L-778,123 (free base) (CHEBI:180478)

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ChEBI Name	L-778,123 (free base)

ChEBI ID	CHEBI:180478

Definition	A member of the class of imidazoles that is 1H-imidazole substituted by (4-cyanophenyl)methyl and [4-(3-chlorophenyl)-3-oxopiperazin-1-yl]methyl groups at positions 1 and 5, respectively. It is a dual inhibitor of FPTase and GGPTase-I.

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

Secondary ChEBI IDs	CHEBI:47167

Supplier Information

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Formula

C22H20ClN5O

Net Charge

Average Mass

405.890

Monoisotopic Mass

405.13564

InChI

InChI=1S/C22H20ClN5O/c23-19-2-1-3-20(10-19)28-9-8-26(15-22(28)29)14-21-12-25-16-27(21)13-18-6-4-17(11-24)5-7-18/h1-7,10,12,16H,8-9,13-15H2

InChIKey

JNUGFGAVPBYSHF-UHFFFAOYSA-N

SMILES

ClC1=CC(=CC=C1)N1CCN(CC2=CN=CN2CC2=CC=C(C=C2)C#N)CC1=O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	EC 2.5.1.58 (protein farnesyltransferase) inhibitor An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of protein farnesyltransferase (EC 2.5.1.58), one of the three enzymes in the prenyltransferase group. EC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitor An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of protein geranylgeranyltransferase type I (EC 2.5.1.59).

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	L-778,123 (free base) (CHEBI:180478) has role antineoplastic agent (CHEBI:35610) L-778,123 (free base) (CHEBI:180478) has role EC 2.5.1.58 (protein farnesyltransferase) inhibitor (CHEBI:64133) L-778,123 (free base) (CHEBI:180478) has role EC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitor (CHEBI:67267) L-778,123 (free base) (CHEBI:180478) is a imidazoles (CHEBI:24780) L-778,123 (free base) (CHEBI:180478) is a monochlorobenzenes (CHEBI:83403) L-778,123 (free base) (CHEBI:180478) is a nitrile (CHEBI:18379) L-778,123 (free base) (CHEBI:180478) is a piperazinone (CHEBI:46846) L-778,123 (free base) (CHEBI:180478) is a tertiary amino compound (CHEBI:50996)

Incoming	L-778,123 hydrochloride (CHEBI:177371) has part L-778,123 (free base) (CHEBI:180478)

IUPAC Name

4-[(5-{[4-(3-chlorophenyl)-3-oxopiperazin-1-yl]methyl}-1H-imidazol-1-yl)methyl]benzonitrile

Registry Number	Type	Source
183499-57-2	CAS Registry Number	ChemIDplus

Last Modified

17 September 2021