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)cyclopropanecarboxamide

ID: ALA393366

PubChem CID: 44430213

Max Phase: Preclinical

Molecular Formula: C17H29NO10

Molecular Weight: 407.42

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)C1CC1

Standard InChI:  InChI=1S/C17H29NO10/c19-5-10-13(23)14(24)11(18-15(25)7-1-2-7)16(28-10)27-9-4-17(26,6-20)3-8(21)12(9)22/h7-14,16,19-24,26H,1-6H2,(H,18,25)/t8-,9-,10-,11-,12-,13-,14-,16+,17+/m1/s1

Standard InChI Key:  LKSUQSKUCGOESJ-FGIQJREJSA-N

Molfile:  

     RDKit          2D

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   10.8206    0.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5350   -0.3012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2540    0.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2540    0.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5350    1.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9424   -0.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9650   -1.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2526   -2.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2574   -2.8441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9735   -3.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6864   -2.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6831   -2.0097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4028   -3.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4068   -4.0712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9773   -4.0795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5449   -3.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9689    1.3526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5338    2.1828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8116   -0.7103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1050    0.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1026    1.3468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5360   -1.6141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8238   -2.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1072   -1.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8279   -2.8551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6714   -1.1871    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6887   -0.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2799   -1.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  8  9  1  0
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  4  7  1  6
  1  6  1  0
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  2  3  1  0
  6 19  1  1
  3  4  1  0
  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
 28 25  1  0
 29 28  1  0
 25 29  1  0
 12 14  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA393366

   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]cyclopropanecarboxamide

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: 407.42

Molecular Weight (Monoisotopic): 407.1791

AlogP: -4.06

#Rotatable Bonds: 6

Polar Surface Area: 189.17

Molecular Species: NEUTRAL

HBA: 10

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.11

CX Basic pKa: ┄

CX LogP: -4.45

CX LogD: -4.45

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.22

Np Likeness Score: 1.44

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