ChemFOnt: Showing chemical card for 9-cis-Retinal (CFc000002665)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:36 UTC

Chemfont ID

CFc000002665

Molecule Identification

Common Name

9-cis-Retinal

Definition

In vivo, 9-cis-retinal is formed through oxidation of 9-cis-retinol by cis-retinol dehydrogenase (cRDH). (PMID:15572038 ). The generation of retinoic acid from retinol is a two-step reaction, with the rate-limiting step being the oxidation of retinol into the intermediate retinaldehyde. Two classes of. unrelated enzymes have been implicated in the oxidation of retinol, the classical cytosolic medium chain alcohol dehydrogenases and recently identified microsomal members of the short chain alcohol dehydrogenase reductase (SDR) superfamily. Further oxidation of the retinaldehyde to the retinoic acid is believed to be catalyzed by several cytosolic aldehyde dehydrogenases. Retinoids are micronutrients required to maintain and promote health of vertebrates. They act physiologically by participating in the visual cycle, in regulating cell differentiation, in embryonic development (PMID:10893430 ), in maintaining normal reproduction, and in the immune response (PMID:8882153 ). In non-ocular tissues, the effects of retinoids within the body are mediated through retinoic acid receptors (RARs) and retinoid X receptors (RXRs), which act to regulate gene expression as ligand-dependent transcription factors. The naturally occurring ligands for these nuclear receptors are thought to be all-trans-retinoic acid for RARs and 9-cis-retinoic acid for RXRs (PMID:10322133 ). While many details of the molecular actions of the RARs and RXRs in regulating gene transcription are understood (PMID:10418975 ), tissue-specific synthetic pathway(s) of their ligands has not been adequately defined. Nevertheless, the therapeutic efficacy of retinoids, including 9-cis-retinoic acid, is well established in both tissue culture and animal models of breast cancer (PMID:8825126 , PMID:12743994 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
all-trans-Retinaldehyde	ChEBI
all-trans-Retinene	ChEBI
all-trans-Vitamin a aldehyde	ChEBI
Retinaldehyde	ChEBI
Retinene	ChEBI
Vitamin a aldehyde	ChEBI
all-trans-Retinal	Kegg
Aldehyde, vitamin a	HMDB
Axerophthal	HMDB
11 cis Retinal	HMDB
11-cis-Retinal	HMDB
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal	HMDB
all-e-Retinal	HMDB
all-epsilon-Retinal	HMDB
alpha-Retinene	HMDB
e-Retinal	HMDB
epsilon-Retinal	HMDB
Retinene 1	HMDB
trans-Retinal	HMDB
trans-Vitamin a aldehyde	HMDB
Vitamin a1 aldehyde	HMDB

Chemical Formula

C₂₀H₂₈O

Average Molecular Weight

284.4357

Monoisotopic Molecular Weight

284.214015518

IUPAC Name

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

Traditional Name

retinaldehyde

CAS Registry Number

514-85-2

SMILES

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

InChI Identifier

InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

InChI Key

NCYCYZXNIZJOKI-OVSJKPMPSA-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
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinal (CHEBI:17898 )
Retinoids (C00376 )
Retinoids (LMPR01090002 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0006218)

Food

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)

Endogenous

Endogenous (HMDB: HMDB0006218)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Retinol Metabolism (PathBank: SMP0087353)

Disease pathway

Vitamin A Deficiency (PathBank: SMP0120500)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	6.62	ALOGPS
logP	4.86	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.87 m³·mol⁻¹	ChemAxon
Polarizability	35.69 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

HMDB0001358

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022576

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00376

BioCyc ID

RETINAL

BiGG ID

Not Available

Wikipedia Link

Retinal

METLIN ID

Not Available

PubChem Compound

638015

PDB ID

Not Available

ChEBI ID

17898

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Ostapenko, I. A.; Furaev, V. V. The 9-cis isomerization of all-trans-retinal during in vitro regeneration of visual pigment. Nature (London), New Biology (1973), 243(127), 185-6.

Showing chemical card for 9-cis-Retinal (CFc000002665)

MOL for CFc000002665 (9-cis-Retinal)

3D MOL for CFc000002665 (9-cis-Retinal)

3D SDF for CFc000002665 (9-cis-Retinal)

3D-SDF for CFc000002665 (9-cis-Retinal)

PDB for CFc000002665 (9-cis-Retinal)

3D PDB for CFc000002665 (9-cis-Retinal)

SMILES for CFc000002665 (9-cis-Retinal)

INCHI for CFc000002665 (9-cis-Retinal)

Structure for CFc000002665 (9-cis-Retinal)

3D Structure for CFc000002665 (9-cis-Retinal)