3-(3,4-dichlorophenyl)-N-((3R,4R,5S,6R)-2,4,5-trihydroxy-6-((4-methylphenylsulfonamido)methyl)tetrahydro-2H-pyran-3-yl)acrylamide

ID: ALA3806250

PubChem CID: 67974063

Max Phase: Preclinical

Molecular Formula: C22H24Cl2N2O7S

Molecular Weight: 531.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)NC[C@H]2OC(O)[C@H](NC(=O)/C=C/c3ccc(Cl)c(Cl)c3)[C@@H](O)[C@@H]2O)cc1

Standard InChI:  InChI=1S/C22H24Cl2N2O7S/c1-12-2-6-14(7-3-12)34(31,32)25-11-17-20(28)21(29)19(22(30)33-17)26-18(27)9-5-13-4-8-15(23)16(24)10-13/h2-10,17,19-22,25,28-30H,11H2,1H3,(H,26,27)/b9-5+/t17-,19-,20-,21-,22?/m1/s1

Standard InChI Key:  QYROCIZAUONYDT-UDOUVNBHSA-N

Molfile:  

     RDKit          2D

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    5.2003   -1.4932    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1622   -2.0952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5549    3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933    3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912    5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4886    5.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8268    5.4110    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -8.8268    8.1110    0.0000 Cl  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
   -2.3383   -1.3500    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
    0.0000   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990   -0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7991   -1.4891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0971   -0.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0949    0.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7948    1.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4969    0.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1333    1.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  2  1  0
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  6  5  1  6
  6  7  1  0
  7  8  1  0
  8  9  1  0
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 10 11  1  1
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 15 16  1  0
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 18 19  2  0
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 20 21  2  0
 21 16  1  0
 20 22  1  0
 19 23  1  0
 10 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  1
 26  6  1  0
  2 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3806250

   (E)-3-(3,4-dichlorophenyl)-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-[[(4-methylphenyl)sulfonylamino]methyl]oxan-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: 531.41

Molecular Weight (Monoisotopic): 530.0681

AlogP: 1.22

#Rotatable Bonds: 7

Polar Surface Area: 145.19

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.37

CX Basic pKa: ┄

CX LogP: 2.18

CX LogD: 2.18

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.34

Np Likeness Score: -0.14

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