NP-MRD: Showing NP-Card for 5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one (NP0289175)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Show more...Show more...

Record Information

Version

2.0

Created at

2022-09-09 19:14:18 UTC

Updated at

2022-09-09 19:14:18 UTC

NP-MRD ID

NP0289175

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Kaempferol-3-O-beta-D-glucopyranosyl-7-O-beta-D-glucopyranoside, also known as kaempferol-3,7- di-beta-D-glucopyranoside or paeonoside, 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. 5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one is found in Allium macrostemon, Allium victorialis, Brassica oleracea, Corydalis bungeana, Crocus sativus, Equisetum ramosissimum, Evolvulus alsinoides, Helichrysum arenarium, Lotus corniculatus, Maclura cochinchinensis, Paeonia lactiflora, Pelargonium graveolens, Pinalia floribunda and Wisteria floribunda. 5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one was first documented in 2009 (PMID: 19768983). Kaempferol-3-O-beta-D-glucopyranosyl-7-O-beta-D-glucopyranoside is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304022019463D          

 43 47  0  0  0  0            999 V2000
   -1.0728    3.9680    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1259    3.4129   -0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4896    5.2627    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5688    4.7262   -0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0563   -1.8759   -1.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0938    0.4915   -0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3473    0.4348    0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1736   -1.9147   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    2.9941   -0.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7510    5.6642    0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7620   -0.7181   -0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6788   -1.8374   -1.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108    0.5377   -0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7522   -0.9911    0.2760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7440   -1.9398    0.4689 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0206   -0.6269   -0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8640   -1.0433   -0.7509 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8295   -1.7202    1.9387 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3455   -0.6047   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3870   -1.8898   -1.8898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7325   -0.3170    2.3669 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0102   -1.3903   -2.2770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0790    0.6120    1.3287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3051    1.6938   -0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0548    0.5945   -0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0397   -1.6830   -1.1489 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1729   -0.1813    0.4988 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5404    1.1622    0.6924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9648   -2.7632    0.6761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2050    6.9682    0.5006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0448   -2.9979   -1.3058 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0307   -1.6078   -0.2536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9452   -2.5721    2.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9507   -1.6860   -0.9943 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2489   -1.9147   -2.9744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9354    0.2323    2.8110 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527   -2.1219   -3.4344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4750    1.6568    2.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1184   -0.6869   -0.9328 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490    1.6189   -0.3837 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7423   -1.8811    0.0435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8961   -1.1502   -0.2008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3986    0.4646   -0.5149 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  9  1  0  0  0  0
  2  4  1  0  0  0  0
  2  9  2  0  0  0  0
  3 10  1  0  0  0  0
  4 10  2  0  0  0  0
  5 11  2  0  0  0  0
  5 12  1  0  0  0  0
  6 11  1  0  0  0  0
  6 13  2  0  0  0  0
 14  7  1  6  0  0  0
  7 28  1  0  0  0  0
 15  8  1  6  0  0  0
  8 29  1  0  0  0  0
  9 24  1  0  0  0  0
 10 30  1  0  0  0  0
 11 39  1  0  0  0  0
 12 16  2  0  0  0  0
 12 31  1  0  0  0  0
 13 16  1  0  0  0  0
 13 40  1  0  0  0  0
 14 17  1  0  0  0  0
 14 41  1  0  0  0  0
 15 18  1  0  0  0  0
 15 42  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 17 32  1  1  0  0  0
 18 21  1  0  0  0  0
 18 33  1  1  0  0  0
 19 25  1  0  0  0  0
 19 34  2  0  0  0  0
 20 22  1  0  0  0  0
 20 35  1  6  0  0  0
 21 23  1  0  0  0  0
 21 36  1  6  0  0  0
 22 26  1  0  0  0  0
 22 37  1  6  0  0  0
 23 27  1  0  0  0  0
 23 38  1  1  0  0  0
 24 25  2  0  0  0  0
 24 40  1  0  0  0  0
 25 43  1  0  0  0  0
 26 39  1  1  0  0  0
 26 41  1  0  0  0  0
 27 42  1  0  0  0  0
 27 43  1  6  0  0  0
M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
   -1.9250    1.8701    1.7879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3165    0.9628    1.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0989   -0.0657    0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4765    0.0005    0.7476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2540    0.8678   -0.0504 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0152    1.7161    0.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2915    1.3259    0.9734 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4299    0.2657    2.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8026   -0.0380    2.1915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0747    0.8544   -0.2278 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2007    1.9358   -1.0948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3331   -0.2385   -0.9661 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4590   -1.4667   -0.3985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9366    0.2640   -1.1941 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1218    1.3481   -2.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4761   -1.0662   -0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1516   -2.1899   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4501   -2.9312   -1.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0703   -4.0430   -2.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260   -4.4622   -1.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8758   -5.5866   -2.3382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0278   -3.7233   -0.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3840   -2.6019   -0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1294   -1.0315   -0.1448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6295   -0.1045    0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9996   -0.1191    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532    0.8615    0.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1535    0.8438    0.6367 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3737    0.5010    0.3355 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2676    0.4452    1.3830 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5833    0.4762    1.1630 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1890    1.7298    1.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5471    1.7995    1.6334 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1108    0.3203   -0.1988 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8425   -0.8812   -0.3649 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1371    0.4217   -1.3135 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6870    0.8764   -2.5120 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9716    1.2763   -0.8665 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9680    1.1876   -1.8645 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2023    1.8974    1.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8353    1.9291    1.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1955    2.9639    2.2861 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0419    0.9370    1.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4664    1.5671   -0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8412    2.2108    1.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1077    0.6832    3.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9320   -0.6847    1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9862   -0.9984    2.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0504    0.4670    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9427    2.7970   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8146   -0.2983   -1.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6670   -2.2264   -0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3575   -0.4599   -1.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3281    1.9461   -2.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4565   -2.6221   -1.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5154   -4.6109   -2.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4428   -5.5385   -3.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0072   -3.9991   -0.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9871   -2.0830    0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4415   -0.9367   -0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3741   -0.5694   -0.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0336   -0.3617    1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9641    1.7453    2.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7084    2.6377    1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7678    2.6217    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8875    1.1138   -0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6369   -0.8536    0.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7238   -0.6194   -1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9196    0.8586   -3.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2208    2.3022   -0.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6377    0.2328   -1.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453    2.6688    1.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7798    3.6813    2.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
 33 32  1  0
 32 31  1  0
 31 30  1  0
 30 29  1  0
 29 28  1  0
 28 27  1  0
 27 40  2  0
 40 41  1  0
 41 42  1  0
 41 43  2  0
 43  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  3 16  2  0
 16 24  1  0
 24 25  1  0
 25 26  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 29 38  1  0
 38 39  1  0
 38 36  1  0
 36 37  1  0
 36 34  1  0
 34 35  1  0
 34 31  1  0
 26 27  1  0
 23 17  1  0
 25 43  1  0
 14  5  1  0
 33 65  1  0
 32 63  1  0
 32 64  1  0
 31 62  1  1
 29 61  1  6
 40 72  1  0
 42 73  1  0
  5 44  1  6
  7 45  1  1
  8 46  1  0
  8 47  1  0
  9 48  1  0
 10 49  1  1
 11 50  1  0
 12 51  1  6
 13 52  1  0
 14 53  1  6
 15 54  1  0
 26 60  1  0
 18 55  1  0
 19 56  1  0
 21 57  1  0
 22 58  1  0
 23 59  1  0
 38 70  1  1
 39 71  1  0
 36 68  1  6
 37 69  1  0
 34 66  1  6
 35 67  1  0
M  END

  Mrv1652304022019463D          

 43 47  0  0  0  0            999 V2000
   -1.0728    3.9680    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1259    3.4129   -0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4896    5.2627    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5688    4.7262   -0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0563   -1.8759   -1.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0938    0.4915   -0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3473    0.4348    0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1736   -1.9147   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    2.9941   -0.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7510    5.6642    0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7620   -0.7181   -0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6788   -1.8374   -1.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108    0.5377   -0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7522   -0.9911    0.2760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7440   -1.9398    0.4689 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0206   -0.6269   -0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8640   -1.0433   -0.7509 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8295   -1.7202    1.9387 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3455   -0.6047   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3870   -1.8898   -1.8898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7325   -0.3170    2.3669 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0102   -1.3903   -2.2770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0790    0.6120    1.3287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3051    1.6938   -0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0548    0.5945   -0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0397   -1.6830   -1.1489 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1729   -0.1813    0.4988 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5404    1.1622    0.6924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9648   -2.7632    0.6761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2050    6.9682    0.5006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0448   -2.9979   -1.3058 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0307   -1.6078   -0.2536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9452   -2.5721    2.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9507   -1.6860   -0.9943 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2489   -1.9147   -2.9744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9354    0.2323    2.8110 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527   -2.1219   -3.4344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4750    1.6568    2.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1184   -0.6869   -0.9328 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490    1.6189   -0.3837 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7423   -1.8811    0.0435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8961   -1.1502   -0.2008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3986    0.4646   -0.5149 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  9  1  0  0  0  0
  2  4  1  0  0  0  0
  2  9  2  0  0  0  0
  3 10  1  0  0  0  0
  4 10  2  0  0  0  0
  5 11  2  0  0  0  0
  5 12  1  0  0  0  0
  6 11  1  0  0  0  0
  6 13  2  0  0  0  0
 14  7  1  6  0  0  0
  7 28  1  0  0  0  0
 15  8  1  6  0  0  0
  8 29  1  0  0  0  0
  9 24  1  0  0  0  0
 10 30  1  0  0  0  0
 11 39  1  0  0  0  0
 12 16  2  0  0  0  0
 12 31  1  0  0  0  0
 13 16  1  0  0  0  0
 13 40  1  0  0  0  0
 14 17  1  0  0  0  0
 14 41  1  0  0  0  0
 15 18  1  0  0  0  0
 15 42  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 17 32  1  1  0  0  0
 18 21  1  0  0  0  0
 18 33  1  1  0  0  0
 19 25  1  0  0  0  0
 19 34  2  0  0  0  0
 20 22  1  0  0  0  0
 20 35  1  6  0  0  0
 21 23  1  0  0  0  0
 21 36  1  6  0  0  0
 22 26  1  0  0  0  0
 22 37  1  6  0  0  0
 23 27  1  0  0  0  0
 23 38  1  1  0  0  0
 24 25  2  0  0  0  0
 24 40  1  0  0  0  0
 25 43  1  0  0  0  0
 26 39  1  1  0  0  0
 26 41  1  0  0  0  0
 27 42  1  0  0  0  0
 27 43  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0289175

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O16/c28-7-14-17(32)20(35)22(37)26(41-14)39-11-5-12(31)16-13(6-11)40-24(9-1-3-10(30)4-2-9)25(19(16)34)43-27-23(38)21(36)18(33)15(8-29)42-27/h1-6,14-15,17-18,20-23,26-33,35-38H,7-8H2/t14-,15-,17-,18-,20+,21+,22-,23-,26-,27+/m1/s1

> <INCHI_KEY>
XFFQVRFGLSBFON-DEFKTLOSSA-N

> <FORMULA>
C27H30O16

> <MOLECULAR_WEIGHT>
610.5175

> <EXACT_MASS>
610.153384912

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
58.085259432611714

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.69

> <JCHEM_LOGP>
-2.1093380676666666

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.556773586700253

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.083346792151727

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483953457595923

> <JCHEM_POLAR_SURFACE_AREA>
265.52

> <JCHEM_REFRACTIVITY>
139.43899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.81e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0      -1.073   3.968   0.502  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.126   3.413  -0.447  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.490   5.263   0.696  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.569   4.726  -0.257  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.056  -1.876  -1.127  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.094   0.492  -0.654  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.347   0.435   0.461  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.174  -1.915  -0.092  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.890   2.994  -0.083  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.751   5.664   0.318  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.762  -0.718  -0.910  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.679  -1.837  -1.089  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.711   0.538  -0.615  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.752  -0.991   0.276  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.744  -1.940   0.469  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.021  -0.627  -0.833  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.864  -1.043  -0.751  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.830  -1.720   1.939  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.345  -0.605  -0.792  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.387  -1.890  -1.890  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.732  -0.317   2.367  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.010  -1.390  -2.277  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.079   0.612   1.329  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.305   1.694  -0.337  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.055   0.595  -0.531  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.040  -1.683  -1.149  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.173  -0.181   0.499  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.540   1.162   0.692  0.00  0.00           O+0
HETATM   29  O   UNK     0      -7.965  -2.763   0.676  0.00  0.00           O+0
HETATM   30  O   UNK     0      -3.205   6.968   0.501  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.045  -2.998  -1.306  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.031  -1.608  -0.254  0.00  0.00           O+0
HETATM   33  O   UNK     0      -4.945  -2.572   2.647  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.951  -1.686  -0.994  0.00  0.00           O+0
HETATM   35  O   UNK     0       8.249  -1.915  -2.974  0.00  0.00           O+0
HETATM   36  O   UNK     0      -6.935   0.232   2.811  0.00  0.00           O+0
HETATM   37  O   UNK     0       5.653  -2.122  -3.434  0.00  0.00           O+0
HETATM   38  O   UNK     0      -4.475   1.657   2.060  0.00  0.00           O+0
HETATM   39  O   UNK     0       4.118  -0.687  -0.933  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.049   1.619  -0.384  0.00  0.00           O+0
HETATM   41  O   UNK     0       5.742  -1.881   0.044  0.00  0.00           O+0
HETATM   42  O   UNK     0      -4.896  -1.150  -0.201  0.00  0.00           O+0
HETATM   43  O   UNK     0      -3.399   0.465  -0.515  0.00  0.00           O+0
CONECT    1    3    9                                                       
CONECT    2    4    9                                                       
CONECT    3    1   10                                                       
CONECT    4    2   10                                                       
CONECT    5   11   12                                                       
CONECT    6   11   13                                                       
CONECT    7   14   28                                                       
CONECT    8   15   29                                                       
CONECT    9    1    2   24                                                  
CONECT   10    3    4   30                                                  
CONECT   11    5    6   39                                                  
CONECT   12    5   16   31                                                  
CONECT   13    6   16   40                                                  
CONECT   14    7   17   41                                                  
CONECT   15    8   18   42                                                  
CONECT   16   12   13   19                                                  
CONECT   17   14   20   32                                                  
CONECT   18   15   21   33                                                  
CONECT   19   16   25   34                                                  
CONECT   20   17   22   35                                                  
CONECT   21   18   23   36                                                  
CONECT   22   20   26   37                                                  
CONECT   23   21   27   38                                                  
CONECT   24    9   25   40                                                  
CONECT   25   19   24   43                                                  
CONECT   26   22   39   41                                                  
CONECT   27   23   42   43                                                  
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30   10                                                            
CONECT   31   12                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
CONECT   34   19                                                            
CONECT   35   20                                                            
CONECT   36   21                                                            
CONECT   37   22                                                            
CONECT   38   23                                                            
CONECT   39   11   26                                                       
CONECT   40   13   24                                                       
CONECT   41   14   26                                                       
CONECT   42   15   27                                                       
CONECT   43   25   27                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
3,7-Bis(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
Kaempferol-3,7- di-beta-D-glucopyranoside	ChEBI
Paeonoside	ChEBI
3,7-Bis(b-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	Generator
3,7-Bis(β-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	Generator
Kaempferol-3,7- di-b-D-glucopyranoside	Generator
Kaempferol-3,7- di-β-D-glucopyranoside	Generator
Kaempferol-3-O-b-D-glucopyranosyl-7-O-b-D-glucopyranoside	Generator
Kaempferol-3-O-β-D-glucopyranosyl-7-O-β-D-glucopyranoside	Generator

Chemical Formula

C₂₇H₃₀O₁₆

Average Mass

610.5175 Da

Monoisotopic Mass

610.15338 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H30O16/c28-7-14-17(32)20(35)22(37)26(41-14)39-11-5-12(31)16-13(6-11)40-24(9-1-3-10(30)4-2-9)25(19(16)34)43-27-23(38)21(36)18(33)15(8-29)42-27/h1-6,14-15,17-18,20-23,26-33,35-38H,7-8H2/t14-,15-,17-,18-,20+,21+,22-,23-,26-,27+/m1/s1

InChI Key

XFFQVRFGLSBFON-DEFKTLOSSA-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
Allium macrostemon	LOTUS Database	35616633
Allium victorialis	LOTUS Database	35616633
Brassica oleracea	LOTUS Database	35616633
Corydalis bungeana	LOTUS Database	35616633
Crocus sativus	LOTUS Database	35616633
Equisetum ramosissimum	LOTUS Database	35616633
Evolvulus alsinoides	LOTUS Database	35616633
Helichrysum arenarium	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Maclura cochinchinensis	LOTUS Database	35616633
Paeonia lactiflora	LOTUS Database	35616633
Pelargonium graveolens	LOTUS Database	35616633
Pinalia floribunda	LOTUS Database	35616633
Wisteria floribunda	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-3-o-glycoside
Flavonoid-7-o-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
Benzopyran
1-benzopyran
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyran
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:67928 )
dihydroxyflavone (CHEBI:67928 )
kaempferol O-glucoside (CHEBI:67928 )

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	-0.69	ALOGPS
logP	-2.1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.08	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	265.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	139.44 m³·mol⁻¹	ChemAxon
Polarizability	58.09 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

6325460

PDB ID

Not Available

ChEBI ID

67928

Good Scents ID

Not Available

References

General References

Ivanova A, Mikhova B, Najdenski H, Tsvetkova I, Kostova I: Chemical composition and antimicrobial activity of wild garlic Allium ursinum of Bulgarian origin. Nat Prod Commun. 2009 Aug;4(8):1059-62. [PubMed:19768983 ]
LOTUS database [Link]

Showing NP-Card for 5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one (NP0289175)

MOL for NP0289175 (5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one)

3D MOL for NP0289175 (5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one)

3D SDF for NP0289175 (5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one)

3D-SDF for NP0289175 (5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one)

PDB for NP0289175 (5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one)

3D PDB for NP0289175 (5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one)

SMILES for NP0289175 (5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one)

INCHI for NP0289175 (5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one)

Structure for NP0289175 (5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one)

3D Structure for NP0289175 (5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})chromen-4-one)