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

ID: ALA4791676

PubChem CID: 162670431

Max Phase: Preclinical

Molecular Formula: C19H26N2O6

Molecular Weight: 378.43

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)c1CCCc1ccccc1

Standard InChI:  InChI=1S/C19H26N2O6/c1-11-13(9-5-8-12-6-3-2-4-7-12)18(21-20-11)27-19-17(25)16(24)15(23)14(10-22)26-19/h2-4,6-7,14-17,19,22-25H,5,8-10H2,1H3,(H,20,21)/t14-,15-,16+,17-,19+/m1/s1

Standard InChI Key:  MIJVOGQOZMHISC-ILYVXUQDSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   27.2438  -15.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2438  -16.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9532  -16.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6626  -16.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6626  -15.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9532  -14.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3757  -14.8147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9532  -17.2725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5349  -14.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5325  -13.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5367  -16.4563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3739  -16.4563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3781  -13.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0429  -13.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7927  -12.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9713  -12.7290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7125  -13.5096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8239  -13.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4361  -13.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2129  -13.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8252  -12.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6033  -13.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2153  -12.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0468  -11.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2611  -11.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6525  -12.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2755  -12.0721    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  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 15 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4791676

   ---

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: 378.43

Molecular Weight (Monoisotopic): 378.1791

AlogP: 0.07

#Rotatable Bonds: 7

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: 1.72

CX LogP: 1.48

CX LogD: 1.48

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.46

Np Likeness Score: 0.81

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