(2R,3S,4R,5R)-2-(Hydroxymethyl)-5-(6-(4-(phenylethynyl)-phenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol

ID: ALA4449169

PubChem CID: 155520320

Max Phase: Preclinical

Molecular Formula: C24H20N4O4

Molecular Weight: 428.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c(-c4ccc(C#Cc5ccccc5)cc4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C24H20N4O4/c29-12-18-21(30)22(31)24(32-18)28-14-27-20-19(25-13-26-23(20)28)17-10-8-16(9-11-17)7-6-15-4-2-1-3-5-15/h1-5,8-11,13-14,18,21-22,24,29-31H,12H2/t18-,21-,22-,24-/m1/s1

Standard InChI Key:  CZWGXQUZWFKCSH-QMBPOEKNSA-N

Molfile:  

 
     RDKit          2D

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    7.8850  -24.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8983  -23.3432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1679  -22.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3410  -25.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5322  -25.4794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2113  -20.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4575  -21.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2223  -19.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2324  -18.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427  -17.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9815  -17.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5243  -16.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5173  -17.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 10  1  1  1
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  9 19  1  0
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 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4449169

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 428.45

Molecular Weight (Monoisotopic): 428.1485

AlogP: 1.50

#Rotatable Bonds: 3

Polar Surface Area: 113.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 2.03

CX LogP: 2.30

CX LogD: 2.30

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.42

Np Likeness Score: 0.36

References

1. Crespo RA, Dang Q, Zhou NE, Guthrie LM, Snavely TC, Dong W, Loesch KA, Suzuki T, You L, Wang W, O'Malley T, Parish T, Olsen DB, Sacchettini JC..  (2019)  Structure-Guided Drug Design of 6-Substituted Adenosine Analogues as Potent Inhibitors of Mycobacterium tuberculosis Adenosine Kinase.,  62  (9): [PMID:31002508] [10.1021/acs.jmedchem.9b00020]

Source

Source(1):

• Scientific Literature