CHEBI:50648 - 9-cis-retinoic acid

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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 No supplier information found for this compound.
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Formula C20H28O2
Net Charge 0
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.
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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
INNs Sources
alitretinoína ChEBI
alitrétinoïne ChEBI
alitretinoinum ChEBI
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
Brand Names Sources
Panretin DrugBank
Panretyn Deprecated term DrugBank
Manual Xrefs Databases
3862 DrugCentral
Alitretinoin Wikipedia
C15493 KEGG COMPOUND
D02815 KEGG DRUG
DB00523 DrugBank
HMDB0002369 HMDB
LMPR01090022 LIPID MAPS
View more database links
Registry Numbers Types Sources
2057222 Reaxys Registry Number Reaxys
5300-03-8 CAS Registry Number ChemIDplus
Citations
Last Modified
10 January 2022