ID: ALA357505

Max Phase: Preclinical

Molecular Formula: C15H23N3O9

Molecular Weight: 389.36

Molecule Type: Small molecule

Representations

Canonical SMILES:  CNC[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/C15H23N3O9/c1-16-4-6-9(20)12(23)14(27-6)25-5-7-10(21)11(22)13(26-7)18-3-2-8(19)17-15(18)24/h2-3,6-7,9-14,16,20-23H,4-5H2,1H3,(H,17,19,24)/t6-,7-,9-,10-,11-,12-,13-,14-/m1/s1

Standard InChI Key:  MDMZIJWDRSBMIS-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: 389.36

Molecular Weight (Monoisotopic): 389.1434

AlogP: -4.16

#Rotatable Bonds: 6

Polar Surface Area: 175.50

Molecular Species: BASE

HBA: 11

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.70

CX Basic pKa: 8.95

CX LogP: -3.63

CX LogD: -4.87

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.28

Np Likeness Score: 1.47

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