Tadehaginoside G

ID: ALA3980175

PubChem CID: 132566160

Max Phase: Preclinical

Molecular Formula: C21H22O10

Molecular Weight: 434.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(O)cc1)O[C@H]1[C@H](Oc2cc(O)cc(O)c2)O[C@H](CO)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C21H22O10/c22-10-16-18(27)19(28)20(21(30-16)29-15-8-13(24)7-14(25)9-15)31-17(26)6-3-11-1-4-12(23)5-2-11/h1-9,16,18-25,27-28H,10H2/b6-3+/t16-,18-,19+,20-,21-/m1/s1

Standard InChI Key:  IKFRTNQSGKBZOF-JSYAWONVSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   20.5923  -17.1726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2942  -16.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0056  -17.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2870  -15.9418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9680  -17.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6562  -18.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6197  -19.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3070  -19.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0338  -19.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0689  -18.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3809  -18.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7225  -19.7399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5807  -15.5297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1771  -18.0030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7556  -17.1924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1614  -15.5440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1257  -16.0860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8784  -15.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8836  -16.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1718  -17.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4632  -16.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4580  -15.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7452  -15.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5568  -14.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2527  -14.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2292  -13.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5093  -13.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8116  -13.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8386  -14.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0909  -13.1324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9249  -13.0438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  9 12  1  0
 17 23  1  0
 22 16  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 18 13  1  1
 19  1  1  6
 20 14  1  1
 21 15  1  6
 13 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 28 30  1  0
 26 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3980175

   ---

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: 434.40

Molecular Weight (Monoisotopic): 434.1213

AlogP: 0.25

#Rotatable Bonds: 6

Polar Surface Area: 166.14

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.97

CX Basic pKa: ┄

CX LogP: 1.52

CX LogD: 1.51

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: 1.92

References

1. Zhang X, Chen C, Li Y, Chen D, Dong L, Na W, Wu C, Zhang J, Li Y..  (2016)  Tadehaginosides A-J, Phenylpropanoid Glucosides from Tadehagi triquetrum, Enhance Glucose Uptake via the Upregulation of PPARγ and GLUT-4 in C2C12 Myotubes.,  79  (5): [PMID:27100993] [10.1021/acs.jnatprod.5b00820]

Source

Source(1):

• Scientific Literature