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

ID: ALA1928901

Chembl Id: CHEMBL1928901

PubChem CID: 482589

Max Phase: Preclinical

Molecular Formula: C16H16N4O4

Molecular Weight: 328.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c(-c4ccccc4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H16N4O4/c21-6-10-13(22)14(23)16(24-10)20-8-19-12-11(17-7-18-15(12)20)9-4-2-1-3-5-9/h1-5,7-8,10,13-14,16,21-23H,6H2/t10-,13-,14-,16-/m1/s1

Standard InChI Key:  MTNIRTDDXIKWCH-DSPGLSBSSA-N

Alternative Forms

1. Parent:

   

   ALA1928901

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

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: 328.33

Molecular Weight (Monoisotopic): 328.1172

AlogP: 0.10

#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: 1.98

CX LogP: 0.18

CX LogD: 0.18

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.62

Np Likeness Score: 0.74

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, Holý A, Votruba I, Dvoráková H..  (2000)  Synthesis and cytostatic activity of substituted 6-phenylpurine bases and nucleosides: application of the Suzuki-Miyaura cross-coupling reactions of 6-chloropurine derivatives with phenylboronic acids.,  43  (9): [PMID:10794698] [10.1021/jm991167+]

3. 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]

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