9-cis-Retinoic acid (CED0004139)

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:36 UTC

Update Date

2026-05-14 16:47:59 UTC

SynCED ID

CED0004139

Secondary Accession Numbers

CHEM002268
T3D2884

Identification

Common Name

9-cis-Retinoic acid

Class

Small Molecule

Description

9-cis-Retinoic acid belongs to the retinoids, a subclass of prenol lipids within the organic compounds. This endogenous solid has the formula C20H28O2 and an average molecular weight of 300.44 g/mol. It functions biologically as a human metabolite, metabolite, signalling molecule, probe (PMC8603351 ), cofactor (PMC2920089 ), retinoic acid receptor agonist, and retinoid X receptor agonist. Chemically, it acts as an antioxidant and an AP-1 antagonist (PMC8603351 ). The compound is used as a keratolytic drug, an anti-inflammatory agent, and an antineoplastic agent (PMC8603351 ). It is recorded as being found in healthcare, pharmaceuticals, and veterinary products, including antineoplastic agents and anti-acne preparations, as well as in household cleaning and consumer products such as soap dispensers and other smoking requisites, and electrical and electronic equipment including video games, antennas, amplifiers, radio transmission systems, and emergency protective devices. Exposure routes include topical and oral administration. 9-cis-Retinoic acid targets 24 proteins, including retinoic acid receptor gamma (RARG), retinoic acid receptor RXR-beta (RXRB), aldehyde dehydrogenase 1A1 (ALDH1A1), and retinoic acid-induced protein 3 (GPRC5A). It also acts as a binder, downregulator, or upregulator of the estrogen receptor (ESR1), bile acid receptor (NR1H4), retinoic acid receptor alpha (RARA), and retinoic acid receptor RXR-alpha (RXRA). Regarding health effects, the compound is associated with inflammation (PMC5739140 ) and has a therapeutic effect on neuropathy (PMC7589133 ). It is used as a treatment for neuroblastoma (PMC10058801 ), acute promyelocytic leukemia (PMC5564849 ), and cancer (PMC13119245 ).

Contaminant Type

Antineoplastic Agent
Cell Stimulant and Proliferant
Drug
Ester
Food Toxin
Keratolytic Agent
Metabolite
Nutraceutical
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid	ChEBI
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ecl)	ChEBI
AGN 100335	ChEBI
all-(e)-Retinoic acid	ChEBI
all-trans-beta-Retinoic acid	ChEBI
all-trans-Tretinoin	ChEBI
all-trans-Vitamin a acid	ChEBI
all-trans-Vitamin a1 acid	ChEBI
beta-Retinoic acid	ChEBI
Eudyna	ChEBI
Renova	ChEBI
Retin-a	ChEBI
Retinoic acid	ChEBI
Retisol-a	ChEBI
Ro 1-5488	ChEBI
Solage	ChEBI
Stieva-a	ChEBI
trans-Retinoic acid	ChEBI
Tretin m	ChEBI
Tretinoin	ChEBI
Vesanoid	ChEBI
Vitamin a acid	ChEBI
Vitinoin	ChEBI
all-trans-Retinoate	Kegg
Avita	Kegg
Retin a	Kegg
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate	Generator
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate (ecl)	Generator
all-(e)-Retinoate	Generator
all-trans-b-Retinoate	Generator
all-trans-b-Retinoic acid	Generator
all-trans-beta-Retinoate	Generator
all-trans-Β-retinoate	Generator
all-trans-Β-retinoic acid	Generator
b-Retinoate	Generator
b-Retinoic acid	Generator
beta-Retinoate	Generator
Β-retinoate	Generator
Β-retinoic acid	Generator
Retinoate	Generator
trans-Retinoate	Generator
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate	HMDB
Tretinoin zinc salt	HMDB
trans Retinoic acid	HMDB
Acid, all-trans-retinoic	HMDB
Salt, tretinoin sodium	HMDB
beta all trans Retinoic acid	HMDB
beta-all-trans-Retinoic acid	HMDB
Acid, vitamin a	HMDB
Potassium salt, tretinoin	HMDB
Sodium salt, tretinoin	HMDB
Acid, beta-all-trans-retinoic	HMDB
Tretinoin potassium salt	HMDB
Zinc salt, tretinoin	HMDB
Acid, retinoic	HMDB
Acid, trans-retinoic	HMDB
Salt, tretinoin potassium	HMDB
Salt, tretinoin zinc	HMDB
Tretinoin sodium salt	HMDB
all trans Retinoic acid	HMDB
Retin-a micro	HMDB
Atralin	HMDB
Tretin-X	HMDB
all-trans-Retinoic acid	MeSH

Chemical Formula

C₂₀H₂₈O₂

Average Molecular Mass

300.442 g/mol

Monoisotopic Mass

300.209 g/mol

CAS Registry Number

302-79-4

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

Traditional Name

tretinoin

SMILES

[H]/C(=C(/[H])\C(\C)=C(/[H])C(O)=O)/C(/[H])=C(\C)/C(/[H])=C(\[H])C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+

InChI Key

SHGAZHPCJJPHSC-YCNIQYBTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoic acid
Diterpenoid
Retinoid skeleton
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Unsaturated fatty acid
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoic acid (CHEBI:15367 )
Retinoids (C00777 )
Retinoids (LMPR01090019 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

human metabolite ?
immunosuppressive agent (PMC13234310 )?
antimicrobial agent (PMC13407702 , PMC6470549 )?
metabolite (PMC12176739 )?A chemical produced during metabolism process, as an intermediate or end-product
immunomodulator (PMC8813210 )?
antiviral agent (PMC9786992 , PMC10223410 )?
neurotoxin (PMC8707050 )?A chemical substance that interferes with the normal functioning of the nervous system
cofactor (PMC2920089 )?A chemical that is required by an enzyme for its intended chemical activity
retinoid X receptor agonist ?
neurotransmitter (PMC12593592 )?A chemical that allows the transmission of signals from one neuron to the next across synapses
signalling molecule (PMC8454266 , PMC6321216 )?
toxin (PMC7912913 )?A chemical substance naturally produced by an organism and poisonous to other organisms
teratogenic agent (PMC4373338 , PMC4373338 )?A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
agonist (PMC8373093 , PMC10977810 )?
cardiotoxic agent (PMC4321749 )?A role played by a chemical compound exihibiting itself through the ability to induce damage to the heart and cardiomyocytes.
retinoic acid receptor agonist (PMC9432570 )?
AP-1 antagonist ?
antioxidant (PMC6943644 , PMC6943644 )?
drug (PMC4464443 )?
inhibitor (PMC7353666 )?
Antidepressant (PMC7583972 )?
ligand (PMC9432570 )?
protective agent (PMC11274592 )?
probe (PMC8603351 )?
antineoplastic agent (PMC7139512 , PMC8439629 )?
ethanol (PMC9786992 , PMC10223410 )?
neuroprotective agent (PMC11274592 )?
farnesoid X receptor agonist (PMC4894417 )?
hepatoprotective agent (PMC8451635 )?
astringent (PMC9786992 )?
chemosensitiser (PMC11274592 )?

Chemical Roles

antioxidant ?A chemical that is used to maintain the quality, integrity, and safety of finished products by inhibiting the oxidative degradation of the ingredients in the formulation. Also referred to as a preservative (EPA).

Organoleptic Effects

bitter taste ?
sweet taste ?
turbid colour ?
pale yellow colour ?

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	181°C
Boiling Point	Not Available
Solubility	<0.1 g/100 mL

Predicted Properties

Property	Value	Source
Water Solubility	0.0048 g/L	ALOGPS
logP	5.66	ALOGPS
logP	5.01	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.79 m³·mol⁻¹	ChemAxon
Polarizability	36.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-000i-2090000000-db078f48efb8038384f2	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0009000000-12dbd83959268dee6dbf	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-066r-4900000000-31c9262cbbf0bad5b738	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fsl-9600000000-c6681587f0a9ae7a712e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0mc0-4941000000-401db468e6db7c5bbb5a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-d05c305f987a713dfaa0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0239000000-09da873ecbe1e09a1602	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0090000000-dca272cadb8a3ba3f819	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-016r-9630000000-553ddaf9452713df67ee	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0390000000-241af7f979164ecfbf34	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0mc0-4941000000-05bed4117d9ed953a2ca	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-9400000000-3ecfeb7f6c8384d2a0d3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0239000000-2c6852256fcbebe1a2aa	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0910000000-a1c1aa8b35e78558cd5b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uei-0494000000-28e6366fdd47e8ba2117	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052r-2980000000-3e7fc78de83c23830416	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052r-5900000000-ef4d86f8bcf86959f794	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052b-0090000000-e07ffb4c1e5c63ab1b59	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052b-0090000000-a0a8411213bbd2543243	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-3690000000-97e6a74798dd69c30ad1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zir-0973000000-3040e9e4a1a5448efbcb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-060c-1950000000-f3b9c9b378f60b8c49a9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ar3-5910000000-de22eb65f274483f3f98	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052b-0090000000-5f942e3b870e7bd0121b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0190000000-22b445382d3977280045	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-016r-4900000000-0005b37f6d54a42a84f6	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2094.0 Log mg/kg [1200:3700]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission (CR). The exact mechanism of action of tretinoin in APL is unknown.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference
lung cancer	Has Therapeutic Effect On	Not Available	A respiratory system cancer that is located in the lung. (DO)	PMC6470549
lung cancer	Not Available	Not Available	A respiratory system cancer that is located in the lung. (DO)	PMC5789320
inflammation	Associated With?	Not Available	Not Available	PMC5739140
inflammation	Associated With?	decrease	Not Available	PMC10244292
inflammation	Has Therapeutic Effect On	Not Available	Not Available	PMC12060933
cancer	Not Available	Not Available	Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. Possible signs and symptoms include a lump, abnormal bleeding, prolonged cough, unexplained weight loss, and a change in bowel movements. There are over 100 types of cancers affect humans. The risk of developing certain cancers can be reduced by not smoking, maintaining a healthy weight, not drinking too much alcohol, eating plenty of vegetables, fruits and whole grains, vaccination against certain infectious diseases, not eating too much processed and red meat and avoiding too much sunlight exposure. Cancer is often treated with some combination of radiation therapy, surgery, chemotherapy and targeted therapy. The majority of cancers, some 90–95% of cases, are due to genetic mutations from environmental and lifestyle factors. The remaining 5–10% are due to inherited genetics.	PMC13119245 , PMC9031226
cancer	Has Therapeutic Effect On	Not Available	Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. Possible signs and symptoms include a lump, abnormal bleeding, prolonged cough, unexplained weight loss, and a change in bowel movements. There are over 100 types of cancers affect humans. The risk of developing certain cancers can be reduced by not smoking, maintaining a healthy weight, not drinking too much alcohol, eating plenty of vegetables, fruits and whole grains, vaccination against certain infectious diseases, not eating too much processed and red meat and avoiding too much sunlight exposure. Cancer is often treated with some combination of radiation therapy, surgery, chemotherapy and targeted therapy. The majority of cancers, some 90–95% of cases, are due to genetic mutations from environmental and lifestyle factors. The remaining 5–10% are due to inherited genetics.	PMC10255398 , PMC11284039
breast cancer	Has Therapeutic Effect On	Not Available	A breast cancer that has material basis in abnormally proliferating cells derives from epithelial cells. (DO)	PMC3703873 , PMC6470549
colorectal cancer	Has Therapeutic Effect On	Not Available	A large intestine cancer that is located in the colon and/or located in the rectum. (DO)	PMC6470549
stroke	Has Therapeutic Effect On	Not Available	Not Available	PMC12101329
Prostate cancer	Not Available	Not Available	A male reproductive organ cancer that is located in the prostate. (DO)	PMC11882781
melanoma	Has Therapeutic Effect On	Not Available	A cell type cancer that has material basis in abnormally proliferating cells derives from melanocytes which are found in skin, the bowel and the eye. (DO)	PMC6470549 , PMC11274592
Hepatocellular carcinoma	Has Therapeutic Effect On	Not Available	A liver carcinoma that has material basis in undifferentiated hepatocytes. (DO)	PMC6470549
necrosis	Has Therapeutic Effect On	Not Available	A disorder characterized as a form of cell injury which results in the premature death of cells in living tissue by autolysis.	PMC8451635
necrosis	Associated With?	Not Available	A disorder characterized as a form of cell injury which results in the premature death of cells in living tissue by autolysis.	PMC9409216
leukemia	Not Available	Not Available	A cancer that affects the blood or bone marrow characterized by an abnormal proliferation of blood cells. (DO)	PMC10014767 , PMC10046612
leukemia	Has Therapeutic Effect On	Not Available	A cancer that affects the blood or bone marrow characterized by an abnormal proliferation of blood cells. (DO)	PMC6470549
psoriasis	Not Available	Not Available	A disorder characterized by a quicker life span of skin cells causing cells to build up rapidly on the surface of the skin.	PMC4464443 , PMC9069627
myocardial infarction	Has Therapeutic Effect On	Not Available	A disorder characterized by gross necrosis of the myocardium; this is due to an interruption of blood supply to the area. (NCI CTCAE)	PMC13234310
edema	Associated With?	Not Available	A disorder characterized by swelling due to an excessive accumulation of fluid (NCI CTCAE)	PMC13234310
Acne	Not Available	Not Available	A disorder of the skin in which oil glands and hair glands become inflamed.	PMC4464443 , PMC6536957
male infertility	Associated With?	Not Available	Not Available	PMC12776080
neuropathy	Has Therapeutic Effect On	Not Available	A nervous system disease that is located in nerves or nerve cells. (do).	PMC7589133
ischemia	Has Therapeutic Effect On	Not Available	A disorder characterized by a decrease or absence of blood supply to an organ or tissue, caused by obstruction (thrombosis or embolism) of an artery. (NCI CTCAE)	PMC12101329 , PMC12101329
ovarian cancer	Not Available	Not Available	A female reproductive organ cancer that is located in the ovary. (DO)	PMC11086401
ovarian cancer	Has Therapeutic Effect On	Not Available	A female reproductive organ cancer that is located in the ovary. (DO)	PMC6470549
neuroblastoma	Not Available	Not Available	An autonomic nervous system neoplasm that derives from immature nerve cells. (DO)	PMC10058801 , PMC7053487
neuroblastoma	Has Therapeutic Effect On	Not Available	An autonomic nervous system neoplasm that derives from immature nerve cells. (DO)	PMC2695280 , PMC8439629
proteinuria	Associated With?	Not Available	A disorder characterized by excess excretion of albumin in the urine. Usually an early sign for CKD.	PMC13234310
myeloid leukemia	Has Therapeutic Effect On	Not Available	Not Available	PMC13362805
skin cancer	Has Therapeutic Effect On	Not Available	Not Available	PMC6470549
breast	Has Therapeutic Effect On	Not Available	Not Available	PMC11274592
Kaposi's sarcoma	Not Available	Not Available	Not Available	PMC2695280
pancreatic cancer	Has Therapeutic Effect On	Not Available	An endocrine gland cancer located in the pancreas. (DO)	PMC9370260
lung	Has Therapeutic Effect On	Not Available	Not Available	PMC11274592
allergic disease	Associated With?	Not Available	Allergic diseases, also known as allergies, are a number of conditions caused by hypersensitivity of the immune system to typically harmless substances in the environment. These diseases include hay fever, food allergies, atopic dermatitis, allergic asthma, and anaphylaxis. Symptoms may include red eyes, an itchy rash, sneezing, a runny nose, shortness of breath, or swelling. Common allergens include pollen and certain foods. Metals and other substances may also cause allergies. Food, insect stings, and medications are common causes of severe allergic reactions. Allergies can be due to both genetic and environmental factors. The underlying mechanism involves immunoglobulin E antibodies (IgE) binding to an allergen and then to a receptor on mast cells or basophils where it triggers the release of inflammatory chemicals such as histamine. Allergies are among the most common conditions in the world. In the developed world, about 20% of people are affected by allergic rhinitis, about 6% of people have at least one food allergy, and about 20% have atopic dermatitis at some point in time.	PMC9483786
acute promyelocytic leukemia	Not Available	Not Available	An acute myeloid leukemia characterized by accumulation of promyelocytes in the bone marrow and by a translocation between chromosomes 15 and 17. (DO)	PMC5564849 , PMC6536957
soft tissue sarcoma	Not Available	Not Available	Not Available	PMC9657890
hematologic cancer	Not Available	Not Available	Not Available	PMC11084730
ovarian carcinoma	Not Available	Not Available	Not Available	PMC2695280
lung adenocarcinoma	Associated With?	Not Available	Not Available	PMC12630483
head and neck squamous cell carcinoma	Not Available	Not Available	Not Available	PMC2695280
cleft palate	Associated With?	increase	Not Available	PMC2643957
cleft palate	Associated With?	Not Available	Not Available	PMC2376161 , PMC7672605
adenoid cystic carcinoma	Has Therapeutic Effect On	Not Available	Not Available	PMC8533791
urinary bladder cancer	Not Available	Not Available	Not Available	PMC2695280
Cell Death	Associated With?	Not Available	Not Available	PMC11486635
Oxidative Stress	Has Therapeutic Effect On	Not Available	Not Available	PMC12060933 , PMC13010960
Oxidative Stress	Associated With?	increase	Not Available	PMC5016891
cardiovascular disorder	Has Therapeutic Effect On	Not Available	Not Available	PMC13234310
Fibrosis	Has Therapeutic Effect On	Not Available	Not Available	PMC8112759 , PMC7036515
nervous system disorder	Has Therapeutic Effect On	Not Available	Not Available	PMC12101329 , PMC12101329
acute lung injury	Has Therapeutic Effect On	Not Available	Not Available	PMC10244292
lip and oral cavity carcinoma	Has Therapeutic Effect On	Not Available	Not Available	PMC6470549
depressive disorder	Associated With?	increase	Not Available	PMC11643848
depressive disorder	Associated With?	Not Available	Not Available	PMC4360223
Fertility	Associated With?	Not Available	Not Available	PMC7502037
Fertility	Associated With?	increase	Not Available	PMC8957012
infectious disease	Associated With?	Not Available	Not Available	PMC9483786
Apoptosis	Associated With?	Not Available	Not Available	PMC9409216
autistic disorder	Decreased in Blood In	decrease	Not Available	PMC12732708
lung non-small cell carcinoma	Has Therapeutic Effect On	Not Available	Not Available	PMC6350198 , PMC11274592
ulcer disease	Associated With?	Not Available	Not Available	PMC13234310
Hematologic Neoplasms	Not Available	Not Available	Not Available	PMC3894235
Neurodegenerative Diseases	Decreased in Blood In	decrease	Not Available	PMC12732708
diabetic kidney disease	Has Therapeutic Effect On	Not Available	Not Available	PMC10244292
Reproductive Health	Has Therapeutic Effect On	Not Available	Not Available	PMC12732580
Skin Aging	Has Therapeutic Effect On	Not Available	Not Available	PMC11783858
hyperlipidemia	Associated With?	increase	Not Available	PMC5016891
Drug Resistance, Multiple	Has Therapeutic Effect On	Not Available	Not Available	PMC11274592
Melasma	Not Available	Not Available	Not Available	PMC11762136
Hearing impairment	Associated With?	inverse	Not Available	PMC12878100
acute liver failure	Not Available	Not Available	Not Available	PMC8451635
Ferroptosis	Has Therapeutic Effect On	Not Available	Not Available	PMC11366759
adult respiratory distress syndrome	Associated With?	Not Available	Not Available	PMC8813210
Lymphoma, T-Cell	Not Available	Not Available	Not Available	PMC4464443 , PMC9069627
keloid	Not Available	Not Available	Not Available	PMC5370439
Abnormality of the skeletal system	Associated With?	Not Available	Not Available	PMC12971886
Pustule	Associated With?	Not Available	Not Available	PMC4154068
Chromosome breakage	Associated With?	Not Available	Not Available	PMC7912913
extrahepatic cholestasis	Has Therapeutic Effect On	Not Available	Not Available	PMC8451635
cheilitis	Associated With?	Not Available	Not Available	PMC9657890

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000010	Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.	Agriculture & land management	PubChem
CEDs000050	Groundwater?Groundwater serves as a vital resource for drinking water and agricultural irrigation but is increasingly susceptible to contamination from synthetic chemicals.	Aquatic systems & sediments	PMC13038014 , PMC13038014
CEDs000233	Brushes?Brushes used in personal care and cosmetics can be a source of synthetic chemical contamination due to the materials and coatings used in their manufacturing.	Personal care & cosmetics	PubChem
CEDs000314	Anti-acne preparations?Anti-acne preparations often contain synthetic chemicals such as benzoyl peroxide, salicylic acid, and various retinoids.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000358	Antineoplastic agents?Antineoplastic agents are a class of synthetic chemicals used primarily in the treatment of cancer.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000505	Amplifiers?Amplifiers, commonly used in various electronic devices to enhance signal strength, can be a source of synthetic chemical contamination due to the materials and processes involved in their production and disposal.	Electrical & Electronic Equipment	PubChem
CEDs000506	Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.	Electrical & Electronic Equipment	PubChem
CEDs000511	Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.	Electrical & Electronic Equipment	PubChem
CEDs000517	Electric Switches?Electric switches, integral components in numerous devices, can be a source of synthetic chemical contamination due to the materials and manufacturing processes involved in their production.	Electrical & Electronic Equipment	PubChem
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000519	Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.	Electrical & Electronic Equipment	PubChem
CEDs000520	Emergency Protective Devices?Emergency protective devices, such as circuit breakers and surge protectors, are essential components in electrical systems designed to prevent damage from overcurrent and surges.	Electrical & Electronic Equipment	PubChem
CEDs000524	Hybrid Capacitors?Hybrid capacitors are energy storage devices that combine the properties of electrolytic and supercapacitors, utilizing a combination of electrochemical principles to achieve higher energy density and power density.	Electrical & Electronic Equipment	PubChem
CEDs000530	Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.	Electrical & Electronic Equipment	PubChem
CEDs000539	Video Games?Video games, through their production and disposal processes, can be a source of synthetic chemical contamination.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	PubChem
CEDs000561	Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.	Household cleaning & consumer products	PubChem
CEDs000563	Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.	Household cleaning & consumer products	PubChem
CEDs000564	Soap Dispensers?Soap dispensers, commonly used for dispensing liquid soaps and sanitizers, can become a source of synthetic chemical contamination due to the materials used in their construction and the products they dispense.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000578	Making Cigars?The process of making cigars involves several steps, including the cultivation of tobacco, fermentation, and the application of various additives to enhance flavor and preservation.	Industrial manufacturing & chemical processing	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000581	Paper Making Machines?Paper making machines utilize various synthetic chemicals throughout the production process, including additives, coatings, and bleaching agents.	Industrial manufacturing & chemical processing	PubChem
CEDs000600	Herbicides And Algicides?Herbicides and algicides are synthetic chemicals primarily used to control unwanted plants and algae in various environments.	Agriculture & land management	PubChem
CEDs000606	Plant Growth Regulators?Plant Growth Regulators (PGRs) are synthetic chemicals designed to influence the growth and development of plants.	Agriculture & land management	PubChem
CEDs000609	Aftershave?Aftershave is a grooming product typically used to soothe and protect the skin following shaving.	Personal care & cosmetics	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000612	Body Washing Or Cleaning Implements?Body washing or cleaning implements, such as synthetic sponges, loofahs, and washcloths, can be sources of synthetic chemical contamination due to the materials used in their production.	Personal care & cosmetics	PubChem
CEDs000613	Depilatories?Depilatories are products designed to remove unwanted hair through the application of synthetic chemicals that break down the protein structure of hair, facilitating its removal.	Personal care & cosmetics	PubChem
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000616	Face Mask Cosmetics?Face mask cosmetics often contain a variety of synthetic chemicals, including preservatives, emulsifiers, and fragrances, which can contribute to chemical contamination.	Personal care & cosmetics	PubChem
CEDs000617	Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	PubChem
CEDs000630	Toys?Toys, particularly those made from synthetic materials such as plastics, can be a source of chemical contamination due to the presence of various additives and compounds used in their production.	Recreation & sports surfaces	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000642	Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.	Textiles, leather & furnishings	PubChem
CEDs000643	Headwear?Headwear made from synthetic materials often incorporates chemicals used in the manufacturing and finishing processes, such as dyes, flame retardants, and water repellents.	Textiles, leather & furnishings	PubChem
CEDs000662	Yarns Or Threads?Yarns or threads used in textiles can be a source of synthetic chemical contamination due to the production processes and treatments they undergo.	Textiles, leather & furnishings	PubChem
CEDs000679	Phosphatic Fertilisers?Phosphatic fertilizers are synthetic chemical products primarily composed of phosphorus, which is essential for plant growth.	Agriculture & land management	PubChem
CEDs000684	Cements?Cements are a composite material primarily used as a binding agent in construction applications, formed by the calcination of limestone and clay minerals at high temperatures.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	PubChem
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	PubChem
CEDs000743	Sludge Treatment?Sludge treatment involves the processing of waste materials generated from wastewater treatment plants, which often contain a variety of organic and inorganic substances.	Wastewater, sanitation & biosolids	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem
CEDs00745	Corn Oil	Agriculture & land management	PMC11274592
CEDs01148	Milk	Food, food processing & cookware	PMC10886360 , PMC10886360
CEDs01162	Dairy Products	Food, food processing & cookware	PMC10886360
CEDs01168	Food Products	Food, food processing & cookware	PMC10886360 , PMC11274592
CEDs01181	Food Items	Food, food processing & cookware	PMC11274592
CEDs01281	Food Formulations	Food, food processing & cookware	PMC11274592
CEDs01300	Animal Foods	Food, food processing & cookware	PMC13066785
CEDs01329	Spices	Food, food processing & cookware	PMC11274592
CEDs01879	Resin	Industrial manufacturing & chemical processing	PMC7696232
CEDs02145	Liquid Wastes	Waste management, landfill & incineration	PMC4492269
CEDs02219	Private Well Water	Drinking water & water supply	PMC13038014
CEDs02255	Water	Aquatic systems & sediments	PMC2695280 , PMC2695280
CEDs02270	River	Aquatic systems & sediments	PMC12197792
CEDs02285	Aquifer	Aquatic systems & sediments	PMC13038014 , PMC13038014
CEDs02361	Stream Sediment	Aquatic systems & sediments	PMC4492269
CEDs02750	Asphalt Binder	Building & Construction	PMC8704828

Pathways

5 pathwaysPathway Source: PathBank

Retinol Metabolism

Vitamin A Deficiency

all-trans-Retinoic acid Drug Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Retinoic acid receptor alpha	P11416	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.9 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 16 E-value 0.0778492
Click to view 3D structure	Retinoic acid receptor gamma	P18911	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.881 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 14 E-value 0.0778492
Click to view 3D structure	Retinoic acid receptor beta	P22605	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.881 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 14 E-value 0.0778492
Click to view 3D structure	Cytochrome P450 2B6	P20813	Humans	Known	Not Available
Click to view 3D structure	Retinoic acid receptor RXR-alpha	P19793	Humans	Predicted (SEA)	Prediction Confidence Score 0.833 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 82 E-value 0.0778492
Click to view 3D structure	Retinoic acid receptor gamma	P13631	Humans	Predicted (SEA)	Prediction Confidence Score 0.806 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 52 E-value 0.0778492
Click to view 3D structure	Retinoic acid receptor RXR-alpha	P28700	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.787 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 17 E-value 0.0778492
Click to view 3D structure	Cellular retinoic acid-binding protein 1	P62965	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.787 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 7 E-value 0.0778492
Click to view 3D structure	Cellular retinoic acid-binding protein 2	P22935	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.787 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 7 E-value 0.0778492
Click to view 3D structure	Catalase	P04040	Humans	Known	Not Available
Click to view 3D structure	Aldehyde dehydrogenase 1A1	P27463	Gallus gallus	Predicted (SEA)	Prediction Confidence Score 0.766 Applicability Domain 0.766 Statistical Significance 1.00e-05 Supporting Reference Compounds 1 E-value 0.0778492
Click to view 3D structure	Cellular retinoic acid-binding protein 1	P40220	Gallus gallus	Predicted (SEA)	Prediction Confidence Score 0.746 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 5 E-value 0.0778492
Click to view 3D structure	Retinoic acid receptor beta	P10826	Humans	Predicted (SEA)	Prediction Confidence Score 0.738 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 47 E-value 0.0778492
Click to view 3D structure	Retinoic acid receptor alpha	P10276	Humans	Predicted (SEA)	Prediction Confidence Score 0.738 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 53 E-value 0.0778492
Click to view 3D structure	Retinoic acid receptor RXR-gamma	P48443	Humans	Predicted (SEA)	Prediction Confidence Score 0.671 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 31 E-value 0.0778492
Click to view 3D structure	Prosaposin	P07602	Humans	Predicted (SEA)	Prediction Confidence Score 0.667 Applicability Domain 0.667 Statistical Significance 2.00e-05 Supporting Reference Compounds 1 E-value 0.155698
Click to view 3D structure	Retinoic acid receptor RXR-beta	P28702	Humans	Predicted (SEA)	Prediction Confidence Score 0.652 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 31 E-value 0.0778492
Click to view 3D structure	Beta-lactoglobulin	P02754	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.613 Applicability Domain 0.696 Statistical Significance 1.00e-05 Supporting Reference Compounds 2 E-value 0.0778492
Click to view 3D structure	Retinoic acid receptor RXR-gamma	P28705	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.601 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 20 E-value 0.0778492
Click to view 3D structure	Retinoic acid receptor RXR-beta	P28704	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.571 Applicability Domain 1.0 Statistical Significance 3.00e-05 Supporting Reference Compounds 19 E-value 0.233548
Click to view 3D structure	Alpha-synuclein	P37840	Humans	Predicted (SEA)	Prediction Confidence Score 0.552 Applicability Domain 1.0 Statistical Significance 6.00e-05 Supporting Reference Compounds 38 E-value 0.467095
Click to view 3D structure	Amyloid-beta precursor protein	P05067	Humans	Predicted (SEA)	Prediction Confidence Score 0.552 Applicability Domain 1.0 Statistical Significance 2.30e-04 Supporting Reference Compounds 109 E-value 1.79053
Click to view 3D structure	Retinoic acid receptor gamma	P13631	Humans	Known	Not Available
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	Prediction Confidence Score 0.493 Applicability Domain 1.0 Statistical Significance 0.0025 Supporting Reference Compounds 686 E-value 19.618
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	Prediction Confidence Score 0.493 Applicability Domain 1.0 Statistical Significance 0.0039 Supporting Reference Compounds 391 E-value 30.2055
Click to view 3D structure	Mitogen-activated protein kinase 1	P28482	Humans	Predicted (SEA)	Prediction Confidence Score 0.479 Applicability Domain 1.0 Statistical Significance 0.0042 Supporting Reference Compounds 763 E-value 33.0081
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	Prediction Confidence Score 0.45 Applicability Domain 1.0 Statistical Significance 3.40e-04 Supporting Reference Compounds 104 E-value 2.64687
Click to view 3D structure	Retinoic acid receptor RXR-alpha	Q05343	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.424 Applicability Domain 1.0 Statistical Significance 3.00e-05 Supporting Reference Compounds 7 E-value 0.233548
Click to view 3D structure	Serine/threonine-protein kinase mTOR	P42345	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 1A1	P00185	Rat	Known	Not Available
Click to view 3D structure	Cytochrome P450 2S1	Q96SQ9	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 26B1	Q9NR63	Humans	Known	Not Available
Click to view 3D structure	Isocitrate lyase	P9WKK7	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Known	Not Available
Click to view 3D structure	Cellular retinoic acid-binding protein 1	P29762	Humans	Known	Not Available
Click to view 3D structure	Cellular retinoic acid-binding protein 2	P29373	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 2C8	P10632	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 26C1	Q6V0L0	Humans	Known	Not Available
Click to view 3D structure	Endoglucanase	P19424	Bacillus sp. (strain KSM-635)	Known	Not Available
Click to view 3D structure	UDP-glucuronosyltransferase 2B7	P16662	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 3A7	P24462	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 2E1	P05181	Humans	Known	Not Available
Click to view 3D structure	Aldehyde dehydrogenase 1A1	P00352	Humans	Known	Not Available
Click to view 3D structure	Retinal dehydrogenase 2	O94788	Humans	Known	Not Available
Click to view 3D structure	Hexokinase-4	P35557	Humans	Known	Not Available
Click to view 3D structure	Vascular endothelial growth factor A, long form	P15692	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 1B1	Q16678	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 7A1	P22680	Humans	Known	Not Available
Click to view 3D structure	Glutathione S-transferase	Q59721	Burkholderia xenovorans (strain LB400)	Known	Not Available
Click to view 3D structure	UDP-glucuronosyltransferase 1A9	O60656	Humans	Known	Not Available
Click to view 3D structure	Aldo-keto reductase family 1 member B10	O60218	Humans	Known	Not Available
Click to view 3D structure	Aldo-keto reductase family 1 member C2	P52895	Humans	Known	Not Available
Click to view 3D structure	Albumin	P02768	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 26A1	O43174	Humans	Known	Not Available
Click to view 3D structure	Retinaldehyde dehydrogenase 3	P47895	Humans	Known	Not Available
Click to view 3D structure	Retinoic acid receptor RXR-alpha	P19793	Humans	Known	Not Available
Click to view 3D structure	Retinoic acid receptor alpha	P10276	Humans	Known	Not Available
Click to view 3D structure	Retinoic acid receptor RXR-beta	P28702	Humans	Known	Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission (CR). The exact mechanism of action of tretinoin in APL is unknown.
Click to view 3D structure	Retinoic acid receptor gamma	P13631	Humans	Known	Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission (CR). The exact mechanism of action of tretinoin in APL is unknown.
Click to view 3D structure	Retinoic acid receptor RXR-gamma	P48443	Humans	Known	Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission (CR). The exact mechanism of action of tretinoin in APL is unknown.
Click to view 3D structure	Retinoic acid receptor beta	P10826	Humans	Known	Not Available
Click to view 3D structure	Aldehyde dehydrogenase 1A1	P00352	Humans	Known	Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission (CR). The exact mechanism of action of tretinoin in APL is unknown.
Click to view 3D structure	Retinal dehydrogenase 2	O94788	Humans	Known	Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission (CR). The exact mechanism of action of tretinoin in APL is unknown.
Click to view 3D structure	Nuclear receptor subfamily 0 group B member 1	P51843	Humans	Known	Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission (CR). The exact mechanism of action of tretinoin in APL is unknown.
Click to view 3D structure	Retinoic acid receptor responder protein 1	P49788	Humans	Known	Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission (CR). The exact mechanism of action of tretinoin in APL is unknown.
Click to view 3D structure	Retinoic acid-induced protein 3	Q8NFJ5	Humans	Known	Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission (CR). The exact mechanism of action of tretinoin in APL is unknown.
Click to view 3D structure	Cellular retinoic acid-binding protein 2	P29373	Humans	Known	Not Available
Click to view 3D structure	Lipocalin-1	P31025	Humans	Known	Not Available
Click to view 3D structure	Odorant-binding protein 2a	Q9NY56	Humans	Known	Not Available
Click to view 3D structure	Protein AMBP	P02760	Humans	Known	Not Available
Click to view 3D structure	Retinol-binding protein 4	P02753	Humans	Known	Not Available
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37231	Humans	Known	Not Available
Click to view 3D structure	Estrogen receptor	P03372	Humans	Known	Not Available
Click to view 3D structure	Bile acid receptor	Q96RI1	Humans	Known	Not Available
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 1A1	P04798	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0001852

FooDB ID

FDB022710

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Link

General References

Huang ME, Ye YC, Chen SR, Chai JR, Lu JX, Zhoa L, Gu LJ, Wang ZY: Use of all-trans retinoic acid in the treatment of acute promyelocytic leukemia. Blood. 1988 Aug;72(2):567-72. [PubMed: 3165295]
Castaigne S, Chomienne C, Daniel MT, Ballerini P, Berger R, Fenaux P, Degos L: All-trans retinoic acid as a differentiation therapy for acute promyelocytic leukemia. I. Clinical results. Blood. 1990 Nov 1;76(9):1704-9. [PubMed: 2224119]
Sanz MA: Treatment of acute promyelocytic leukemia. Hematology Am Soc Hematol Educ Program. 2006:147-55. [PubMed: 17124054]
Mao JT, Goldin JG, Dermand J, Ibrahim G, Brown MS, Emerick A, McNitt-Gray MF, Gjertson DW, Estrada F, Tashkin DP, Roth MD: A pilot study of all-trans-retinoic acid for the treatment of human emphysema. Am J Respir Crit Care Med. 2002 Mar 1;165(5):718-23. [PubMed: 11874821]
Roth MD, Connett JE, D'Armiento JM, Foronjy RF, Friedman PJ, Goldin JG, Louis TA, Mao JT, Muindi JR, O'Connor GT, Ramsdell JW, Ries AL, Scharf SM, Schluger NW, Sciurba FC, Skeans MA, Walter RE, Wendt CH, Wise RA: Feasibility of retinoids for the treatment of emphysema study. Chest. 2006 Nov;130(5):1334-45. [PubMed: 17099008]
Mertz JR, Shang E, Piantedosi R, Wei S, Wolgemuth DJ, Blaner WS: Identification and characterization of a stereospecific human enzyme that catalyzes 9-cis-retinol oxidation. A possible role in 9-cis-retinoic acid formation. J Biol Chem. 1997 May 2;272(18):11744-9. [PubMed: 9115228]
Drugs.com - http://www.drugs.com/cons/Tretinoin.html

9-cis-Retinoic acid (CED0004139)

Structure for CHEM002268: 9-cis-Retinoic acid

Structure