3-(2-chloro-6-fluorophenyl)-N-((2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-((1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyloxy)-tetrahydro-2H-pyran-3-yl)-5-methylisoxazole-4-carboxamide

ID: ALA393566

PubChem CID: 44430224

Max Phase: Preclinical

Molecular Formula: C24H30ClFN2O11

Molecular Weight: 576.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1onc(-c2c(F)cccc2Cl)c1C(=O)N[C@H]1[C@@H](O[C@@H]2C[C@](O)(CO)C[C@@H](O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C24H30ClFN2O11/c1-9-15(17(28-39-9)16-10(25)3-2-4-11(16)26)22(35)27-18-21(34)20(33)14(7-29)38-23(18)37-13-6-24(36,8-30)5-12(31)19(13)32/h2-4,12-14,18-21,23,29-34,36H,5-8H2,1H3,(H,27,35)/t12-,13-,14-,18-,19-,20-,21-,23+,24+/m1/s1

Standard InChI Key:  YIHIXBMJRBVOLD-DSEHCLGPSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA393566

   3-(2-chloro-6-fluorophenyl)-N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxyoxan-3-yl]-5-methyl-1,2-oxazole-4-carboxamide

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

Calculated Properties

Molecular Weight: 576.96

Molecular Weight (Monoisotopic): 576.1522

AlogP: -1.40

#Rotatable Bonds: 7

Polar Surface Area: 215.20

Molecular Species: NEUTRAL

HBA: 12

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.63

CX Basic pKa: ┄

CX LogP: -2.03

CX LogD: -2.03

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.19

Np Likeness Score: 0.33

References

1. Metaferia BB, Ray S, Smith JA, Bewley CA..  (2007)  Design and synthesis of substrate-mimic inhibitors of mycothiol-S-conjugate amidase from Mycobacterium tuberculosis.,  17  (2): [PMID:17084627] [10.1016/j.bmcl.2006.10.031]

Source

Source(1):

• Scientific Literature