(2S)-cyclopentyl 2-((((2R,5R)-5-(6-amino-9H-purin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yloxy)methyl)(phenoxy)phosphorylamino)propanoate

ID: ALA1095425

PubChem CID: 11519593

Max Phase: Preclinical

Molecular Formula: C24H28FN6O6P

Molecular Weight: 546.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NP(=O)(CO[C@@H]1C=C(F)[C@H](n2cnc3c(N)ncnc32)O1)Oc1ccccc1)C(=O)OC1CCCC1

Standard InChI:  InChI=1S/C24H28FN6O6P/c1-15(24(32)35-16-7-5-6-8-16)30-38(33,37-17-9-3-2-4-10-17)14-34-19-11-18(25)23(36-19)31-13-29-20-21(26)27-12-28-22(20)31/h2-4,9-13,15-16,19,23H,5-8,14H2,1H3,(H,30,33)(H2,26,27,28)/t15-,19-,23+,38?/m0/s1

Standard InChI Key:  DTJVIZODBBCRCW-XHVABEAOSA-N

Molfile:  

     RDKit          2D

 38 42  0  0  0  0  0  0  0  0999 V2000
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    3.2755   -4.1097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2573   -4.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9627   -5.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157   -6.1572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8285   -4.9016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514   -3.3412    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -2.5740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048   -5.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2310   -3.7462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8062   -3.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3614   -4.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1905   -6.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5318   -2.8894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8810   -3.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1997   -2.9322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4280   -2.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9923   -1.4388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3813   -0.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2059   -0.6871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6414   -1.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2525   -2.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4467   -1.2151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8060   -2.8373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4750   -3.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2157   -4.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3907   -4.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1416   -3.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3518   -3.0570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6982   -4.7826    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -3.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
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  1  6  1  0
  3  2  1  1
  7  8  2  0
  7  2  1  0
  1  3  1  0
  6  9  1  0
  3  4  1  0
  7 10  1  0
  1  5  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 21 29  1  0
 24 29  1  0
 28 30  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 35 36  1  1
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 31 35  1  0
 32 23  1  1
 33 37  1  0
  9 17  1  0
 36 38  1  0
 38  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1095425

   cyclopentyl (2S)-2-[[[(2R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yl]oxymethyl-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: 546.50

Molecular Weight (Monoisotopic): 546.1792

AlogP: 3.83

#Rotatable Bonds: 10

Polar Surface Area: 152.71

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.36

CX Basic pKa: 4.89

CX LogP: 2.42

CX LogD: 2.42

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.28

Np Likeness Score: 0.01

References

1. Mackman RL, Ray AS, Hui HC, Zhang L, Birkus G, Boojamra CG, Desai MC, Douglas JL, Gao Y, Grant D, Laflamme G, Lin KY, Markevitch DY, Mishra R, McDermott M, Pakdaman R, Petrakovsky OV, Vela JE, Cihlar T..  (2010)  Discovery of GS-9131: Design, synthesis and optimization of amidate prodrugs of the novel nucleoside phosphonate HIV reverse transcriptase (RT) inhibitor GS-9148.,  18  (10): [PMID:20409721] [10.1016/j.bmc.2010.03.041]

Source

Source(1):

• Scientific Literature