(2S)-isopropyl 2-((((2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-bromo-4-fluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorylamino)propanoate

ID: ALA4540766

PubChem CID: 155550131

Max Phase: Preclinical

Molecular Formula: C22H27BrFN6O8P

Molecular Weight: 633.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)[C@H](C)NP(=O)(OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)[C@](F)(Br)[C@H]1O)Oc1ccccc1

Standard InChI:  InChI=1S/C22H27BrFN6O8P/c1-11(2)36-19(33)12(3)29-39(34,38-13-7-5-4-6-8-13)35-9-14-16(31)22(23,24)20(37-14)30-10-26-15-17(30)27-21(25)28-18(15)32/h4-8,10-12,14,16,20,31H,9H2,1-3H3,(H,29,34)(H3,25,27,28,32)/t12-,14+,16-,20+,22-,39?/m0/s1

Standard InChI Key:  DYLSVKLQSKKAAB-GFHVOXQRSA-N

Molfile:  

 
     RDKit          2D

 39 42  0  0  0  0  0  0  0  0999 V2000
    9.1379   -3.9169    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.3421   -3.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5560   -4.4998    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5212   -3.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6030   -2.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9337   -2.4335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2687   -2.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4839   -2.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3119   -1.8587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0353   -4.3712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3880   -2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4687   -1.8834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6436   -1.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7226   -2.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0531   -3.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1366   -3.9695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8891   -4.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5588   -3.8201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4718   -3.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1392   -2.5180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9742   -5.1279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5272   -1.6041    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.3552   -0.7972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9143   -2.1564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5211   -2.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3045   -3.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5051   -3.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2883   -4.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8695   -4.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6705   -4.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8836   -3.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295   -1.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9577   -1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -2.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7319   -2.1995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6886   -3.2611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1190   -2.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3342   -2.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2909   -3.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  2  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  4  1  0
  7  8  1  1
  8  9  1  0
  4 10  1  1
  5 11  1  1
 11 15  1  0
 14 12  1  0
 12 13  2  0
 13 11  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 14  1  0
 19 20  2  0
 17 21  1  0
  9 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 24 32  1  0
 32 33  1  6
 32 34  1  0
 34 35  1  0
 34 36  2  0
 35 37  1  0
 37 38  1  0
 37 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4540766

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 633.37

Molecular Weight (Monoisotopic): 632.0795

AlogP: 2.15

#Rotatable Bonds: 10

Polar Surface Area: 192.91

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.89

CX Basic pKa: 0.43

CX LogP: 1.53

CX LogD: 1.53

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.14

Np Likeness Score: 0.18

References

1. Mengshetti S, Zhou L, Sari O, De Schutter C, Zhang H, Cho JH, Tao S, Bassit LC, Verma K, Domaoal RA, Ehteshami M, Jiang Y, Ovadia R, Kasthuri M, Ollinger Russell O, McBrayer T, Whitaker T, Pattassery J, Pascual ML, Uher L, Lin BY, Lee S, Amblard F, Coats SJ, Schinazi RF..  (2019)  Discovery of a Series of 2'-α-Fluoro,2'-β-bromo-ribonucleosides and Their Phosphoramidate Prodrugs as Potent Pan-Genotypic Inhibitors of Hepatitis C Virus.,  62  (4): [PMID:30653317] [10.1021/acs.jmedchem.8b01300]

Source

Source(1):

• Scientific Literature