(1S,2R,3S,4R,5S)-4-(5-((5-chlorothiophen-2-yl)ethynyl)-7-(methylamino)-3H-imidazo[4,5-b]pyridin-3-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide

ID: ALA3612939

Chembl Id: CHEMBL3612939

PubChem CID: 122188578

Max Phase: Preclinical

Molecular Formula: C21H20ClN5O3S

Molecular Weight: 457.94

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H20ClN5O3S/c1-23-13-7-10(3-4-11-5-6-14(22)31-11)26-19-15(13)25-9-27(19)16-12-8-21(12,20(30)24-2)18(29)17(16)28/h5-7,9,12,16-18,28-29H,8H2,1-2H3,(H,23,26)(H,24,30)/t12-,16-,17+,18+,21+/m1/s1

Standard InChI Key:  DVEWTVCBLKZYMV-NEWQXWLQSA-N

Alternative Forms

1. Parent:

   

   ALA3612939

   ---

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: 457.94

Molecular Weight (Monoisotopic): 457.0975

AlogP: 1.62

#Rotatable Bonds: 3

Polar Surface Area: 112.30

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.13

CX Basic pKa: 3.81

CX LogP: 1.31

CX LogD: 1.31

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: -0.01

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