CHEBI:167660 - LB42908

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ChEBI Name LB42908
ChEBI ID CHEBI:167660
Definition A member of the class of pyrrolecarboxamides that is 1H-pyrrole substituted by [1-(3a,7a-dihydro-1,3-benzodioxol-5-ylmethyl)-1H-imidazol-5-yl]methyl, (4-methylpiperazin-1-yl)carbonyl, and naphthalen-1-yl groups at positions 1, 3 and 4, respectively. It is a potent inhibitor of Ras farnesyltransferase (IC50= 0.9nM against H-Ras and 2.4nM against K-Ras) with potential anticancer activity.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter R. Stephan
Supplier Information
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Formula C32H33N5O3
Net Charge 0
Average Mass 535.648
Monoisotopic Mass 535.25834
InChI InChI=1S/C32H33N5O3/c1-34-11-13-36(14-12-34)32(38)29-20-35(19-28(29)27-8-4-6-24-5-2-3-7-26(24)27)18-25-16-33-21-37(25)17-23-9-10-30-31(15-23)40-22-39-30/h2-10,15-16,19-21,30-31H,11-14,17-18,22H2,1H3
InChIKey VZWZHIJGBPHRDI-UHFFFAOYSA-N
SMILES CN1CCN(CC1)C(=O)C1=CN(CC2=CN=CN2CC2=CC3OCOC3C=C2)C=C1C1=CC=CC2=CC=CC=C12
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.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing LB42908 (CHEBI:167660) has role antineoplastic agent (CHEBI:35610)
LB42908 (CHEBI:167660) has role apoptosis inducer (CHEBI:68495)
LB42908 (CHEBI:167660) has role EC 2.5.1.58 (protein farnesyltransferase) inhibitor (CHEBI:64133)
LB42908 (CHEBI:167660) is a N-acylpiperazine (CHEBI:46844)
LB42908 (CHEBI:167660) is a N-methylpiperazine (CHEBI:46920)
LB42908 (CHEBI:167660) is a benzodioxole (CHEBI:38733)
LB42908 (CHEBI:167660) is a imidazoles (CHEBI:24780)
LB42908 (CHEBI:167660) is a naphthalenes (CHEBI:25477)
LB42908 (CHEBI:167660) is a pyrrolecarboxamide (CHEBI:48611)
IUPAC Name
[1-{[1-(3a,7a-dihydro-1,3-benzodioxol-5-ylmethyl)-1H-imidazol-5-yl]methyl}-4-(naphthalen-1-yl)-1H-pyrrol-3-yl](4-methylpiperazin-1-yl)methanone
Synonyms Sources
(1-((1-(benzo[d][1,3]dioxol-5-ylmethyl)-1H-imidazol-5-yl)methyl)-4-(naphthalen-1-yl)-1H-pyrrol-3-yl)(4-methylpiperazin-1-yl)methanone ChEBI
[1-[[3-(3a,7a-dihydro-1,3-benzodioxol-5-ylmethyl)imidazol-4-yl]methyl]-4-naphthalen-1-ylpyrrol-3-yl]-(4-methylpiperazin-1-yl)methanone ChEBI
[1-{[1-(1,3-benzodioxol-5-ylmethyl)-1H-imidazol-5-yl]-methyl}-4-(1-naphtyl)-1H-pyrrol-3-yl](4-methyl-1-piperazynyl)methanone ChEBI
LB 42908 ChEBI
LB-42908 ChEBI
Manual Xref Database
34980887 ChemSpider
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Registry Number Type Source
226927-89-5 CAS Registry Number ChEBI
Citations Waiting for Citations Types Sources
11714612 PubMed citation SUBMITTER
15812228 PubMed citation Europe PMC
16331612 PubMed citation Europe PMC
16712893 PubMed citation SUBMITTER
22497764 PubMed citation SUBMITTER
24059235 PubMed citation Europe PMC
Last Modified
18 March 2021