5-(6-Amino-2-chloro-purin-9-yl)-4-fluoro-2-hydroxymethyl-tetrahydro-furan-3-ol

ID: ALA3142980

Chembl Id: CHEMBL3142980

PubChem CID: 9882903

Max Phase: Preclinical

Molecular Formula: C10H11ClFN5O3

Molecular Weight: 303.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1F

Standard InChI:  InChI=1S/C10H11ClFN5O3/c11-10-15-7(13)5-8(16-10)17(2-14-5)9-4(12)6(19)3(1-18)20-9/h2-4,6,9,18-19H,1H2,(H2,13,15,16)/t3-,4-,6-,9-/m1/s1

Standard InChI Key:  WDDPHFBMKLOVOX-DXTOWSMRSA-N

Alternative Forms

1. Parent:

   

   ALA3142980

   2-Chloro-9-(2-deoxy-2-fluoro-beta-d-ribofuranosyl)adenine

Molecule Features

Natural Product: Yes

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: 303.68

Molecular Weight (Monoisotopic): 303.0534

AlogP: -0.35

#Rotatable Bonds: 2

Polar Surface Area: 119.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.71

CX Basic pKa: 2.20

CX LogP: -0.29

CX LogD: -0.29

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.65

Np Likeness Score: 0.63

References

1. Siddiqi SM, Jacobson KA, Esker JL, Olah ME, Ji XD, Melman N, Tiwari KN, Secrist JA, Schneller SW, Cristalli G..  (1995)  Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.,  38  (7): [PMID:7707320] [10.1021/jm00007a014]

2. Ma T, Lin JS, Newton MG, Cheng YC, Chu CK..  (1997)  Synthesis and anti-hepatitis B virus activity of 9-(2-deoxy-2-fluoro-beta-L-arabinofuranosyl) purine nucleosides.,  40  (17): [PMID:9276020] [10.1021/jm970233+]

3. Zaitseva GV, Sivets GG, Kazimierczuk Z, Vilpo JA, Mikhailopulo IA.  (1995)  Convergent syntheses and cytostatic properties of 2-chloro-2-deoxy-2-fluoroadenosine and its N7-isomer,  5  (24): [10.1016/0960-894X(95)00524-5]

4. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays