ID: ALA435585

Max Phase: Preclinical

Molecular Formula: C21H22N4O4S2

Molecular Weight: 458.57

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc2ccc(S(=O)(=O)N[C@H]3CCN(Cc4ccc(C(=N)N)s4)C3=O)cc2c1

Standard InChI:  InChI=1S/C21H22N4O4S2/c1-29-15-4-2-13-3-6-17(11-14(13)10-15)31(27,28)24-18-8-9-25(21(18)26)12-16-5-7-19(30-16)20(22)23/h2-7,10-11,18,24H,8-9,12H2,1H3,(H3,22,23)/t18-/m0/s1

Standard InChI Key:  HKCOOJZUUOHZDF-SFHVURJKSA-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: 458.57

Molecular Weight (Monoisotopic): 458.1082

AlogP: 2.27

#Rotatable Bonds: 7

Polar Surface Area: 125.58

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.06

CX Basic pKa: 8.85

CX LogP: 1.28

CX LogD: 0.11

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.37

Np Likeness Score: -1.14

References

1. Ewing WR, Becker MR, Manetta VE, Davis RS, Pauls HW, Mason H, Choi-Sledeski YM, Green D, Cha D, Spada AP, Cheney DL, Mason JS, Maignan S, Guilloteau JP, Brown K, Colussi D, Bentley R, Bostwick J, Kasiewski CJ, Morgan SR, Leadley RJ, Dunwiddie CT, Perrone MH, Chu V..  (1999)  Design and structure-activity relationships of potent and selective inhibitors of blood coagulation factor Xa.,  42  (18): [PMID:10479288] [10.1021/jm990040h]

2. Liang G, Chen X, Aldous S, Pu SF, Mehdi S, Powers E, Giovanni A, Kongsamut S, Xia T, Zhang Y, Wang R, Gao Z, Merriman G, McLean LR, Morize I..  (2012)  Virtual Screening and X-ray Crystallography for Human Kallikrein 6 Inhibitors with an Amidinothiophene P1 Group.,  3  (2): [PMID:24900446] [10.1021/ml200291e]

Source

Source(1):

• Scientific Literature