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

ID: ALA2323695

Chembl Id: CHEMBL2323695

PubChem CID: 10009210

Max Phase: Preclinical

Molecular Formula: C32H49N5O8

Molecular Weight: 631.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(CCCC(=O)NC(C)(C)C(=O)N2CCNCC2)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/C32H49N5O8/c1-18(2)25-22(29(36-35-25)45-30-28(42)27(41)26(40)23(17-38)44-30)16-21-10-9-20(15-19(21)3)7-6-8-24(39)34-32(4,5)31(43)37-13-11-33-12-14-37/h9-10,15,18,23,26-28,30,33,38,40-42H,6-8,11-14,16-17H2,1-5H3,(H,34,39)(H,35,36)/t23-,26-,27+,28-,30+/m1/s1

Standard InChI Key:  HZIRWWOSGYBPSU-RHBSMATHSA-N

Alternative Forms

1. Parent:

   

   ALA2323695

   N-(2-methyl-1-oxo-1-piperazin-1-ylpropan-2-yl)-4-[3-methyl-4-[[5-propan-2-yl-3-[(2S,3R,4S,5S,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: 631.77

Molecular Weight (Monoisotopic): 631.3581

AlogP: 0.26

#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: 12.11

CX Basic pKa: 7.82

CX LogP: 1.52

CX LogD: 0.96

Aromatic Rings: 2

Heavy Atoms: 45

QED Weighted: 0.17

Np Likeness Score: 0.06

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