ID: ALA198262

Max Phase: Preclinical

Molecular Formula: C28H27BrN2O7S

Molecular Weight: 615.50

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1c(Br)ccc2oc(C(=O)Nc3ccc(-c4ccc(S(=O)(=O)N[C@H](C(=O)O)C(C)C)cc4)cc3)c(C)c12

Standard InChI:  InChI=1S/C28H27BrN2O7S/c1-15(2)24(28(33)34)31-39(35,36)20-11-7-18(8-12-20)17-5-9-19(10-6-17)30-27(32)25-16(3)23-22(38-25)14-13-21(29)26(23)37-4/h5-15,24,31H,1-4H3,(H,30,32)(H,33,34)/t24-/m0/s1

Standard InChI Key:  HHHAELOQIYTSIY-DEOSSOPVSA-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: 615.50

Molecular Weight (Monoisotopic): 614.0722

AlogP: 5.82

#Rotatable Bonds: 9

Polar Surface Area: 134.94

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.33

CX Basic pKa:

CX LogP: 5.68

CX LogD: 2.26

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.22

Np Likeness Score: -0.84

References

1. 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]

2. 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]

3. 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