C0088485

ID: ALA4537408

Cas Number: 1808797-88-7

PubChem CID: 77528802

Max Phase: Preclinical

Molecular Formula: C24H28N6O3

Molecular Weight: 448.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1ccc2ncc(=O)n3c2n1CC3CN1CCC(NCc2cc3c(cn2)OCCC3)CC1

Standard InChI:  InChI=1S/C24H28N6O3/c31-22-4-3-20-24-29(22)15-19(30(24)23(32)13-27-20)14-28-7-5-17(6-8-28)25-11-18-10-16-2-1-9-33-21(16)12-26-18/h3-4,10,12-13,17,19,25H,1-2,5-9,11,14-15H2

Standard InChI Key:  PZFAZQUREQIODZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 38  0  0  0  0  0  0  0  0999 V2000
   -3.5750    0.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5371    0.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5371   -1.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2594   -1.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2594    0.9674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674    2.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8944    2.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8575    3.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492    4.9837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3141    6.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8020    7.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    7.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6400    6.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1279    5.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904    9.2130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6686    9.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1839   10.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6711   11.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1837   12.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6582   12.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1707   14.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2088   15.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7344   15.1130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2218   13.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7473   13.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   12.0289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2777    0.9674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553    0.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5932    0.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -1.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2777   -1.9530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  3
  6  7  1  0
  7  2  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 11  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 21  2  0
 26 27  1  0
 27 28  2  0
 28 19  1  0
  9 29  1  0
 29  6  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  3
 33  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4537408

   GSK 2140944;GSK2140944;Gepotidacin

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: 448.53

Molecular Weight (Monoisotopic): 448.2223

AlogP: 1.09

#Rotatable Bonds: 5

Polar Surface Area: 94.28

Molecular Species: BASE

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.62

CX LogP: 0.16

CX LogD: -1.09

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.62

Np Likeness Score: -0.89

References

1. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Pandemic Response Box,  [10.6019/CHEMBL4513161]

2. Lu Y, Mann CA, Nolan S, Collins JA, Parker E, Papa J, Vibhute S, Jahanbakhsh S, Thwaites M, Hufnagel D, Hazbón MH, Moreno J, Stedman TT, Wittum T, Wozniak DJ, Osheroff N, Yalowich JC, Mitton-Fry MJ..  (2022)  1,3-Dioxane-Linked Novel Bacterial Topoisomerase Inhibitors: Expanding Structural Diversity and the Antibacterial Spectrum.,  13  (6.0): [PMID:35707162] [10.1021/acsmedchemlett.2c00111]

Source

Source(2):

• Scientific Literature
• CO-ADD antimicrobial screening data