ID: ALA454743

Max Phase: Preclinical

Molecular Formula: C12H16N4O3

Molecular Weight: 264.29

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=c1[nH]cnc2c(CN3C[C@@H](CO)[C@H](O)C3)c[nH]c12

Standard InChI:  InChI=1S/C12H16N4O3/c17-5-8-3-16(4-9(8)18)2-7-1-13-11-10(7)14-6-15-12(11)19/h1,6,8-9,13,17-18H,2-5H2,(H,14,15,19)/t8-,9+/m0/s1

Standard InChI Key:  AFNHHLILYQEHKK-DTWKUNHWSA-N

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

Properties

Molecular Weight: 264.29

Molecular Weight (Monoisotopic): 264.1222

AlogP: -0.96

#Rotatable Bonds: 3

Polar Surface Area: 105.24

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.03

CX Basic pKa: 7.47

CX LogP: -1.77

CX LogD: -2.11

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.57

Np Likeness Score: -0.02

References

1. Clinch K, Evans GB, Fröhlich RF, Furneaux RH, Kelly PM, Legentil L, Murkin AS, Li L, Schramm VL, Tyler PC, Woolhouse AD..  (2009)  Third-generation immucillins: syntheses and bioactivities of acyclic immucillin inhibitors of human purine nucleoside phosphorylase.,  52  (4): [PMID:19170524] [10.1021/jm801421q]

2. Mason JM, Murkin AS, Li L, Schramm VL, Gainsford GJ, Skelton BW..  (2008)  A beta-fluoroamine inhibitor of purine nucleoside phosphorylase.,  51  (18): [PMID:18800772] [10.1021/jm800792b]

3. Cheviet T, Lefebvre-Tournier I, Wein S, Peyrottes S..  (2019)  Plasmodium Purine Metabolism and Its Inhibition by Nucleoside and Nucleotide Analogues.,  62  (18): [PMID:30964283] [10.1021/acs.jmedchem.9b00182]

Source

Source(1):

• Scientific Literature