NP-MRD: Showing NP-Card for Avicularin (NP0043848)

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Record Information

Version

1.0

Created at

2021-06-22 17:25:36 UTC

Updated at

2021-08-20 00:00:45 UTC

NP-MRD ID

NP0043848

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Avicularin

Description

Avicularin belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Thus, avicularin is considered to be a flavonoid. Avicularin 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. Avicularin is found in Alhagi persarum, Asplenium viride, Astilbe arendsii, Aureolaria virginica, Berchemia floribunda, Betula pubescens, Bistorta officinalis, Bupleurum falcatum, Bursera graveolens, Camellia sinensis, Caragana spinosa, Chaenomeles sinensis, Chimaphila umbellata, Cinnamomum philippinense, Coriaria ruscifolia, Cosmos sulphureus, Crataegus rhipidophylla, Elliottia paniculata, Empetrum nigrum, Eugenia myrcianthes, Euphorbia maculata, Filipendula ulmaria, Geranium pusillum, Hedysarum alpinum, Hedysarum gmelinii, Hedysarum sachalinense, Hypericum hyssopifolium, Hypericum maculatum, Hypericum perforatum, Hypericum sikokumontanum, Japonolirion osense, Koenigia coriaria, Koenigia divaricata, Laserpitium latifolium, Malus sylvestris, Mangifera indica , Mimosa pudica, Myriophyllum aquaticum, Phoebe formosana, Polygonum cuspidatum , Fallopia sachalinensis, Polygonum sachalinensis, Polygonum scabrum, Prunus salicina, Pyrola elliptica, Rhododendron brachycarpum, Rhododendron dauricum, Rhododendron schlippenbachii, Rhododendron spinuliferum, Rodgersia podophylla, Rosa canina, Rosa rugosa, Rumex acetosa, Rumex crispus, Saxifraga tricuspidata, Sorbus intermedia, Tapirira guianensis , Pleroma semidecandrum, Vaccinium ovalifolium and Viscum album. It was first documented in 1987 (PMID: 17269066). Based on a literature review a significant number of articles have been published on avicularin (PMID: 27719955) (PMID: 12787957) (PMID: 14600382) (PMID: 17177509).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306222119252D          

 31 34  0  0  1  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.1434   -1.2375    0.0000 C   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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6674    1.3099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4125    2.0945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4125    2.0945    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6674    1.3099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974    2.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5619    3.5157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974    2.7620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521    1.0550    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
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 14 18  1  0  0  0  0
 12 19  1  0  0  0  0
  8 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 24 26  1  6  0  0  0
 26 27  1  0  0  0  0
 23 28  1  1  0  0  0
 22 29  1  6  0  0  0
  4 30  1  0  0  0  0
  3 31  1  0  0  0  0
M  END

NP0043848
     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
   -0.1000   -2.9721   -0.0072 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911   -2.1048   -0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029   -0.8073   -0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093   -0.5731   -0.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446   -0.2371    0.1594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6524   -1.2988    0.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7701   -0.7961    0.8978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7787   -0.9773    2.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9069   -0.4684    2.9917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9132    0.6284    0.4702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9873    0.8257   -0.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870    0.9201   -0.1906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0712    2.1404    0.2818 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5273    0.0819   -0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3725    1.4703   -1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864    2.3714   -0.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3530    3.6702   -1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753    4.1521   -1.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2830    5.4756   -2.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2657    3.2564   -2.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8289    3.6474   -2.9691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156    1.9282   -1.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7494   -0.3059   -0.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720   -1.4777    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537   -1.8352    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6727   -3.0947    1.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9835   -3.4351    1.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6801   -4.0428    1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3904   -3.7079    0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3557   -4.6373    0.8005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732   -2.4432    0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2212   -0.0629    1.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6606   -1.3506    0.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8001   -2.0938    2.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8651   -0.6117    2.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6585   -0.3116    2.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0001    1.3067    1.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6192    1.4709    0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7542    0.9903   -1.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3488    2.8281   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2310    1.9889   -0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741    4.3256   -0.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5246    5.8414   -2.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    4.5712   -3.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985    1.2829   -2.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1448   -1.0988    0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6102   -3.8041    0.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9274   -5.0423    1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878   -5.5834    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  3 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 14 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31  2  1  0
 12  5  1  0
 22 15  1  0
 31 24  1  0
  5 32  1  1
  7 33  1  6
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  1
 11 38  1  0
 12 39  1  6
 13 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
 25 46  1  0
 27 47  1  0
 28 48  1  0
 30 49  1  0
M  END


  Mrv1652306222119252D          

 31 34  0  0  1  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.1434   -1.2375    0.0000 C   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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6674    1.3099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4125    2.0945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4125    2.0945    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6674    1.3099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974    2.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5619    3.5157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974    2.7620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521    1.0550    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
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 14 18  1  0  0  0  0
 12 19  1  0  0  0  0
  8 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 24 26  1  6  0  0  0
 26 27  1  0  0  0  0
 23 28  1  1  0  0  0
 22 29  1  6  0  0  0
  4 30  1  0  0  0  0
  3 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043848

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20-/m0/s1

> <INCHI_KEY>
BDCDNTVZSILEOY-UXYNSRGZSA-N

> <FORMULA>
C20H18O11

> <MOLECULAR_WEIGHT>
434.353

> <EXACT_MASS>
434.0849114

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
41.05455230130117

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
0.76

> <JCHEM_LOGP>
0.4854996460000001

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.872523610896667

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.372405621031869

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981152416465515

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
103.31299999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
avicularin

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043848
     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
   -0.1000   -2.9721   -0.0072 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911   -2.1048   -0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029   -0.8073   -0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093   -0.5731   -0.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446   -0.2371    0.1594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6524   -1.2988    0.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7701   -0.7961    0.8978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7787   -0.9773    2.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9069   -0.4684    2.9917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9132    0.6284    0.4702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9873    0.8257   -0.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870    0.9201   -0.1906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0712    2.1404    0.2818 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5273    0.0819   -0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3725    1.4703   -1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864    2.3714   -0.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3530    3.6702   -1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753    4.1521   -1.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2830    5.4756   -2.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2657    3.2564   -2.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8289    3.6474   -2.9691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156    1.9282   -1.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7494   -0.3059   -0.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720   -1.4777    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537   -1.8352    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6727   -3.0947    1.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9835   -3.4351    1.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6801   -4.0428    1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3904   -3.7079    0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3557   -4.6373    0.8005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732   -2.4432    0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2212   -0.0629    1.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6606   -1.3506    0.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8001   -2.0938    2.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8651   -0.6117    2.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6585   -0.3116    2.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0001    1.3067    1.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6192    1.4709    0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7542    0.9903   -1.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3488    2.8281   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2310    1.9889   -0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741    4.3256   -0.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5246    5.8414   -2.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    4.5712   -3.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985    1.2829   -2.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1448   -1.0988    0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6102   -3.8041    0.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9274   -5.0423    1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878   -5.5834    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  3 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 14 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31  2  1  0
 12  5  1  0
 22 15  1  0
 31 24  1  0
  5 32  1  1
  7 33  1  6
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  1
 11 38  1  0
 12 39  1  6
 13 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
 25 46  1  0
 27 47  1  0
 28 48  1  0
 30 49  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.246   2.445   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.770   3.910   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.770   3.910   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.246   2.445   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.675   5.156   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.049   6.563   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.675   5.156   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -2.711   1.969   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16    7                                                       
CONECT   18   14                                                            
CONECT   19   12                                                            
CONECT   20    8   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   21                                                       
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   23                                                            
CONECT   29   22                                                            
CONECT   30    4                                                            
CONECT   31    3                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    NP0043848
HETATM    1  O1  UNL     1      -0.100  -2.972  -0.007  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.791  -2.105  -0.080  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.503  -0.807  -0.530  1.00  0.00           C  
HETATM    4  O2  UNL     1      -0.809  -0.573  -0.868  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.745  -0.237   0.159  1.00  0.00           C  
HETATM    6  O3  UNL     1      -2.652  -1.299   0.298  1.00  0.00           O  
HETATM    7  C4  UNL     1      -3.770  -0.796   0.898  1.00  0.00           C  
HETATM    8  C5  UNL     1      -3.779  -0.977   2.398  1.00  0.00           C  
HETATM    9  O4  UNL     1      -4.907  -0.468   2.992  1.00  0.00           O  
HETATM   10  C6  UNL     1      -3.913   0.628   0.470  1.00  0.00           C  
HETATM   11  O5  UNL     1      -4.987   0.826  -0.393  1.00  0.00           O  
HETATM   12  C7  UNL     1      -2.587   0.920  -0.191  1.00  0.00           C  
HETATM   13  O6  UNL     1      -2.071   2.140   0.282  1.00  0.00           O  
HETATM   14  C8  UNL     1       1.527   0.082  -0.586  1.00  0.00           C  
HETATM   15  C9  UNL     1       1.372   1.470  -1.044  1.00  0.00           C  
HETATM   16  C10 UNL     1       2.386   2.371  -0.778  1.00  0.00           C  
HETATM   17  C11 UNL     1       2.353   3.670  -1.220  1.00  0.00           C  
HETATM   18  C12 UNL     1       1.275   4.152  -1.972  1.00  0.00           C  
HETATM   19  O7  UNL     1       1.283   5.476  -2.398  1.00  0.00           O  
HETATM   20  C13 UNL     1       0.266   3.256  -2.238  1.00  0.00           C  
HETATM   21  O8  UNL     1      -0.829   3.647  -2.969  1.00  0.00           O  
HETATM   22  C14 UNL     1       0.316   1.928  -1.778  1.00  0.00           C  
HETATM   23  O9  UNL     1       2.749  -0.306  -0.210  1.00  0.00           O  
HETATM   24  C15 UNL     1       3.072  -1.478   0.211  1.00  0.00           C  
HETATM   25  C16 UNL     1       4.354  -1.835   0.590  1.00  0.00           C  
HETATM   26  C17 UNL     1       4.673  -3.095   1.037  1.00  0.00           C  
HETATM   27  O10 UNL     1       5.984  -3.435   1.417  1.00  0.00           O  
HETATM   28  C18 UNL     1       3.680  -4.043   1.113  1.00  0.00           C  
HETATM   29  C19 UNL     1       2.390  -3.708   0.739  1.00  0.00           C  
HETATM   30  O11 UNL     1       1.356  -4.637   0.801  1.00  0.00           O  
HETATM   31  C20 UNL     1       2.073  -2.443   0.291  1.00  0.00           C  
HETATM   32  H1  UNL     1      -1.221  -0.063   1.141  1.00  0.00           H  
HETATM   33  H2  UNL     1      -4.661  -1.351   0.496  1.00  0.00           H  
HETATM   34  H3  UNL     1      -3.800  -2.094   2.568  1.00  0.00           H  
HETATM   35  H4  UNL     1      -2.865  -0.612   2.880  1.00  0.00           H  
HETATM   36  H5  UNL     1      -5.658  -0.312   2.397  1.00  0.00           H  
HETATM   37  H6  UNL     1      -4.000   1.307   1.367  1.00  0.00           H  
HETATM   38  H7  UNL     1      -5.619   1.471   0.043  1.00  0.00           H  
HETATM   39  H8  UNL     1      -2.754   0.990  -1.307  1.00  0.00           H  
HETATM   40  H9  UNL     1      -2.349   2.828  -0.376  1.00  0.00           H  
HETATM   41  H10 UNL     1       3.231   1.989  -0.185  1.00  0.00           H  
HETATM   42  H11 UNL     1       3.174   4.326  -0.980  1.00  0.00           H  
HETATM   43  H12 UNL     1       0.525   5.841  -2.936  1.00  0.00           H  
HETATM   44  H13 UNL     1      -0.927   4.571  -3.324  1.00  0.00           H  
HETATM   45  H14 UNL     1      -0.498   1.283  -2.045  1.00  0.00           H  
HETATM   46  H15 UNL     1       5.145  -1.099   0.536  1.00  0.00           H  
HETATM   47  H16 UNL     1       6.610  -3.804   0.710  1.00  0.00           H  
HETATM   48  H17 UNL     1       3.927  -5.042   1.466  1.00  0.00           H  
HETATM   49  H18 UNL     1       1.488  -5.583   1.114  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   31
CONECT    3    4   14   14
CONECT    4    5
CONECT    5    6   12   32
CONECT    6    7
CONECT    7    8   10   33
CONECT    8    9   34   35
CONECT    9   36
CONECT   10   11   12   37
CONECT   11   38
CONECT   12   13   39
CONECT   13   40
CONECT   14   15   23
CONECT   15   16   16   22
CONECT   16   17   41
CONECT   17   18   18   42
CONECT   18   19   20
CONECT   19   43
CONECT   20   21   22   22
CONECT   21   44
CONECT   22   45
CONECT   23   24
CONECT   24   25   25   31
CONECT   25   26   46
CONECT   26   27   28   28
CONECT   27   47
CONECT   28   29   48
CONECT   29   30   31   31
CONECT   30   49
END

NP0043848
     RDKit          3D

49 52  0  0  0  0  0  0  0  0999 V2000
   -0.1000   -2.9721   -0.0072 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911   -2.1048   -0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029   -0.8073   -0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093   -0.5731   -0.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446   -0.2371    0.1594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6524   -1.2988    0.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7701   -0.7961    0.8978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7787   -0.9773    2.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9069   -0.4684    2.9917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9132    0.6284    0.4702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9873    0.8257   -0.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870    0.9201   -0.1906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0712    2.1404    0.2818 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5273    0.0819   -0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3725    1.4703   -1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864    2.3714   -0.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3530    3.6702   -1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753    4.1521   -1.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2830    5.4756   -2.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2657    3.2564   -2.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8289    3.6474   -2.9691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156    1.9282   -1.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7494   -0.3059   -0.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720   -1.4777    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537   -1.8352    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6727   -3.0947    1.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9835   -3.4351    1.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6801   -4.0428    1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3904   -3.7079    0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3557   -4.6373    0.8005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732   -2.4432    0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2212   -0.0629    1.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6606   -1.3506    0.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8001   -2.0938    2.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8651   -0.6117    2.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6585   -0.3116    2.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0001    1.3067    1.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6192    1.4709    0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7542    0.9903   -1.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3488    2.8281   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2310    1.9889   -0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741    4.3256   -0.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5246    5.8414   -2.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    4.5712   -3.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985    1.2829   -2.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1448   -1.0988    0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6102   -3.8041    0.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9274   -5.0423    1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878   -5.5834    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  3 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 14 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31  2  1  0
 12  5  1  0
 22 15  1  0
 31 24  1  0
  5 32  1  1
  7 33  1  6
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  1
 11 38  1  0
 12 39  1  6
 13 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
 25 46  1  0
 27 47  1  0
 28 48  1  0
 30 49  1  0
M  END

View in JSmol

Synonyms

Value	Source
Avicularine	ChEBI
Avicularoside	ChEBI
Fenicularin	ChEBI
Quercetin 3-alpha-L-arabinofuranoside	ChEBI
Quercetin 3-a-L-arabinofuranoside	Generator
Quercetin 3-α-L-arabinofuranoside	Generator

Chemical Formula

C₂₀H₁₈O₁₁

Average Mass

434.3530 Da

Monoisotopic Mass

434.08491 Da

IUPAC Name

3-{[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

Traditional Name

avicularin

CAS Registry Number

Not Available

SMILES

OC[C@@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20-/m0/s1

InChI Key

BDCDNTVZSILEOY-UXYNSRGZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alhagi persarum	LOTUS Database	35616633
Arctostaphylos uva-ursi	KNApSAcK Database	22123792
Asplenium viride	LOTUS Database	35616633
Astilbe arendsii	LOTUS Database	35616633
Aureolaria virginica	LOTUS Database	35616633
Berchemia floribunda	LOTUS Database	35616633
Betula pubescens	LOTUS Database	35616633
Bistorta officinalis	LOTUS Database	35616633
Bupleurum falcatum	LOTUS Database	35616633
Bursera graveolens	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Caragana spinosa	LOTUS Database	35616633
Chaenomeles sinensis	LOTUS Database	35616633
Chaenomeles sinensis KOEHNE	KNApSAcK Database	22123792
Chimaphila umbellata	LOTUS Database	35616633
Cinnamomum philippinense	LOTUS Database	35616633
Coriaria ruscifolia	LOTUS Database	35616633
Cosmos sulphureus	LOTUS Database	35616633
Cowania mexicana	KNApSAcK Database	22123792
Crataegus rhipidophylla	LOTUS Database	35616633
Dryas octopetala	KNApSAcK Database	22123792
Elliottia paniculata	LOTUS Database	35616633
Empetrum nigrum	LOTUS Database	35616633
Eugenia myrcianthes	LOTUS Database	35616633
Euphorbia maculata	LOTUS Database	35616633
Filipendula ulmaria	LOTUS Database	35616633
Foeniculum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Geranium pusillum	LOTUS Database	35616633
Hedysarum alpinum	LOTUS Database	35616633
Hedysarum gmelinii	LOTUS Database	35616633
Hedysarum sachalinense	Plant	KNApSAcK
Hypericum hyssopifolium	LOTUS Database	35616633
Hypericum maculatum	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Hypericum scabrum	KNApSAcK Database	22123792
Hypericum sikokumontanum	LOTUS Database	35616633
Japonolirion osense	Plant	KNApSAcK
Juglans regia	KNApSAcK Database	22123792
Koenigia coriaria	LOTUS Database	35616633
Koenigia divaricata	LOTUS Database	35616633
Laserpitium latifolium	LOTUS Database	35616633
Ledum palustre	KNApSAcK Database	22123792
Malus pumila	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Malus sylvestris	LOTUS Database	35616633
Mangifera indica	Plant	KNApSAcK
Mimosa pudica	LOTUS Database	35616633
Myriophyllum aquaticum	LOTUS Database	35616633
Phoebe formosana	LOTUS Database	35616633
Photinia melanocarpa	FooDB	PHENOL EXPLORER
Pimenta dioica	KNApSAcK Database	22123792
Polygonum aviculare	KNApSAcK Database	22123792
Polygonum cuspidatum	Plant	KNApSAcK
Polygonum sachalinense	LOTUS Database	35616633
Polygonum sachalinensis	Plant	KNApSAcK
Polygonum scabrum	LOTUS Database	35616633
Prunus salicina	LOTUS Database	35616633
Psidium guajava	KNApSAcK Database	22123792
Pyrola elliptica	LOTUS Database	35616633
Pyrus communis	FooDB	PHENOL EXPLORER
Rhododendron brachycarpum	LOTUS Database	35616633
Rhododendron dauricum	LOTUS Database	35616633
Rhododendron schlippenbachii	LOTUS Database	35616633
Rhododendron spinuliferum	LOTUS Database	35616633
Richea angustifolia	KNApSAcK Database	22123792
Richea scoparia	KNApSAcK Database	22123792
Rodgersia podophylla	LOTUS Database	35616633
Rosa canina	LOTUS Database	35616633
Rosa rugosa	LOTUS Database	35616633
Rumex acetosa	LOTUS Database	35616633
Rumex crispus	LOTUS Database	35616633
Saxifraga tricuspidata	LOTUS Database	35616633
Scandosorbus intermedia	LOTUS Database	35616633
Solanum glaucophyllum	KNApSAcK Database	22123792
Tapirira guianensis	-	KNApSAcK
Taxodium distichum	KNApSAcK Database	22123792
Tibouchina semidecandra	LOTUS Database	35616633
Vaccinium corymbosum	FooDB	PHENOL EXPLORER
Vaccinium macrocarpon	FooDB	PHENOL EXPLORER
Vaccinium myritillus	KNApSAcK Database	22123792
Vaccinium myrtillus	KNApSAcK Database	22123792
Vaccinium ovalifolium	LOTUS Database	35616633
Vaccinium vitis-idaea	FooDB	PHENOL EXPLORER
Viscum album	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Pentose monosaccharide
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Tetrahydrofuran
Secondary alcohol
Oxacycle
Acetal
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:65460 )
tetrahydroxyflavone (CHEBI:65460 )
quercetin O-glycoside (CHEBI:65460 )
alpha-L-arabinofuranoside (CHEBI:65460 )
Flavones and Flavonols (LMPK12112167 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	17670 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.76	ALOGPS
logP	0.49	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.31 m³·mol⁻¹	ChemAxon
Polarizability	41.05 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00005367

Chemspider ID

20130086

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Avicularin

METLIN ID

Not Available

PubChem Compound

5490064

PDB ID

Not Available

ChEBI ID

65460

Good Scents ID

rw1823221

References

General References

Blunder M, Orthaber A, Bauer R, Bucar F, Kunert O: Efficient identification of flavones, flavanones and their glycosides in routine analysis via off-line combination of sensitive NMR and HPLC experiments. Food Chem. 2017 Mar 1;218:600-609. doi: 10.1016/j.foodchem.2016.09.077. Epub 2016 Sep 13. [PubMed:27719955 ]
Cakir A, Mavi A, Yildirim A, Duru ME, Harmandar M, Kazaz C: Isolation and characterization of antioxidant phenolic compounds from the aerial parts of Hypericum hyssopifolium L. by activity-guided fractionation. J Ethnopharmacol. 2003 Jul;87(1):73-83. doi: 10.1016/s0378-8741(03)00112-0. [PubMed:12787957 ]
Gao H, Wu L, Kuroyanagi M, Harada K, Kawahara N, Nakane T, Umehara K, Hirasawa A, Nakamura Y: Antitumor-promoting constituents from Chaenomeles sinensis KOEHNE and their activities in JB6 mouse epidermal cells. Chem Pharm Bull (Tokyo). 2003 Nov;51(11):1318-21. doi: 10.1248/cpb.51.1318. [PubMed:14600382 ]
Ek S, Kartimo H, Mattila S, Tolonen A: Characterization of phenolic compounds from lingonberry (Vaccinium vitis-idaea). J Agric Food Chem. 2006 Dec 27;54(26):9834-42. doi: 10.1021/jf0623687. [PubMed:17177509 ]
Pachaly P, Klein M: Constituents of Andromeda polifolia. Planta Med. 1987 Oct;53(5):442-4. doi: 10.1055/s-2006-962769. [PubMed:17269066 ]

Showing NP-Card for Avicularin (NP0043848)

MOL for NP0043848 (Avicularin)

3D MOL for NP0043848 (Avicularin)

3D SDF for NP0043848 (Avicularin)

3D-SDF for NP0043848 (Avicularin)

PDB for NP0043848 (Avicularin)

3D PDB for NP0043848 (Avicularin)

SMILES for NP0043848 (Avicularin)

INCHI for NP0043848 (Avicularin)

Structure for NP0043848 (Avicularin)

3D Structure for NP0043848 (Avicularin)