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

ID: ALA3612931

Chembl Id: CHEMBL3612931

PubChem CID: 122188570

Max Phase: Preclinical

Molecular Formula: C21H21ClN6O3S

Molecular Weight: 472.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNc1nc(C#Cc2ccc(Cl)s2)nc2c1ncn2[C@H]1[C@H](O)[C@H](O)[C@]2(C(=O)NC)C[C@H]12

Standard InChI:  InChI=1S/C21H21ClN6O3S/c1-3-24-18-14-19(27-13(26-18)7-5-10-4-6-12(22)32-10)28(9-25-14)15-11-8-21(11,20(31)23-2)17(30)16(15)29/h4,6,9,11,15-17,29-30H,3,8H2,1-2H3,(H,23,31)(H,24,26,27)/t11-,15-,16+,17+,21+/m1/s1

Standard InChI Key:  QINHVPXTCNLQAU-RUZZFIIFSA-N

Alternative Forms

1. Parent:

   

   ALA3612931

   ---

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: 472.96

Molecular Weight (Monoisotopic): 472.1084

AlogP: 1.40

#Rotatable Bonds: 4

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: 3.38

CX LogP: 1.79

CX LogD: 1.79

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.42

Np Likeness Score: -0.06

References

1. 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]

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]

Source

Source(1):

• Scientific Literature