4-(2-Benzyloxyphenylmethyl)-5-isopropyl-1H-pyrazol-3-ylbeta-D-glucopyranoside

ID: ALA2159091

Chembl Id: CHEMBL2159091

PubChem CID: 9956975

Max Phase: Preclinical

Molecular Formula: C26H32N2O7

Molecular Weight: 484.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccccc1OCc1ccccc1

Standard InChI:  InChI=1S/C26H32N2O7/c1-15(2)21-18(12-17-10-6-7-11-19(17)33-14-16-8-4-3-5-9-16)25(28-27-21)35-26-24(32)23(31)22(30)20(13-29)34-26/h3-11,15,20,22-24,26,29-32H,12-14H2,1-2H3,(H,27,28)/t20-,22-,23+,24-,26+/m1/s1

Standard InChI Key:  VKJYZOHVADWABC-TXKDOCKMSA-N

Alternative Forms

1. Parent:

   

   ALA2159091

   4-(2-Benzyloxybenzyl)-3-(beta-D-glucopyranosyloxy)-5-isopropyl-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: 484.55

Molecular Weight (Monoisotopic): 484.2210

AlogP: 1.88

#Rotatable Bonds: 9

Polar Surface Area: 137.29

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: 1.59

CX LogP: 3.05

CX LogD: 3.05

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.31

Np Likeness Score: 0.54

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