4-Benzyl-5-methyl-1H-pyrazol-3-yl beta-D-glucopyranoside

ID: ALA4793115

PubChem CID: 9841314

Max Phase: Preclinical

Molecular Formula: C17H22N2O6

Molecular Weight: 350.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccccc1

Standard InChI:  InChI=1S/C17H22N2O6/c1-9-11(7-10-5-3-2-4-6-10)16(19-18-9)25-17-15(23)14(22)13(21)12(8-20)24-17/h2-6,12-15,17,20-23H,7-8H2,1H3,(H,18,19)/t12-,13-,14+,15-,17+/m1/s1

Standard InChI Key:  OFVXIEBOPMVNOI-GAGVYUBLSA-N

Molfile:  

 
     RDKit          2D

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    3.4834  -15.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1928  -16.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9022  -15.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9022  -15.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1928  -14.7383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6152  -14.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1928  -17.2023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7704  -14.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7680  -13.9232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7721  -16.3861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6134  -16.3861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6176  -13.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2825  -13.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0281  -12.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2067  -12.6588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9521  -13.4394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0634  -13.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6715  -13.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4512  -13.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0632  -12.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8947  -12.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1090  -11.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5004  -12.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5093  -12.0007    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
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 14 15  2  0
 15 16  1  0
 16 17  1  0
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 14 18  1  0
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 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
M  END

Alternative Forms

1. Parent:

   

   ALA4793115

   (2S,3R,4S,5S,6R)-2-[(4-benzyl-5-methyl-1H-pyrazol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

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: 350.37

Molecular Weight (Monoisotopic): 350.1478

AlogP: -0.51

#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: 0.59

CX LogD: 0.59

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.49

Np Likeness Score: 0.82

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