(2S)-Benzyl2-((((2R,3R,4R,5R)-5-(4-Aminopyrrolo[1,2-f]-[1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorylamino)propanoate

ID: ALA3120790

PubChem CID: 76325302

Max Phase: Preclinical

Molecular Formula: C29H31N6O8P

Molecular Weight: 622.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NP(=O)(OC[C@H]1O[C@@](C#N)(c2ccc3c(N)ncnn23)[C@](C)(O)[C@@H]1O)Oc1ccccc1)C(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C29H31N6O8P/c1-19(27(37)40-15-20-9-5-3-6-10-20)34-44(39,43-21-11-7-4-8-12-21)41-16-23-25(36)28(2,38)29(17-30,42-23)24-14-13-22-26(31)32-18-33-35(22)24/h3-14,18-19,23,25,36,38H,15-16H2,1-2H3,(H,34,39)(H2,31,32,33)/t19-,23+,25+,28+,29-,44?/m0/s1

Standard InChI Key:  DTGIRBDEUUOOOE-ZLPYKPOHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3120790

   benzyl (2S)-2-[[[(2R,3R,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxy-4-methyloxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate

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: 622.58

Molecular Weight (Monoisotopic): 622.1941

AlogP: 2.47

#Rotatable Bonds: 11

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: 1.88

CX LogD: 1.88

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.14

Np Likeness Score: -0.02

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]

Source

Source(1):

• Scientific Literature