1-(6-Amino-purin-9-yl)-4-hydroxymethyl-bicyclo[3.1.0]hexane-2,3-diol

ID: ALA2112095

Chembl Id: CHEMBL2112095

PubChem CID: 71450842

Max Phase: Preclinical

Molecular Formula: C12H15N5O3

Molecular Weight: 277.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@]12C[C@H]1[C@H](CO)[C@@H](O)[C@H]2O

Standard InChI:  InChI=1S/C12H15N5O3/c13-10-7-11(15-3-14-10)17(4-16-7)12-1-6(12)5(2-18)8(19)9(12)20/h3-6,8-9,18-20H,1-2H2,(H2,13,14,15)/t5-,6-,8+,9+,12-/m0/s1

Standard InChI Key:  PNZMMPDHUWWITO-CEQXEPLDSA-N

Alternative Forms

1. Parent:

   

   ALA2112095

   (1S,2S,3R,4R,5S)-1-(6-aminopurin-9-yl)-4-(hydroxymethyl)bicyclo[3.1.0]hexane-2,3-diol

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: 277.28

Molecular Weight (Monoisotopic): 277.1175

AlogP: -1.53

#Rotatable Bonds: 2

Polar Surface Area: 130.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: 3.64

CX LogP: -2.32

CX LogD: -2.32

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.52

Np Likeness Score: 1.07

References

1. Jacobson KA, Ji X, Li AH, Melman N, Siddiqui MA, Shin KJ, Marquez VE, Ravi RG..  (2000)  Methanocarba analogues of purine nucleosides as potent and selective adenosine receptor agonists.,  43  (11): [PMID:10841798] [10.1021/jm9905965]

2. Jacobson KA, Salmaso V, Suresh RR, Tosh DK..  (2021)  Expanding the repertoire of methanocarba nucleosides from purinergic signaling to diverse targets.,  12  (11.0): [PMID:34825182] [10.1039/D1MD00167A]

Source

Source(1):

• Scientific Literature