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CHEBI:167660 - LB42908

Default Structure
ChEBI IDCHEBI:167660
ChEBI NameLB42908
Stars
DefinitionA 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.
Last Modified18 March 2021
SubmitterR. Stephan
DownloadsMolfile
FormulaC32H33N5O3
Net Charge0
Average Mass535.648
Monoisotopic Mass535.25834
SMILESCN1CCN(C(=O)c2cn(Cc3cncn3CC3=CC4OCOC4C=C3)cc2-c2cccc3ccccc23)CC1
InChIInChI=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
InChIKeyVZWZHIJGBPHRDI-UHFFFAOYSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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  Source
[1-{[1-(1,3-benzodioxol-5-ylmethyl)-1H-imidazol-5-yl]-methyl}-4-(1-naphtyl)-1H-pyrrol-3-yl](4-methyl-1-piperazynyl)methanoneChEBI
(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)methanoneChEBI
[1-[[3-(3a,7a-dihydro-1,3-benzodioxol-5-ylmethyl)imidazol-4-yl]methyl]-4-naphthalen-1-ylpyrrol-3-yl]-(4-methylpiperazin-1-yl)methanoneChEBI
LB 42908ChEBI
LB-42908ChEBI
Manual XrefsDatabases
34980887ChemSpider
Registry NumbersSources
CAS:226927-89-5ChEBI
Citations