(1S,2R,3S,4R,5S)-2,3-dihydroxy-4-(2-iodo-6-(phenethylamino)-9H-purin-9-yl)-N-methylbicyclo[3.1.0]hexane-1-carboxamide

ID: ALA3746512

Chembl Id: CHEMBL3746512

PubChem CID: 127040305

Max Phase: Preclinical

Molecular Formula: C21H23IN6O3

Molecular Weight: 534.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)[C@@]12C[C@@H]1[C@@H](n1cnc3c(NCCc4ccccc4)nc(I)nc31)[C@H](O)[C@@H]2O

Standard InChI:  InChI=1S/C21H23IN6O3/c1-23-19(31)21-9-12(21)14(15(29)16(21)30)28-10-25-13-17(26-20(22)27-18(13)28)24-8-7-11-5-3-2-4-6-11/h2-6,10,12,14-16,29-30H,7-9H2,1H3,(H,23,31)(H,24,26,27)/t12-,14-,15+,16+,21+/m1/s1

Standard InChI Key:  DILMSJYJOSOLCR-DYRGRVSNSA-N

Alternative Forms

1. Parent:

   

   ALA3746512

   ---

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: 534.36

Molecular Weight (Monoisotopic): 534.0876

AlogP: 1.11

#Rotatable Bonds: 6

Polar Surface Area: 125.19

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.12

CX Basic pKa: 2.27

CX LogP: 1.07

CX LogD: 1.07

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.28

Np Likeness Score: 0.09

References

1. Tosh DK, Paoletta S, Chen Z, Crane S, Lloyd J, Gao ZG, Gizewski ET, Auchampach JA, Salvemini D, Jacobson KA..  (2015)  Structure-Based Design, Synthesis by Click Chemistry and in Vivo Activity of Highly Selective A3 Adenosine Receptor Agonists.,  6  (4): [PMID:26236460] [10.1039/c4md00571f]

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