(S)-2-{4'-[(Benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid

ID: ALA187523

Chembl Id: CHEMBL187523

PubChem CID: 6852146

Max Phase: Preclinical

Molecular Formula: C26H24N2O6S

Molecular Weight: 492.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@H](NS(=O)(=O)c1ccc(-c2ccc(NC(=O)c3cc4ccccc4o3)cc2)cc1)C(=O)O

Standard InChI:  InChI=1S/C26H24N2O6S/c1-16(2)24(26(30)31)28-35(32,33)21-13-9-18(10-14-21)17-7-11-20(12-8-17)27-25(29)23-15-19-5-3-4-6-22(19)34-23/h3-16,24,28H,1-2H3,(H,27,29)(H,30,31)/t24-/m0/s1

Standard InChI Key:  HJFONKSERLWIGE-DEOSSOPVSA-N

Alternative Forms

1. Parent:

   

   ALA187523

   N-({4'-[(1-Benzofuran-2-ylcarbonyl)amino]-1,1'-biphenyl-4-YL}sulfonyl)-L-valine

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

Calculated Properties

Molecular Weight: 492.55

Molecular Weight (Monoisotopic): 492.1355

AlogP: 4.74

#Rotatable Bonds: 8

Polar Surface Area: 125.71

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.33

CX Basic pKa: ┄

CX LogP: 4.56

CX LogD: 1.14

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.33

Np Likeness Score: -1.07

References

1. Wu J, Rush TS, Hotchandani R, Du X, Geck M, Collins E, Xu ZB, Skotnicki J, Levin JI, Lovering FE..  (2005)  Identification of potent and selective MMP-13 inhibitors.,  15  (18): [PMID:16005220] [10.1016/j.bmcl.2005.06.019]

2. Li J, Rush TS, Li W, DeVincentis D, Du X, Hu Y, Thomason JR, Xiang JS, Skotnicki JS, Tam S, Cunningham KM, Chockalingam PS, Morris EA, Levin JI..  (2005)  Synthesis and SAR of highly selective MMP-13 inhibitors.,  15  (22): [PMID:16153831] [10.1016/j.bmcl.2005.08.001]

3. Li W, Li J, Wu Y, Wu J, Hotchandani R, Cunningham K, McFadyen I, Bard J, Morgan P, Schlerman F, Xu X, Tam S, Goldman SJ, Williams C, Sypek J, Mansour TS..  (2009)  A selective matrix metalloprotease 12 inhibitor for potential treatment of chronic obstructive pulmonary disease (COPD): discovery of (S)-2-(8-(methoxycarbonylamino)dibenzo[b,d]furan-3-sulfonamido)-3-methylbutanoic acid (MMP408).,  52  (7): [PMID:19278250] [10.1021/jm900093d]

4. Li W, Li J, Wu Y, Rancati F, Vallese S, Raveglia L, Wu J, Hotchandani R, Fuller N, Cunningham K, Morgan P, Fish S, Krykbaev R, Xu X, Tam S, Goldman SJ, Abraham W, Williams C, Sypek J, Mansour TS..  (2009)  Identification of an orally efficacious matrix metalloprotease 12 inhibitor for potential treatment of asthma.,  52  (17): [PMID:19725580] [10.1021/jm900809r]

5. Li W, Hu Y, Li J, Thomason JR, DeVincentis D, Du X, Wu J, Hotchandani R, Rush TS, Skotnicki JS, Tam S, Chockalingam PS, Morris EA, Levin JI..  (2009)  3,4-Disubstituted benzofuran P1' MMP-13 inhibitors: optimization of selectivity and reduction of protein binding.,  19  (16): [PMID:19625186] [10.1016/j.bmcl.2009.07.008]

Source

Source(1):

• Scientific Literature