1-((2R,3R,4S,5S)-5-((S)-1-((2R,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yloxy)prop-2-ynyl)-3,4-dihydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

ID: ALA4556639

Chembl Id: CHEMBL4556639

PubChem CID: 155556933

Max Phase: Preclinical

Molecular Formula: C16H21N3O9

Molecular Weight: 399.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C#C[C@H](O[C@@H]1O[C@H](CN)[C@@H](O)[C@H]1O)[C@H]1O[C@@H](n2ccc(=O)[nH]c2=O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H21N3O9/c1-2-6(26-15-12(24)9(21)7(5-17)27-15)13-10(22)11(23)14(28-13)19-4-3-8(20)18-16(19)25/h1,3-4,6-7,9-15,21-24H,5,17H2,(H,18,20,25)/t6-,7+,9+,10-,11+,12+,13+,14+,15+/m0/s1

Standard InChI Key:  ZMPJDHGJNDQVLQ-LNBGRKRMSA-N

Alternative Forms

1. Parent:

   

   ALA4556639

   ---

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: 399.36

Molecular Weight (Monoisotopic): 399.1278

AlogP: -4.42

#Rotatable Bonds: 5

Polar Surface Area: 189.49

Molecular Species: BASE

HBA: 11

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.70

CX Basic pKa: 8.75

CX LogP: -3.66

CX LogD: -4.78

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.26

Np Likeness Score: 1.42

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. Kusaka S, Yamamoto K, Shinohara M, Minato Y, Ichikawa S..  (2022)  Design, synthesis and conformation-activity relationship analysis of LNA/BNA-type 5'-O-aminoribosyluridine as MraY inhibitors.,  65  [PMID:35500521] [10.1016/j.bmc.2022.116744]

3. Okamoto K, Ishikawa A, Okawa R, Yamamoto K, Sato T, Yokota SI, Chiba K, Ichikawa S..  (2021)  Design, synthesis and biological evaluation of simplified analogues of MraY inhibitory natural product with rigid scaffold.,  55  [PMID:35016115] [10.1016/j.bmc.2021.116556]

Source

Source(1):

• Scientific Literature