[(S)-4-Guanidino-1-({[4-guanidino-1-(4-nitro-phenylcarbamoyl)-butylcarbamoyl]-methyl}-carbamoyl)-butyl]-carbamic acid benzyl ester

ID: ALA32044

PubChem CID: 44287771

Max Phase: Preclinical

Molecular Formula: C28H39N11O7

Molecular Weight: 641.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCCCC(NC(=O)CNC(=O)[C@H](CCCN=C(N)N)NC(=O)OCc1ccccc1)C(=O)Nc1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C28H39N11O7/c29-26(30)33-14-4-8-21(38-28(43)46-17-18-6-2-1-3-7-18)24(41)35-16-23(40)37-22(9-5-15-34-27(31)32)25(42)36-19-10-12-20(13-11-19)39(44)45/h1-3,6-7,10-13,21-22H,4-5,8-9,14-17H2,(H,35,41)(H,36,42)(H,37,40)(H,38,43)(H4,29,30,33)(H4,31,32,34)/t21-,22?/m0/s1

Standard InChI Key:  WIQWZMXJFYDPOU-HMTLIYDFSA-N

Molfile:  

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M  CHG  2   1   1  13  -1
M  END

Alternative Forms

1. Parent:

   

   ALA32044

   [(S)-4-Guanidino-1-({[4-guanidino-1-(4-nitro-phenylcarbamoyl)-butylcarbamoyl]-methyl}-carbamoyl)-butyl]-carbamic acid benzyl ester

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: 641.69

Molecular Weight (Monoisotopic): 641.3034

AlogP: -0.25

#Rotatable Bonds: 18

Polar Surface Area: 295.07

Molecular Species: BASE

HBA: 9

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.69

CX Basic pKa: 11.52

CX LogP: -1.09

CX LogD: -5.35

Aromatic Rings: 2

Heavy Atoms: 46

QED Weighted: 0.03

Np Likeness Score: -0.41

References

1. Marlowe CK, Sinha U, Gunn AC, Scarborough RM..  (2000)  Design, synthesis and structure-activity relationship of a series of arginine aldehyde factor Xa inhibitors. Part 1: structures based on the (D)-Arg-Gly-Arg tripeptide sequence.,  10  (1): [PMID:10636232] [10.1016/s0960-894x(99)00582-x]

Source

Source(1):

• Scientific Literature