{2-[1-(6-Amino-purin-9-yl)-meth-(Z)-ylidene]-1-hydroxymethyl-cyclopropyl}-methanol

ID: ALA157102

Chembl Id: CHEMBL157102

PubChem CID: 3006039

Max Phase: Preclinical

Molecular Formula: C11H13N5O2

Molecular Weight: 247.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2/C=C1/CC1(CO)CO

Standard InChI:  InChI=1S/C11H13N5O2/c12-9-8-10(14-5-13-9)16(6-15-8)2-7-1-11(7,3-17)4-18/h2,5-6,17-18H,1,3-4H2,(H2,12,13,14)/b7-2-

Standard InChI Key:  PXYOVTOZMPOHBK-UQCOIBPSSA-N

Alternative Forms

1. Parent:

   

   ALA157102

   [2-(6-Amino-purin-9-ylmethylene)-1-hydroxymethyl-cyclopropyl]-methanol

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: 247.26

Molecular Weight (Monoisotopic): 247.1069

AlogP: -0.38

#Rotatable Bonds: 3

Polar Surface Area: 110.08

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.50

CX LogP: -1.61

CX LogD: -1.61

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.68

Np Likeness Score: 0.35

References

1. Zhou S, Breitenbach JM, Borysko KZ, Drach JC, Kern ER, Gullen E, Cheng YC, Zemlicka J..  (2004)  Synthesis and antiviral activity of (Z)- and (E)-2,2-[bis(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines: second-generation methylenecyclopropane analogues of nucleosides.,  47  (3): [PMID:14736238] [10.1021/jm030316s]

2. Yan Z, Kern ER, Gullen E, Cheng YC, Drach JC, Zemlicka J..  (2005)  Nucleotides and pronucleotides of 2,2-bis(hydroxymethyl)methylenecyclopropane analogues of purine nucleosides: synthesis and antiviral activity.,  48  (1): [PMID:15634003] [10.1021/jm040149b]

3. Prado-Prado FJ, Martinez de la Vega O, Uriarte E, Ubeira FM, Chou KC, González-Díaz H..  (2009)  Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.,  17  (2): [PMID:19112024] [10.1016/j.bmc.2008.11.075]

4. Randhawa P, Zemlicka J, Sauerbrei A, Meier C, Hostetler KY, Beadle JR, Farasati NA, Huang Y, Bradley M..  (2008)  Anti-BK virus activity of nucleoside analogs.,  52  (4): [PMID:18285481] [10.1128/aac.01241-07]

Source

Source(1):

• Scientific Literature