3-(3,4-dichlorophenyl)-N-((3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3-yl)acrylamide

ID: ALA3805806

PubChem CID: 67974101

Max Phase: Preclinical

Molecular Formula: C16H19Cl2NO6

Molecular Weight: 392.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1NC(=O)/C=C/c1ccc(Cl)c(Cl)c1

Standard InChI:  InChI=1S/C16H19Cl2NO6/c1-24-16-13(15(23)14(22)11(7-20)25-16)19-12(21)5-3-8-2-4-9(17)10(18)6-8/h2-6,11,13-16,20,22-23H,7H2,1H3,(H,19,21)/b5-3+/t11-,13-,14-,15-,16?/m1/s1

Standard InChI Key:  KYEAJBCDOXSFNK-OFRTXUDVSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    2.6003   -1.4977    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
   -1.3070   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078   -5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109   -7.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9099   -8.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9099   -9.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109  -10.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3119   -9.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118   -8.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2727  -10.3497    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109  -11.6997    0.0000 Cl  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
   -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
    3.6387   -0.8963    0.0000 C   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  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 16 18  1  0
 15 19  1  0
  9 20  2  0
  6 21  1  1
  5 22  1  6
  4 23  1  1
 24 23  1  0
  1 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3805806

   (E)-3-(3,4-dichlorophenyl)-N-[(3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]prop-2-enamide

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: 392.24

Molecular Weight (Monoisotopic): 391.0589

AlogP: 0.58

#Rotatable Bonds: 5

Polar Surface Area: 108.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: ┄

CX LogP: 0.99

CX LogD: 0.99

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.55

Np Likeness Score: 0.82

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