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)-4-nitrobenzamide

ID: ALA232697

PubChem CID: 44430215

Max Phase: Preclinical

Molecular Formula: C20H28N2O12

Molecular Weight: 488.45

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)c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C20H28N2O12/c23-7-13-16(27)17(28)14(21-18(29)9-1-3-10(4-2-9)22(31)32)19(34-13)33-12-6-20(30,8-24)5-11(25)15(12)26/h1-4,11-17,19,23-28,30H,5-8H2,(H,21,29)/t11-,12-,13-,14-,15-,16-,17-,19+,20+/m1/s1

Standard InChI Key:  KNNGPTOEHPPYFL-JHBMTMDISA-N

Molfile:  

     RDKit          2D

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    5.7012   -7.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8395   -8.3602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  4  7  1  6
  1  6  1  0
  5 18  1  1
  2  3  1  0
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  3  4  1  0
  2 20  1  0
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  5  6  1  0
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  9 23  1  1
  9 10  1  0
 23 24  1  0
 10 11  1  0
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  8 27  1  6
 25 28  2  0
 12 14  1  6
 28 29  1  0
  1  2  1  0
 29 30  2  0
 14 15  1  0
 30 31  1  0
  8  7  1  0
 31 32  2  0
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 11 16  1  1
  8  9  1  0
 10 17  1  6
 33 34  2  0
 33 35  1  0
 30 33  1  0
M  CHG  2  33   1  35  -1
M  END

Alternative Forms

1. Parent:

   

   ALA232697

   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]-4-nitrobenzamide

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: 488.45

Molecular Weight (Monoisotopic): 488.1642

AlogP: -3.24

#Rotatable Bonds: 7

Polar Surface Area: 232.31

Molecular Species: NEUTRAL

HBA: 12

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.63

CX Basic pKa: ┄

CX LogP: -3.43

CX LogD: -3.43

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.14

Np Likeness Score: 0.89

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