5-Methyl-4-(3-methylbenzyl)-1H-pyrazol-3-yl beta-D-glucopyranoside

ID: ALA4752053

PubChem CID: 162652619

Max Phase: Preclinical

Molecular Formula: C18H24N2O6

Molecular Weight: 364.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)c1

Standard InChI:  InChI=1S/C18H24N2O6/c1-9-4-3-5-11(6-9)7-12-10(2)19-20-17(12)26-18-16(24)15(23)14(22)13(8-21)25-18/h3-6,13-16,18,21-24H,7-8H2,1-2H3,(H,19,20)/t13-,14-,15+,16-,18+/m1/s1

Standard InChI Key:  UAXACTDVVIZWHB-QFXBJFAPSA-N

Molfile:  

 
     RDKit          2D

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   14.3091  -24.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3091  -25.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0185  -25.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7279  -25.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7279  -24.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0185  -24.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4409  -24.3403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0185  -26.7981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5961  -24.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5937  -23.5190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5979  -25.9819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4392  -25.9819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4433  -23.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1082  -23.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8538  -22.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0325  -22.2546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7778  -23.0352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8891  -23.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4973  -22.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2770  -23.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8889  -22.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7205  -21.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9347  -21.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3261  -21.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3350  -21.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6655  -22.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  1
  3  8  1  1
  1  9  1  1
  9 10  1  0
  2 11  1  6
  4 12  1  6
  7 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 13  2  0
 14 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 15 25  1  0
 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4752053

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 364.40

Molecular Weight (Monoisotopic): 364.1634

AlogP: -0.20

#Rotatable Bonds: 5

Polar Surface Area: 128.06

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: 1.69

CX LogP: 1.11

CX LogD: 1.11

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.50

Np Likeness Score: 0.62

References

1. Shimizu K,Fujikura H,Fushimi N,Nishimura T,Tatani K,Katsuno K,Fujimori Y,Watanabe S,Hiratochi M,Nakabayashi T,Kamada N,Arakawa K,Hikawa H,Azumaya I,Isaji M.  (2021)  Discovery of remogliflozin etabonate: A potent and highly selective SGLT2 inhibitor.,  34  [PMID:33581390] [10.1016/j.bmc.2021.116033]

Source

Source(1):

• Scientific Literature