ChemFOnt: Showing chemical card for 4-Hydroxyretinoic acid (CFc000002688)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:38 UTC

Chemfont ID

CFc000002688

Molecule Identification

Common Name

4-Hydroxyretinoic acid

Definition

4-Hydroxyretinoic acid is an NADPH-dependent hydroxylation metabolite of retinoic acid in the microsomes, via the cytochrome P-450 system. Retinoic acid is an activated metabolite of retinol that supports the systemic functions of vitamin A in vivo. (PMID: 1538719 , 1932598 , 2851384 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid	ChEBI
(2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid	ChEBI
(7E,9E,11E,13E)-4-Hydroxyretinoic acid	ChEBI
4-Hydroxy-(7E,9E,11E,13E)-retinoic acid	ChEBI
4-Hydroxy-all-trans-retinoic acid	ChEBI
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate	Generator
(2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoate	Generator
(7E,9E,11E,13E)-4-Hydroxyretinoate	Generator
4-Hydroxy-(7E,9E,11E,13E)-retinoate	Generator
4-Hydroxy-all-trans-retinoate	Generator
4-Hydroxyretinoate	Generator
4-Hydroxy-13-cis-retinoate	HMDB
4-Hydroxy-13-cis-retinoic acid	HMDB, MeSH
4-Hydroxy-retinoate	HMDB
4-Hydroxy-retinoic acid	HMDB
4-OH-Retinoate	HMDB
4-OH-Retinoic acid	HMDB
all-trans-4-Hydroxyretinoate	HMDB
all-trans-4-Hydroxyretinoic acid	HMDB
rac-4-Hydroxy-all-trans-retinoate	HMDB
rac-4-Hydroxy-all-trans-retinoic acid	HMDB
4-Hydroxy-13-retinoic acid	MeSH, HMDB
4-Hydroxyretinoic acid, (13-cis)-isomer	MeSH, HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

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

Traditional Name

4-hydroxyretinoic acid

CAS Registry Number

66592-72-1

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/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+

InChI Key

KGUMXGDKXYTTEY-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
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoid (CHEBI:63795 )
Retinoids (C16677 )
Retinoids (LMPR01090025 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006254)

Cellular substructure

Organelle

Nucleus (HMDB: HMDB0006254)

Organ

Kidney (HMDB: HMDB0006254)
Liver (HMDB: HMDB0006254)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006254)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006254)

Source

Endogenous

Endogenous (HMDB: HMDB0006254)

Animal

Animal (HMDB: HMDB0006254)

Exogenous

Food

Food (HMDB: HMDB0006254)

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: HMDB0006254)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006254)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.009 g/L	ALOGPS
logP	5.04	ALOGPS
logP	3.78	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.31 m³·mol⁻¹	ChemAxon
Polarizability	37.33 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

External Links

HMDB ID

HMDB0006254

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023862

KNApSAcK ID

Not Available

Chemspider ID

4943093

KEGG Compound ID

C16677

BioCyc ID

Not Available

BiGG ID

2299866

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6438629

PDB ID

Not Available

ChEBI ID

63795

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Rosenberger, Michael. Retinoic acid metabolites. 1. Total synthesis of 4-hydroxy- and 4-oxoretinoic acid. Journal of Organic Chemistry (1982), 47(9), 1698-701.

Showing chemical card for 4-Hydroxyretinoic acid (CFc000002688)

MOL for CFc000002688 (4-Hydroxyretinoic acid)

3D MOL for CFc000002688 (4-Hydroxyretinoic acid)

3D SDF for CFc000002688 (4-Hydroxyretinoic acid)

3D-SDF for CFc000002688 (4-Hydroxyretinoic acid)

PDB for CFc000002688 (4-Hydroxyretinoic acid)

3D PDB for CFc000002688 (4-Hydroxyretinoic acid)

SMILES for CFc000002688 (4-Hydroxyretinoic acid)

INCHI for CFc000002688 (4-Hydroxyretinoic acid)

Structure for CFc000002688 (4-Hydroxyretinoic acid)

3D Structure for CFc000002688 (4-Hydroxyretinoic acid)