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

ID: ALA1093423

Cas Number: 898537-18-3

PubChem CID: 11988953

Max Phase: Preclinical

Molecular Formula: C23H30O6S

Molecular Weight: 434.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc(Cc2cc([C@@H]3S[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(OC)cc2C)cc1

Standard InChI:  InChI=1S/C23H30O6S/c1-4-29-16-7-5-14(6-8-16)10-15-11-17(18(28-3)9-13(15)2)23-22(27)21(26)20(25)19(12-24)30-23/h5-9,11,19-27H,4,10,12H2,1-3H3/t19-,20-,21+,22-,23+/m1/s1

Standard InChI Key:  WHSOLWOTCHFFBK-ZQGJOIPISA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -3.2679  -10.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2679  -11.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534  -11.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8343  -11.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8343  -10.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534  -10.0741    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1195  -10.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4080  -10.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3048  -10.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3099   -9.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4040   -8.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1230   -9.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0173  -10.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7337  -10.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4424  -10.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1583  -10.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1627   -9.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4453   -8.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7323   -9.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9834  -10.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6969  -10.4946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824  -11.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5546  -12.5583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1205  -11.7343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8786   -8.8699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -9.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8372   -8.8454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367   -8.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0263   -8.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888  -10.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 13 14  1  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093423

   Luseogliflozin

2. Alternative Forms:

   

   ALA1093423

   Luseogliflozin hydrate

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: 434.55

Molecular Weight (Monoisotopic): 434.1763

AlogP: 2.22

#Rotatable Bonds: 7

Polar Surface Area: 99.38

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.85

CX Basic pKa: ┄

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.53

Np Likeness Score: 0.22

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]

2. Li Z, Xu X, Deng L, Liao R, Liang R, Zhang B, Zhang L..  (2018)  Design, synthesis and biological evaluation of nitric oxide releasing derivatives of dapagliflozin as potential anti-diabetic and anti-thrombotic agents.,  26  (14): [PMID:29954682] [10.1016/j.bmc.2018.06.017]

3. Haider K, Pathak A, Rohilla A, Haider MR, Ahmad K, Yar MS..  (2019)  Synthetic strategy and SAR studies of C-glucoside heteroaryls as SGLT2 inhibitor: A review.,  184  [PMID:31630053] [10.1016/j.ejmech.2019.111773]

4. Romero FA, Jones CT, Xu Y, Fenaux M, Halcomb RL..  (2020)  The Race to Bash NASH: Emerging Targets and Drug Development in a Complex Liver Disease.,  63  (10): [PMID:31930920] [10.1021/acs.jmedchem.9b01701]

5. Wang Y, Lou Y, Wang J, Li D, Chen H, Zheng T, Xia C, Song X, Dong T, Li J, Li J, Liu H..  (2019)  Design, synthesis and biological evaluation of 6-deoxy O-spiroketal C-arylglucosides as novel renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.,  180  [PMID:31325786] [10.1016/j.ejmech.2019.07.032]

Source

Source(1):

• Scientific Literature