1-((2R,3R,4S,5S)-5-((S)-1-((2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yloxy)-2-(4-(5-hydroxypentyl)-1H-1,2,3-triazol-1-yl)ethyl)-3,4-dihydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

ID: ALA4470560

Chembl Id: CHEMBL4470560

PubChem CID: 155534756

Max Phase: Preclinical

Molecular Formula: C22H34N6O10

Molecular Weight: 542.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC[C@H]1O[C@@H](O[C@@H](Cn2cc(CCCCCO)nn2)[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/C22H34N6O10/c23-8-12-15(31)18(34)21(36-12)37-13(10-27-9-11(25-26-27)4-2-1-3-7-29)19-16(32)17(33)20(38-19)28-6-5-14(30)24-22(28)35/h5-6,9,12-13,15-21,29,31-34H,1-4,7-8,10,23H2,(H,24,30,35)/t12-,13+,15-,16+,17-,18-,19-,20-,21+/m1/s1

Standard InChI Key:  XSNYCLMECAHSGZ-KNBHMFLWSA-N

Alternative Forms

1. Parent:

   

   ALA4470560

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 542.55

Molecular Weight (Monoisotopic): 542.2336

AlogP: -4.06

#Rotatable Bonds: 12

Polar Surface Area: 240.43

Molecular Species: BASE

HBA: 15

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.70

CX Basic pKa: 8.75

CX LogP: -3.31

CX LogD: -4.43

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.13

Np Likeness Score: 0.75

References

1. 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]

2. Bugg TD, Rodolis MT, Mihalyi A, Jamshidi S..  (2016)  Inhibition of phospho-MurNAc-pentapeptide translocase (MraY) by nucleoside natural product antibiotics, bacteriophage ϕX174 lysis protein E, and cationic antibacterial peptides.,  24  (24): [PMID:27021004] [10.1016/j.bmc.2016.03.018]

Source

Source(1):

• Scientific Literature