[2-(4-Trifluoromethylbenzyl)phenyl]-5a-carba-beta-D-gluco pyranoside

ID: ALA1819496

Chembl Id: CHEMBL1819496

PubChem CID: 11517178

Max Phase: Preclinical

Molecular Formula: C21H23F3O5

Molecular Weight: 412.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1C[C@@H](Oc2ccccc2Cc2ccc(C(F)(F)F)cc2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C21H23F3O5/c22-21(23,24)15-7-5-12(6-8-15)9-13-3-1-2-4-16(13)29-17-10-14(11-25)18(26)20(28)19(17)27/h1-8,14,17-20,25-28H,9-11H2/t14-,17-,18-,19+,20+/m1/s1

Standard InChI Key:  VESYLBNKBDGTSC-SBUWESJJSA-N

Alternative Forms

1. Parent:

   

   ALA1819496

   (1R,2S,3R,4R,6R)-4-(hydroxymethyl)-6-[2-[[4-(trifluoromethyl)phenyl]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: 412.40

Molecular Weight (Monoisotopic): 412.1498

AlogP: 2.14

#Rotatable Bonds: 5

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: 2.33

CX LogD: 2.33

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: 0.73

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