N(2)-([biphenyl]-4-ylsulfonyl)-N-hydroxy-N(2)-isopropoxy-D-valinamide (CHEBI:93296)

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ChEBI Name	N²-([biphenyl]-4-ylsulfonyl)-N-hydroxy-N²-isopropoxy-D-valinamide

ChEBI ID	CHEBI:93296

ChEBI ASCII Name	N(2)-([biphenyl]-4-ylsulfonyl)-N-hydroxy-N(2)-isopropoxy-D-valinamide

Definition	A hydroxamic acid that is N-hydroxy-D-valinamide in which the α-amino group has been substituted by isopropoxy and [biphenyl]-4-ylsulfonyl groups. A selective matrix metalloproteinase-2 (MMP-2) inhibitor, it is one of the most potent inducers of autophagy. Its physiological roles include angiogenesis, cancer metastasis, embryogenesis, tissue remodeling in development, and wound healing.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C20H26N2O5S

Net Charge

Average Mass

406.498

Monoisotopic Mass

406.15624

InChI

InChI=1S/C20H26N2O5S/c1-14(2)19(20(23)21-24)22(27-15(3)4)28(25,26)18-12-10-17(11-13-18)16-8-6-5-7-9-16/h5-15,19,24H,1-4H3,(H,21,23)/t19-/m1/s1

InChIKey

DGZZVIWCMGVHGV-LJQANCHMSA-N

SMILES

CC(C)[C@H](C(=O)NO)N(OC(C)C)S(=O)(=O)C1=CC=C(C=C1)C2=CC=CC=C2

Roles Classification
Biological Role(s):	EC 3.4.24.24 (gelatinase A) inhibitor An EC 3.4.24.* (metalloendopeptidase) inhibitor that interferes with the action of gelatinase A (EC 3.4.24.24). autophagy inducer Any compound that induces the process of autophagy (the self-digestion of one or more components of a cell through the action of enzymes originating within the same cell).

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. melanin synthesis inhibitor A depigmentation agent which inhibits the synthesis of melanin.

ChEBI Ontology
Outgoing	N²-([biphenyl]-4-ylsulfonyl)-N-hydroxy-N²-isopropoxy-D-valinamide (CHEBI:93296) has role antineoplastic agent (CHEBI:35610) N²-([biphenyl]-4-ylsulfonyl)-N-hydroxy-N²-isopropoxy-D-valinamide (CHEBI:93296) has role autophagy inducer (CHEBI:138880) N²-([biphenyl]-4-ylsulfonyl)-N-hydroxy-N²-isopropoxy-D-valinamide (CHEBI:93296) has role EC 3.4.24.24 (gelatinase A) inhibitor (CHEBI:84036) N²-([biphenyl]-4-ylsulfonyl)-N-hydroxy-N²-isopropoxy-D-valinamide (CHEBI:93296) has role melanin synthesis inhibitor (CHEBI:64933) N²-([biphenyl]-4-ylsulfonyl)-N-hydroxy-N²-isopropoxy-D-valinamide (CHEBI:93296) is a D-valine derivative (CHEBI:84130) N²-([biphenyl]-4-ylsulfonyl)-N-hydroxy-N²-isopropoxy-D-valinamide (CHEBI:93296) is a hydroxamic acid (CHEBI:24650)

IUPAC Name

N²-([biphenyl]-4-ylsulfonyl)-N-hydroxy-N²-isopropoxy-D-valinamide

Synonyms	Sources
(2R)-2-[([1,1'-biphenyl]-4-ylsulfonyl)(1-methylethoxy)amino]-N-hydroxy-3-methyl-butanamide	ChEBI
(2R)-N-hydroxy-3-methyl-2-[(4-phenylphenyl)sulfonyl-propan-2-yloxyamino]butanamide	LINCS
(R)-N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)-3-methylbutanamide	ChEBI
ARP 101	ChEBI
ARP-101	ChEBI
ARP101	ChEBI
N²-([biphenyl]-4-ylsulfonyl)-N-hydroxy-N²-(propan-2-yloxy)-D-valinamide	IUPAC

Last Modified

26 October 2017