NP-MRD: Showing NP-Card for 2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one (NP0054064)

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Record Information

Version

2.0

Created at

2022-04-28 00:32:18 UTC

Updated at

2022-04-28 00:32:18 UTC

NP-MRD ID

NP0054064

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one

Description

Isoswertiajaponin belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Thus, isoswertiajaponin is considered to be a flavonoid. 2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one is found in Gnetum gnemon , Iris florentina, Iris germanica, Passiflora sexflora, Phragmites australis and Zantedeschia aethiopica. 2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one was first documented in 2004 (PMID: 15008460). Based on a literature review a significant number of articles have been published on Isoswertiajaponin (PMID: 22041076) (PMID: 26262599) (PMID: 25789809) (PMID: 21830883) (PMID: 20839125).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304282202322D          

 33 36  0  0  1  0            999 V2000
   -0.7145   -0.4125    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   -1.6500    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
    0.7145   -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
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
   -1.4289    0.8250    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
    2.1434   -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
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
  1  2  2  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
  1  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  1  0  0  0
 13 14  1  0  0  0  0
 10 15  1  6  0  0  0
  9 16  1  1  0  0  0
  8 17  1  6  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 26 29  1  0  0  0  0
 25 30  1  0  0  0  0
  3 31  1  0  0  0  0
  1 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -3.7806   -2.9497    1.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9054   -1.9248    0.9403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5290   -2.1574    0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0746   -3.4018    1.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -3.6347    0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7242   -4.8930    1.1067 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1592   -2.6099    0.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5126   -2.8082    0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0037   -3.9234    0.5490 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2703   -1.7188   -0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7216   -0.4500   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6197    0.6306   -0.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3313    1.6408   -1.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2916    2.6012   -1.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5606    2.5651   -1.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4930    3.5396   -1.5706 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8740    1.5479   -0.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1579    1.5175    0.2151 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9251    0.6282   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280   -0.3286   -0.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -1.3335    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -1.0983    0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3621    0.2361    0.3627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4952    0.1823    1.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2981    1.3205    0.9568 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4455    1.1696    1.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3254    2.2326    1.8406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6987    1.2604   -0.5035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8664    1.9594   -0.7405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5229    1.7081   -1.3172 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7615    1.6116   -2.6871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837    0.8861   -0.9327 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1464    1.6424   -1.1334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7810   -2.6016    1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3779   -3.5394    2.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9120   -3.6389    0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6947   -4.2354    1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5605   -5.3709    1.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3455   -1.8276   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3690    1.6887   -1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0463    3.3809   -2.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4272    3.5370   -1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3016    0.7413    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1535   -0.1616    0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5775    0.8520    1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7322    2.2519    1.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9775    0.2233    1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0051    1.1419    2.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9509    3.0330    1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8460    0.1555   -0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3588    1.4243   -1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2913    2.7700   -1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0612    2.5120   -2.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3101    0.0480   -1.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1725    1.9674   -2.0850 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 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 11 12  1  0
 12 19  2  0
 19 17  1  0
 17 18  1  0
 17 15  2  0
 15 16  1  0
 15 14  1  0
 14 13  2  0
 22  3  1  0
 32 23  1  0
 13 12  1  0
 21  7  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  6 38  1  0
 10 39  1  0
 23 45  1  1
 25 46  1  6
 26 47  1  0
 26 48  1  0
 27 49  1  0
 28 50  1  6
 29 51  1  0
 30 52  1  6
 31 53  1  0
 32 54  1  6
 33 55  1  0
 19 44  1  0
 18 43  1  0
 16 42  1  0
 14 41  1  0
 13 40  1  0
M  END

  Mrv1652304282202322D          

 33 36  0  0  1  0            999 V2000
   -0.7145   -0.4125    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   -1.6500    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
    0.7145   -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
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
   -1.4289    0.8250    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
    2.1434   -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
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
  1  2  2  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
  1  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  1  0  0  0
 13 14  1  0  0  0  0
 10 15  1  6  0  0  0
  9 16  1  1  0  0  0
  8 17  1  6  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 26 29  1  0  0  0  0
 25 30  1  0  0  0  0
  3 31  1  0  0  0  0
  1 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054064

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C=C(OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O11/c1-31-14-6-12(27)16-11(26)5-13(8-2-3-9(24)10(25)4-8)32-21(16)17(14)22-20(30)19(29)18(28)15(7-23)33-22/h2-6,15,18-20,22-25,27-30H,7H2,1H3/t15-,18-,19+,20-,22+/m1/s1

> <INCHI_KEY>
BRYZTZMVXZZLPD-PGPONNFDSA-N

> <FORMULA>
C22H22O11

> <MOLECULAR_WEIGHT>
462.407

> <EXACT_MASS>
462.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.52007097248043

> <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-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

> <ALOGPS_LOGP>
0.47

> <JCHEM_LOGP>
-0.20830303699999952

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.720338955203967

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.289490504415673

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979192630016531

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
112.49539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000  -4.620   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  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   10                                                            
CONECT   16    9                                                            
CONECT   17    8                                                            
CONECT   18    5   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20    4   22                                                  
CONECT   22   21                                                            
CONECT   23   19   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   26                                                            
CONECT   30   25                                                            
CONECT   31    3                                                            
CONECT   32    1   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₁₁

Average Mass

462.4070 Da

Monoisotopic Mass

462.11621 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C=C(OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C22H22O11/c1-31-14-6-12(27)16-11(26)5-13(8-2-3-9(24)10(25)4-8)32-21(16)17(14)22-20(30)19(29)18(28)15(7-23)33-22/h2-6,15,18-20,22-25,27-30H,7H2,1H3/t15-,18-,19+,20-,22+/m1/s1

InChI Key

BRYZTZMVXZZLPD-PGPONNFDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Gnetum gnemon	Plant	KNApSAcK
Iris florentina	Plant	KNApSAcK
Iris germanica	LOTUS Database	35616633
Passiflora sexflora	Plant	KNApSAcK
Phragmites australis	Plant	KNApSAcK
Zantedeschia aethiopica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
7-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Hexose monosaccharide
C-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
Catechol
Anisole
Phenol ether
Pyranone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monosaccharide
Benzenoid
Oxane
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
1,2-diol
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Primary alcohol
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
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	0.47	ALOGPS
logP	-0.21	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.29	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.5 m³·mol⁻¹	ChemAxon
Polarizability	44.52 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00006122

Chemspider ID

10306142

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21721993

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wu LZ, Wu HF, Xu XD, Yang JS: Two new flavone C-glycosides from Trollius ledebourii. Chem Pharm Bull (Tokyo). 2011;59(11):1393-5. doi: 10.1248/cpb.59.1393. [PubMed:22041076 ]
Qin Y, Liang Y, Ren D, Qiu X, Li X: Separation of phenolic acids and flavonoids from Trollius chinensis Bunge by high speed counter-current chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Sep 15;1001:82-9. doi: 10.1016/j.jchromb.2015.07.051. Epub 2015 Aug 1. [PubMed:26262599 ]
Liu L, Guo L, Zhao C, Wu X, Wang R, Liu C: Characterization of the intestinal absorption of seven flavonoids from the flowers of Trollius chinensis using the Caco-2 cell monolayer model. PLoS One. 2015 Mar 19;10(3):e0119263. doi: 10.1371/journal.pone.0119263. eCollection 2015. [PubMed:25789809 ]
Perveen S, El-Shafae AM, Al-Taweel A, Fawzy GA, Malik A, Afza N, Latif M, Iqbal L: Antioxidant and urease inhibitory C-glycosylflavonoids from Celtis africana. J Asian Nat Prod Res. 2011 Sep;13(9):799-804. doi: 10.1080/10286020.2011.593171. [PubMed:21830883 ]
Dong FY, Guan LN, Zhang YH, Cui ZH, Wang L, Wang W: Acylated flavone C-glycosides from Hemistepta lyrata. J Asian Nat Prod Res. 2010 Sep;12(9):776-80. doi: 10.1080/10286020.2010.504183. [PubMed:20839125 ]
Wang RF, Yang XW, Ma CM, Liu HY, Shang MY, Zhang QY, Cai SQ, Park JH: Trollioside, a new compound from the flowers of Trollius chinensis. J Asian Nat Prod Res. 2004 Jun;6(2):139-44. doi: 10.1080/1028602031000147393. [PubMed:15008460 ]

Showing NP-Card for 2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one (NP0054064)

MOL for NP0054064 (2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one)

3D MOL for NP0054064 (2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one)

3D SDF for NP0054064 (2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one)

3D-SDF for NP0054064 (2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one)

PDB for NP0054064 (2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one)

3D PDB for NP0054064 (2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one)

SMILES for NP0054064 (2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one)

INCHI for NP0054064 (2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one)

Structure for NP0054064 (2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one)

3D Structure for NP0054064 (2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one)