[2-(4-Isopropylbenzyl)phenyl]-5a-carba-beta-D-glucopyranoside

ID: ALA1819488

Chembl Id: CHEMBL1819488

PubChem CID: 11718002

Max Phase: Preclinical

Molecular Formula: C23H30O5

Molecular Weight: 386.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc(Cc2ccccc2O[C@@H]2C[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C23H30O5/c1-14(2)16-9-7-15(8-10-16)11-17-5-3-4-6-19(17)28-20-12-18(13-24)21(25)23(27)22(20)26/h3-10,14,18,20-27H,11-13H2,1-2H3/t18-,20-,21-,22+,23+/m1/s1

Standard InChI Key:  YPTBUFXDOWDOME-FXILAVBZSA-N

Alternative Forms

1. Parent:

   

   ALA1819488

   (1R,2S,3R,4R,6R)-4-(hydroxymethyl)-6-[2-[(4-propan-2-ylphenyl)methyl]phenoxy]cyclohexane-1,2,3-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: 386.49

Molecular Weight (Monoisotopic): 386.2093

AlogP: 2.24

#Rotatable Bonds: 6

Polar Surface Area: 90.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.79

CX Basic pKa: ┄

CX LogP: 2.70

CX LogD: 2.70

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: 1.03

References

1. Ohtake Y, Sato T, Matsuoka H, Nishimoto M, Taka N, Takano K, Yamamoto K, Ohmori M, Higuchi T, Murakata M, Kobayashi T, Morikawa K, Shimma N, Suzuki M, Hagita H, Ozawa K, Yamaguchi K, Kato M, Ikeda S..  (2011)  5a-Carba-β-D-glucopyranose derivatives as novel sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.,  19  (18): [PMID:21873071] [10.1016/j.bmc.2011.08.005]

Source

Source(1):

• Scientific Literature