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

ID: ALA3407784

Chembl Id: CHEMBL3407784

PubChem CID: 118730351

Max Phase: Preclinical

Molecular Formula: C20H19ClN6O3S

Molecular Weight: 458.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)[C@@]12C[C@@H]1[C@@H](n1cnc3c(NC)nc(C#Cc4ccc(Cl)s4)nc31)[C@H](O)[C@@H]2O

Standard InChI:  InChI=1S/C20H19ClN6O3S/c1-22-17-13-18(26-12(25-17)6-4-9-3-5-11(21)31-9)27(8-24-13)14-10-7-20(10,19(30)23-2)16(29)15(14)28/h3,5,8,10,14-16,28-29H,7H2,1-2H3,(H,23,30)(H,22,25,26)/t10-,14-,15+,16+,20+/m1/s1

Standard InChI Key:  RVLAHZAHALVQKF-AQPYCOETSA-N

Alternative Forms

1. Parent:

   

   ALA3407784

   ---

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: 458.93

Molecular Weight (Monoisotopic): 458.0928

AlogP: 1.01

#Rotatable Bonds: 3

Polar Surface Area: 125.19

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.12

CX Basic pKa: 3.41

CX LogP: 1.44

CX LogD: 1.44

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: 0.05

References

1. Tosh DK, Finley A, Paoletta S, Moss SM, Gao ZG, Gizewski ET, Auchampach JA, Salvemini D, Jacobson KA..  (2014)  In vivo phenotypic screening for treating chronic neuropathic pain: modification of C2-arylethynyl group of conformationally constrained A3 adenosine receptor agonists.,  57  (23): [PMID:25422861] [10.1021/jm501021n]

2. Tosh DK, Crane S, Chen Z, Paoletta S, Gao ZG, Gizewski E, Auchampach JA, Salvemini D, Jacobson KA..  (2015)  Rigidified A3 Adenosine Receptor Agonists: 1-Deazaadenine Modification Maintains High in Vivo Efficacy.,  6  (7): [PMID:26191370] [10.1021/acsmedchemlett.5b00150]

3. 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]

4. Yu J, Mannes P, Jung YH, Ciancetta A, Bitant A, Lieberman DI, Khaznadar S, Auchampach JA, Gao ZG, Jacobson KA..  (2018)  Structure activity relationship of 2-arylalkynyl-adenine derivatives as human A₃ adenosine receptor antagonists.,  9  (11): [PMID:30568760] [10.1039/C8MD00317C]

5. 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]

6. Suresh RR, Gao ZG, Salmaso V, Chen E, Campbell RG, Poe RB, Liston TE, Jacobson KA..  (2022)  Selective A₃ Adenosine Receptor Antagonist Radioligand for Human and Rodent Species.,  13  (4.0): [PMID:35450351] [10.1021/acsmedchemlett.1c00685]

Source

Source(1):

• Scientific Literature