4-(2-Benzyloxyphenylmethyl)-5-trifluoromethyl-1Hpyrazol-3-ylbeta-D-glucopyranoside

ID: ALA2159094

Chembl Id: CHEMBL2159094

PubChem CID: 10301121

Max Phase: Preclinical

Molecular Formula: C24H25F3N2O7

Molecular Weight: 510.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccccc2OCc2ccccc2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C24H25F3N2O7/c25-24(26,27)21-15(10-14-8-4-5-9-16(14)34-12-13-6-2-1-3-7-13)22(29-28-21)36-23-20(33)19(32)18(31)17(11-30)35-23/h1-9,17-20,23,30-33H,10-12H2,(H,28,29)/t17-,18-,19+,20-,23+/m1/s1

Standard InChI Key:  VRWBPJPUNCXWHA-MZSWFSNMSA-N

Alternative Forms

1. Parent:

   

   ALA2159094

   4-(2-benzyloxybenzyl)-3-(beta-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole

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: 510.47

Molecular Weight (Monoisotopic): 510.1614

AlogP: 1.78

#Rotatable Bonds: 8

Polar Surface Area: 137.29

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.13

CX Basic pKa: 0.76

CX LogP: 2.76

CX LogD: 2.76

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.31

Np Likeness Score: 0.40

References

1. Fushimi N, Fujikura H, Shiohara H, Teranishi H, Shimizu K, Yonekubo S, Ohno K, Miyagi T, Itoh F, Shibazaki T, Tomae M, Ishikawa-Takemura Y, Nakabayashi T, Kamada N, Ozawa T, Kobayashi S, Isaji M..  (2012)  Structure-activity relationship studies of 4-benzyl-1H-pyrazol-3-yl β-d-glucopyranoside derivatives as potent and selective sodium glucose co-transporter 1 (SGLT1) inhibitors with therapeutic activity on postprandial hyperglycemia.,  20  (22): [PMID:23062824] [10.1016/j.bmc.2012.09.037]

Source

Source(1):

• Scientific Literature