NP-MRD: Showing NP-Card for 2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0286951)

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Record Information

Version

2.0

Created at

2022-09-09 15:46:30 UTC

Updated at

2022-09-09 15:46:30 UTC

NP-MRD ID

NP0286951

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

Description

Pongamoside d belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Thus, pongamoside D is considered to be a flavonoid. 2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one is found in Hyoscyamus niger and Pongamia pinnata. 2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one was first documented in 2004 (PMID: 15081295). Based on a literature review very few articles have been published on Pongamoside d (PMID: 19401911).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309092217462D          

 34 38  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860    2.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0420    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    2.1434   -1.2375    0.0000 C   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
    1.4289   -2.4750    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  1  0  0  0
 17 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
   -2.2081   -2.5051   -5.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812   -2.9817   -4.3803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7790   -2.1924   -3.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2318   -2.3880   -2.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1093   -3.5035   -1.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4670   -4.5529   -2.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3386   -5.5576   -1.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8666   -5.5172   -0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5214   -4.4699    0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670   -3.4910   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1984   -4.6977    1.2875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5123   -6.0927    1.3542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7490   -6.3816   -0.0290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8711   -1.5392   -1.0383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0968   -0.5206   -1.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    0.3234   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    1.4304   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    2.2021    0.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1517    3.3236    0.8399 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2730    2.9888    1.6030 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1044    2.9636    2.9462 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0506    1.9790    3.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    2.0716    4.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8470    4.3372    3.4943 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0114    4.9015    4.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575    5.2193    2.4473 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4729    6.2428    3.0170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3970    4.4660    1.4720 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1025    5.3874    0.4394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5439    1.6428   -1.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2146    0.8138   -2.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858   -0.2858   -2.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0613   -1.1100   -3.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193   -0.8710   -4.6920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9801   -2.2363   -4.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9066   -1.5972   -5.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5830   -3.3025   -5.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0519   -4.6349   -3.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5749   -6.3644   -2.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -2.6843    0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6691   -6.6738    1.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4522   -6.1956    1.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1537    0.1247    0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4895    3.6128   -0.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0585    2.5956    3.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0453    2.1893    3.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3737    0.9702    3.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8478    1.6616    5.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0729    4.2041    4.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7706    4.5004    3.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1195    5.6923    1.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1269    6.8132    3.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4425    4.1933    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    6.3058    0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1945    2.4935   -1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5783    0.9611   -3.6858 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 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 17 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
 33  3  1  0
 10  5  1  0
 32 15  1  0
  9  8  1  0
 28 19  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 16 43  1  0
 19 44  1  6
 21 45  1  1
 22 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  1
 25 50  1  0
 26 51  1  6
 27 52  1  0
 28 53  1  1
 29 54  1  0
 30 55  1  0
 31 56  1  0
  6 38  1  0
  7 39  1  0
 12 41  1  0
 12 42  1  0
 10 40  1  0
M  END

  Mrv1652309092217462D          

 34 38  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860    2.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0420    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    2.1434   -1.2375    0.0000 C   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
    1.4289   -2.4750    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  1  0  0  0
 17 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0286951

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC2=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2C1=O)C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O11/c1-29-22-17(25)12-4-3-11(32-23-20(28)19(27)18(26)16(8-24)34-23)7-14(12)33-21(22)10-2-5-13-15(6-10)31-9-30-13/h2-7,16,18-20,23-24,26-28H,8-9H2,1H3/t16-,18-,19+,20-,23-/m1/s1

> <INCHI_KEY>
RQSSRCUNGIYPIQ-PUIBNRJISA-N

> <FORMULA>
C23H22O11

> <MOLECULAR_WEIGHT>
474.418

> <EXACT_MASS>
474.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
46.666257562810145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2H-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <JCHEM_LOGP>
-0.11501180733333302

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.196090790996788

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20014001339205

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343722586

> <JCHEM_POLAR_SURFACE_AREA>
153.37

> <JCHEM_REFRACTIVITY>
113.58200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(2H-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.654   3.816   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.185   3.977   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.812   2.570   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    4   15                                                       
CONECT   15   14   16   32                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   19   29                                                  
CONECT   29   28                                                            
CONECT   30   17   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   15   33                                                  
CONECT   33   32    3   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₁₁

Average Mass

474.4180 Da

Monoisotopic Mass

474.11621 Da

IUPAC Name

2-(2H-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

2-(2H-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(OC2=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2C1=O)C1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C23H22O11/c1-29-22-17(25)12-4-3-11(32-23-20(28)19(27)18(26)16(8-24)34-23)7-14(12)33-21(22)10-2-5-13-15(6-10)31-9-30-13/h2-7,16,18-20,23-24,26-28H,8-9H2,1H3/t16-,18-,19+,20-,23-/m1/s1

InChI Key

RQSSRCUNGIYPIQ-PUIBNRJISA-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
Hyoscyamus niger	LOTUS Database	35616633
Pongamia pinnata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3-methoxyflavonoid-skeleton
Flavone
Phenolic glycoside
3-methoxychromone
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Benzodioxole
Pyranone
Alkyl aryl ether
Pyran
Monosaccharide
Oxane
Benzenoid
Heteroaromatic compound
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	-0.12	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	153.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.58 m³·mol⁻¹	ChemAxon
Polarizability	46.67 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00011170

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101731481

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Begum AS, Verma S, Sahai M, Schneider K, Sussmuth R: Hyoscyamal, a new tetrahydrofurano lignan from Hyoscyamus niger Linn. Nat Prod Res. 2009;23(7):595-600. doi: 10.1080/14786410802113961. [PubMed:19401911 ]
Ahmad G, Yadav PP, Maurya R: Furanoflavonoid glycosides from Pongamia pinnata fruits. Phytochemistry. 2004 Apr;65(7):921-4. doi: 10.1016/j.phytochem.2004.01.020. [PubMed:15081295 ]
LOTUS database [Link]

Showing NP-Card for 2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0286951)

MOL for NP0286951 (2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0286951 (2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0286951 (2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0286951 (2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

PDB for NP0286951 (2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0286951 (2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

SMILES for NP0286951 (2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

INCHI for NP0286951 (2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

Structure for NP0286951 (2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0286951 (2-(2h-1,3-benzodioxol-5-yl)-3-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)