2-Hydroxymethyl-5-(6-thiophen-2-yl-purin-9-ylmethyl)-tetrahydro-furan-3,4-diol

ID: ALA236070

Chembl Id: CHEMBL236070

PubChem CID: 6475823

Max Phase: Preclinical

Molecular Formula: C14H14N4O4S

Molecular Weight: 334.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c(-c4cccs4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H14N4O4S/c19-4-7-11(20)12(21)14(22-7)18-6-17-10-9(8-2-1-3-23-8)15-5-16-13(10)18/h1-3,5-7,11-12,14,19-21H,4H2/t7-,11-,12-,14-/m1/s1

Standard InChI Key:  JJGFWBKSCRSUKK-UBPLGANQSA-N

Alternative Forms

1. Parent:

   

   ALA236070

   5-(Hydroxymethyl)-2-(6-(2-thienyl)purin-9-yl)oxolane-3,4-diol

2. Alternative Forms:

   

   ALA236070

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3. 

   ALA236070

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4. 

   ALA236070

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5. 

   ALA236070

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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: 334.36

Molecular Weight (Monoisotopic): 334.0736

AlogP: 0.17

#Rotatable Bonds: 3

Polar Surface Area: 113.52

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 0.97

CX LogP: -0.05

CX LogD: -0.05

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.63

Np Likeness Score: 0.25

References

1. Gundersen LL, Nissen-Meyer J, Spilsberg B..  (2002)  Synthesis and antimycobacterial activity of 6-arylpurines: the requirements for the N-9 substituent in active antimycobacterial purines.,  45  (6): [PMID:11882008] [10.1021/jm0110284]

2. Hocek M, Naus P, Pohl R, Votruba I, Furman PA, Tharnish PM, Otto MJ..  (2005)  Cytostatic 6-arylpurine nucleosides. 6. SAR in anti-HCV and cytostatic activity of extended series of 6-hetarylpurine ribonucleosides.,  48  (18): [PMID:16134952] [10.1021/jm050335x]

3. Kimoto M, Moriyama K, Yokoyama S, Hirao I..  (2007)  Cytostatic evaluations of nucleoside analogs related to unnatural base pairs for a genetic expansion system.,  17  (20): [PMID:17804231] [10.1016/j.bmcl.2007.07.088]

4. Hassan AE, Abou-Elkhair RA, Riordan JM, Allan PW, Parker WB, Khare R, Waud WR, Montgomery JA, Secrist JA..  (2012)  Synthesis and evaluation of the substrate activity of C-6 substituted purine ribosides with E. coli purine nucleoside phosphorylase: palladium mediated cross-coupling of organozinc halides with 6-chloropurine nucleosides.,  47  [PMID:22112758] [10.1016/j.ejmech.2011.10.039]

5. Bera S, Mondal D..  (2019)  Insights of synthetic analogues of anti-leprosy agents.,  27  (13): [PMID:31103404] [10.1016/j.bmc.2019.04.032]

Source

Source(1):

• Scientific Literature