ChemFOnt: Showing chemical card for 5,8-Epoxy-13-cis-retinoic acid (CFc000042824)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:32 UTC

Chemfont ID

CFc000042824

Molecule Identification

Common Name

5,8-Epoxy-13-cis-retinoic acid

Definition

5,8-Epoxy-13-cis-retinoic acid is an oxygenated metabolite of 13-cis-retinoic acid. It is formed from the hydroperoxide-dependent co-oxidation of 13-cis-retinoic acid by prostaglandin H (PGH) synthase (PMID: 3115987 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5,8-Epoxy-13-cis-retinoate	Generator
5,8-Oxy-13-cis-retinoic acid	HMDB
5,8-Oxy-13-cis-retinoate	Generator, HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.441

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

(2Z,4E,6E)-7-(4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-yl)-3-methylocta-2,4,6-trienoic acid

Traditional Name

(2Z,4E,6E)-7-(4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl)-3-methylocta-2,4,6-trienoic acid

CAS Registry Number

112018-12-9

SMILES

C\C(\C=C\C=C(/C)C1OC2(C)CCCC(C)(C)C2=C1)=C\C(O)=O

InChI Identifier

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

InChI Key

QDOSIDVGVRAXSE-DYIZZJGFSA-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

Diterpenoid
Retinoid skeleton
Benzofuran
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Dihydrofuran
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062412)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0062 g/L	ALOGPS
logP	5.38	ALOGPS
logP	4.27	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	96.4 m³·mol⁻¹	ChemAxon
Polarizability	36.56 Å³	ChemAxon
Number of Rings	2	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

HMDB0062412

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71316382

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 5,8-Epoxy-13-cis-retinoic acid (CFc000042824)

MOL for CFc000042824 (5,8-Epoxy-13-cis-retinoic acid)

3D MOL for CFc000042824 (5,8-Epoxy-13-cis-retinoic acid)

3D SDF for CFc000042824 (5,8-Epoxy-13-cis-retinoic acid)

3D-SDF for CFc000042824 (5,8-Epoxy-13-cis-retinoic acid)

PDB for CFc000042824 (5,8-Epoxy-13-cis-retinoic acid)

3D PDB for CFc000042824 (5,8-Epoxy-13-cis-retinoic acid)

SMILES for CFc000042824 (5,8-Epoxy-13-cis-retinoic acid)

INCHI for CFc000042824 (5,8-Epoxy-13-cis-retinoic acid)

Structure for CFc000042824 (5,8-Epoxy-13-cis-retinoic acid)

3D Structure for CFc000042824 (5,8-Epoxy-13-cis-retinoic acid)