4-Benzyl-5-isopropyl-1H-pyrazol-3-ylbeta-D-glucopyranoside

ID: ALA2160193

Chembl Id: CHEMBL2160193

PubChem CID: 71455055

Max Phase: Preclinical

Molecular Formula: C19H26N2O6

Molecular Weight: 378.43

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)c1Cc1ccccc1

Standard InChI:  InChI=1S/C19H26N2O6/c1-10(2)14-12(8-11-6-4-3-5-7-11)18(21-20-14)27-19-17(25)16(24)15(23)13(9-22)26-19/h3-7,10,13,15-17,19,22-25H,8-9H2,1-2H3,(H,20,21)/t13-,15-,16+,17-,19+/m1/s1

Standard InChI Key:  KOUKLJGYBYZYJQ-YRHQEJDOSA-N

Alternative Forms

1. Parent:

   

   ALA2160193

   (2S,3R,4S,5S,6R)-2-[(4-benzyl-5-propan-2-yl-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: Small molecule

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: 0.30

#Rotatable Bonds: 6

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: 1.59

CX LogP: 1.48

CX LogD: 1.48

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: 0.99

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]

2. Fushimi N, Teranishi H, Shimizu K, Yonekubo S, Ohno K, Miyagi T, Itoh F, Shibazaki T, Tomae M, Ishikawa-Takemura Y, Nakabayashi T, Kamada N, Yamauchi Y, Kobayashi S, Isaji M..  (2013)  Design, synthesis, and structure-activity relationships of a series of 4-benzyl-5-isopropyl-1H-pyrazol-3-yl β-D-glycopyranosides substituted with novel hydrophilic groups as highly potent inhibitors of sodium glucose co-transporter 1 (SGLT1).,  21  (3): [PMID:23273606] [10.1016/j.bmc.2012.11.041]

Source

Source(1):

• Scientific Literature