ID: ALA523034

Max Phase: Preclinical

Molecular Formula: C19H20N2O7S

Molecular Weight: 420.44

Molecule Type: Small molecule

Representations

Canonical SMILES:  COC(=O)Nc1ccc2oc3cc(S(=O)(=O)N[C@H](C(=O)O)C(C)C)ccc3c2c1

Standard InChI:  InChI=1S/C19H20N2O7S/c1-10(2)17(18(22)23)21-29(25,26)12-5-6-13-14-8-11(20-19(24)27-3)4-7-15(14)28-16(13)9-12/h4-10,17,21H,1-3H3,(H,20,24)(H,22,23)/t17-/m0/s1

Standard InChI Key:  MKAIHDAGQJQAHA-KRWDZBQOSA-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: 420.44

Molecular Weight (Monoisotopic): 420.0991

AlogP: 3.15

#Rotatable Bonds: 6

Polar Surface Area: 134.94

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.86

CX Basic pKa:

CX LogP: 2.77

CX LogD: -0.46

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: -1.01

References

1. 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]

2. 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]

3. Wu Y, Li J, Wu J, Morgan P, Xu X, Rancati F, Vallese S, Raveglia L, Hotchandani R, Fuller N, Bard J, Cunningham K, Fish S, Krykbaev R, Tam S, Goldman SJ, Williams C, Mansour TS, Saiah E, Sypek J, Li W..  (2012)  Discovery of potent and selective matrix metalloprotease 12 inhibitors for the potential treatment of chronic obstructive pulmonary disease (COPD).,  22  (1): [PMID:22153340] [10.1016/j.bmcl.2011.11.046]

Source

Source(1):

• Scientific Literature