NP-MRD: Showing NP-Card for Apigenin 7-O-glucuronide (NP0045253)

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Record Information

Version

2.0

Created at

2022-03-17 19:16:42 UTC

Updated at

2022-03-17 19:16:42 UTC

NP-MRD ID

NP0045253

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apigenin 7-O-glucuronide

Description

Apigenin 7-glucuronide belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Apigenin 7-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Apigenin 7-glucuronide is found, on average, in the highest concentration within globe artichokes. Apigenin 7-O-glucuronide is found in Acanthus ebracteatus, Acanthus ilicifolius, Agrimonia eupatoria, Antirrhinum majus, Aster koraiensis, Bellis perennis , Broussonetia papyrifera, Callicarpa japonica Thunb.var.luxurians Rehd., Centaurea aspera, Centaurea bracteata, Chaenomeles sinensis, Chamaemelum nobile, Chrysanthemum morifolium, Leucanthemum vulgare , Clinopodium umbrosum, Cynara cardunculus, Echinop ritro, Erigeron annuus, Fernandoa adenophylla, Fuchsia excorticata , Fuchsia procumbens, Galeopsis angustifolia, Glechoma hederacea L. , Hyssopus officinalis, Jacaranda mimosifolia, Keiskea japonica, Lippia alba , Lycopus virginicus, Marchantia berteroana, Medicago polymorpha, Medicago sativa, Medicago truncatula, Meehania fargesii, Meehania urticifolia, Millingtonia hortensis, Monarda punctata, Ocimum tenuiflorum, Onopordum illyricum, Origanum vulgare, Pedicularis longiflora, Phlomoides tuberosa, Picria fel-terrae , Riccia fluitans L, Salvia fruticosa, Salvia palaestina, Salvia triloba , Santolina chamaecyperissus, Scutellaria alpina, Scutellaria galericulata, Scutellaria indica, Strobilanthes crispus , Tanacetum parthenium, Tanacetum parthenium (L.) Schulz Bip. , Thalictrum thunbergii, Torilis arvensis and Veronica spicata. This could make apigenin 7-glucuronide a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310081920332D          

 37 40  0  0  1  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    4.2868    0.8250    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
    6.4302   -1.2375    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    1.2375    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  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   -2.8875    0.0000 C   0  0  1  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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  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
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  6  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 19 20  1  1  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  2  0  0  0  0
 16 25  1  6  0  0  0
 17 26  1  1  0  0  0
 18 27  1  1  0  0  0
 28 20  2  0  0  0  0
 29 20  1  0  0  0  0
 30 10  1  0  0  0  0
 21 30  1  6  0  0  0
 31 13  1  0  0  0  0
 31 14  1  0  0  0  0
 32 19  1  0  0  0  0
 32 21  1  0  0  0  0
 16 33  1  1  0  0  0
 17 34  1  6  0  0  0
 18 35  1  6  0  0  0
 19 36  1  1  0  0  0
 21 37  1  1  0  0  0
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -5.0402   -3.1953   -1.3536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5990   -2.3406   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7887   -2.6238    0.0281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9535   -1.0178   -0.4642 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7694   -0.9336   -1.1952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0700    0.1650   -0.6681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7264    0.1491   -0.9897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7046    0.0613   -0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8460   -0.0229    1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2253   -0.1109    2.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0581   -0.1884    3.5104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4894   -0.1123    1.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176   -0.1950    2.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5019   -0.2715    3.7134 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8504   -0.1878    1.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0155   -0.1042    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3267   -0.0968   -0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4033   -0.0092   -1.5501 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6150    0.0009   -2.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8046   -0.0770   -1.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0136   -0.0684   -2.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7459   -0.1645   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5086   -0.1733    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9260   -0.0284   -0.2127 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6968   -0.0292    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203    0.0555   -0.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7511    1.4566   -1.0940 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5505    2.4331   -0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1802    1.2831   -1.4484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3208    1.3446   -2.8541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8525    0.0968   -0.8659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6841    0.4415    0.2250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6732   -2.6604   -0.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6577   -0.8848    0.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2139    0.0984    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8409   -0.0239    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5051   -0.2538    4.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7312   -0.2525    2.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5101    0.0529   -2.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6850    0.0691   -3.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8732   -0.1240   -1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6833   -0.2247    0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5204   -0.2429    1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7810    0.1202   -1.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1680    1.8123   -1.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5132    2.0718    0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7321    2.1976   -1.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2499    2.2756   -3.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5643   -0.3105   -1.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1420    0.7431    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 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
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  4 31  1  0
 31 32  1  0
 31 29  1  0
 29 30  1  0
 29 27  1  0
 27 28  1  0
 27  6  1  0
 26  8  1  0
 23 17  1  0
 25 12  1  0
  6 35  1  1
  9 36  1  0
 11 37  1  0
 15 38  1  0
 26 44  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
  4 34  1  1
  3 33  1  0
 31 49  1  6
 32 50  1  0
 29 47  1  1
 30 48  1  0
 27 45  1  6
 28 46  1  0
M  END


  Mrv1652310081920332D          

 37 40  0  0  1  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    4.2868    0.8250    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
    6.4302   -1.2375    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    1.2375    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  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   -2.8875    0.0000 C   0  0  1  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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  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
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  6  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 19 20  1  1  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  2  0  0  0  0
 16 25  1  6  0  0  0
 17 26  1  1  0  0  0
 18 27  1  1  0  0  0
 28 20  2  0  0  0  0
 29 20  1  0  0  0  0
 30 10  1  0  0  0  0
 21 30  1  6  0  0  0
 31 13  1  0  0  0  0
 31 14  1  0  0  0  0
 32 19  1  0  0  0  0
 32 21  1  0  0  0  0
 16 33  1  1  0  0  0
 17 34  1  6  0  0  0
 18 35  1  6  0  0  0
 19 36  1  1  0  0  0
 21 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0045253

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O11/c22-9-3-1-8(2-4-9)13-7-12(24)15-11(23)5-10(6-14(15)31-13)30-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21-23,25-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1

> <INCHI_KEY>
JBFOLLJCGUCDQP-ZFORQUDYSA-N

> <FORMULA>
C21H18O11

> <MOLECULAR_WEIGHT>
446.361

> <EXACT_MASS>
446.084911418

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
41.804929980311336

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
0.7588955783333331

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.29767661727884

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.739209987804226

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686826778068572

> <JCHEM_POLAR_SURFACE_AREA>
183.21

> <JCHEM_REFRACTIVITY>
104.92569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-19         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       0.000  -6.160   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.667  -6.160   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.334  -3.850   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5   10   11                                                       
CONECT    6   10   14                                                       
CONECT    7   12   13                                                       
CONECT    8    1    2   13                                                  
CONECT    9    3    4   22                                                  
CONECT   10    5    6   30                                                  
CONECT   11    5   15   23                                                  
CONECT   12    7   15   24                                                  
CONECT   13    7    8   31                                                  
CONECT   14    6   15   31                                                  
CONECT   15   11   12   14                                                  
CONECT   16   17   18   25   33                                             
CONECT   17   16   19   26   34                                             
CONECT   18   16   21   27   35                                             
CONECT   19   17   20   32   36                                             
CONECT   20   19   28   29                                                  
CONECT   21   18   30   32   37                                             
CONECT   22    9                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
CONECT   25   16                                                            
CONECT   26   17                                                            
CONECT   27   18                                                            
CONECT   28   20                                                            
CONECT   29   20                                                            
CONECT   30   10   21                                                       
CONECT   31   13   14                                                       
CONECT   32   19   21                                                       
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   18                                                            
CONECT   36   19                                                            
CONECT   37   21                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
Apigenin-7-O-beta-D-glucuronide	MeSH
Apigenin-7-O-glucuronide	MeSH

Chemical Formula

C₂₁H₁₈O₁₁

Average Mass

446.3610 Da

Monoisotopic Mass

446.08491 Da

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H18O11/c22-9-3-1-8(2-4-9)13-7-12(24)15-11(23)5-10(6-14(15)31-13)30-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21-23,25-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1

InChI Key

JBFOLLJCGUCDQP-ZFORQUDYSA-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
Acanthus ebracteatus	Plant	KNApSAcK
Acanthus ilicifolius	LOTUS Database	35616633
Agrimonia eupatoria	LOTUS Database	35616633
Antirrhinum majus	LOTUS Database	35616633
Aster koraiensis	LOTUS Database	35616633
Bellis perennis	Plant	KNApSAcK
Broussonetia papyrifera	LOTUS Database	35616633
Callicarpa japonica Thunb.var.luxurians Rehd.	Plant	KNApSAcK
Centaurea aspera	LOTUS Database	35616633
Centaurea bracteata	LOTUS Database	35616633
Chaenomeles sinensis	LOTUS Database	35616633
Chamaemelum nobile	LOTUS Database	35616633
Chrysanthemum morifolium	LOTUS Database	35616633
Chrysanthemum vulgare	Plant	KNApSAcK
Clinopodium umbrosum	LOTUS Database	35616633
Cynara cardunculus	LOTUS Database	35616633
Cynara scolymus	FooDB	PHENOL EXPLORER
Echinop ritro	-	KNApSAcK
Erigeron annuus	LOTUS Database	35616633
Fernandoa adenophylla	Plant	KNApSAcK
Fuchsia excorticata	Plant	KNApSAcK
Fuchsia procumbens	Plant	KNApSAcK
Galeopsis angustifolia	LOTUS Database	35616633
Glechoma hederacea	Plant	KNApSAcK
Hyssopus officinalis L.	LOTUS Database	35616633
Jacaranda mimosifolia	LOTUS Database	35616633
Keiskea japonica	LOTUS Database	35616633
Lippia alba	Plant	KNApSAcK
Lycopus virginicus	LOTUS Database	35616633
Marchantia berteroana	Plant	KNApSAcK
Medicago polymorpha	LOTUS Database	35616633
Medicago sativa	LOTUS Database	35616633
Medicago truncatula	LOTUS Database	35616633
Meehania fargesii	LOTUS Database	35616633
Meehania urticifolia	LOTUS Database	35616633
Millingtonia hortensis	LOTUS Database	35616633
Monarda punctata	LOTUS Database	35616633
Ocimum tenuiflorum	LOTUS Database	35616633
Onopordum illyricum	LOTUS Database	35616633
Origanum vulgare	LOTUS Database	35616633
Pedicularis longiflora	LOTUS Database	35616633
Phlomoides tuberosa	LOTUS Database	35616633
Picria fel-terrae	Plant	KNApSAcK
Riccia fluitans L	Plant	KNApSAcK
Salvia fruticosa	LOTUS Database	35616633
Salvia palaestina	LOTUS Database	35616633
Salvia triloba	Plant	KNApSAcK
Santolina chamaecyperissus	Plant	KNApSAcK
Scutellaria alpina	LOTUS Database	35616633
Scutellaria galericulata	LOTUS Database	35616633
Scutellaria indica	LOTUS Database	35616633
Strobilanthes crispus	Plant	KNApSAcK
Tanacetum parthenium	LOTUS Database	35616633
Tanacetum parthenium (L.) Schulz Bip.	Plant	KNApSAcK
Thalictrum minus var. hypoleucum	Plant	KNApSAcK
Torilis arvensis	LOTUS Database	35616633
Veronica spicata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
2-heteroaryl carboxamide
Furoic acid or derivatives
Furan
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Organopnictogen compound
Aromatic alcohol
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.03	ALOGPS
logP	0.76	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.74	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.93 m³·mol⁻¹	ChemAxon
Polarizability	41.8 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

HMDB0240480

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000138

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

5319484

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Apigenin 7-O-glucuronide (NP0045253)

MOL for NP0045253 (Apigenin 7-O-glucuronide)

3D MOL for NP0045253 (Apigenin 7-O-glucuronide)

3D SDF for NP0045253 (Apigenin 7-O-glucuronide)

3D-SDF for NP0045253 (Apigenin 7-O-glucuronide)

PDB for NP0045253 (Apigenin 7-O-glucuronide)

3D PDB for NP0045253 (Apigenin 7-O-glucuronide)

SMILES for NP0045253 (Apigenin 7-O-glucuronide)

INCHI for NP0045253 (Apigenin 7-O-glucuronide)

Structure for NP0045253 (Apigenin 7-O-glucuronide)

3D Structure for NP0045253 (Apigenin 7-O-glucuronide)