Showing Compound 4-Hydroxyretinoic acid (FDB023862)

Record Information

Version

1.0

Creation date

2011-09-21 00:35:56 UTC

Update date

2015-07-21 06:57:54 UTC

Primary ID

FDB023862

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-Hydroxyretinoic acid

Description

4-Hydroxyretinoic acid 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. Based on a literature review a significant number of articles have been published on 4-Hydroxyretinoic acid.

CAS Number

66592-72-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(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)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate	Generator
(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)-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-tetraenoate	Generator
(2e,4e,6e,8e)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoate	Generator
(2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic 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-Hydroxyretinoate	Generator
(7e,9e,11e,13e)-4-Hydroxyretinoate	Generator

Showing 1 to 10 of 41 entries

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

Chemical Formula

C20H28O3

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

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

Isomeric SMILES

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

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Organ and components:

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	4-Hydroxyretinoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0k92-1093000000-7f88a5d83645fa2a79e9	Spectrum
Predicted GC-MS	4-Hydroxyretinoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0092-5008900000-f94c9a4b723e495dbc22	Spectrum
Predicted GC-MS	4-Hydroxyretinoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxyretinoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0292000000-4d5a6c9335a4fa5db05e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zg1-0590000000-0b50fabd74e810e935c0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pba-3920000000-8958845f26cb19e0194b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0089000000-cdb17ed778c9480eb63e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gi1-0094000000-b75b3689212cfa9472cb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-4390000000-5614482c4d64bf67afaf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-0291000000-7a67cccc8b73d68d76e3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f8i-0490000000-891d9992953ed919a7c3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000l-5920000000-8f663f06367ea569c02e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0096000000-123a0c931fe8f0c0d401	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0190000000-3eec1ef4274b19e5f537	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-016r-4910000000-9e73ac1032f900dd901d	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06254

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

2299866

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB