NP-MRD: Showing NP-Card for Juglanin (NP0044804)

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Record Information

Version

2.0

Created at

2022-02-24 21:16:47 UTC

Updated at

2022-02-24 21:16:47 UTC

NP-MRD ID

NP0044804

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Juglanin

Description

Kaempferol 3-alpha-L-arabinofuranoside, also known as euglanin, 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. Kaempferol 3-alpha-L-arabinofuranoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Kaempferol 3-alpha-L-arabinofuranoside has been detected, but not quantified in, several different foods, such as pears, fennels, rose hips, common walnuts, and jutes. Juglanin is found in Abies homolepis, Acer mandshuricum, Acer pictum, Aesculus hippocastanum , Foeniculum vulgare , Asplenium trichomanes-ramosum, Asplenium viride, Astilbe thunbergii, Calluna vulgaris, Cinnamomum philippinense, Corchorus olitorius , Diplusodon speciosus, Epilobium hirsutum, Erythroxylum barbatum, Erythroxylum ulei, Eugenia selloi, Tetradium glabrifolium, Excoecaria agallocha, Fuchsia excorticata, Fuchsia pilaloensis, Geranium platyanthum, Guatteria rupestris, Guatteria villosissima, Juglans regia , Licania pyrifolia, Lindera glauca, Lysimachia congestiflora, Oenothera fruticosa, Oldenlandia herbacea, Persea americana, Phlebodium aureum, Phlebodium decumanum, Phoebe formosana, Prunus spinosa , Pyrola chlorantha, Rodgersia podophylla , Rosa damascena, Rosa rugosa, Rosa spp., Rubus rigidus, Saxifraga tricuspidata, Sorbaria sorbifolia , Speranskia tuberculata, Tapirira guianensis and Warburgia ugandensis. Juglanin was first documented in 1994 (Kim, et al.). This could make kaempferol 3-alpha-L-arabinofuranoside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241216022D          

 30 33  0  0  0  0            999 V2000
   -3.2152   -1.9640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -1.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -1.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567   -0.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567    0.5108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -0.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866    0.5108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567   -1.9640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569   -1.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569   -0.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.3141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050    0.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6593    1.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1739    2.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5095    3.2014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695    2.4480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    1.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7386    0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5237    0.7418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -1.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -2.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -3.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -2.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -1.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152   -3.2014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  2  0  0  0  0
  6 13  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 28  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 22  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  2  0  0  0  0
 24 29  1  0  0  0  0
 25 26  1  0  0  0  0
 25 30  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 48 51  0  0  0  0  0  0  0  0999 V2000
   -0.1199   -3.0471   -0.1782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9042   -2.0659   -0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5138   -0.7505   -0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8359   -0.5117   -0.5316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -0.4116    0.5395 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2164    0.8611    0.6699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885    1.0186   -0.0114 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4711    1.3727    1.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1654    2.5430    1.6944 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7661   -0.3235   -0.6015 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1278   -0.5614   -0.5223 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9990   -1.2246    0.3780 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8603   -2.4904   -0.0861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4582    0.2301   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1919    1.6685   -0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0571    2.2036   -1.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1331    3.5868   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8407    4.4570   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6836    5.8456   -0.7572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0009    3.9455   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1543    2.5829   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7291   -0.1340   -0.1023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1641   -1.3297    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5270   -1.5993    0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9381   -2.8826    0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2997   -3.1072    0.6791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0185   -3.9061    0.4417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6713   -3.6619    0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7346   -4.7022    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2530   -2.3619    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2847   -0.6851    1.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3509    1.8099   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6203    0.5582    1.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4244    1.5219    0.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8752    3.2349    1.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3536   -0.3897   -1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2774   -1.5042   -0.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5660   -1.1394    1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5694   -3.0817    0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181    1.5621   -1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0403    3.9849   -1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816    6.4765   -0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7615    4.6444    0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0686    2.1919    0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2117   -0.7459    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7195   -3.1142    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3725   -4.9102    0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -5.6580    0.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3 14  2  0
 14 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30  2  1  0
  2  1  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  2  0
  5 12  1  0
 12 13  1  0
 12 10  1  0
 10 11  1  0
 10  7  1  0
  2  3  1  0
 21 15  1  0
 30 23  1  0
  9 35  1  0
  8 33  1  0
  8 34  1  0
  7 32  1  6
  5 31  1  1
 24 45  1  0
 26 46  1  0
 27 47  1  0
 29 48  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 12 38  1  1
 13 39  1  0
 10 36  1  6
 11 37  1  0
M  END


  Mrv0541 02241216022D          

 30 33  0  0  0  0            999 V2000
   -3.2152   -1.9640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -1.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -1.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567   -0.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567    0.5108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -0.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866    0.5108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567   -1.9640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569   -1.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569   -0.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.3141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050    0.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6593    1.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1739    2.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5095    3.2014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695    2.4480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    1.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7386    0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5237    0.7418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -1.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -2.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -3.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -2.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -1.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152   -3.2014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  2  0  0  0  0
  6 13  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 28  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 22  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  2  0  0  0  0
 24 29  1  0  0  0  0
 25 26  1  0  0  0  0
 25 30  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0044804

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O10/c21-7-13-15(25)17(27)20(29-13)30-19-16(26)14-11(24)5-10(23)6-12(14)28-18(19)8-1-3-9(22)4-2-8/h1-6,13,15,17,20-25,27H,7H2

> <INCHI_KEY>
POQICXMTUPVZMX-UHFFFAOYSA-N

> <FORMULA>
C20H18O10

> <MOLECULAR_WEIGHT>
418.3509

> <EXACT_MASS>
418.089996796

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
39.7486104591771

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
0.7890649676666666

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.440214953827674

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.433890258159877

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981152416465515

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
101.33210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -6.002  -3.666   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.667  -2.896   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.335  -3.666   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.001  -2.896   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001  -1.356   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.666  -0.586   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.666   0.953   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.667  -1.356   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.335  -0.586   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.335   0.953   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.666  -3.666   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.666  -2.896   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.666  -1.356   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.001  -0.586   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.001   0.953   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.756   1.859   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.231   3.325   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.325   4.570   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.951   5.976   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.676   4.570   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.771   3.325   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.245   1.859   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.711   1.385   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.667  -3.666   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.667  -5.206   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.335  -5.976   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.001  -5.206   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.001  -3.666   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.335  -2.896   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.002  -5.976   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6                                                            
CONECT    8    2    9                                                       
CONECT    9    5    8   10                                                  
CONECT   10    9                                                            
CONECT   11    4   12                                                       
CONECT   12   11   13   28                                                  
CONECT   13    6   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21   17   20   22                                                  
CONECT   22   15   21   23                                                  
CONECT   23   22                                                            
CONECT   24   25   29                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   12   27   29                                                  
CONECT   29   24   28                                                       
CONECT   30   25                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Kaempferol 3-a-L-arabinofuranoside	Generator
Kaempferol 3-α-L-arabinofuranoside	Generator
Euglanin	HMDB
Juglanin?	HMDB
Kaempferol-3-O-alpha-L-arabinofuranoside	MeSH

Chemical Formula

C₂₀H₁₈O₁₀

Average Mass

418.3509 Da

Monoisotopic Mass

418.09000 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(O)C1O

InChI Identifier

InChI=1S/C20H18O10/c21-7-13-15(25)17(27)20(29-13)30-19-16(26)14-11(24)5-10(23)6-12(14)28-18(19)8-1-3-9(22)4-2-8/h1-6,13,15,17,20-25,27H,7H2

InChI Key

POQICXMTUPVZMX-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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

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
Abies homolepis	LOTUS Database	35616633
Acer mandshuricum	LOTUS Database	35616633
Acer pictum	LOTUS Database	35616633
Aesculus hippocastanum	Plant	KNApSAcK
Anethum foeniculum	Plant	KNApSAcK
Asplenium trichomanes-ramosum	Plant	KNApSAcK
Asplenium viride	LOTUS Database	35616633
Astilbe thunbergii	LOTUS Database	35616633
Calluna vulgaris	LOTUS Database	35616633
Cinnamomum philippinense	LOTUS Database	35616633
Corchorus olitorius	Plant	KNApSAcK
Corylus avellana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Diplusodon speciosus	LOTUS Database	35616633
Epilobium hirsutum	LOTUS Database	35616633
Erythroxylum barbatum	LOTUS Database	35616633
Erythroxylum ulei	LOTUS Database	35616633
Eugenia selloi	LOTUS Database	35616633
Euodia fargesii	LOTUS Database	35616633
Excoecaria agallocha	LOTUS Database	35616633
Foeniculum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Fuchsia excorticata	LOTUS Database	35616633
Fuchsia pilaloensis	LOTUS Database	35616633
Geranium platyanthum	LOTUS Database	35616633
Guatteria rupestris	Plant	KNApSAcK
Guatteria villosissima	Plant	KNApSAcK
Juglans regia	Plant	KNApSAcK
Laurus nobilis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Licania pyrifolia	LOTUS Database	35616633
Lindera glauca	LOTUS Database	35616633
Lysimachia congestiflora	LOTUS Database	35616633
Oenothera fruticosa	LOTUS Database	35616633
Oldenlandia herbacea	LOTUS Database	35616633
Persea americana	LOTUS Database	35616633
Phlebodium aureum	LOTUS Database	35616633
Phlebodium decumanum	LOTUS Database	35616633
Phoebe formosana	LOTUS Database	35616633
Prunus spinosa	Plant	KNApSAcK
Pyrola chlorantha	LOTUS Database	35616633
Rodgersia podophylla	Plant	KNApSAcK
Rosa damascena	LOTUS Database	35616633
Rosa rugosa	LOTUS Database	35616633
Rosa spp.	Plant	KNApSAcK
Rubus rigidus	LOTUS Database	35616633
Saxifraga tricuspidata	LOTUS Database	35616633
Sorbaria sorbifolia	Plant	KNApSAcK
Speranskia tuberculata	Plant	KNApSAcK
Tapirira guianensis	-	KNApSAcK
Warburgia ugandensis	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
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
O-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
Pentose monosaccharide
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monosaccharide
Pyran
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.99	ALOGPS
logP	0.79	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.33 m³·mol⁻¹	ChemAxon
Polarizability	39.75 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029502

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000636

KNApSAcK ID

C00005132

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

13245583

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hyoung Ja Kim, Eun-Rhan Woo, and Hokoon Park (1994). Hyoung Ja Kim, Eun-Rhan Woo, and Hokoon Park. A Novel Lignan and Flavonoids from Polygonum aviculare. Journal of Natural Products 1994 57 (5), 581-586 DOI: 10.1021/np50107a003. Journal of Natural Products.

Showing NP-Card for Juglanin (NP0044804)

MOL for NP0044804 (Juglanin)

3D MOL for NP0044804 (Juglanin)

3D SDF for NP0044804 (Juglanin)

3D-SDF for NP0044804 (Juglanin)

PDB for NP0044804 (Juglanin)

3D PDB for NP0044804 (Juglanin)

SMILES for NP0044804 (Juglanin)

INCHI for NP0044804 (Juglanin)

Structure for NP0044804 (Juglanin)

3D Structure for NP0044804 (Juglanin)