gamendazole (CHEBI:90703)

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ChEBI Name	gamendazole

ChEBI ID	CHEBI:90703

Definition	A member of the class of indazoles that is 3-(indazol-3-yl}prop-2-enoic acid carrying additional 2,4-dichlorobenzyl and trifluoromethyl substituents at positions 1 and 6 respectively. An orally active antispermatogenic compound with antifertility effects that is a potential male contraceptive drug.

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

Submitter	Stan Laulederkind

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Formula

C18H11Cl2F3N2O2

Net Charge

Average Mass

415.194

Monoisotopic Mass

414.01497

InChI

InChI=1S/C18H11Cl2F3N2O2/c19-12-3-1-10(14(20)8-12)9-25-16-7-11(18(21,22)23)2-4-13(16)15(24-25)5-6-17(26)27/h1-8H,9H2,(H,26,27)/b6-5+

InChIKey

KYYQMVUKYQCSQY-AATRIKPKSA-N

SMILES

N=1N(C2=C(C1\C=C\C(O)=O)C=CC(=C2)C(F)(F)F)CC3=CC=C(C=C3Cl)Cl

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):	Hsp90 inhibitor An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90. eukaryotic translation elongation factor 1alpha 1 inhibitor Any compound that inihibits the human protein, eukaryotic translation elongation factor 1alpha 1.

Application(s):	synthetic oral contraceptive An oral contraceptive which owes its effectiveness to synthetic preparation. antispermatogenic agent An agent that destroy spermatozoa in the male genitalia and block spermatogenesis.

ChEBI Ontology
Outgoing	gamendazole (CHEBI:90703) has functional parent lonidamine (CHEBI:50138) gamendazole (CHEBI:90703) has role antispermatogenic agent (CHEBI:145047) gamendazole (CHEBI:90703) has role eukaryotic translation elongation factor 1_α 1 inhibitor (CHEBI:90767) gamendazole (CHEBI:90703) has role Hsp90 inhibitor (CHEBI:63962) gamendazole (CHEBI:90703) has role synthetic oral contraceptive (CHEBI:49326) gamendazole (CHEBI:90703) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020) gamendazole (CHEBI:90703) is a dichlorobenzene (CHEBI:23697) gamendazole (CHEBI:90703) is a indazoles (CHEBI:38769) gamendazole (CHEBI:90703) is a olefinic compound (CHEBI:78840) gamendazole (CHEBI:90703) is a organofluorine compound (CHEBI:37143)

IUPAC Name

(2E)-3-{1-[(2,4-dichlorophenyl)methyl]-6-(trifluoromethyl)-1H-indazol-3-yl}prop-2-enoic acid

Synonym	Source
trans-3-(1-benzyl-6-(trifluoromethyl)-1H-indazol-3-yl)acrylic acid	SUBMITTER

Registry Number	Type	Source
12542895	Reaxys Registry Number	Reaxys

Last Modified

08 October 2019