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)isonicotinamide

ID: ALA393367

PubChem CID: 16215347

Max Phase: Preclinical

Molecular Formula: C19H28N2O10

Molecular Weight: 444.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(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)c1ccncc1

Standard InChI:  InChI=1S/C19H28N2O10/c22-7-12-15(26)16(27)13(21-17(28)9-1-3-20-4-2-9)18(31-12)30-11-6-19(29,8-23)5-10(24)14(11)25/h1-4,10-16,18,22-27,29H,5-8H2,(H,21,28)/t10-,11-,12-,13-,14-,15-,16-,18+,19+/m1/s1

Standard InChI Key:  SYUAXOTYUROTGH-DVPZWMNYSA-N

Molfile:  

     RDKit          2D

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   17.5492    0.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2637    0.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.6710    0.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6937   -1.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9812   -1.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9862   -2.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7023   -2.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4151   -2.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4118   -1.4598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1316   -2.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1357   -3.5214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.2736   -2.7100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6975    1.9026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2625    2.7329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5401   -0.1604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8336    1.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8313    1.8968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2647   -1.0641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5524   -1.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8358   -1.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5566   -2.3052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4001   -0.6371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8357   -0.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1200    0.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4066   -0.2561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4135   -1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1299   -1.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 16  1  1
  8  9  1  0
 10 17  1  6
  4  7  1  6
  1  6  1  0
  5 18  1  1
  2  3  1  0
  6 19  1  1
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  2 20  1  0
  4  5  1  0
  2 21  1  6
  5  6  1  0
 21 22  1  0
  8 13  1  0
  9 23  1  1
  9 10  1  0
 23 24  1  0
 10 11  1  0
 24 25  1  0
 11 12  1  0
 24 26  2  0
 12 13  1  0
  8 27  1  6
 25 28  2  0
 12 14  1  6
 28 29  1  0
  1  2  1  0
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 14 15  1  0
 30 31  1  0
  8  7  1  0
 31 32  2  0
 32 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA393367

   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]pyridine-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: 444.44

Molecular Weight (Monoisotopic): 444.1744

AlogP: -3.76

#Rotatable Bonds: 6

Polar Surface Area: 202.06

Molecular Species: NEUTRAL

HBA: 11

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.65

CX Basic pKa: 3.39

CX LogP: -4.59

CX LogD: -4.59

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.21

Np Likeness Score: 1.20

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