ID: ALA3343304

Max Phase: Preclinical

Molecular Formula: C23H27ClN2O9S

Molecular Weight: 542.99

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1c(OCCCO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cccc1OCc1cc(-c2ccc(Cl)s2)on1

Standard InChI:  InChI=1S/C23H27ClN2O9S/c24-18-6-5-17(36-18)15-9-12(26-35-15)11-33-14-4-1-3-13(19(14)25)31-7-2-8-32-23-22(30)21(29)20(28)16(10-27)34-23/h1,3-6,9,16,20-23,27-30H,2,7-8,10-11,25H2/t16-,20-,21+,22-,23-/m1/s1

Standard InChI Key:  VXGSYPULPXOYEC-UJGPHIHISA-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: 542.99

Molecular Weight (Monoisotopic): 542.1126

AlogP: 1.80

#Rotatable Bonds: 11

Polar Surface Area: 169.89

Molecular Species: NEUTRAL

HBA: 12

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.21

CX Basic pKa: 4.17

CX LogP: 0.71

CX LogD: 0.71

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.18

Np Likeness Score: -0.15

References

1. Belviso BD, Caliandro R, de Candia M, Zaetta G, Lopopolo G, Incampo F, Colucci M, Altomare CD..  (2014)  How a β-D-glucoside side chain enhances binding affinity to thrombin of inhibitors bearing 2-chlorothiophene as P1 moiety: crystallography, fragment deconstruction study, and evaluation of antithrombotic properties.,  57  (20): [PMID:25268757] [10.1021/jm5010754]

Source

Source(1):

• Scientific Literature