((4aR,6R)-9-{2-[(1R,4S)-5-((S)-3-Fluoro-phenyl)-pyridin-2-yl]-vinyl}-1-methyl-3-oxo-dodecahydro-naphtho[2,3-c]furan-6-yl)-carbamic acid(R)-2-hydroxy-ethyl ester

ID: ALA3542381

Chembl Id: CHEMBL3542381

Cas Number: 1256919-03-5

PubChem CID: 49838773

Max Phase: Preclinical

Molecular Formula: C29H33FN2O5

Molecular Weight: 508.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1OC(=O)[C@@H]2C[C@@H]3C[C@H](NC(=O)OCCO)CC[C@H]3[C@H](/C=C/c3ccc(-c4cccc(F)c4)cn3)[C@H]12

Standard InChI:  InChI=1S/C29H33FN2O5/c1-17-27-25(10-7-22-6-5-19(16-31-22)18-3-2-4-21(30)13-18)24-9-8-23(32-29(35)36-12-11-33)14-20(24)15-26(27)28(34)37-17/h2-7,10,13,16-17,20,23-27,33H,8-9,11-12,14-15H2,1H3,(H,32,35)/b10-7+/t17-,20+,23-,24-,25+,26-,27+/m1/s1

Standard InChI Key:  ZHYYTGYLGLSISZ-VERGWIBFSA-N

Alternative Forms

1. Parent:

   

   ALA3542381

   Vorapaxar metabolite M20

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: 508.59

Molecular Weight (Monoisotopic): 508.2374

AlogP: 4.60

#Rotatable Bonds: 6

Polar Surface Area: 97.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.32

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.55

Np Likeness Score: 0.10

References

1. Ghosal A, Lu X, Penner N, Gao L, Ramanathan R, Chowdhury SK, Kishnani NS, Alton KB..  (2011)  Identification of human liver cytochrome P450 enzymes involved in the metabolism of SCH 530348 (Vorapaxar), a potent oral thrombin protease-activated receptor 1 antagonist.,  39  (1): [PMID:20926621] [10.1124/dmd.110.035493]

Source

Source(1):

• Scientific Literature