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

ID: ALA391010

PubChem CID: 44435066

Max Phase: Preclinical

Molecular Formula: C22H29FN2O6S

Molecular Weight: 468.55

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)C1COC(c2cccc(F)c2)=N1

Standard InChI:  InChI=1S/C22H29FN2O6S/c23-13-6-4-5-12(9-13)21-24-15(11-30-21)20(29)25-17-19(28)18(27)16(10-26)31-22(17)32-14-7-2-1-3-8-14/h4-6,9,14-19,22,26-28H,1-3,7-8,10-11H2,(H,25,29)/t15?,16-,17-,18-,19-,22-/m0/s1

Standard InChI Key:  RNGOHNDBGLSAEQ-CJJUXZNXSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  1  0  0  0  0  0999 V2000
   14.0153  -19.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0153  -20.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7297  -20.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4488  -20.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4488  -19.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7297  -18.7817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1636  -18.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1644  -17.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1626  -20.4418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7285  -21.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3008  -20.4408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2998  -18.7880    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.2979  -17.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0166  -17.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0166  -16.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3031  -16.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5878  -16.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5861  -17.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3008  -21.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5868  -21.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0153  -21.6783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8058  -21.4158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3106  -22.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7851  -22.7505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5735  -22.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4858  -22.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0877  -21.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2636  -21.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8392  -22.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2450  -22.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0678  -22.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8240  -23.4713    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  4  9  1  6
 11 19  1  0
  2  3  1  0
 20 19  1  0
  3 10  1  1
 19 21  2  0
 20 22  1  0
  3  4  1  0
  2 11  1  6
  4  5  1  0
  1 12  1  6
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 20  1  0
  5  6  1  0
 23 26  1  0
 12 13  1  0
 26 27  2  0
 13 14  1  0
 27 28  1  0
 28 29  2  0
  5  7  1  1
 29 30  1  0
  1  2  1  0
 30 31  2  0
 31 26  1  0
  7  8  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA391010

   N-((2R,3R,4R,5S,6R)-2-(cyclohexylthio)-4,5-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-3-yl)-2-(3-fluorophenyl)-4,5-dihydrooxazole-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: 468.55

Molecular Weight (Monoisotopic): 468.1730

AlogP: 0.96

#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: 12.03

CX Basic pKa: 0.53

CX LogP: 1.59

CX LogD: 1.59

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: 0.26

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