(1S)-1,5-Anhydro-1-[2-methoxy-4-methyl-5-[4-(propan-2-yl)-benzyl]phenyl]-1-thio-D-glucitol

ID: ALA1093778

PubChem CID: 46205461

Max Phase: Preclinical

Molecular Formula: C24H32O5S

Molecular Weight: 432.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C)c(Cc2ccc(C(C)C)cc2)cc1[C@@H]1S[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C24H32O5S/c1-13(2)16-7-5-15(6-8-16)10-17-11-18(19(29-4)9-14(17)3)24-23(28)22(27)21(26)20(12-25)30-24/h5-9,11,13,20-28H,10,12H2,1-4H3/t20-,21-,22+,23-,24+/m1/s1

Standard InChI Key:  HTWHMNISZAPAQO-SJSRKZJXSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1093778

   (2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-[2-methoxy-4-methyl-5-[(4-propan-2-ylphenyl)methyl]phenyl]thiane-3,4,5-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: 432.58

Molecular Weight (Monoisotopic): 432.1970

AlogP: 2.95

#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: 3.32

CX LogD: 3.32

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.56

Np Likeness Score: 0.37

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