(1S)-1,5-Anhydro-1-[5-(4-ethylbenzyl)-2-methoxy-4-methylphenyl]-1-thio-D-glucitol

ID: ALA1093777

PubChem CID: 46205143

Max Phase: Preclinical

Molecular Formula: C23H30O5S

Molecular Weight: 418.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(Cc2cc([C@@H]3S[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(OC)cc2C)cc1

Standard InChI:  InChI=1S/C23H30O5S/c1-4-14-5-7-15(8-6-14)10-16-11-17(18(28-3)9-13(16)2)23-22(27)21(26)20(25)19(12-24)29-23/h5-9,11,19-27H,4,10,12H2,1-3H3/t19-,20-,21+,22-,23+/m1/s1

Standard InChI Key:  WLDMZNZGTUEQJN-ZQGJOIPISA-N

Molfile:  

     RDKit          2D

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   11.8547  -11.9724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8538   -9.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5668   -9.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1380   -9.0836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1385   -8.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0016   -9.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA1093777

   (1S)-1,5-Anhydro-1-[5-(4-ethylbenzyl)-2-methoxy-4-methylphenyl]-1-thio-D-glucitol

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: 418.56

Molecular Weight (Monoisotopic): 418.1814

AlogP: 2.39

#Rotatable Bonds: 6

Polar Surface Area: 90.15

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.85

CX Basic pKa: ┄

CX LogP: 3.04

CX LogD: 3.04

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: 0.35

References

1. Kakinuma H, Oi T, Hashimoto-Tsuchiya Y, Arai M, Kawakita Y, Fukasawa Y, Iida I, Hagima N, Takeuchi H, Chino Y, Asami J, Okumura-Kitajima L, Io F, Yamamoto D, Miyata N, Takahashi T, Uchida S, Yamamoto K..  (2010)  (1S)-1,5-anhydro-1-[5-(4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio-D-glucitol (TS-071) is a potent, selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for type 2 diabetes treatment.,  53  (8): [PMID:20302302] [10.1021/jm901893x]

Source

Source(1):

• Scientific Literature