NP-MRD: Showing NP-Card for androechin (NP0206499)

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Record Information

Version

2.0

Created at

2022-09-05 02:46:10 UTC

Updated at

2022-09-05 02:46:10 UTC

NP-MRD ID

NP0206499

Secondary Accession Numbers

None

Natural Product Identification

Common Name

androechin

Description

Androechin belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. androechin is found in Andrographis echioides. androechin was first documented in 2001 (PMID: 11355769). Based on a literature review very few articles have been published on Androechin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052204462D          

 32 34  0  0  1  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 19 32  2  0  0  0  0
  3 32  1  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
   -0.9032    5.3343    2.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4826    4.1496    2.1563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328    3.2321    1.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5974    3.4306    1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3048    2.4519    0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6061    2.8387    0.2363 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171    1.3156   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4106    0.1616   -0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5137   -0.6946   -1.1337 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6913   -0.3986   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8714   -0.1152   -0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0898   -0.9060   -0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1010   -2.0277   -1.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2573   -2.7599   -1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4162   -2.3070   -0.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4470   -1.1977   -0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864   -0.4623    0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4245    0.6437    0.8695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6822    1.1635    0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2905    0.0518   -0.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6077   -0.3899   -0.0928 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5834   -1.5927    0.5503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7334   -2.3096    0.6313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7883   -1.7960    1.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2106   -0.5441    1.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2555   -2.5797   -0.7622 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4983   -3.2078   -0.6628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4285   -1.3149   -1.5580 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5869   -1.6757   -2.8960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2398   -0.3983   -1.4624 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2816   -0.7833   -2.3936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3586    2.1032    0.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2525    5.8260    1.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6735    6.0739    2.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2330    5.0592    3.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745    4.3170    1.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.4936   -0.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7395   -1.3425   -1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9348    0.7019    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -2.4033   -1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2279   -3.6325   -2.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3398   -2.8548   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3886   -0.8738    0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6719    1.2296    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1730    0.3212    0.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4476   -3.3293    1.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184   -1.8277    2.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6884   -2.4734    1.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1727    0.1273    1.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5499   -3.2496   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4360   -4.1152   -0.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3792   -0.8238   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1280   -0.9810   -3.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6122    0.6313   -1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3413   -0.3208   -3.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    2.0312    1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  7 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 19 32  2  0
 32  3  1  0
 17 12  1  0
 30 21  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
 10 38  1  0
 11 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 18 44  1  0
 21 45  1  1
 23 46  1  1
 24 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  6
 27 51  1  0
 28 52  1  1
 29 53  1  0
 30 54  1  6
 31 55  1  0
 32 56  1  0
M  END


  Mrv1652309052204462D          

 32 34  0  0  1  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 19 32  2  0  0  0  0
  3 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206499

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C(=O)\C=C\C2=CC=CC=C2O)C(O[C@@H]2OC(CO)[C@@H](O)[C@H](O)C2O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O10/c1-30-12-8-15(26)18(14(25)7-6-11-4-2-3-5-13(11)24)16(9-12)31-22-21(29)20(28)19(27)17(10-23)32-22/h2-9,17,19-24,26-29H,10H2,1H3/b7-6+/t17?,19-,20+,21?,22-/m1/s1

> <INCHI_KEY>
DBDVNEPYCHFXLY-FDWXWSKHSA-N

> <FORMULA>
C22H24O10

> <MOLECULAR_WEIGHT>
448.424

> <EXACT_MASS>
448.136946973

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.979937450082225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(2-hydroxy-4-methoxy-6-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one

> <JCHEM_LOGP>
1.203889985

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.866309168845323

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.132804088972921

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092346309496

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
111.42730000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
androechin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   19                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
CONECT   19    7   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   21   31                                                  
CONECT   31   30                                                            
CONECT   32   19    3                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₁₀

Average Mass

448.4240 Da

Monoisotopic Mass

448.13695 Da

IUPAC Name

(2E)-1-(2-hydroxy-4-methoxy-6-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one

Traditional Name

androechin

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C(=O)\C=C\C2=CC=CC=C2O)C(O[C@@H]2OC(CO)[C@@H](O)[C@H](O)C2O)=C1

InChI Identifier

InChI=1S/C22H24O10/c1-30-12-8-15(26)18(14(25)7-6-11-4-2-3-5-13(11)24)16(9-12)31-22-21(29)20(28)19(27)17(10-23)32-22/h2-9,17,19-24,26-29H,10H2,1H3/b7-6+/t17?,19-,20+,21?,22-/m1/s1

InChI Key

DBDVNEPYCHFXLY-FDWXWSKHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Andrographis echioides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid o-glycoside
2'-hydroxychalcone
Linear 1,3-diarylpropanoid
Phenolic glycoside
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Hexose monosaccharide
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Methoxyphenol
Phenoxy compound
Phenol ether
Styrene
Anisole
Benzoyl
Aryl ketone
Methoxybenzene
Alkyl aryl ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Enone
Vinylogous acid
Alpha,beta-unsaturated ketone
Secondary alcohol
Ketone
Ether
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Aldehyde
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120199 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.2	ChemAxon
pKa (Strongest Acidic)	7.13	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	111.43 m³·mol⁻¹	ChemAxon
Polarizability	43.98 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00014503

Chemspider ID

24845949

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42607586

PDB ID

Not Available

ChEBI ID

185807

Good Scents ID

Not Available

References

General References

Jayaprakasam B, Gunasekar D, Rao KV, Blond A, Bodo B: Androechin, a new chalcone glucoside from Andrographis echioides. J Asian Nat Prod Res. 2001;3(1):43-8. doi: 10.1080/10286020108042837. [PubMed:11355769 ]
LOTUS database [Link]

Showing NP-Card for androechin (NP0206499)

MOL for NP0206499 (androechin)

3D MOL for NP0206499 (androechin)

3D SDF for NP0206499 (androechin)

3D-SDF for NP0206499 (androechin)

PDB for NP0206499 (androechin)

3D PDB for NP0206499 (androechin)

SMILES for NP0206499 (androechin)

INCHI for NP0206499 (androechin)

Structure for NP0206499 (androechin)

3D Structure for NP0206499 (androechin)