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

ID: ALA3612932

Chembl Id: CHEMBL3612932

PubChem CID: 122188571

Max Phase: Preclinical

Molecular Formula: C22H23ClN6O3S

Molecular Weight: 486.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNc1nc(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/C22H23ClN6O3S/c1-3-8-25-19-15-20(28-14(27-19)7-5-11-4-6-13(23)33-11)29(10-26-15)16-12-9-22(12,21(32)24-2)18(31)17(16)30/h4,6,10,12,16-18,30-31H,3,8-9H2,1-2H3,(H,24,32)(H,25,27,28)/t12-,16-,17+,18+,22+/m1/s1

Standard InChI Key:  CPDWVNNYXONUCC-YWNJHDJRSA-N

Alternative Forms

1. Parent:

   

   ALA3612932

   ---

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: 486.99

Molecular Weight (Monoisotopic): 486.1241

AlogP: 1.79

#Rotatable Bonds: 5

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: 2.28

CX LogD: 2.28

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.41

Np Likeness Score: -0.13

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. 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]

4. 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]

5. Jacobson KA, Salmaso V, Suresh RR, Tosh DK..  (2021)  Expanding the repertoire of methanocarba nucleosides from purinergic signaling to diverse targets.,  12  (11.0): [PMID:34825182] [10.1039/D1MD00167A]

Source

Source(1):

• Scientific Literature