3-(4-Propyloxyphenyl)-1-[3-(beta-D-glucopyranosyl)-2,4,6-trihydroxyphenyl]propan-1-one

ID: ALA4099324

PubChem CID: 137661404

Max Phase: Preclinical

Molecular Formula: C24H30O10

Molecular Weight: 478.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOc1ccc(CCC(=O)c2c(O)cc(O)c([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c2O)cc1

Standard InChI:  InChI=1S/C24H30O10/c1-2-9-33-13-6-3-12(4-7-13)5-8-14(26)18-15(27)10-16(28)19(21(18)30)24-23(32)22(31)20(29)17(11-25)34-24/h3-4,6-7,10,17,20,22-25,27-32H,2,5,8-9,11H2,1H3/t17-,20-,22+,23-,24+/m1/s1

Standard InChI Key:  URDMZBKELOFRSX-VYJJCVKJSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   34.7119   -9.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7161  -10.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9979  -10.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0062   -8.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2922  -10.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3004   -9.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4218  -10.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9979  -11.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5864  -10.4951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5947   -8.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8806   -9.2652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.8355   -8.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1256   -9.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8355   -8.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1256  -10.0869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   35.4199   -8.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5413  -10.0869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.2470   -8.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5413   -7.6354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.6668   -8.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0824   -8.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9610   -9.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7141   -7.6436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.0824   -8.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3643   -7.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3767   -9.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6585   -8.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7889   -7.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.4978   -8.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5004   -8.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2094   -9.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  0
  5  6  1  0
  6  4  1  0
  2  7  1  6
  3  8  1  1
  5  9  1  6
  6 10  1  1
 11 10  1  0
  3  5  1  0
 12 13  2  0
 13 15  1  0
 14 12  1  0
 16 13  1  0
 17 19  1  0
 18 12  1  0
 19 16  2  0
 20 18  2  0
 21 18  1  0
 22 14  1  0
 23 25  1  0
 24 28  1  0
 25 21  1  0
 26 19  1  0
 27 29  1  0
 28 30  2  0
 29 23  2  0
 30 23  1  0
 17 14  2  0
 24 27  2  0
  1 16  1  1
 24 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099324

   ---

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: 478.49

Molecular Weight (Monoisotopic): 478.1839

AlogP: 0.92

#Rotatable Bonds: 9

Polar Surface Area: 177.14

Molecular Species: NEUTRAL

HBA: 10

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.55

CX Basic pKa: ┄

CX LogP: 2.16

CX LogD: 1.93

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.26

Np Likeness Score: 1.40

References

1. Jesus AR, Vila-Viçosa D, Machuqueiro M, Marques AP, Dore TM, Rauter AP..  (2017)  Targeting Type 2 Diabetes with C-Glucosyl Dihydrochalcones as Selective Sodium Glucose Co-Transporter 2 (SGLT2) Inhibitors: Synthesis and Biological Evaluation.,  60  (2): [PMID:28098449] [10.1021/acs.jmedchem.6b01134]

Source

Source(1):

• Scientific Literature