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

ID: ALA1090786

PubChem CID: 46205462

Max Phase: Preclinical

Molecular Formula: C22H27ClO5S

Molecular Weight: 438.97

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)cc2Cl)cc1

Standard InChI:  InChI=1S/C22H27ClO5S/c1-3-12-4-6-13(7-5-12)8-14-9-15(17(28-2)10-16(14)23)22-21(27)20(26)19(25)18(11-24)29-22/h4-7,9-10,18-22,24-27H,3,8,11H2,1-2H3/t18-,19-,20+,21-,22+/m1/s1

Standard InChI Key:  ZCUPHXMNGVNWAQ-BDHVOXNPSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
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    8.9557  -17.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6701  -17.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3892  -17.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3892  -16.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6701  -15.8443    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.1041  -15.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8155  -16.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5283  -15.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5334  -15.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8195  -14.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1006  -15.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2408  -16.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9572  -15.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6659  -16.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3818  -15.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3862  -15.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6688  -14.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9558  -15.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2402  -15.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5267  -16.2649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2412  -17.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6689  -18.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1031  -17.5044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1021  -14.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8152  -15.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3863  -14.6155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3869  -13.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2498  -14.6249    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  5  7  1  1
 14 15  2  0
  7  8  1  0
 15 16  1  0
  1  2  1  0
 16 17  2  0
  1  6  1  0
 17 18  1  0
  2  3  1  0
 18 19  2  0
 19 14  1  0
  3  4  1  0
  1 20  1  1
  4  5  1  0
 20 21  1  0
  7 12  2  0
  2 22  1  6
  8  9  2  0
  3 23  1  1
  9 10  1  0
  4 24  1  6
 10 11  2  0
 17 25  1  0
 11 12  1  0
 25 26  1  0
  5  6  1  0
 12 27  1  0
  9 13  1  0
 27 28  1  0
 10 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1090786

   (1S)-1,5-Anhydro-1-[4-chloro-5-(4-ethylbenzyl)-2-methoxyphenyl]-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: 438.97

Molecular Weight (Monoisotopic): 438.1268

AlogP: 2.73

#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: 3.13

CX LogD: 3.13

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: 0.14

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