NP-MRD: Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0189716)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 06:14:34 UTC

Updated at

2022-09-04 06:14:34 UTC

NP-MRD ID

NP0189716

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

Description

Pedaliin 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. Pedaliin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Pedaliin has been detected, but not quantified in, fats and oils. 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one is found in Dracocephalum tanguticum, Pterogyne nitens and Sesamum indicum. This could make pedaliin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305312D          

 34 37  0  0  0  0            999 V2000
    4.2868    0.8250    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
    0.0000    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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
   -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
    1.4289   -1.6500    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
    2.1434   -0.4125    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
    5.7158    0.0000    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
    6.4302   -0.4125    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
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  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    2.0625    0.0000 O   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
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  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   -2.4750    0.0000 O   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
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  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  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  1  0  0  0  0
 12  5  2  0  0  0  0
 12  8  1  0  0  0  0
 13  6  2  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21 14  2  0  0  0  0
 21 18  1  0  0  0  0
 22 20  1  0  0  0  0
 23  7  1  0  0  0  0
 24  9  1  0  0  0  0
 25 10  1  0  0  0  0
 26 11  2  0  0  0  0
 27 17  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  0  0  0  0
 30 20  1  0  0  0  0
 31  1  1  0  0  0  0
 31 14  1  0  0  0  0
 32 12  1  0  0  0  0
 32 13  1  0  0  0  0
 33 15  1  0  0  0  0
 33 22  1  0  0  0  0
 34 21  1  0  0  0  0
 34 22  1  0  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
   -0.1713    3.8318    0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    2.6289    0.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2563    1.4125    0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1162    1.3574    0.5686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7670    0.1381    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0760    0.1003    0.4421 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7659   -0.9990    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2243   -0.9633    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9729   -2.0816    0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3651   -2.0152    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9864   -0.8082    0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3699   -0.7004    0.6031 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2216    0.3463    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8681    1.5385    0.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8615    0.2365    0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0436   -2.1364    0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6600   -2.1615   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0551   -3.2437   -0.2404 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9705   -0.9870    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111   -0.9367    0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1783   -2.0258   -0.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0349    0.3158    0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212    0.3302    0.2191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1654    0.5263   -0.9405 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8467   -0.6611   -1.2345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5963   -0.9740   -0.0977 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0342   -2.4135   -0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8026   -2.4953   -1.4117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7791   -0.0278   -0.0669 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5256   -0.0556   -1.2194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1811    1.3600    0.2028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1474    2.3303    0.2484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1700    1.6272   -0.8878 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5915    2.8643   -0.7585 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1655    3.9258    1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7358    3.9347    0.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7947    4.7208    0.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7460    2.2210    0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753   -3.0605    0.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9737   -2.9049    0.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9473   -1.5228    0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3356    2.3704    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890    1.1641    0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5702   -3.0725   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0059   -2.9485   -0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4929    0.6929   -1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0351   -0.7992    0.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1181   -3.0150   -0.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6080   -2.7852    0.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4938   -3.1913   -2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3803   -0.2958    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9751   -0.1790   -2.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6286    1.2591    1.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9056    3.0997    0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7458    1.5751   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2912    3.5532   -0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 22 20  1  0
 20 21  1  0
 20 19  2  0
 19 17  1  0
 17 18  2  0
 17 16  1  0
 16  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  7  8  1  0
  8 15  2  0
 15 13  1  0
 13 14  1  0
 13 11  2  0
 11 12  1  0
 11 10  1  0
 10  9  2  0
  4  3  1  0
  9  8  1  0
 33 24  1  0
  5 19  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 24 46  1  6
 26 47  1  1
 27 48  1  0
 27 49  1  0
 28 50  1  0
 29 51  1  1
 30 52  1  0
 31 53  1  1
 32 54  1  0
 33 55  1  6
 34 56  1  0
 21 45  1  0
 16 44  1  0
  4 38  1  0
 15 43  1  0
 14 42  1  0
 12 41  1  0
 10 40  1  0
  9 39  1  0
M  END


  Mrv0541 05061305312D          

 34 37  0  0  0  0            999 V2000
    4.2868    0.8250    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
    0.0000    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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
   -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
    1.4289   -1.6500    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
    2.1434   -0.4125    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
    5.7158    0.0000    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
    6.4302   -0.4125    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
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  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    2.0625    0.0000 O   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
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  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   -2.4750    0.0000 O   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
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  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  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  1  0  0  0  0
 12  5  2  0  0  0  0
 12  8  1  0  0  0  0
 13  6  2  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21 14  2  0  0  0  0
 21 18  1  0  0  0  0
 22 20  1  0  0  0  0
 23  7  1  0  0  0  0
 24  9  1  0  0  0  0
 25 10  1  0  0  0  0
 26 11  2  0  0  0  0
 27 17  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  0  0  0  0
 30 20  1  0  0  0  0
 31  1  1  0  0  0  0
 31 14  1  0  0  0  0
 32 12  1  0  0  0  0
 32 13  1  0  0  0  0
 33 15  1  0  0  0  0
 33 22  1  0  0  0  0
 34 21  1  0  0  0  0
 34 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0189716

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC2OC(CO)C(O)C(O)C2O)C(O)=C2C(=O)C=C(OC2=C1)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O12/c1-31-14-6-13-16(11(26)5-12(32-13)8-2-3-9(24)10(25)4-8)18(28)21(14)34-22-20(30)19(29)17(27)15(7-23)33-22/h2-6,15,17,19-20,22-25,27-30H,7H2,1H3

> <INCHI_KEY>
WLDSVYQTJXGHOT-UHFFFAOYSA-N

> <FORMULA>
C22H22O12

> <MOLECULAR_WEIGHT>
478.4029

> <EXACT_MASS>
478.111126168

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
46.42102915188818

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
-0.02261554700000007

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.17530202776951

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.5245089556235

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923662130335

> <JCHEM_POLAR_SURFACE_AREA>
195.59999999999994

> <JCHEM_REFRACTIVITY>
113.50239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1   31                                                            
CONECT    2    3    8                                                       
CONECT    3    2    9                                                       
CONECT    4    8   10                                                       
CONECT    5   11   12                                                       
CONECT    6   13   14                                                       
CONECT    7   15   23                                                       
CONECT    8    2    4   12                                                  
CONECT    9    3   10   24                                                  
CONECT   10    4    9   25                                                  
CONECT   11    5   16   26                                                  
CONECT   12    5    8   32                                                  
CONECT   13    6   16   32                                                  
CONECT   14    6   21   31                                                  
CONECT   15    7   17   33                                                  
CONECT   16   11   13   18                                                  
CONECT   17   15   19   27                                                  
CONECT   18   16   21   28                                                  
CONECT   19   17   20   29                                                  
CONECT   20   19   22   30                                                  
CONECT   21   14   18   34                                                  
CONECT   22   20   33   34                                                  
CONECT   23    7                                                            
CONECT   24    9                                                            
CONECT   25   10                                                            
CONECT   26   11                                                            
CONECT   27   17                                                            
CONECT   28   18                                                            
CONECT   29   19                                                            
CONECT   30   20                                                            
CONECT   31    1   14                                                       
CONECT   32   12   13                                                       
CONECT   33   15   22                                                       
CONECT   34   21   22                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxyluteolin 7-methyl ether 6-glucoside	HMDB

Chemical Formula

C₂₂H₂₂O₁₂

Average Mass

478.4029 Da

Monoisotopic Mass

478.11113 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(OC2OC(CO)C(O)C(O)C2O)C(O)=C2C(=O)C=C(OC2=C1)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C22H22O12/c1-31-14-6-13-16(11(26)5-12(32-13)8-2-3-9(24)10(25)4-8)18(28)21(14)34-22-20(30)19(29)17(27)15(7-23)33-22/h2-6,15,17,19-20,22-25,27-30H,7H2,1H3

InChI Key

WLDSVYQTJXGHOT-UHFFFAOYSA-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
Dracocephalum tanguticum	LOTUS Database	35616633
Pterogyne nitens	LOTUS Database	35616633
Sesamum indicum	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-6-o-glycoside
Flavonoid o-glycoside
7-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Anisole
Catechol
Pyranone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monocyclic benzene moiety
Monosaccharide
Pyran
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Polyol
Organic oxide
Primary alcohol
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	0.66	ALOGPS
logP	-0.023	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.52	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.5 m³·mol⁻¹	ChemAxon
Polarizability	46.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030805

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002747

KNApSAcK ID

Not Available

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

73981696

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0189716)

MOL for NP0189716 (2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0189716 (2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0189716 (2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0189716 (2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

PDB for NP0189716 (2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0189716 (2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

SMILES for NP0189716 (2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

INCHI for NP0189716 (2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

Structure for NP0189716 (2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0189716 (2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)