ID: ALA474121

Max Phase: Preclinical

Molecular Formula: C11H14N4O4

Molecular Weight: 266.26

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=c1[nH]cnc2c([C@H]3N[C@@H](CO)[C@H](O)[C@@H]3O)c[nH]c12

Standard InChI:  InChI=1S/C11H14N4O4/c16-2-5-9(17)10(18)7(15-5)4-1-12-8-6(4)13-3-14-11(8)19/h1,3,5,7,9-10,12,15-18H,2H2,(H,13,14,19)/t5-,7+,9-,10+/m0/s1

Standard InChI Key:  IWKXDMQDITUYRK-LBHYJYKWSA-N

Molecule Features

Natural Product: Yes

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: 266.26

Molecular Weight (Monoisotopic): 266.1015

AlogP: -2.02

#Rotatable Bonds: 2

Polar Surface Area: 134.26

Molecular Species: NEUTRAL

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.03

CX Basic pKa: 7.94

CX LogP: -2.72

CX LogD: -3.37

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.37

Np Likeness Score: 1.06

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. 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