ChemFOnt: Showing chemical card for 9,13-cis-Retinoic acid (CFc000008104)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:44 UTC

Chemfont ID

CFc000008104

Molecule Identification

Common Name

9,13-cis-Retinoic acid

Definition

9,13-cis-Retinoic 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. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
9,13-cis-Retinoate	Generator
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-(2E,4Z,6E,8Z)-nonatetraen-1-Oate	HMDB
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-(2E,4Z,6E,8Z)-nonatetraen-1-Oic acid	HMDB
9,13-cis-Retinoic acid	HMDB, Generator
9,13-cis-Retinoic acid anion	HMDB
9,13-cis-Vitamin-a-acid	HMDB
9,13-cis-Vitamin-alpha-acid	HMDB
9,13-Di-cis-ra	HMDB
9-cis,13-cis-Retinoate	HMDB
9-cis,13-cis-Retinoic acid	HMDB
DcVA	HMDB
9,13-Retinoic acid	MeSH, HMDB
9,13-Di-cis-retinoate	Generator

Chemical Formula

C₂₀H₂₈O₂

Average Molecular Weight

300.4351

Monoisotopic Molecular Weight

300.20893014

IUPAC Name

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

Traditional Name

9,13-di-cis-retinoic acid

CAS Registry Number

5352-74-9

SMILES

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

InChI Identifier

InChI=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 Key

SHGAZHPCJJPHSC-CDMOMSTLSA-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
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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

Retinoids (LMPR01090023 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012874)

Source

Endogenous

Endogenous (HMDB: HMDB0012874)

Animal

Animal (HMDB: HMDB0012874)

Exogenous

Food

Food (HMDB: HMDB0012874)

Exogenous (HMDB: HMDB0012874)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012874)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012874)

Lipid metabolism pathway (HMDB: HMDB0012874)

Cellular process

Cell signaling (HMDB: HMDB0012874)

Biochemical process

Lipid transport (HMDB: HMDB0012874)

Role

Biological role

Energy source (HMDB: HMDB0012874)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012874)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0048 g/L	ALOGPS
logP	5.66	ALOGPS
logP	5.01	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.79 m³·mol⁻¹	ChemAxon
Polarizability	35.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012874

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029194

KNApSAcK ID

Not Available

Chemspider ID

4925342

KEGG Compound ID

C00777

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6419708

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 9,13-cis-Retinoic acid (CFc000008104)

MOL for CFc000008104 (9,13-cis-Retinoic acid)

3D MOL for CFc000008104 (9,13-cis-Retinoic acid)

3D SDF for CFc000008104 (9,13-cis-Retinoic acid)

3D-SDF for CFc000008104 (9,13-cis-Retinoic acid)

PDB for CFc000008104 (9,13-cis-Retinoic acid)

3D PDB for CFc000008104 (9,13-cis-Retinoic acid)

SMILES for CFc000008104 (9,13-cis-Retinoic acid)

INCHI for CFc000008104 (9,13-cis-Retinoic acid)

Structure for CFc000008104 (9,13-cis-Retinoic acid)

3D Structure for CFc000008104 (9,13-cis-Retinoic acid)