3,5-dinitro-N-((3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzamide

ID: ALA3805765

PubChem CID: 88537798

Max Phase: Preclinical

Molecular Formula: C13H15N3O10

Molecular Weight: 373.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C13H15N3O10/c17-4-8-10(18)11(19)9(13(21)26-8)14-12(20)5-1-6(15(22)23)3-7(2-5)16(24)25/h1-3,8-11,13,17-19,21H,4H2,(H,14,20)/t8-,9-,10-,11-,13?/m1/s1

Standard InChI Key:  GNVPUHGUOBDPSL-FGDGVPSKSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421   -3.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6060   -6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6060   -7.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -8.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080   -7.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0079   -6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2933   -8.2481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2954   -9.4481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3317   -7.6467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043   -8.2534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9445   -7.6551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9026   -9.4533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432    3.5994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  7  6  1  0
  2  7  1  0
  7  8  1  6
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 13 20  1  0
 20 21  1  0
 20 22  2  0
  6 23  1  1
  5 24  1  6
  4 25  1  1
 26 25  1  0
M  CHG  4  17   1  18  -1  20   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3805765

   3,5-dinitro-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]benzamide

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: 373.27

Molecular Weight (Monoisotopic): 373.0757

AlogP: -1.97

#Rotatable Bonds: 5

Polar Surface Area: 205.53

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.62

CX Basic pKa: ┄

CX LogP: -1.49

CX LogD: -1.49

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.28

Np Likeness Score: 0.41

References

1. Lin H, Zeng J, Xie R, Schulz MJ, Tedesco R, Qu J, Erhard KF, Mack JF, Raha K, Rendina AR, Szewczuk LM, Kratz PM, Jurewicz AJ, Cecconie T, Martens S, McDevitt PJ, Martin JD, Chen SB, Jiang Y, Nickels L, Schwartz BJ, Smallwood A, Zhao B, Campobasso N, Qian Y, Briand J, Rominger CM, Oleykowski C, Hardwicke MA, Luengo JI..  (2016)  Discovery of a Novel 2,6-Disubstituted Glucosamine Series of Potent and Selective Hexokinase 2 Inhibitors.,  7  (3): [PMID:26985301] [10.1021/acsmedchemlett.5b00214]

Source

Source(1):

• Scientific Literature