ID: ALA147455

Max Phase: Preclinical

Molecular Formula: C15H22N4O9

Molecular Weight: 402.36

Molecule Type: Small molecule

Representations

Canonical SMILES:  N/C=N/C[C@H]1O[C@@H](OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H22N4O9/c16-5-17-3-6-9(21)12(24)14(28-6)26-4-7-10(22)11(23)13(27-7)19-2-1-8(20)18-15(19)25/h1-2,5-7,9-14,21-24H,3-4H2,(H2,16,17)(H,18,20,25)/t6-,7-,9-,10-,11-,12-,13-,14-/m1/s1

Standard InChI Key:  SRKPSJFMWNAHDA-RBUSVLPKSA-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: 402.36

Molecular Weight (Monoisotopic): 402.1387

AlogP: -4.39

#Rotatable Bonds: 6

Polar Surface Area: 201.85

Molecular Species: BASE

HBA: 11

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.62

CX Basic pKa: 10.47

CX LogP: -4.73

CX LogD: -6.12

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.20

Np Likeness Score: 1.42

References

1. Dini C, Drochon N, Feteanu S, Guillot JC, Peixoto C, Aszodi J..  (2001)  Synthesis of analogues of the O-beta-D-ribofuranosyl nucleoside moiety of liposidomycins. Part 1: contribution of the amino group and the uracil moiety upon the inhibition of MraY.,  11  (4): [PMID:11229763] [10.1016/s0960-894x(00)00715-0]

2. Patel B, Ryan P, Makwana V, Zunk M, Rudrawar S, Grant G..  (2019)  Caprazamycins: Promising lead structures acting on a novel antibacterial target MraY.,  171  [PMID:30933853] [10.1016/j.ejmech.2019.01.071]

3. Serpi M, Ferrari V, Pertusati F..  (2016)  Nucleoside Derived Antibiotics to Fight Microbial Drug Resistance: New Utilities for an Established Class of Drugs?,  59  (23): [PMID:27607900] [10.1021/acs.jmedchem.6b00325]

Source

Source(1):

• Scientific Literature