2-(2,2'-dihydroxy-5'-ureidomethyl-biphenyl-3-yl)-1H-benzoimidazole-5-carboxamidine

ID: ALA378916

Chembl Id: CHEMBL378916

PubChem CID: 135528873

Max Phase: Preclinical

Molecular Formula: C22H20N6O3

Molecular Weight: 416.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc2[nH]c(-c3cccc(-c4cc(CNC(N)=O)ccc4O)c3O)nc2c1

Standard InChI:  InChI=1S/C22H20N6O3/c23-20(24)12-5-6-16-17(9-12)28-21(27-16)14-3-1-2-13(19(14)30)15-8-11(4-7-18(15)29)10-26-22(25)31/h1-9,29-30H,10H2,(H3,23,24)(H,27,28)(H3,25,26,31)

Standard InChI Key:  AEOYTBFWYXDAMX-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA378916

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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: 416.44

Molecular Weight (Monoisotopic): 416.1597

AlogP: 2.76

#Rotatable Bonds: 5

Polar Surface Area: 174.13

Molecular Species: BASE

HBA: 5

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.48

CX Basic pKa: 10.60

CX LogP: 1.48

CX LogD: 0.50

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.20

Np Likeness Score: -0.41

References

1. Riggs JR, Hu H, Kolesnikov A, Leahy EM, Wesson KE, Shrader WD, Vijaykumar D, Wahl TA, Tong Z, Sprengeler PA, Green MJ, Yu C, Katz BA, Sanford E, Nguyen M, Cabuslay R, Young WB..  (2006)  Novel 5-azaindole factor VIIa inhibitors.,  16  (12): [PMID:16621549] [10.1016/j.bmcl.2006.03.049]

2. Vijaykumar D, Rai R, Shaghafi M, Ton T, Torkelson S, Leahy EM, Riggs JR, Hu H, Sprengeler PA, Shrader WD, O'Bryan C, Cabuslay R, Sanford E, Gjerstadt E, Liu L, Sukbuntherng J, Young WB..  (2006)  Efforts toward oral bioavailability in factor VIIa inhibitors.,  16  (14): [PMID:16650987] [10.1016/j.bmcl.2006.04.018]

3. Hu H, Kolesnikov A, Riggs JR, Wesson KE, Stephens R, Leahy EM, Shrader WD, Sprengeler PA, Green MJ, Sanford E, Nguyen M, Gjerstad E, Cabuslay R, Young WB..  (2006)  Potent 4-amino-5-azaindole factor VIIa inhibitors.,  16  (17): [PMID:16793264] [10.1016/j.bmcl.2006.06.016]

Source

Source(1):

• Scientific Literature