(R)-9-(2-phosphonylmethoxypropyl)-2,6-diaminopurine

ID: ALA482690

Chembl Id: CHEMBL482690

Cas Number: 147057-10-1

PubChem CID: 461307

Max Phase: Preclinical

Molecular Formula: C9H15N6O4P

Molecular Weight: 302.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](Cn1cnc2c(N)nc(N)nc21)OCP(=O)(O)O

Standard InChI:  InChI=1S/C9H15N6O4P/c1-5(19-4-20(16,17)18)2-15-3-12-6-7(10)13-9(11)14-8(6)15/h3,5H,2,4H2,1H3,(H2,16,17,18)(H4,10,11,13,14)/t5-/m1/s1

Standard InChI Key:  LWEKFDHXJHJYGB-RXMQYKEDSA-N

Alternative Forms

1. Parent:

   

   ALA482690

   (R)-9-(2-Phosphonomethoxypropyl)-2,6-diaminopurine

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: 302.23

Molecular Weight (Monoisotopic): 302.0892

AlogP: -0.47

#Rotatable Bonds: 5

Polar Surface Area: 162.40

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -5.31

CX Basic pKa: 6.56

CX LogP: -4.26

CX LogD: -3.68

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.53

Np Likeness Score: -0.29

References

1. Shi M, Wang X, De Clercq E, Takao S, Baba M..  (2007)  Selective inhibition of porcine endogenous retrovirus replication in human cells by acyclic nucleoside phosphonates.,  51  (7): [PMID:17470654] [10.1128/aac.00212-07]

2. Jansa P, Baszczyňski O, Dračínský M, Votruba I, Zídek Z, Bahador G, Stepan G, Cihlar T, Mackman R, Holý A, Janeba Z..  (2011)  A novel and efficient one-pot synthesis of symmetrical diamide (bis-amidate) prodrugs of acyclic nucleoside phosphonates and evaluation of their biological activities.,  46  (9): [PMID:21664011] [10.1016/j.ejmech.2011.05.040]

3. Krečmerová M, Jansa P, Dračínský M, Sázelová P, Kašička V, Neyts J, Auwerx J, Kiss E, Goris N, Stepan G, Janeba Z..  (2013)  9-[2-(R)-(Phosphonomethoxy)propyl]-2,6-diaminopurine (R)-PMPDAP and its prodrugs: optimized preparation, including identification of by-products formed, and antiviral evaluation in vitro.,  21  (5): [PMID:23375089] [10.1016/j.bmc.2012.12.044]

Source

Source(1):

• Scientific Literature