(1S,2S,3R,4R,5S)-5-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-1-cyclopropoxy-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol

ID: ALA4097849

PubChem CID: 137661793

Max Phase: Preclinical

Molecular Formula: C24H27ClO7

Molecular Weight: 462.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc(Cc2cc([C@]34OC[C@](OC5CC5)(O3)[C@@H](O)[C@H](O)[C@H]4O)ccc2Cl)cc1

Standard InChI:  InChI=1S/C24H27ClO7/c1-2-29-17-6-3-14(4-7-17)11-15-12-16(5-10-19(15)25)24-22(28)20(26)21(27)23(32-24,13-30-24)31-18-8-9-18/h3-7,10,12,18,20-22,26-28H,2,8-9,11,13H2,1H3/t20-,21-,22+,23-,24-/m0/s1

Standard InChI Key:  UIWNXSSAMKJOET-LKTXNROYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    5.5658  -10.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5715  -11.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2676  -11.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9580  -11.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9524  -10.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2563  -10.0180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6939  -10.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7946   -9.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5360   -9.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1727   -9.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9101   -9.1782    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.0679  -10.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7046  -10.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4460  -10.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5508   -9.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2882   -9.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9249   -9.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6663   -9.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3030  -10.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0445   -9.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8242  -10.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0827  -10.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3305  -10.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9193   -9.6474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658   -9.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6582  -11.6062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2773  -12.4215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8809  -11.6316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7861  -10.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2187  -10.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4304  -11.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0185  -11.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  5  7  1  1
  7  8  2  0
  9  8  1  0
 10  9  2  0
 10 11  1  0
 12 10  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 16 15  1  0
 17 16  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 21 17  1  0
 22 21  2  0
 14 22  1  0
 23 12  2  0
  7 23  1  0
  5 24  1  0
 25 24  1  0
  1 25  1  0
  4 26  1  6
  3 27  1  1
  2 28  1  6
  1 29  1  1
 29 30  1  0
 31 30  1  0
 32 31  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097849

   ---

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: 462.93

Molecular Weight (Monoisotopic): 462.1445

AlogP: 2.50

#Rotatable Bonds: 7

Polar Surface Area: 97.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.79

CX Basic pKa: ┄

CX LogP: 4.00

CX LogD: 4.00

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.58

Np Likeness Score: 0.52

References

1. Li Y, Shi Z, Chen L, Zheng S, Li S, Xu B, Liu Z, Liu J, Deng C, Ye F..  (2017)  Discovery of a Potent, Selective Renal Sodium-Dependent Glucose Cotransporter 2 (SGLT2) Inhibitor (HSK0935) for the Treatment of Type 2 Diabetes.,  60  (10): [PMID:28447791] [10.1021/acs.jmedchem.6b01818]

Source

Source(1):

• Scientific Literature