4-{4-[3-(beta-D-Galactopyranosyloxy)-5-isopropyl-1Hpyrazol-4-ylmethyl]phenyl}-N-[1,1-dimethyl-2-oxo-2-(piperazin-1-yl)ethyl]butanamide

ID: ALA2323694

Chembl Id: CHEMBL2323694

PubChem CID: 11758523

Max Phase: Preclinical

Molecular Formula: C31H47N5O8

Molecular Weight: 617.74

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)c1Cc1ccc(CCCC(=O)NC(C)(C)C(=O)N2CCNCC2)cc1

Standard InChI:  InChI=1S/C31H47N5O8/c1-18(2)24-21(28(35-34-24)44-29-27(41)26(40)25(39)22(17-37)43-29)16-20-10-8-19(9-11-20)6-5-7-23(38)33-31(3,4)30(42)36-14-12-32-13-15-36/h8-11,18,22,25-27,29,32,37,39-41H,5-7,12-17H2,1-4H3,(H,33,38)(H,34,35)/t22-,25+,26+,27-,29+/m1/s1

Standard InChI Key:  XLGGPHXVLBTVEQ-HUSNPGIHSA-N

Alternative Forms

1. Parent:

   

   ALA2323694

   N-(2-methyl-1-oxo-1-piperazin-1-ylpropan-2-yl)-4-[4-[[5-propan-2-yl-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-pyrazol-4-yl]methyl]phenyl]butanamide

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: 617.74

Molecular Weight (Monoisotopic): 617.3425

AlogP: -0.05

#Rotatable Bonds: 12

Polar Surface Area: 189.50

Molecular Species: NEUTRAL

HBA: 10

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.10

CX Basic pKa: 7.82

CX LogP: 1.01

CX LogD: 0.45

Aromatic Rings: 2

Heavy Atoms: 44

QED Weighted: 0.17

Np Likeness Score: 0.15

References

1. 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