(2S,2'S)-dipropyl 2,2'-((((2R,5R)-5-(6-amino-9H-purin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yloxy)methyl)phosphoryl)bis(azanediyl)bis(3-phenylpropanoate)

ID: ALA1094327

PubChem CID: 46887048

Max Phase: Preclinical

Molecular Formula: C34H41FN7O7P

Molecular Weight: 709.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOC(=O)[C@H](Cc1ccccc1)NP(=O)(CO[C@@H]1C=C(F)[C@H](n2cnc3c(N)ncnc32)O1)N[C@@H](Cc1ccccc1)C(=O)OCCC

Standard InChI:  InChI=1S/C34H41FN7O7P/c1-3-15-46-33(43)26(17-23-11-7-5-8-12-23)40-50(45,41-27(34(44)47-16-4-2)18-24-13-9-6-10-14-24)22-48-28-19-25(35)32(49-28)42-21-39-29-30(36)37-20-38-31(29)42/h5-14,19-21,26-28,32H,3-4,15-18,22H2,1-2H3,(H2,36,37,38)(H2,40,41,45)/t26-,27-,28-,32+/m0/s1

Standard InChI Key:  HPIWMPNXEFPOBY-BQUCCUTGSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1094327

   propyl (2S)-2-[[[(2R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yl]oxymethyl-[[(2S)-1-oxo-3-phenyl-1-propoxypropan-2-yl]amino]phosphoryl]amino]-3-phenylpropanoate

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: 709.72

Molecular Weight (Monoisotopic): 709.2789

AlogP: 4.59

#Rotatable Bonds: 18

Polar Surface Area: 181.81

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.47

CX Basic pKa: 4.89

CX LogP: 3.97

CX LogD: 3.97

Aromatic Rings: 4

Heavy Atoms: 50

QED Weighted: 0.10

Np Likeness Score: -0.08

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