CHEBI:90739 - BMS-453

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name BMS-453
ChEBI ID CHEBI:90739
Definition A member of the class of dihydronaphthalenes that is 1,2-dihydronaphthalene which is substituted at positions 1, 1, 4, and 6 by methyl, methyl, phenyl, and 2-(p-carboxyphenyl)vinyl groups, respectively (the E isomer). It is a potent retinoic acid receptor γ (RARβ) agonist that acts as an antagonist against RARα and RARγ.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H24O2
Net Charge 0
Average Mass 380.479
Monoisotopic Mass 380.17763
InChI InChI=1S/C27H24O2/c1-27(2)17-16-23(21-6-4-3-5-7-21)24-18-20(12-15-25(24)27)9-8-19-10-13-22(14-11-19)26(28)29/h3-16,18H,17H2,1-2H3,(H,28,29)/b9-8+
InChIKey VUODRPPTYLBGFM-CMDGGOBGSA-N
SMILES C(=O)(C1=CC=C(C=C1)/C=C/C2=CC3=C(C(CC=C3C4=CC=CC=C4)(C)C)C=C2)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): teratogenic agent
A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
retinoic acid receptor beta agonist
Any retinoic acid receptor (RAR) agonist with specificity for RARbeta.
retinoic acid receptor gamma antagonist
A retinoic acid receptor antagonist that antagonises retinoic acid receptor gamma.
retinoic acid receptor alpha antagonist
A retinoic acid receptor antagonist that antagonises retinoic acid receptor alpha.
Application(s): retinoic acid receptor beta agonist
Any retinoic acid receptor (RAR) agonist with specificity for RARbeta.
retinoic acid receptor gamma antagonist
A retinoic acid receptor antagonist that antagonises retinoic acid receptor gamma.
retinoic acid receptor alpha antagonist
A retinoic acid receptor antagonist that antagonises retinoic acid receptor alpha.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing BMS-453 (CHEBI:90739) has role retinoic acid receptor α antagonist (CHEBI:90713)
BMS-453 (CHEBI:90739) has role retinoic acid receptor β agonist (CHEBI:90742)
BMS-453 (CHEBI:90739) has role retinoic acid receptor γ antagonist (CHEBI:90744)
BMS-453 (CHEBI:90739) has role teratogenic agent (CHEBI:50905)
BMS-453 (CHEBI:90739) is a benzoic acids (CHEBI:22723)
BMS-453 (CHEBI:90739) is a dihydronaphthalenes (CHEBI:90740)
BMS-453 (CHEBI:90739) is a stilbenoid (CHEBI:26776)
IUPAC Name
4-[(E)-2-(5,5-dimethyl-8-phenyl-5,6-dihydronaphthalen-2-yl)vinyl]benzoic acid
Synonyms Sources
BMS 189453 ChemIDplus
BMS 453 ChemIDplus
BMS-189453 ChEBI
BMS189453 ChEBI
BMS453 ChemIDplus
Registry Numbers Types Sources
166977-43-1 CAS Registry Number ChemIDplus
24186643 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12563696 PubMed citation Europe PMC
21107276 PubMed citation Europe PMC
22423954 PubMed citation Europe PMC
24720764 PubMed citation Europe PMC
26469117 PubMed citation Europe PMC
27261179 PubMed citation Europe PMC
Last Modified
15 May 2019