(4-{2-(5-Carbamimidoyl-2-hydroxy-phenoxy)-3,5-difluoro-6-[3-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)-phenoxy]-pyridin-4-yloxy}-piperidin-1-yl)-acetic acid

ID: ALA332322

Chembl Id: CHEMBL332322

PubChem CID: 135515290

Max Phase: Preclinical

Molecular Formula: C29H30F2N6O6

Molecular Weight: 596.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN=C1c1cccc(Oc2nc(Oc3cc(C(=N)N)ccc3O)c(F)c(OC3CCN(CC(=O)O)CC3)c2F)c1

Standard InChI:  InChI=1S/C29H30F2N6O6/c1-36-12-9-34-27(36)17-3-2-4-19(13-17)42-28-23(30)25(41-18-7-10-37(11-8-18)15-22(39)40)24(31)29(35-28)43-21-14-16(26(32)33)5-6-20(21)38/h2-6,13-14,18,38H,7-12,15H2,1H3,(H3,32,33)(H,39,40)

Standard InChI Key:  ZKPMPXGSEXIYPL-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA332322

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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: 596.59

Molecular Weight (Monoisotopic): 596.2195

AlogP: 3.55

#Rotatable Bonds: 10

Polar Surface Area: 166.82

Molecular Species: ZWITTERION

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.41

CX Basic pKa: 12.35

CX LogP: -1.39

CX LogD: -2.64

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.20

Np Likeness Score: -0.41

References

1. Phillips GB, Buckman BO, Davey DD, Eagen KA, Guilford WJ, Hinchman J, Ho E, Koovakkat S, Liang A, Light DR, Mohan R, Ng HP, Post JM, Shaw KJ, Smith D, Subramanyam B, Sullivan ME, Trinh L, Vergona R, Walters J, White K, Whitlow M, Wu S, Xu W, Morrissey MM..  (1998)  Discovery of N-[2-[5-[Amino(imino)methyl]-2-hydroxyphenoxy]-3, 5-difluoro-6-[3-(4, 5-dihydro-1-methyl-1H-imidazol-2-yl)phenoxy]pyridin-4-yl]-N-methylgl y cine (ZK-807834): a potent, selective, and orally active inhibitor of the blood coagulation enzyme factor Xa.,  41  (19): [PMID:9733480] [10.1021/jm980280h]

Source

Source(1):

• Scientific Literature