(1R,2R,3S,4R,5S)-4-(6-((4-Hydroxy-3-methoxyphenethyl)amino)-2-(phenylethynyl)-9H-purin-9-yl)bicyclo[3.1.0]hexane-2,3-diol

ID: ALA4571380

Chembl Id: CHEMBL4571380

PubChem CID: 155562467

Max Phase: Preclinical

Molecular Formula: C28H27N5O4

Molecular Weight: 497.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(CCNc2nc(C#Cc3ccccc3)nc3c2ncn3[C@H]2[C@H](O)[C@H](O)[C@@H]3C[C@@H]32)ccc1O

Standard InChI:  InChI=1S/C28H27N5O4/c1-37-21-13-17(7-9-20(21)34)11-12-29-27-23-28(32-22(31-27)10-8-16-5-3-2-4-6-16)33(15-30-23)24-18-14-19(18)25(35)26(24)36/h2-7,9,13,15,18-19,24-26,34-36H,11-12,14H2,1H3,(H,29,31,32)/t18-,19+,24+,25+,26-/m0/s1

Standard InChI Key:  VNPDINLPSRFSFN-OMUDAWCKSA-N

Alternative Forms

1. Parent:

   

   ALA4571380

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 497.56

Molecular Weight (Monoisotopic): 497.2063

AlogP: 2.51

#Rotatable Bonds: 6

Polar Surface Area: 125.55

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.23

CX Basic pKa: 2.98

CX LogP: 3.43

CX LogD: 3.43

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.30

Np Likeness Score: 0.12

References

1. Tosh DK, Salmaso V, Rao H, Bitant A, Fisher CL, Lieberman DI, Vorbrüggen H, Reitman ML, Gavrilova O, Gao ZG, Auchampach JA, Jacobson KA..  (2020)  Truncated (N)-Methanocarba Nucleosides as Partial Agonists at Mouse and Human A3 Adenosine Receptors: Affinity Enhancement by N6-(2-Phenylethyl) Substitution.,  63  (8): [PMID:32271569] [10.1021/acs.jmedchem.0c00235]

2. Tosh DK, Salmaso V, Campbell RG, Rao H, Bitant A, Pottie E, Stove CP, Liu N, Gavrilova O, Gao ZG, Auchampach JA, Jacobson KA..  (2022)  A₃ adenosine receptor agonists containing dopamine moieties for enhanced interspecies affinity.,  228  [PMID:34844790] [10.1016/j.ejmech.2021.113983]

Source

Source(1):

• Scientific Literature