Retinal (CED0000471)

Record Information

Version

1.0

Creation Date

2016-05-22 03:59:53 UTC

Update Date

2026-04-03 01:07:03 UTC

Accession Number

CHEM017186

Identification

Common Name

Retinal

Class

Small Molecule

Description

Retinal is an organic compound with the formula $\text{C}_{20}\text{H}_{28}\text{O}$ and an average molecular weight of 284.44 g/mol. Retinal belongs to the retinoids, a subclass of prenol lipids within the organic compounds. In biological contexts, the compound serves as a chromophore (PMC12361693). Industrially, it is utilized as a softener and conditioner (PMC12361693). Retinal is associated with 12 recorded sources. Within the category of electrical and electronic equipment, it is found in amplifiers, antennas, coils, electric hearing aids, loudspeakers, and three additional sources. In the sector of household cleaning and consumer products, it is identified in tobacco product cases and non-electric simulated smoking devices. Furthermore, it is found in floors within building and construction, as well as in the preparation of vinegar within food, food processing and cookware.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(13cis)-Retinal	ChEBI
(2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal	ChEBI
13-cis-Retinaldehyde	ChEBI
RETINAL	ChEBI
13Z-Retinal	HMDB
cis-13-Retinal	HMDB
Neoretinene a	HMDB
Neovitamin a aldehyde	HMDB
13-cis-Retinal	MeSH, HMDB

Chemical Formula

C₂₀H₂₈O

Average Molecular Mass

284.436 g/mol

Monoisotopic Mass

284.214 g/mol

CAS Registry Number

116-31-4

IUPAC Name

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

Traditional Name

13-cis retinal

SMILES

C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O

InChI Identifier

InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

InChI Key

NCYCYZXNIZJOKI-OVSJKPMPSA-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

Retinoid skeleton
Diterpenoid
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinal (CHEBI:45487 )
Retinoids (LMPR01090018 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

chromophore

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
logP	4.86	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.87 m³·mol⁻¹	ChemAxon
Polarizability	35.47 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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	splash10-014i-2290000000-df9d2aa7545cc60a54f9	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-9700000000-c2e22000dfae0765c367	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03g0-0950000000-bccf87de037f98873f41	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01t9-1910000000-5fe7643c395769c68286	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-9700000000-fca532f917595376d653	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0490000000-f543f08fbaf94a2e3f8e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-3940000000-74f087cc812b3715e7ac	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fri-9830000000-72a5d01c6181340ad986	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0090000000-bad35938b77f181c29b9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0090000000-1aadad0770df07f98436	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00ko-4690000000-f624d342f88456375b9c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00n3-1960000000-43f8c66f164764c37361	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0609-3920000000-dbeab0a82b306761cf6a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-7900000000-d2bb7c1aeeb87d8833d2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a59-0090000000-2ec2f8f314943441fa15	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pb9-0190000000-312cebb17ccd0189ab4d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-1590000000-b2551eac481c0c930a4d	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2498.0	Log mg/kg	[1400:4400]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
497	Floors	Building & Construction	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
508	Coils	Electrical & Electronic Equipment	Not Available
516	Electric Hearing Aids	Electrical & Electronic Equipment	Not Available
526	Loudspeakers	Electrical & Electronic Equipment	Not Available
527	Magnets	Electrical & Electronic Equipment	Not Available
531	Relays	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
548	Preparation Of Vinegar	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
567	Tobacco Product Cases	Household cleaning & consumer products	Not Available
612	Body Washing Or Cleaning Implements	Personal care & cosmetics	Not Available
616	Face Mask Cosmetics	Personal care & cosmetics	Not Available
619	Manicure Pedicure	Personal care & cosmetics	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
658	Touch Fasteners	Textiles, leather & furnishings	Not Available

Pathways

3 pathways

Retinol Metabolism

Vitamin A Deficiency

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Aldehyde dehydrogenase 1A1	P27463	Gallus gallus	Predicted (SEA)	0.155698
Click to view 3D structure	Retinoic acid receptor alpha	P11416	Mus musculus	Predicted (SEA)	0.155698
Click to view 3D structure	Retinoic acid receptor gamma	P18911	Mus musculus	Predicted (SEA)	0.155698
Click to view 3D structure	Retinoic acid receptor beta	P22605	Mus musculus	Predicted (SEA)	0.155698
Click to view 3D structure	Retinoic acid receptor RXR-alpha	P19793	Humans	Predicted (SEA)	0.544945
Click to view 3D structure	Retinoic acid receptor gamma	P13631	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Prosaposin	P07602	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Beta-lactoglobulin	P02754	Bos taurus	Predicted (SEA)	0.155698
Click to view 3D structure	Retinoic acid receptor RXR-alpha	P28700	Mus musculus	Predicted (SEA)	0.155698
Click to view 3D structure	Cellular retinoic acid-binding protein 1	P62965	Mus musculus	Predicted (SEA)	0.0778492
Click to view 3D structure	Cellular retinoic acid-binding protein 2	P22935	Mus musculus	Predicted (SEA)	0.0778492
Click to view 3D structure	Cellular retinoic acid-binding protein 1	P40220	Gallus gallus	Predicted (SEA)	0.155698
Click to view 3D structure	Retinoic acid receptor beta	P10826	Humans	Predicted (SEA)	0.778492
Click to view 3D structure	Retinoic acid receptor alpha	P10276	Humans	Predicted (SEA)	1.24559
Click to view 3D structure	Alpha-synuclein	P37840	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Amyloid-beta precursor protein	P05067	Humans	Predicted (SEA)	1.79053
Click to view 3D structure	Retinoic acid receptor RXR-gamma	P48443	Humans	Predicted (SEA)	0.778492
Click to view 3D structure	Retinoic acid receptor RXR-beta	P28702	Humans	Predicted (SEA)	0.934191
Click to view 3D structure	Retinoic acid receptor RXR-gamma	P28705	Mus musculus	Predicted (SEA)	1.08989
Click to view 3D structure	Retinoic acid receptor RXR-beta	P28704	Mus musculus	Predicted (SEA)	1.16774
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	3.42537
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	67.5731
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	81.8195
Click to view 3D structure	Mitogen-activated protein kinase 1	P28482	Humans	Predicted (SEA)	154.764
Click to view 3D structure	Retinal dehydrogenase 2	O93344	Gallus gallus	Predicted (SEA)	0.0778492