(2R,15R)-2-[(1-Amino-4-fluoroisoquinolin-6-yl)amino]-7-(cyclopropanesulfonyl)-4,15,17-trimethyl-13-oxa-4,11-diazatricyclo-[14.2.2.1(6,10)]henicosa-1(18),6,8,10(21),16,19-hexaene-3,12-dione

ID: ALA3902498

PubChem CID: 72551247

Max Phase: Preclinical

Molecular Formula: C33H34FN5O5S

Molecular Weight: 631.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2ccc1[C@@H](C)COC(=O)Nc1ccc(S(=O)(=O)C3CC3)c(c1)CN(C)C(=O)[C@@H]2Nc1ccc2c(N)ncc(F)c2c1

Standard InChI:  InChI=1S/C33H34FN5O5S/c1-18-12-20-4-9-25(18)19(2)17-44-33(41)38-22-6-11-29(45(42,43)24-7-8-24)21(13-22)16-39(3)32(40)30(20)37-23-5-10-26-27(14-23)28(34)15-36-31(26)35/h4-6,9-15,19,24,30,37H,7-8,16-17H2,1-3H3,(H2,35,36)(H,38,41)/t19-,30+/m0/s1

Standard InChI Key:  ZVYUEFHDJYEETD-WWOZWPLTSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3902498

   US9174974, Example 19

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: 631.73

Molecular Weight (Monoisotopic): 631.2265

AlogP: 5.68

#Rotatable Bonds: 4

Polar Surface Area: 143.72

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.41

CX Basic pKa: 6.53

CX LogP: 4.29

CX LogD: 4.24

Aromatic Rings: 4

Heavy Atoms: 45

QED Weighted: 0.26

Np Likeness Score: -0.25

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