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CHEBI:167660 - LB42908

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:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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.
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-[[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
(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-{[1-(1,3-benzodioxol-5-ylmethyl)-1H-imidazol-5-yl]-methyl}-4-(1-naphtyl)-1H-pyrrol-3-yl](4-methyl-1-piperazynyl)methanoneChEBI
Manual XrefsDatabases
34980887ChemSpider
Registry NumbersSources
CAS:226927-89-5ChEBI
Citations