Diethyl [(2R,15R)-2-[(1-Aminoisoquinolin-6-yl)amino]-4,15,17-trimethyl-3,12-dioxo-13-oxa-4,11-diazatricyclo[14.2.2.1(6,10)]henicosa-1(18),6,8,10(21),16,19-hexaen-7-yl]phosphonate

ID: ALA3980787

PubChem CID: 72550807

Max Phase: Preclinical

Molecular Formula: C34H40N5O6P

Molecular Weight: 645.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=O)(OCC)c1ccc2cc1CN(C)C(=O)[C@H](Nc1ccc3c(N)nccc3c1)c1ccc(c(C)c1)[C@@H](C)COC(=O)N2

Standard InChI:  InChI=1S/C34H40N5O6P/c1-6-44-46(42,45-7-2)30-13-10-27-18-25(30)19-39(5)33(40)31(37-26-9-12-29-23(17-26)14-15-36-32(29)35)24-8-11-28(21(3)16-24)22(4)20-43-34(41)38-27/h8-18,22,31,37H,6-7,19-20H2,1-5H3,(H2,35,36)(H,38,41)/t22-,31+/m0/s1

Standard InChI Key:  YIXUXJDCYJOAHT-WKRVVKTRSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA3980787

   US9174974, Example 12

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: 645.70

Molecular Weight (Monoisotopic): 645.2716

AlogP: 6.49

#Rotatable Bonds: 7

Polar Surface Area: 145.11

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.49

CX Basic pKa: 9.17

CX LogP: 5.52

CX LogD: 4.02

Aromatic Rings: 4

Heavy Atoms: 46

QED Weighted: 0.19

Np Likeness Score: 0.15

References

1. Zhang X, Glunz PW, Johnson JA, Jiang W, Jacutin-Porte S, Ladziata V, Zou Y, Phillips MS, Wurtz NR, Parkhurst B, Rendina AR, Harper TM, Cheney DL, Luettgen JM, Wong PC, Seiffert D, Wexler RR, Priestley ES..  (2016)  Discovery of a Highly Potent, Selective, and Orally Bioavailable Macrocyclic Inhibitor of Blood Coagulation Factor VIIa-Tissue Factor Complex.,  59  (15): [PMID:27455395] [10.1021/acs.jmedchem.6b00469]

2.  (2015)  Macrocyclic factor VIIa inhibitors, 

Source

Source(2):

• Scientific Literature
• BindingDB Database