ChemFOnt: Showing chemical card for all-trans-5,6-Epoxyretinoic acid (CFc000007976)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:34 UTC

Chemfont ID

CFc000007976

Molecule Identification

Common Name

all-trans-5,6-Epoxyretinoic acid

Definition

all-trans-5,6-Epoxyretinoic acid, also known as 5,6-epoxy-atRA, is classified as a member of the retinoids. Retinoids are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. all-trans-5,6-Epoxyretinoic acid is considered to be a practically insoluble (in water) and a weak acidic compound. all-trans-5,6-Epoxyretinoic acid is an isoprenoid lipid molecule. all-trans-5,6-Epoxyretinoic acid can be found primarily in human kidney and liver tissues; and in blood and urine. Within a cell, all-trans-5,6-epoxyretinoic acid is primarily located in the cytoplasm, in the extracellular space, or near the membrane.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
all-trans-5,6-Epoxy-5,6-dihydroretinoic acid	ChEBI
all-trans-5,6-Epoxy-5,6-dihydroretinoate	Generator
all-trans-5,6-Epoxyretinoate	Generator
5,6-Epoxy-5,6-dihydro-retinoate	HMDB
5,6-Epoxy-5,6-dihydro-retinoic acid	HMDB
5,6-Epoxyretinoic acid, (13-cis)-isomer	MeSH, HMDB
5,6-Epoxyretinoic acid, sodium salt	MeSH, HMDB
5,6-Epoxyretinoic acid	MeSH, HMDB
5,6-Epoxy-5,6-dihydroretinoic acid	HMDB
5,6-Epoxy-atRA	HMDB
all-trans-5,6-Epoxyretinoic acid	HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

Traditional Name

(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

CAS Registry Number

13100-69-1

SMILES

C\C(\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(O)=O

InChI Identifier

InChI=1S/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14+

InChI Key

KEEHJLBAOLGBJZ-WEDZBJJJSA-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
Epoxy fatty acid
Heterocyclic fatty acid
Oxepane
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Ether
Oxacycle
Oxirane
Dialkyl ether
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

retinoid (CHEBI:80658 )
Retinoids (C16680 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0012451)

Cellular substructure

Organ

Liver (HMDB: HMDB0012451)
Kidney (HMDB: HMDB0012451)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0012451)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012451)

Source

Endogenous

Endogenous (HMDB: HMDB0012451)

Animal

Animal (HMDB: HMDB0012451)

Exogenous

Food

Food (HMDB: HMDB0012451)

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: HMDB0012451)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012451)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0039 g/L	ALOGPS
logP	5.74	ALOGPS
logP	4.54	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.94	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.52 m³·mol⁻¹	ChemAxon
Polarizability	37.19 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

HMDB0012451

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029067

KNApSAcK ID

Not Available

Chemspider ID

4515523

KEGG Compound ID

C16680

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5363137

PDB ID

Not Available

ChEBI ID

80658

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for all-trans-5,6-Epoxyretinoic acid (CFc000007976)

MOL for CFc000007976 (all-trans-5,6-Epoxyretinoic acid)

3D MOL for CFc000007976 (all-trans-5,6-Epoxyretinoic acid)

3D SDF for CFc000007976 (all-trans-5,6-Epoxyretinoic acid)

3D-SDF for CFc000007976 (all-trans-5,6-Epoxyretinoic acid)

PDB for CFc000007976 (all-trans-5,6-Epoxyretinoic acid)

3D PDB for CFc000007976 (all-trans-5,6-Epoxyretinoic acid)

SMILES for CFc000007976 (all-trans-5,6-Epoxyretinoic acid)

INCHI for CFc000007976 (all-trans-5,6-Epoxyretinoic acid)

Structure for CFc000007976 (all-trans-5,6-Epoxyretinoic acid)

3D Structure for CFc000007976 (all-trans-5,6-Epoxyretinoic acid)