ID: ALA3120789

Max Phase: Preclinical

Molecular Formula: C28H37N6O8P

Molecular Weight: 616.61

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCC(CC)COC(=O)[C@H](C)NP(=O)(OC[C@H]1O[C@@](C#N)(c2ccc3c(N)ncnn23)[C@](C)(O)[C@@H]1O)Oc1ccccc1

Standard InChI:  InChI=1S/C28H37N6O8P/c1-5-19(6-2)14-39-26(36)18(3)33-43(38,42-20-10-8-7-9-11-20)40-15-22-24(35)27(4,37)28(16-29,41-22)23-13-12-21-25(30)31-17-32-34(21)23/h7-13,17-19,22,24,35,37H,5-6,14-15H2,1-4H3,(H,33,38)(H2,30,31,32)/t18-,22+,24+,27+,28-,43?/m0/s1

Standard InChI Key:  AJUZSILXPPXOCL-MOJYSVATSA-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: 616.61

Molecular Weight (Monoisotopic): 616.2410

AlogP: 2.70

#Rotatable Bonds: 13

Polar Surface Area: 203.55

Molecular Species: NEUTRAL

HBA: 13

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.23

CX Basic pKa: 0.65

CX LogP: 2.29

CX LogD: 2.29

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.16

Np Likeness Score: 0.12

References

1. Cho A, Zhang L, Xu J, Lee R, Butler T, Metobo S, Aktoudianakis V, Lew W, Ye H, Clarke M, Doerffler E, Byun D, Wang T, Babusis D, Carey AC, German P, Sauer D, Zhong W, Rossi S, Fenaux M, McHutchison JG, Perry J, Feng J, Ray AS, Kim CU..  (2014)  Discovery of the first C-nucleoside HCV polymerase inhibitor (GS-6620) with demonstrated antiviral response in HCV infected patients.,  57  (5): [PMID:23547794] [10.1021/jm400201a]

2. Siegel D, Hui HC, Doerffler E, Clarke MO, Chun K, Zhang L, Neville S, Carra E, Lew W, Ross B, Wang Q, Wolfe L, Jordan R, Soloveva V, Knox J, Perry J, Perron M, Stray KM, Barauskas O, Feng JY, Xu Y, Lee G, Rheingold AL, Ray AS, Bannister R, Strickley R, Swaminathan S, Lee WA, Bavari S, Cihlar T, Lo MK, Warren TK, Mackman RL..  (2017)  Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses.,  60  (5): [PMID:28124907] [10.1021/acs.jmedchem.6b01594]

Source

Source(1):

• Scientific Literature