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

ID: ALA3612940

Chembl Id: CHEMBL3612940

PubChem CID: 122188579

Max Phase: Preclinical

Molecular Formula: C22H22ClN5O3S

Molecular Weight: 471.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNc1cc(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/C22H22ClN5O3S/c1-3-25-14-8-11(4-5-12-6-7-15(23)32-12)27-20-16(14)26-10-28(20)17-13-9-22(13,21(31)24-2)19(30)18(17)29/h6-8,10,13,17-19,29-30H,3,9H2,1-2H3,(H,24,31)(H,25,27)/t13-,17-,18+,19+,22+/m1/s1

Standard InChI Key:  DTTFXWQRYRYGNI-RQEHDQILSA-N

Alternative Forms

1. Parent:

   

   ALA3612940

   ---

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: 471.97

Molecular Weight (Monoisotopic): 471.1132

AlogP: 2.01

#Rotatable Bonds: 4

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: 3.80

CX LogP: 1.67

CX LogD: 1.67

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -0.10

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, 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]

3. 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