(2S,3S,4R,5R)-5-(2-((5-Chlorothiophen-2-yl)ethynyl)-6-(n-propylamino)-9H-purin-9-yl)-3,4-dihydroxy-N-methyltetrahydrofuran-2-carboxamide

ID: ALA4086593

Chembl Id: CHEMBL4086593

PubChem CID: 137641762

Max Phase: Preclinical

Molecular Formula: C20H21ClN6O4S

Molecular Weight: 476.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNc1nc(C#Cc2ccc(Cl)s2)nc2c1ncn2[C@@H]1O[C@H](C(=O)NC)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C20H21ClN6O4S/c1-3-8-23-17-13-18(26-12(25-17)7-5-10-4-6-11(21)32-10)27(9-24-13)20-15(29)14(28)16(31-20)19(30)22-2/h4,6,9,14-16,20,28-29H,3,8H2,1-2H3,(H,22,30)(H,23,25,26)/t14-,15+,16-,20+/m0/s1

Standard InChI Key:  VVAIUXGEZUTKDN-KSVNGYGVSA-N

Alternative Forms

1. Parent:

   

   ALA4086593

   ---

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: 476.95

Molecular Weight (Monoisotopic): 476.1034

AlogP: 1.13

#Rotatable Bonds: 5

Polar Surface Area: 134.42

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.39

CX Basic pKa: 3.19

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: -0.08

References

1. Tosh DK, Janowsky A, Eshleman AJ, Warnick E, Gao ZG, Chen Z, Gizewski E, Auchampach JA, Salvemini D, Jacobson KA..  (2017)  Scaffold Repurposing of Nucleosides (Adenosine Receptor Agonists): Enhanced Activity at the Human Dopamine and Norepinephrine Sodium Symporters.,  60  (7): [PMID:28319392] [10.1021/acs.jmedchem.7b00141]

2. Tosh DK,Salmaso V,Rao H,Campbell R,Bitant A,Gao ZG,Auchampach JA,Jacobson KA.  (2020)  Direct Comparison of (N)-Methanocarba and Ribose-Containing 2-Arylalkynyladenosine Derivatives as A Receptor Agonists.,  11  (10): [PMID:33062176] [10.1021/acsmedchemlett.9b00637]

3. Abel B, Murakami M, Tosh DK, Yu J, Lusvarghi S, Campbell RG, Gao ZG, Jacobson KA, Ambudkar SV..  (2022)  Interaction of A₃ adenosine receptor ligands with the human multidrug transporter ABCG2.,  231  [PMID:35152062] [10.1016/j.ejmech.2022.114103]

Source

Source(1):

• Scientific Literature