5-Isopropyl-4-[4-(methylsulfanyl)benzyl]-1H-pyrazol-3-yl beta-D-glucopyranoside

ID: ALA4795938

PubChem CID: 57802443

Max Phase: Preclinical

Molecular Formula: C20H28N2O6S

Molecular Weight: 424.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C(C)C)cc1

Standard InChI:  InChI=1S/C20H28N2O6S/c1-10(2)15-13(8-11-4-6-12(29-3)7-5-11)19(22-21-15)28-20-18(26)17(25)16(24)14(9-23)27-20/h4-7,10,14,16-18,20,23-26H,8-9H2,1-3H3,(H,21,22)/t14-,16-,17+,18-,20+/m1/s1

Standard InChI Key:  CMIQVSDCEJLDOR-NWDGLCLDSA-N

Molfile:  

 
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   41.4479   -2.4233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   43.0271   -5.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8087   -5.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4224   -5.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2469   -4.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9778   -6.6688    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   44.7547   -6.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4795938

   (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[4-[(4-methylsulfanylphenyl)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: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 424.52

Molecular Weight (Monoisotopic): 424.1668

AlogP: 1.02

#Rotatable Bonds: 7

Polar Surface Area: 128.06

Molecular Species: NEUTRAL

HBA: 8

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: 2.11

CX LogD: 2.11

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: 0.65

References

1. Shimizu K,Fujikura H,Fushimi N,Nishimura T,Tatani K,Katsuno K,Fujimori Y,Watanabe S,Hiratochi M,Nakabayashi T,Kamada N,Arakawa K,Hikawa H,Azumaya I,Isaji M.  (2021)  Discovery of remogliflozin etabonate: A potent and highly selective SGLT2 inhibitor.,  34  [PMID:33581390] [10.1016/j.bmc.2021.116033]

Source

Source(1):

• Scientific Literature