(2S)-methyl 2-((((2R,3S,4S,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorylamino)-3-methylbutanoate

ID: ALA515584

PubChem CID: 44572056

Max Phase: Preclinical

Molecular Formula: C22H29N6O8P

Molecular Weight: 536.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@H](NP(=O)(OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@@H](O)[C@@H]1O)Oc1ccccc1)C(C)C

Standard InChI:  InChI=1S/C22H29N6O8P/c1-12(2)15(22(31)33-3)27-37(32,36-13-7-5-4-6-8-13)34-9-14-17(29)18(30)21(35-14)28-11-26-16-19(23)24-10-25-20(16)28/h4-8,10-12,14-15,17-18,21,29-30H,9H2,1-3H3,(H,27,32)(H2,23,24,25)/t14-,15+,17-,18+,21-,37?/m1/s1

Standard InChI Key:  HPXBTPGTPDQDJY-SKKHLDJQSA-N

Molfile:  

     RDKit          2D

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  7  8  2  0
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 13 17  1  1
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M  END

Alternative Forms

1. Parent:

   

   ALA515584

   methyl (2S)-2-[[[(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]-3-methylbutanoate

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: 536.48

Molecular Weight (Monoisotopic): 536.1784

AlogP: 1.02

#Rotatable Bonds: 10

Polar Surface Area: 193.17

Molecular Species: NEUTRAL

HBA: 13

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.22

CX Basic pKa: 4.92

CX LogP: 0.55

CX LogD: 0.55

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.21

Np Likeness Score: 0.56

References

1. Shen W, Kim JS, Kish PE, Zhang J, Mitchell S, Gentry BG, Breitenbach JM, Drach JC, Hilfinger J..  (2009)  Design and synthesis of vidarabine prodrugs as antiviral agents.,  19  (3): [PMID:19097789] [10.1016/j.bmcl.2008.12.031]

2. Wang Z, Zang R, Niu Z, Wang W, Wang X, Tang Y..  (2021)  Synthesis and antiviral effect of phosphamide modified vidarabine for treating HSV 1 infections.,  52  [PMID:34624489] [10.1016/j.bmcl.2021.128405]

Source

Source(1):

• Scientific Literature