ID: ALA143418

Max Phase: Preclinical

Molecular Formula: C21H23F2N7O2

Molecular Weight: 443.46

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1nc(N)ccc1CNC(=O)Cn1c(C)cnc(NCC(F)(F)c2ccccn2)c1=O

Standard InChI:  InChI=1S/C21H23F2N7O2/c1-13-9-27-19(28-12-21(22,23)16-5-3-4-8-25-16)20(32)30(13)11-18(31)26-10-15-6-7-17(24)29-14(15)2/h3-9H,10-12H2,1-2H3,(H2,24,29)(H,26,31)(H,27,28)

Standard InChI Key:  OWCMVQFLPIOYNL-UHFFFAOYSA-N

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

Properties

Molecular Weight: 443.46

Molecular Weight (Monoisotopic): 443.1881

AlogP: 1.75

#Rotatable Bonds: 8

Polar Surface Area: 127.82

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.32

CX LogP: 0.42

CX LogD: 0.16

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.48

Np Likeness Score: -1.44

References

1. Burgey CS, Robinson KA, Lyle TA, Sanderson PE, Lewis SD, Lucas BJ, Krueger JA, Singh R, Miller-Stein C, White RB, Wong B, Lyle EA, Williams PD, Coburn CA, Dorsey BD, Barrow JC, Stranieri MT, Holahan MA, Sitko GR, Cook JJ, McMasters DR, McDonough CM, Sanders WM, Wallace AA, Clayton FC, Bohn D, Leonard YM, Detwiler TJ, Lynch JJ, Yan Y, Chen Z, Kuo L, Gardell SJ, Shafer JA, Vacca JP..  (2003)  Metabolism-directed optimization of 3-aminopyrazinone acetamide thrombin inhibitors. Development of an orally bioavailable series containing P1 and P3 pyridines.,  46  (4): [PMID:12570369] [10.1021/jm020311f]

2. Stepan AF, Mascitti V, Beaumont K, Kalgutkar AS.  (2013)  Metabolism-guided drug design,  4  (4): [10.1039/C2MD20317K]

3. Gillis EP, Eastman KJ, Hill MD, Donnelly DJ, Meanwell NA..  (2015)  Applications of Fluorine in Medicinal Chemistry.,  58  (21): [PMID:26200936] [10.1021/acs.jmedchem.5b00258]

4. Xie Z, Tian Y, Lv X, Xiao X, Zhan M, Cheng K, Li S, Liao C..  (2018)  The selectivity and bioavailability improvement of novel oral anticoagulants: An overview.,  146  [PMID:29407959] [10.1016/j.ejmech.2018.01.067]

Source

Source(1):

• Scientific Literature