NP-MRD: Showing NP-Card for 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one (NP0210830)

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Record Information

Version

2.0

Created at

2022-09-05 08:49:25 UTC

Updated at

2022-09-05 08:49:25 UTC

NP-MRD ID

NP0210830

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

Description

Swertisin, also known as flavocommelitin, belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Thus, swertisin is considered to be a flavonoid. Swertisin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one is found in Aleurites moluccanus, Alliaria petiolata, Aquilegia oxysepala, Carex fraseriana, Echinodorus grandiflorus, Gaillardia aristata, Gaillardia pulchella, Galipea trifoliata, Gentiana algida, Gentiana brachyphylla, Gentianella austriaca, Gnetum gnemon, Iris germanica, Iris gracilipes, Justicia pectoralis, Justicia ramosa, Knautia montana, Lophatherum gracile, Machaerium isadelphum, Passiflora biflora, Passiflora incarnata, Saccharum officinarum, Swertia japonica, Swertia mussotii, Swertia paniculata, Swertia tetrapetala, Syzygium cumini, Triticum aestivum, Wilbrandia ebracteata and Ziziphus jujuba. 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one was first documented in 2021 (PMID: 34634740). Based on a literature review a small amount of articles have been published on swertisin (PMID: 35855584) (PMID: 35843397) (PMID: 35655066) (PMID: 35528477).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052210492D          

 32 35  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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
    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 O   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 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
    5.0013    1.2375    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
    6.4302    1.2375    0.0000 O   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
    5.0013   -0.4125    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
    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 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
    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
    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  2  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
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  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  1  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
  7 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  3 21  2  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -0.9037    0.3956    3.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4015    0.3655    2.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236    0.2756    0.9782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8447    0.2327    1.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6091    0.1361   -0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052    0.0966    0.0342 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7330    0.0221   -0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1805   -0.0346   -0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1842    0.2895   -1.5048 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5099    0.0816   -1.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8659   -0.4357    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1559   -0.6572    0.4965 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8527   -0.7689    0.9805 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5397   -0.5658    0.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2924   -0.0252   -2.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8966    0.0073   -2.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4398   -0.0322   -3.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0549    0.0835   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    0.1222   -1.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9450    0.0790   -2.6761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041    0.2182   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5378    0.3695   -0.4393 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2350    0.8222    0.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5569    1.1112    0.2168 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3290    1.6860    1.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6492    1.9967    0.9606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2555   -0.1742   -0.2384 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6783   -0.0792   -1.5830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2985   -1.3332   -0.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8883   -1.4423    1.1835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0739   -0.9589   -1.0152 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3712   -0.9667   -2.3378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0981    1.1715    3.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4183   -0.5882    3.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7070    0.6319    4.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3015    0.2673    2.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9145    0.7104   -2.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3038    0.3570   -1.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6903    0.0782    1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1350   -1.1893    1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7477   -0.8181    1.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -0.0801   -3.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    0.0069   -3.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7098    1.0935   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5913    1.8110   -0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8137    2.6021    1.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4226    0.9897    2.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7519    1.8286   -0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1436   -0.3863    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8236   -1.0471   -1.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6951   -2.2643   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5767   -2.3644    1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3308   -1.7935   -0.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2434   -1.9339   -2.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 21 19  1  0
 19 20  1  0
 19 18  2  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  4  3  1  0
 14  8  1  0
 31 22  1  0
  5 18  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 22 44  1  6
 24 45  1  6
 25 46  1  0
 25 47  1  0
 26 48  1  0
 27 49  1  1
 28 50  1  0
 29 51  1  6
 30 52  1  0
 31 53  1  6
 32 54  1  0
 20 43  1  0
 15 42  1  0
  4 36  1  0
  9 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
M  END


  Mrv1652309052210492D          

 32 35  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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
    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 O   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 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
    5.0013    1.2375    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
    6.4302    1.2375    0.0000 O   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
    5.0013   -0.4125    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
    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 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
    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
    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  2  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
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  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  1  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
  7 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  3 21  2  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
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 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0210830

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O10/c1-30-13-7-14-16(11(25)6-12(31-14)9-2-4-10(24)5-3-9)19(27)17(13)22-21(29)20(28)18(26)15(8-23)32-22/h2-7,15,18,20-24,26-29H,8H2,1H3/t15-,18-,20+,21-,22+/m1/s1

> <INCHI_KEY>
ABRULANJVVJLFI-DGHBBABESA-N

> <FORMULA>
C22H22O10

> <MOLECULAR_WEIGHT>
446.408

> <EXACT_MASS>
446.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.618123100753266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.09526228466666686

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.731803084458539

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.925745368568145

> <JCHEM_PKA_STRONGEST_BASIC>
-2.97919262769486

> <JCHEM_POLAR_SURFACE_AREA>
166.14

> <JCHEM_REFRACTIVITY>
110.51449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

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

> <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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8                                                       
CONECT   15    7   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    5   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3   22                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
5,4'-Dihydroxy-7-methoxy-6-C-beta-D-glucopyranosyl flavonoside	ChEBI
6-beta-D-Glucopyranosyl-4',5-dihydroxy-7-methoxyflavone	ChEBI
6-beta-D-Glucopyranosyl-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one	ChEBI
6-C-Glucopyranosyl-7-O-methylapigenin	ChEBI
7-O-Methyl-6-C-beta-D-glucopyranosylapigenin	ChEBI
7-O-Methylapigenin 6-C-beta-D-glucopyranoside	ChEBI
Flavocommelitin	ChEBI
5,4'-Dihydroxy-7-methoxy-6-C-b-D-glucopyranosyl flavonoside	Generator
5,4'-Dihydroxy-7-methoxy-6-C-β-D-glucopyranosyl flavonoside	Generator
6-b-D-Glucopyranosyl-4',5-dihydroxy-7-methoxyflavone	Generator
6-Β-D-glucopyranosyl-4',5-dihydroxy-7-methoxyflavone	Generator
6-b-D-Glucopyranosyl-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one	Generator
6-Β-D-glucopyranosyl-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one	Generator
7-O-Methyl-6-C-b-D-glucopyranosylapigenin	Generator
7-O-Methyl-6-C-β-D-glucopyranosylapigenin	Generator
7-O-Methylapigenin 6-C-b-D-glucopyranoside	Generator
7-O-Methylapigenin 6-C-β-D-glucopyranoside	Generator

Chemical Formula

C₂₂H₂₂O₁₀

Average Mass

446.4080 Da

Monoisotopic Mass

446.12130 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C22H22O10/c1-30-13-7-14-16(11(25)6-12(31-14)9-2-4-10(24)5-3-9)19(27)17(13)22-21(29)20(28)18(26)15(8-23)32-22/h2-7,15,18,20-24,26-29H,8H2,1H3/t15-,18-,20+,21-,22+/m1/s1

InChI Key

ABRULANJVVJLFI-DGHBBABESA-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
Aleurites moluccanus	LOTUS Database	35616633
Alliaria petiolata	LOTUS Database	35616633
Aquilegia oxysepala	LOTUS Database	35616633
Cymophyllus fraseri	LOTUS Database	35616633
Echinodorus grandiflorus	LOTUS Database	35616633
Gaillardia aristata	LOTUS Database	35616633
Gaillardia pulchella	LOTUS Database	35616633
Galipea trifoliata	LOTUS Database	35616633
Gentiana algida	LOTUS Database	35616633
Gentiana brachyphylla	LOTUS Database	35616633
Gentianella austriaca	LOTUS Database	35616633
Gnetum gnemon	LOTUS Database	35616633
Iris germanica	LOTUS Database	35616633
Iris gracilipes	LOTUS Database	35616633
Justicia pectoralis	LOTUS Database	35616633
Justicia ramosa	LOTUS Database	35616633
Knautia montana	LOTUS Database	35616633
Lophatherum gracile	LOTUS Database	35616633
Machaerium isadelphum	LOTUS Database	35616633
Passiflora biflora	LOTUS Database	35616633
Passiflora incarnata	LOTUS Database	35616633
Saccharum officinarum	LOTUS Database	35616633
Swertia japonica	LOTUS Database	35616633
Swertia mussotii	LOTUS Database	35616633
Swertia paniculata	LOTUS Database	35616633
Swertia tetrapetala	LOTUS Database	35616633
Syzygium cumini	LOTUS Database	35616633
Triticum aestivum	LOTUS Database	35616633
Wilbrandia ebracteata	LOTUS Database	35616633
Ziziphus jujuba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-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 C-glycosides

Alternative Parents

Substituents

Flavonoid c-glycoside
7-methoxyflavonoid-skeleton
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
Chromone
C-glycosyl compound
1-benzopyran
Benzopyran
Anisole
Alkyl aryl ether
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
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	0.095	ChemAxon
pKa (Strongest Acidic)	6.93	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.51 m³·mol⁻¹	ChemAxon
Polarizability	44.62 Å³	ChemAxon
Number of Rings	4	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

C00006125

Chemspider ID

110548

KEGG Compound ID

C17835

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124034

PDB ID

Not Available

ChEBI ID

131838

Good Scents ID

Not Available

References

General References

Hu Y, Liu L, Wang Z, Jiang CP, Zhu Z, Li H, Zeng Q, Xue Y, Wu Y, Wang Y, Yi Y, Zhu H, Shen C, Liu Q: Network pharmacology, molecular docking and in vivo and in vitro experiments to explore the molecular mechanism of licorice green tea beverage to scavenge oxygen free radicals. J Food Biochem. 2022 Oct;46(10):e14315. doi: 10.1111/jfbc.14315. Epub 2022 Jul 19. [PubMed:35855584 ]
Sadeghi M, Miroliaei M, Ghanadian M: Inhibitory effect of flavonoid glycosides on digestive enzymes: In silico, in vitro, and in vivo studies. Int J Biol Macromol. 2022 Sep 30;217:714-730. doi: 10.1016/j.ijbiomac.2022.07.086. Epub 2022 Jul 14. [PubMed:35843397 ]
Liu H, Zhang X, Liu Y, Xin N, Deng Y, Li Y: Semen Ziziphi Spinosae attenuates blood-brain barrier dysfunction induced by lipopolysaccharide by targeting the FAK-DOCK180-Rac1-WAVE2-Arp3 signaling pathway. NPJ Sci Food. 2022 Jun 2;6(1):27. doi: 10.1038/s41538-022-00142-6. [PubMed:35655066 ]
Fernandes DC, Martins BP, Silva GPD, Fonseca END, Santos SVM, Velozo LSM, Gayer CRM, Sabino KCC, Coelho MGP: Echinodorus macrophyllus fraction with a high level of flavonoid inhibits peripheral and central mechanisms of nociception. J Tradit Complement Med. 2021 Jul 15;12(2):123-130. doi: 10.1016/j.jtcme.2021.07.001. eCollection 2022 Mar. [PubMed:35528477 ]
Zhu Y, Wang W, Liu Z, Jiang S, Tao Y, Jiang L, Mei L: Comprehensive screening and separation of cyclooxygenase-2 inhibitors from Pterocephalus hookeri by affinity solid-phase extraction coupled with preparative high-performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2021 Oct 15;1183:122981. doi: 10.1016/j.jchromb.2021.122981. Epub 2021 Oct 6. [PubMed:34634740 ]
LOTUS database [Link]

Showing NP-Card for 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one (NP0210830)

MOL for NP0210830 (5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one)

3D MOL for NP0210830 (5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one)

3D SDF for NP0210830 (5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one)

3D-SDF for NP0210830 (5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one)

PDB for NP0210830 (5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one)

3D PDB for NP0210830 (5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one)

SMILES for NP0210830 (5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one)

INCHI for NP0210830 (5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one)

Structure for NP0210830 (5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one)

3D Structure for NP0210830 (5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one)