(S)-1-(5-(((6,7-Dihydro-[1,4]oxathiino[2,3-c]pyridazin-3-yl)methyl)amino)-trans-1,3-dioxan-2-yl)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethan-1-ol

ID: ALA4852949

PubChem CID: 162640929

Max Phase: Preclinical

Molecular Formula: C22H24FN5O5S

Molecular Weight: 489.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2ncc(F)c(C[C@H](O)[C@H]3OC[C@H](NCc4cc5c(nn4)OCCS5)CO3)c2n1

Standard InChI:  InChI=1S/C22H24FN5O5S/c1-30-19-3-2-16-20(26-19)14(15(23)9-25-16)7-17(29)22-32-10-13(11-33-22)24-8-12-6-18-21(28-27-12)31-4-5-34-18/h2-3,6,9,13,17,22,24,29H,4-5,7-8,10-11H2,1H3/t13-,17-,22-/m0/s1

Standard InChI Key:  QUTCIOKBWBLIHI-SRMJIJMDSA-N

Molfile:  

 
     RDKit          2D

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   32.9545  -10.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6614  -11.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3682  -10.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3682  -10.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   37.1779   -6.0722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.8841   -6.4797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.5882   -6.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5882   -5.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8802   -4.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2924   -4.8362    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   39.2946   -6.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4723   -8.1100    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.2467   -9.7569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2467   -8.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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 15 20  1  0
 18 21  1  6
 21 22  1  0
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 23 24  2  0
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 15 33  1  6
  1 34  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4852949

   ---

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: 489.53

Molecular Weight (Monoisotopic): 489.1482

AlogP: 1.49

#Rotatable Bonds: 7

Polar Surface Area: 120.74

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.11

CX Basic pKa: 7.02

CX LogP: 1.46

CX LogD: 1.31

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.50

Np Likeness Score: -0.67

References

1. Lu Y, Vibhute S, Li L, Okumu A, Ratigan SC, Nolan S, Papa JL, Mann CA, English A, Chen A, Seffernick JT, Koci B, Duncan LR, Roth B, Cummings JE, Slayden RA, Lindert S, McElroy CA, Wozniak DJ, Yalowich J, Mitton-Fry MJ..  (2021)  Optimization of TopoIV Potency, ADMET Properties, and hERG Inhibition of 5-Amino-1,3-dioxane-Linked Novel Bacterial Topoisomerase Inhibitors: Identification of a Lead with In Vivo Efficacy against MRSA.,  64  (20.0): [PMID:34614347] [10.1021/acs.jmedchem.1c01250]

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(1):

• Scientific Literature