(1-Benzhydryl-2-{2-[(5-carbamimidoyl-thiophen-2-ylmethyl)-carbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylamino)-acetic acid

ID: ALA420540

Chembl Id: CHEMBL420540

Cas Number: 280780-95-2

PubChem CID: 9871765

Max Phase: Preclinical

Molecular Formula: C28H31N5O4S

Molecular Weight: 533.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc(CNC(=O)[C@@H]2CCCN2C(=O)[C@H](NCC(=O)O)C(c2ccccc2)c2ccccc2)s1

Standard InChI:  InChI=1S/C28H31N5O4S/c29-26(30)22-14-13-20(38-22)16-32-27(36)21-12-7-15-33(21)28(37)25(31-17-23(34)35)24(18-8-3-1-4-9-18)19-10-5-2-6-11-19/h1-6,8-11,13-14,21,24-25,31H,7,12,15-17H2,(H3,29,30)(H,32,36)(H,34,35)/t21-,25+/m0/s1

Standard InChI Key:  BIHPYGVYKSQDLA-SQJMNOBHSA-N

Alternative Forms

1. Parent:

   

   ALA420540

   Unii-FS64O4K98A

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: 533.65

Molecular Weight (Monoisotopic): 533.2097

AlogP: 2.51

#Rotatable Bonds: 11

Polar Surface Area: 148.61

Molecular Species: ZWITTERION

HBA: 6

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.81

CX Basic pKa: 9.21

CX LogP: 0.53

CX LogD: 0.34

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.19

Np Likeness Score: -0.65

References

1. Lee K, Park CW, Jung WH, Park HD, Lee SH, Chung KH, Park SK, Kwon OH, Kang M, Park DH, Lee SK, Kim EE, Yoon SK, Kim A..  (2003)  Efficacious and orally bioavailable thrombin inhibitors based on a 2,5-thienylamidine at the P1 position: discovery of N-carboxymethyl-d-diphenylalanyl-l-prolyl[(5-amidino-2-thienyl)methyl]amide.,  46  (17): [PMID:12904065] [10.1021/jm030025j]

Source

Source(1):

• Scientific Literature