4-(4-Hydroxy-2-methylphenylmethyl)-5-isopropyl-1Hpyrazol-3-ylbeta-D-glucopyranoside

ID: ALA2159101

Chembl Id: CHEMBL2159101

PubChem CID: 10431578

Max Phase: Preclinical

Molecular Formula: C20H28N2O7

Molecular Weight: 408.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(O)ccc1Cc1c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)n[nH]c1C(C)C

Standard InChI:  InChI=1S/C20H28N2O7/c1-9(2)15-13(7-11-4-5-12(24)6-10(11)3)19(22-21-15)29-20-18(27)17(26)16(25)14(8-23)28-20/h4-6,9,14,16-18,20,23-27H,7-8H2,1-3H3,(H,21,22)/t14-,16-,17+,18-,20+/m1/s1

Standard InChI Key:  WVGZFGBLAOTZSN-NWDGLCLDSA-N

Alternative Forms

1. Parent:

   

   ALA2159101

   (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[4-[(4-hydroxy-2-methylphenyl)methyl]-5-propan-2-yl-1H-pyrazol-3-yl]oxy]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: 408.45

Molecular Weight (Monoisotopic): 408.1897

AlogP: 0.32

#Rotatable Bonds: 6

Polar Surface Area: 148.29

Molecular Species: NEUTRAL

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.14

CX Basic pKa: 1.59

CX LogP: 1.69

CX LogD: 1.69

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.40

Np Likeness Score: 1.07

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