9-(S)-(3-Fluoro-2-phosphonylmethoxypropyl)adenine

ID: ALA2021513

Chembl Id: CHEMBL2021513

PubChem CID: 70693907

Max Phase: Preclinical

Molecular Formula: C8H11FN5O4P

Molecular Weight: 291.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2C[C@@H](F)OCP(=O)(O)O

Standard InChI:  InChI=1S/C8H11FN5O4P/c9-5(18-4-19(15,16)17)1-14-3-13-6-7(10)11-2-12-8(6)14/h2-3,5H,1,4H2,(H2,10,11,12)(H2,15,16,17)/t5-/m0/s1

Standard InChI Key:  BRBMEZUIFJSKOB-YFKPBYRVSA-N

Alternative Forms

1. Parent:

   

   ALA2021513

   [(1R)-2-(6-aminopurin-9-yl)-1-fluoroethoxy]methylphosphonic acid

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: 291.18

Molecular Weight (Monoisotopic): 291.0533

AlogP: -0.14

#Rotatable Bonds: 5

Polar Surface Area: 136.38

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.35

CX Basic pKa: 3.67

CX LogP: -3.50

CX LogD: -3.66

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.65

Np Likeness Score: -0.52

References

1. Duraffour S, Snoeck R, Krecmerová M, van Den Oord J, De Vos R, Holy A, Crance JM, Garin D, De Clercq E, Andrei G..  (2007)  Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.,  51  (12): [PMID:17893157] [10.1128/aac.00838-07]

2. Baszczyňski O, Jansa P, Dračínský M, Klepetářová B, Holý A, Votruba I, de Clercq E, Balzarini J, Janeba Z..  (2011)  Synthesis and antiviral activity of N9-[3-fluoro-2-(phosphonomethoxy)propyl] analogues derived from N6-substituted adenines and 2,6-diaminopurines.,  19  (7): [PMID:21429755] [10.1016/j.bmc.2011.02.050]

3. 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]

Source

Source(1):

• Scientific Literature