ID: ALA151287

Max Phase: Preclinical

Molecular Formula: C14H21N3O8

Molecular Weight: 359.34

Molecule Type: Small molecule

Representations

Canonical SMILES:  NC[C@H]1O[C@@H](OC[C@@H]2C[C@@H](O)[C@H](n3ccc(=O)[nH]c3=O)O2)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H21N3O8/c15-4-8-10(20)11(21)13(25-8)23-5-6-3-7(18)12(24-6)17-2-1-9(19)16-14(17)22/h1-2,6-8,10-13,18,20-21H,3-5,15H2,(H,16,19,22)/t6-,7+,8+,10+,11+,12+,13+/m0/s1

Standard InChI Key:  LKNRCKGTNKUSFH-PJXXCCFTSA-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: 359.34

Molecular Weight (Monoisotopic): 359.1329

AlogP: -3.39

#Rotatable Bonds: 5

Polar Surface Area: 169.26

Molecular Species: BASE

HBA: 10

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.70

CX Basic pKa: 8.75

CX LogP: -3.26

CX LogD: -4.38

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.36

Np Likeness Score: 1.74

References

1. Dini C, Drochon N, Guillot JC, Mauvais P, Walter P, Aszodi J..  (2001)  Synthesis of analogues of the O-beta-D-ribofuranosyl nucleoside moiety of liposidomycins. Part 2: role of the hydroxyl groups upon the inhibition of MraY.,  11  (4): [PMID:11229764] [10.1016/s0960-894x(00)00714-9]

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