Retinoic acid, 13-cis- (CED0003035)

Record Information
Version1.0
Creation Date2016-05-19 03:56:03 UTC
Update Date2026-05-14 16:54:51 UTC
Accession NumberCHEM012455
Identification
Common NameRetinoic acid, 13-cis-
ClassSmall Molecule
Description
Retinoic acid, 13-cis- belongs to the retinoids, a subclass of prenol lipids within the organic compounds. This compound, which falls under the superclass of lipids and lipid-like molecules, has the chemical formula C20H28O2 and an average molecular weight of 300.44 g/mol. It is used for industrial pharmaceutical purposes. The compound is found in seven recorded sources, including anti-acne preparations within healthcare, pharmaceuticals, and veterinary products. It is also present in floors used in building and construction, line transmission systems in electrical and electronic equipment, and the preparation of vinegar in food, food processing, and cookware. Additionally, it is found in household cleaning and consumer products, specifically other smoking requisites, pipe accessories, and non-electric simulated smoking devices. Recorded exposure routes for this substance include topical and oral administration. Regarding its biological activity, retinoic acid, 13-cis- has two recorded protein targets. It acts as an agonist for both the retinoic acid receptor alpha (RARA) and the retinoic acid receptor gamma (RARG), although its interaction with RARG is also categorized as other/unknown.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(7E,9E,11E,13Z)-Retinoic acidChEBI
13-cis-Vitamin a acidChEBI
13-RAChEBI
AccutaneChEBI
AmnesteemChEBI
cis-RAChEBI
ClaravisChEBI
IsotretinoinaChEBI
IsotretinoineChEBI
IsotretinoinoChEBI
IsotretinoinumChEBI
Neovitamin a acidChEBI
AbsoricaKegg
SotretKegg
(7E,9E,11E,13Z)-RetinoateGenerator
13-cis-RetinoateGenerator
(13-cis)-RetinoateHMDB
(13-cis)-Retinoic acidHMDB
CIP-isotretinoinHMDB
cis-RetinoateHMDB
cis-Retinoic acidHMDB
IsotretinoinHMDB
IsotrexHMDB
RetinoateHMDB
Retinoic acidHMDB
RoaccutanHMDB
RoaccutaneHMDB
RoacutanHMDB
TeriosalHMDB
Isotretinoin zinc salt, 13 cis isomerHMDB
Isotretinoin zinc salt, 13-cis-isomerHMDB
13 cis Retinoic acidHMDB
13-cis-Retinoate,isotretinoinHMDB
13-cis-Retinoic acidChEBI
Chemical FormulaC20H28O2
Average Molecular Mass300.435 g/mol
Monoisotopic Mass300.209 g/mol
CAS Registry Number4759-48-2
IUPAC Name(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
Traditional Nameisotretinoin
SMILESC\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C\C(O)=O
InChI IdentifierInChI=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 KeySHGAZHPCJJPHSC-XFYACQKRSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
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 FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0048 g/LALOGPS
logP5.66ALOGPS
logP5.01ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.79 m³·mol⁻¹ChemAxon
Polarizability36.15 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-052r-2090000000-42b8aa0666b5a088671bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-5139000000-29caedb85908ca2b99f4Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-12dbd83959268dee6dbfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-066r-4900000000-31c9262cbbf0bad5b738Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fsl-9600000000-c6681587f0a9ae7a712eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uei-0494000000-28e6366fdd47e8ba2117Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-2980000000-3e7fc78de83c23830416Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-5900000000-ef4d86f8bcf86959f794Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052b-0090000000-e07ffb4c1e5c63ab1b59Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052b-0090000000-a0a8411213bbd2543243Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-3690000000-97e6a74798dd69c30ad1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zir-0973000000-3040e9e4a1a5448efbcbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-060c-1950000000-f3b9c9b378f60b8c49a9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ar3-5910000000-de22eb65f274483f3f98Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052b-0090000000-5f942e3b870e7bd0121bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0190000000-22b445382d3977280045Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016r-4900000000-0005b37f6d54a42a84f6Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2094.0Log mg/kg[1200:3700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
rosaceais_treatment_forNot AvailablePMC9724583
Exposure Sources
Source IDSourceSectorReference
314Anti-acne preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
497FloorsBuilding & ConstructionNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Alpha-synuclein structureClick to view 3D structureAlpha-synucleinP37840HumansPredicted (SEA)0.467095
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)1.79053
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)19.618
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)30.2055
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)33.0081
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)2.64687
Click to view 3D structureRetinoic acid receptor RXR-alphaQ05343Rattus norvegicusPredicted (SEA)0.233548
Click to view 3D structureRetinoic acid receptor alphaP11416Mus musculusPredicted (SEA)0.0778492
Click to view 3D structureRetinoic acid receptor gammaP18911Mus musculusPredicted (SEA)0.0778492
Click to view 3D structureRetinoic acid receptor betaP22605Mus musculusPredicted (SEA)0.0778492
Retinoic acid receptor RXR-alpha structureClick to view 3D structureRetinoic acid receptor RXR-alphaP19793HumansPredicted (SEA)0.0778492
Retinoic acid receptor gamma structureClick to view 3D structureRetinoic acid receptor gammaP13631HumansPredicted (SEA)0.0778492
Click to view 3D structureRetinoic acid receptor RXR-alphaP28700Mus musculusPredicted (SEA)0.0778492
Click to view 3D structureCellular retinoic acid-binding protein 1P62965Mus musculusPredicted (SEA)0.0778492
Click to view 3D structureCellular retinoic acid-binding protein 2P22935Mus musculusPredicted (SEA)0.0778492
Click to view 3D structureAldehyde dehydrogenase 1A1P27463Gallus gallusPredicted (SEA)0.0778492
Click to view 3D structureCellular retinoic acid-binding protein 1P40220Gallus gallusPredicted (SEA)0.0778492
Retinoic acid receptor beta structureClick to view 3D structureRetinoic acid receptor betaP10826HumansPredicted (SEA)0.0778492
Retinoic acid receptor alpha structureClick to view 3D structureRetinoic acid receptor alphaP10276HumansPredicted (SEA)0.0778492
Retinoic acid receptor RXR-gamma structureClick to view 3D structureRetinoic acid receptor RXR-gammaP48443HumansPredicted (SEA)0.0778492
Prosaposin structureClick to view 3D structureProsaposinP07602HumansPredicted (SEA)0.155698
Retinoic acid receptor RXR-beta structureClick to view 3D structureRetinoic acid receptor RXR-betaP28702HumansPredicted (SEA)0.0778492
Click to view 3D structureBeta-lactoglobulinP02754Bos taurusPredicted (SEA)0.0778492
Click to view 3D structureRetinoic acid receptor RXR-gammaP28705Mus musculusPredicted (SEA)0.0778492
Click to view 3D structureRetinoic acid receptor RXR-betaP28704Mus musculusPredicted (SEA)0.233548
Concentrations
Not Available
External Links
DrugBank IDDB00982
HMDB IDHMDB0006219
FooDB IDFDB023843
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2430432
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIsotretinoin
Chemspider ID4445539
ChEBI ID6067
PubChem Compound ID5282379
Kegg Compound IDC07058
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Blaner WS: Cellular metabolism and actions of 13-cis-retinoic acid. J Am Acad Dermatol. 2001 Nov;45(5):S129-35.
2. Chen H, Juchau MR: Recombinant human glutathione S-transferases catalyse enzymic isomerization of 13-cis-retinoic acid to all-trans-retinoic acid in vitro. Biochem J. 1998 Nov 15;336 ( Pt 1):223-6.
3. Tsukada M, Schroder M, Roos TC, Chandraratna RA, Reichert U, Merk HF, Orfanos CE, Zouboulis CC: 13-cis retinoic acid exerts its specific activity on human sebocytes through selective intracellular isomerization to all-trans retinoic acid and binding to retinoid acid receptors. J Invest Dermatol. 2000 Aug;115(2):321-7.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11606947
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11866680
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15304471
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18077132
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18788179
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19568610
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=20482692
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23676507
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=9807973