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

ID: ALA1819491

Chembl Id: CHEMBL1819491

PubChem CID: 10133993

Max Phase: Preclinical

Molecular Formula: C21H26O6

Molecular Weight: 374.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cc2ccccc2O[C@@H]2C[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C21H26O6/c1-26-16-8-6-13(7-9-16)10-14-4-2-3-5-17(14)27-18-11-15(12-22)19(23)21(25)20(18)24/h2-9,15,18-25H,10-12H2,1H3/t15-,18-,19-,20+,21+/m1/s1

Standard InChI Key:  YUCULZXMVCSQQI-WIGAVFHRSA-N

Alternative Forms

1. Parent:

   

   ALA1819491

   (1R,2S,3R,4R,6R)-4-(hydroxymethyl)-6-[2-[(4-methoxyphenyl)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: 374.43

Molecular Weight (Monoisotopic): 374.1729

AlogP: 1.13

#Rotatable Bonds: 6

Polar Surface Area: 99.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.79

CX Basic pKa: ┄

CX LogP: 1.29

CX LogD: 1.29

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: 1.11

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]

2. Ohtake Y, Sato T, Matsuoka H, Kobayashi T, Nishimoto M, Taka N, Takano K, Yamamoto K, Ohmori M, Higuchi T, Murakata M, Morikawa K, Shimma N, Suzuki M, Hagita H, Ozawa K, Yamaguchi K, Kato M, Ikeda S..  (2012)  C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.,  20  (13): [PMID:22652255] [10.1016/j.bmc.2012.04.053]

Source

Source(1):

• Scientific Literature