ChemFOnt: Showing chemical card for 4-Oxoretinal (CFc000008086)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:43 UTC

Chemfont ID

CFc000008086

Molecule Identification

Common Name

4-Oxoretinal

Definition

4-Oxoretinal is a predominant retinoids during morphogenesis in mouse skin in vivo. Topical 4-oxoretinal and 4-oxoretinol promoted significant epidermal hyperplasia and metaplasia in mouse tail. They induced a moderate response for epidermal inflammation, compared with retinal, whereas neither 4-oxoretinal nor 4-oxoretinol prevented menadione-induced epidermal lipid peroxidation, unlike retinal and retinol. As analyzed by quantitative PCR, 4-oxoretinal and 4-oxoretinol did not reproduce the significant increased expression of genes coding for keratin 4, amphiregulin, heparin-EGF and CYP26A1, that did induce retinal and retinol. However, both retinal and 4-oxoretinal significantly inhibited the lipopolysaccharide-induced maturation of human dendritic cells in vitro. As analyzed in vivo and in vitro, 4-oxoretinal and 4-oxoretinol were not converted into retinoic acid. We conclude that 4-oxoretinal and 4-oxoretinol exert a moderate direct retinoid-like activity in vivo, thus confirming previous in vitro studies in amphibians showing 4-oxometabolites of vitamin A as bioactive agents rather than inactive catabolites.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,7-Dimethyl-9-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-all-trans-2,4,6,8-nonatetraenal	HMDB
4-Ketoretinal	HMDB
4-oxo-all-trans-Retinal	HMDB
4OVA	HMDB

Chemical Formula

C₂₀H₂₆O₂

Average Molecular Weight

298.4192

Monoisotopic Molecular Weight

298.193280076

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

Traditional Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

CAS Registry Number

33532-44-4

SMILES

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

InChI Identifier

InChI=1S/C20H26O2/c1-15(7-6-8-16(2)13-14-21)9-11-18-17(3)10-12-19(22)20(18,4)5/h6-9,11,13-14H,10,12H2,1-5H3/b8-6+,11-9+,15-7+,16-13+

InChI Key

ZORDCCAUKPDLPN-ZBSJWCJSSA-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

Retinoid skeleton
Diterpenoid
Cyclohexenone
Enal
Alpha,beta-unsaturated aldehyde
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012794)

Source

Endogenous

Endogenous (HMDB: HMDB0012794)

Animal

Animal (HMDB: HMDB0012794)

Exogenous

Food

Food (HMDB: HMDB0012794)

Exogenous (HMDB: HMDB0012794)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012794)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012794)

Lipid metabolism pathway (HMDB: HMDB0012794)

Cellular process

Cell signaling (HMDB: HMDB0012794)

Biochemical process

Lipid transport (HMDB: HMDB0012794)

Role

Biological role

Energy source (HMDB: HMDB0012794)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012794)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.007 g/L	ALOGPS
logP	5.47	ALOGPS
logP	4.19	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	19.84	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.56 m³·mol⁻¹	ChemAxon
Polarizability	35.76 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012794

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029176

KNApSAcK ID

Not Available

Chemspider ID

30776653

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481523

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4-Oxoretinal (CFc000008086)

MOL for CFc000008086 (4-Oxoretinal)

3D MOL for CFc000008086 (4-Oxoretinal)

3D SDF for CFc000008086 (4-Oxoretinal)

3D-SDF for CFc000008086 (4-Oxoretinal)

PDB for CFc000008086 (4-Oxoretinal)

3D PDB for CFc000008086 (4-Oxoretinal)

SMILES for CFc000008086 (4-Oxoretinal)

INCHI for CFc000008086 (4-Oxoretinal)

Structure for CFc000008086 (4-Oxoretinal)

3D Structure for CFc000008086 (4-Oxoretinal)