GI254023X (CHEBI:143102)

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CHEBI:143102 - GI254023X

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ChEBI ID	CHEBI:143102
ChEBI Name	GI254023X
Stars
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.
Last Modified	20 March 2019
Submitter	Sandra Orchard
Downloads	Molfile

Formula	C21H33N3O4
Net Charge	0
Average Mass	391.512
Monoisotopic Mass	391.24711
SMILES	CNC(=O)[C@@H](NC(=O)[C@H](CCCc1ccccc1)[C@H](C)N(O)C=O)C(C)(C)C
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

Roles Classification

Biological Roles:	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.*). apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. matrix metalloproteinase inhibitor
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	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	Source
(2R)-N-[(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]-propyl]-2-[(1S)-1-[formyl(hydroxy)amino]ethyl]-5-phenylpentanamide	ChEBI
GI4023	ChEBI
GI-4023	ChEBI
GI-254023X	ChEBI
(2R,3S)-3-(formyl-hydroxyamino)-2-(3-phenyl-1-propyl)butanoic acid [(1S)-2,2-dimethyl-1-methylcarbamoyl-1-propyl]amide	ChEBI

Registry Numbers	Sources
CAS:260264-93-5	ChEBI

Citations