(Rp)-adenosine-5'-O-(P3-(m-nitrobenzyl)-(P1-thio)-triphosphate

ID: ALA3973528

Chembl Id: CHEMBL3973528

PubChem CID: 134153259

Max Phase: Preclinical

Molecular Formula: C16H19N6O14P3S

Molecular Weight: 644.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO[P@@](O)(=S)OP(=O)(O)OP(=O)(O)Oc2cccc([N+](=O)[O-])c2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C16H19N6O14P3S/c17-14-11-15(19-6-18-14)21(7-20-11)16-13(24)12(23)10(33-16)5-32-39(31,40)36-38(29,30)35-37(27,28)34-9-3-1-2-8(4-9)22(25)26/h1-4,6-7,10,12-13,16,23-24H,5H2,(H,27,28)(H,29,30)(H,31,40)(H2,17,18,19)/t10-,12-,13-,16-,39-/m1/s1

Standard InChI Key:  JMAKBEVBTYWSFB-WENHWCAASA-N

Alternative Forms

1. Parent:

   

   ALA3973528

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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: 644.34

Molecular Weight (Monoisotopic): 643.9893

AlogP: 0.48

#Rotatable Bonds: 11

Polar Surface Area: 294.20

Molecular Species: ACID

HBA: 17

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.97

CX Basic pKa: 4.92

CX LogP: -2.68

CX LogD: -7.32

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.09

Np Likeness Score: 0.48

References

1. Kaczmarek R, Krakowiak A, Korczyński D, Baraniak J, Nawrot B..  (2016)  Phosphorothioate analogs of P1,P3-di(nucleosid-5'-yl) triphosphates: Synthesis, assignment of the absolute configuration at P-atoms and P-stereodependent recognition by Fhit hydrolase.,  24  (21): [PMID:27591011] [10.1016/j.bmc.2016.08.027]

Source

Source(1):

• Scientific Literature