ChemFOnt: Showing chemical card for 4-oxo-Retinoic acid (CFc000002704)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:39 UTC

Chemfont ID

CFc000002704

Molecule Identification

Common Name

4-oxo-Retinoic acid

Definition

4-oxo-Retinoic acid is a biologically active geometric isomer of retinoic acid (RA). 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in cells. Metabolic transformation of all-trans RA to 4-hydroxylated RA appears to be primarily catalyzed by the cytochrome P 450 (CYP) 26AI in human skin cells. Cellular levels of all-trans RA are meticulously regulated utilizing an array of systems to balance uptake, biosynthesis, catabolism, and efflux transport. RA is a critical regulator of gene expression during embryonic development and in the maintenance of adult epithelial tissues. (PMID: 8794203 , 7893159 , 17330217 , 16778795 , 17460545 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-oxo-all-trans-Retinoic acid	ChEBI
4-oxo-AtRA	ChEBI
4-oxo-all-trans-Retinoate	Generator
4-oxo-Retinoate	Generator
4-keto-Retinoate	HMDB
4-keto-Retinoic acid	HMDB
4-Ketoretinoate	HMDB
4-Ketoretinoic acid	HMDB, MeSH
4-Oxoretinoate	HMDB
4-Oxoretinoic acid	HMDB, MeSH
4-Oxotretinoin	HMDB
all-trans-4-Oxoretinoate	HMDB
all-trans-4-Oxoretinoic acid	HMDB
ro 11-4824	HMDB
ro 12-4824	HMDB
4-oxo-13-cis-Retinoic acid	MeSH, HMDB
4-oxo-Isotretinoin	MeSH, HMDB
4-oxo-trans-Retinoic acid	MeSH, HMDB
4-Oxoretinoic acid, (13-cis)-isomer	MeSH, HMDB

Chemical Formula

C₂₀H₂₆O₃

Average Molecular Weight

314.4186

Monoisotopic Molecular Weight

314.188194698

IUPAC Name

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

Traditional Name

4-oxo-retinoic acid

CAS Registry Number

38030-57-8

SMILES

C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O

InChI Identifier

InChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+

InChI Key

GGCUJPCCTQNTJF-FRCNGJHJSA-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
Cyclohexenone
Methyl-branched fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoid (CHEBI:80656 )
Retinoids (C16678 )
Retinoids (LMPR01090026 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006285)

Cellular substructure

Organelle

Nucleus (HMDB: HMDB0006285)

Organ

Liver (HMDB: HMDB0006285)
Kidney (HMDB: HMDB0006285)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006285)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006285)

Source

Endogenous

Endogenous (HMDB: HMDB0006285)

Animal

Animal (HMDB: HMDB0006285)

Exogenous

Food

Food (HMDB: HMDB0006285)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Role

Biological role

Energy source (HMDB: HMDB0006285)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006285)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0062 g/L	ALOGPS
logP	4.94	ALOGPS
logP	4.35	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.48 m³·mol⁻¹	ChemAxon
Polarizability	36.62 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon