N-((2R,3R,4R,5S,6R)-2-(cyclohexylthio)-4,5-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-3-yl)-2-(3-fluorophenyl)-5,6-dihydro-4H-1,3-oxazine-4-carboxamide

ID: ALA239416

PubChem CID: 44435068

Max Phase: Preclinical

Molecular Formula: C23H31FN2O6S

Molecular Weight: 482.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1SC1CCCCC1)C1CCOC(c2cccc(F)c2)=N1

Standard InChI:  InChI=1S/C23H31FN2O6S/c24-14-6-4-5-13(11-14)22-25-16(9-10-31-22)21(30)26-18-20(29)19(28)17(12-27)32-23(18)33-15-7-2-1-3-8-15/h4-6,11,15-20,23,27-29H,1-3,7-10,12H2,(H,26,30)/t16?,17-,18-,19-,20-,23-/m0/s1

Standard InChI Key:  ZPFSWDAMAHIEOS-NDRYKJPLSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA239416

   N-((2R,3R,4R,5S,6R)-2-(cyclohexylthio)-4,5-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-3-yl)-2-(3-fluorophenyl)-5,6-dihydro-4H-1,3-oxazine-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: 482.57

Molecular Weight (Monoisotopic): 482.1887

AlogP: 1.35

#Rotatable Bonds: 6

Polar Surface Area: 120.61

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.12

CX Basic pKa: 1.34

CX LogP: 1.65

CX LogD: 1.65

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.48

Np Likeness Score: 0.10

References

1. Metaferia BB, Fetterolf BJ, Shazad-Ul-Hussan S, Moravec M, Smith JA, Ray S, Gutierrez-Lugo MT, Bewley CA..  (2007)  Synthesis of natural product-inspired inhibitors of Mycobacterium tuberculosis mycothiol-associated enzymes: the first inhibitors of GlcNAc-Ins deacetylase.,  50  (25): [PMID:18020307] [10.1021/jm070669h]

Source

Source(1):

• Scientific Literature