ID: ALA20154

Max Phase: Preclinical

Molecular Formula: C20H31N3O4

Molecular Weight: 377.49

Molecule Type: Small molecule

Representations

Canonical SMILES:  CNC(=O)[C@@H](NC(=O)[C@H](CCCc1ccccc1)CC(=O)NO)C(C)(C)C

Standard InChI:  InChI=1S/C20H31N3O4/c1-20(2,3)17(19(26)21-4)22-18(25)15(13-16(24)23-27)12-8-11-14-9-6-5-7-10-14/h5-7,9-10,15,17,27H,8,11-13H2,1-4H3,(H,21,26)(H,22,25)(H,23,24)/t15-,17-/m1/s1

Standard InChI Key:  LPZWIAVKYXCHGC-NVXWUHKLSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 377.49

Molecular Weight (Monoisotopic): 377.2315

AlogP: 1.80

#Rotatable Bonds: 9

Polar Surface Area: 107.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.90

CX Basic pKa:

CX LogP: 1.95

CX LogD: 1.93

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.39

Np Likeness Score: 0.42

References

1. Yamamoto M, Tsujishita H, Hori N, Ohishi Y, Inoue S, Ikeda S, Okada Y..  (1998)  Inhibition of membrane-type 1 matrix metalloproteinase by hydroxamate inhibitors: an examination of the subsite pocket.,  41  (8): [PMID:9548812] [10.1021/jm970404a]

2. Fray MJ, Burslem MF, Dickinson RP..  (2001)  Selectivity of inhibition of matrix metalloproteases MMP-3 and MMP-2 by succinyl hydroxamates and their carboxylic acid analogues is dependent on P3' group chirality.,  11  (4): [PMID:11229773] [10.1016/s0960-894x(00)00719-8]

3. Fray MJ, Dickinson RP..  (2001)  Discovery of potent and selective succinyl hydroxamate inhibitors of matrix metalloprotease-3 (stromelysin-1).,  11  (4): [PMID:11229774] [10.1016/s0960-894x(00)00720-4]

4. Verma RP, Hansch C..  (2007)  Matrix metalloproteinases (MMPs): chemical-biological functions and (Q)SARs.,  15  (6): [PMID:17275314] [10.1016/j.bmc.2007.01.011]

Source

Source(1):

• Scientific Literature