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

ID: ALA2159102

Chembl Id: CHEMBL2159102

PubChem CID: 71453232

Max Phase: Preclinical

Molecular Formula: C21H30N2O6

Molecular Weight: 406.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C(C)C)c(C)c1

Standard InChI:  InChI=1S/C21H30N2O6/c1-10(2)16-14(8-13-6-5-11(3)7-12(13)4)20(23-22-16)29-21-19(27)18(26)17(25)15(9-24)28-21/h5-7,10,15,17-19,21,24-27H,8-9H2,1-4H3,(H,22,23)/t15-,17-,18+,19-,21+/m1/s1

Standard InChI Key:  JDMDCYIKMZGDNP-UVPIGPOJSA-N

Alternative Forms

1. Parent:

   

   ALA2159102

   (2S,3R,4S,5S,6R)-2-[[4-[(2,4-dimethylphenyl)methyl]-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: 406.48

Molecular Weight (Monoisotopic): 406.2104

AlogP: 0.92

#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: 2.51

CX LogD: 2.51

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: 0.68

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