CHEBI:143102 - GI254023X

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ChEBI Name GI254023X
ChEBI ID CHEBI:143102
Definition A L-valine derivative that is 3-methyl-L-valine in which carboxy OH group is replaced by a methylnitrilo group and the one of the amino hydrogens is replaced by a (2R)-2-{(1S)-1-[formyl(hydroxy)amino]ethyl}-5-phenylpentanoyl group. It is a potent MMP9 and ADAM10 metalloprotease inhibitor with IC50 of 2.5 and 5.3 nM, respectively.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Sandra Orchard
Supplier Information
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Formula C21H33N3O4
Net Charge 0
Average Mass 391.512
Monoisotopic Mass 391.24711
InChI InChI=1S/C21H33N3O4/c1-15(24(28)14-25)17(13-9-12-16-10-7-6-8-11-16)19(26)23-18(20(27)22-5)21(2,3)4/h6-8,10-11,14-15,17-18,28H,9,12-13H2,1-5H3,(H,22,27)(H,23,26)/t15-,17+,18+/m0/s1
InChIKey GHVMTHKJUAOZJP-CGTJXYLNSA-N
SMILES [C@H](C(NC)=O)(NC([C@H](CCCC=1C=CC=CC1)[C@@H](N(O)C=O)C)=O)C(C)(C)C
Roles Classification
Biological Role(s): apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
matrix metalloproteinase inhibitor

EC 3.4.24.* (metalloendopeptidase) inhibitor
Any EC 3.4.* (hydrolases acting on peptide bond) inhibitor that interferes with the activity of a metalloendopeptidase (EC 3.4.24.*).
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing GI254023X (CHEBI:143102) has role antineoplastic agent (CHEBI:35610)
GI254023X (CHEBI:143102) has role apoptosis inducer (CHEBI:68495)
GI254023X (CHEBI:143102) has role EC 3.4.24.* (metalloendopeptidase) inhibitor (CHEBI:59107)
GI254023X (CHEBI:143102) has role matrix metalloproteinase inhibitor (CHEBI:50664)
GI254023X (CHEBI:143102) is a L-valine derivative (CHEBI:84129)
GI254023X (CHEBI:143102) is a aldehyde (CHEBI:17478)
GI254023X (CHEBI:143102) is a hydroxylamines (CHEBI:24709)
IUPAC Name
N2-[(2R)-2-{(1S)-1-[formyl(hydroxy)amino]ethyl}-5-phenylpentanoyl]-N,3-dimethyl-L-valinamide
Synonyms Sources
(2R)-N-[(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]-propyl]-2-[(1S)-1-[formyl(hydroxy)amino]ethyl]-5-phenylpentanamide ChEBI
(2R,3S)-3-(formyl-hydroxyamino)-2-(3-phenyl-1-propyl)butanoic acid [(1S)-2,2-dimethyl-1-methylcarbamoyl-1-propyl]amide ChEBI
GI-254023X ChEBI
GI-4023 ChEBI
GI4023 ChEBI
Registry Number Type Source
260264-93-5 CAS Registry Number ChEBI
Citations Waiting for Citations Types Sources
12714508 PubMed citation Europe PMC
20197648 PubMed citation Europe PMC
24518602 PubMed citation Europe PMC
26314424 PubMed citation Europe PMC
26708884 PubMed citation Europe PMC
27043625 PubMed citation Europe PMC
27549131 PubMed citation Europe PMC
28801670 PubMed citation Europe PMC
Last Modified
20 March 2019