9-cis-retinoic acid (CHEBI:50648)

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ChEBI Name	*9-cis-retinoic acid*

ChEBI ID	CHEBI:50648

ChEBI ASCII Name	9-cis-retinoic acid

Definition	A retinoic acid in which the exocyclic double bonds have 7E,9Z,11E,13E geometry.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:63793

Supplier Information	ChemicalBook:CB7852954, eMolecules:478134, ZINC000000895323

Download	Molfile XML SDF

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Wikipedia	License
Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes. Phenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma–active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. Therefore will eventually be hydrolyzed and oxidized to yield phenylacetic acid that will be excreted primarily in the urine in conjugated form.
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Formula

C20H28O2

Net Charge

Average Mass

300.43512

Monoisotopic Mass

300.20893

InChI

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+

InChIKey

SHGAZHPCJJPHSC-ZVCIMWCZSA-N

SMILES

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

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	retinoid X receptor agonist An agonist that selectively binds to and activates a retinoid X receptor. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via retinoic acid )

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. keratolytic drug A drug that softens, separates, and causes desquamation of the cornified epithelium or horny layer of skin. Keratolytic drugs are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases.

ChEBI Ontology
Outgoing	9-cis-retinoic acid (CHEBI:50648) has role antineoplastic agent (CHEBI:35610) 9-cis-retinoic acid (CHEBI:50648) has role keratolytic drug (CHEBI:50176) 9-cis-retinoic acid (CHEBI:50648) has role metabolite (CHEBI:25212) 9-cis-retinoic acid (CHEBI:50648) has role retinoid X receptor agonist (CHEBI:63794) 9-cis-retinoic acid (CHEBI:50648) is a retinoic acid (CHEBI:26536) 9-cis-retinoic acid (CHEBI:50648) is conjugate acid of 9-cis-retinoate (CHEBI:78630)

Incoming	9-cis-4-hydroxyretinoic acid (CHEBI:63802) has functional parent 9-cis-retinoic acid (CHEBI:50648) 9-cis-4-oxoretinoic acid (CHEBI:139255) has functional parent 9-cis-retinoic acid (CHEBI:50648) 9-cis-retinoyl-β-D-glucuronide (CHEBI:172945) has functional parent 9-cis-retinoic acid (CHEBI:50648) 9-cis-retinoate (CHEBI:78630) is conjugate base of 9-cis-retinoic acid (CHEBI:50648)

IUPAC Name

(9cis)-retinoic acid

Synonyms	Sources
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid	IUPAC
(7E,9Z,11E,13E)-retinoic acid	ChEBI
9(Z)-Retinoic acid	ChemIDplus
9-cis-Tretinoin	ChemIDplus
Alitretinoin	KEGG DRUG

Last Modified

10 January 2022