Methyl (2S,3S,4R,5R)-5-(2-((5-Chlorothiophen-2-yl)ethynyl)-6-(methylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

ID: ALA4092411

Chembl Id: CHEMBL4092411

PubChem CID: 137653203

Max Phase: Preclinical

Molecular Formula: C18H16ClN5O5S

Molecular Weight: 449.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1nc(C#Cc2ccc(Cl)s2)nc2c1ncn2[C@@H]1O[C@H](C(=O)OC)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C18H16ClN5O5S/c1-20-15-11-16(23-10(22-15)6-4-8-3-5-9(19)30-8)24(7-21-11)17-13(26)12(25)14(29-17)18(27)28-2/h3,5,7,12-14,17,25-26H,1-2H3,(H,20,22,23)/t12-,13+,14-,17+/m0/s1

Standard InChI Key:  QHRWVXZCSCFZGP-QDEZUTFSSA-N

Alternative Forms

1. Parent:

   

   ALA4092411

   ---

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: 449.88

Molecular Weight (Monoisotopic): 449.0561

AlogP: 0.77

#Rotatable Bonds: 3

Polar Surface Area: 131.62

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.38

CX Basic pKa: 3.22

CX LogP: 1.86

CX LogD: 1.86

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.39

Np Likeness Score: 0.36

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