NP-MRD: Showing NP-Card for epigallocatechin (NP0031142)

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Record Information

Version

2.0

Created at

2021-06-19 22:18:29 UTC

Updated at

2021-08-20 00:00:22 UTC

NP-MRD ID

NP0031142

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epigallocatechin

Provided By

JEOL Database JEOL Logo

Description

(-)-Epigallocatechin, also known as epigallocatechol or antiscurvy factor C2, belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety (-)-Epigallocatechin is a bitter tasting compound (-)-Epigallocatechin is found, on average, in the highest concentration within a few different foods, such as cocoa beans (Theobroma cacao), green tea, and black tea and in a lower concentration in pistachios (Pistacia vera), peaches (Prunus persica), and muskmelons (Cucumis melo) (-)-Epigallocatechin has also been detected, but not quantified in, several different foods, such as quinces (Cydonia oblonga), common persimmons (Diospyros virginiana), macadamia nut (m. Tetraphylla), cucumbers (Cucumis sativus), and chocolate. This could make (-)-epigallocatechin a potential biomarker for the consumption of these foods (-)-Epigallocatechin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. epigallocatechin is found in Acacia binervia, Vachellia karroo, Acacia melanoxylon, Vachellia pennatula, Senegalia polyacantha, Alhagi maurorum, Alhagi sparsifolia, Apis cerana, Apocynum venetum, Azadirachta indica, Caragana spinosa, Chrysophyllum cainito, Croton draconoides, Cycas circinalis, Dicranopteris pedata, Distylium racemosum, Elaeagnus glabra, Entada phaseoloides, Ephedra sinica, Eschweilera coriacea, Esenbeckia grandiflora, Geranium thunbergii, Gossypium hirsutum, Gymnosporia montana, Helianthemum glomeratum, Hippophae rhamnoides, Koenigia coriaria, Leptarrhena pyrolifolia, Limonium gmelinii, Limonium sinense, Lindera aggregata, Lotus corniculatus, Lotus pedunculatus, Matricaria chamomilla, Gymnosporia senegalensis, Morella rubra, Morus alba, Myrtus communis, Onobrychis viciifolia, Parkia biglobosa, Phyllanthus niruri, Phyllanthus reticulatus, Platanus orientalis, Platycarya strobilacea, Dasiphora fruticosa, Pteroxygonum giraldii, Quercus glauca, Quercus robur, Rhodiola rosea, Rhodiola semenovii, Rhus glabra, Rhus typhina, Salacia chinensis, Salacia reticulata, Sempervivum tectorum, Syzygium aqueum, Tectaria subtriphylla, Trifolium repens, Uncaria guianensis, Vitellaria paradoxa, Vitis vinifera, Xanthoceras sorbifolium, Ziziphus jujuba and Ziziphus spina-christi. epigallocatechin was first documented in 2000 (PMID: 10775337). Based on a literature review a small amount of articles have been published on (-)-Epigallocatechin (PMID: 16131288) (PMID: 12375264) (PMID: 16823496) (PMID: 19653629).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100183D          

 36 38  0  0  0  0            999 V2000
   -2.9748    0.1261   -4.4757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0132    0.8271   -3.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322    1.9486   -3.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003    2.6855   -2.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6974    3.7932   -1.9979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628    2.3140   -0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225    1.1951   -1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587    0.4400   -2.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518    0.7451    0.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2854    1.7514    1.0049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4648    1.1319    2.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8195   -0.1061    2.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0553   -0.6409    3.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3679   -1.8349    4.3190 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605    0.0395    4.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179   -0.4799    5.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174    1.2593    3.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5120    1.9290    4.1098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6660    1.8123    2.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    2.3803    1.5058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5143    1.3908    2.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2587    3.1128    0.3352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3536   -0.6149   -4.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4045    2.2288   -4.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1476    3.9125   -2.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130   -0.4317   -2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6639    2.5244    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6939   -0.6345    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -2.1551    3.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3709   -1.3234    5.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655    1.3539    4.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9691    2.7705    2.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    3.0849    2.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6739    0.7601    1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7504    4.0711    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3116    3.3071    0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
 10 11  1  0  0  0  0
  4  3  1  0  0  0  0
 11 12  2  0  0  0  0
  6  4  2  0  0  0  0
 12 13  1  0  0  0  0
  3  2  2  0  0  0  0
 13 15  2  0  0  0  0
 15 17  1  0  0  0  0
  2  8  1  0  0  0  0
 17 19  2  0  0  0  0
 19 11  1  0  0  0  0
  8  7  2  0  0  0  0
  2  1  1  0  0  0  0
  7  9  1  0  0  0  0
  4  5  1  0  0  0  0
  6 22  1  0  0  0  0
 20 21  1  0  0  0  0
 22 20  1  0  0  0  0
 15 16  1  0  0  0  0
 20 10  1  0  0  0  0
 13 14  1  0  0  0  0
 10  9  1  0  0  0  0
 17 18  1  0  0  0  0
  3 24  1  0  0  0  0
  8 26  1  0  0  0  0
 22 35  1  0  0  0  0
 22 36  1  0  0  0  0
 20 33  1  1  0  0  0
 10 27  1  6  0  0  0
 12 28  1  0  0  0  0
 19 32  1  0  0  0  0
  1 23  1  0  0  0  0
  5 25  1  0  0  0  0
 21 34  1  0  0  0  0
 16 30  1  0  0  0  0
 14 29  1  0  0  0  0
 18 31  1  0  0  0  0
M  END

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -2.9748    0.1261   -4.4757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0132    0.8271   -3.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322    1.9486   -3.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003    2.6855   -2.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6974    3.7932   -1.9979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628    2.3140   -0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225    1.1951   -1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587    0.4400   -2.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518    0.7451    0.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2854    1.7514    1.0049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4648    1.1319    2.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8195   -0.1061    2.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0553   -0.6409    3.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3679   -1.8349    4.3190 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605    0.0395    4.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179   -0.4799    5.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174    1.2593    3.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5120    1.9290    4.1098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6660    1.8123    2.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    2.3803    1.5058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5143    1.3908    2.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2587    3.1128    0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3536   -0.6149   -4.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4045    2.2288   -4.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1476    3.9125   -2.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130   -0.4317   -2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6639    2.5244    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6939   -0.6345    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -2.1551    3.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3709   -1.3234    5.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655    1.3539    4.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9691    2.7705    2.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    3.0849    2.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6739    0.7601    1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7504    4.0711    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3116    3.3071    0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
 10 11  1  0
  4  3  1  0
 11 12  2  0
  6  4  2  0
 12 13  1  0
  3  2  2  0
 13 15  2  0
 15 17  1  0
  2  8  1  0
 17 19  2  0
 19 11  1  0
  8  7  2  0
  2  1  1  0
  7  9  1  0
  4  5  1  0
  6 22  1  0
 20 21  1  0
 22 20  1  0
 15 16  1  0
 20 10  1  0
 13 14  1  0
 10  9  1  0
 17 18  1  0
  3 24  1  0
  8 26  1  0
 22 35  1  0
 22 36  1  0
 20 33  1  1
 10 27  1  6
 12 28  1  0
 19 32  1  0
  1 23  1  0
  5 25  1  0
 21 34  1  0
 16 30  1  0
 14 29  1  0
 18 31  1  0
M  END


  Mrv1652306202100183D          

 36 38  0  0  0  0            999 V2000
   -2.9748    0.1261   -4.4757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0132    0.8271   -3.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322    1.9486   -3.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003    2.6855   -2.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6974    3.7932   -1.9979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628    2.3140   -0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225    1.1951   -1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587    0.4400   -2.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518    0.7451    0.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2854    1.7514    1.0049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4648    1.1319    2.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8195   -0.1061    2.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0553   -0.6409    3.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3679   -1.8349    4.3190 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605    0.0395    4.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179   -0.4799    5.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174    1.2593    3.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5120    1.9290    4.1098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6660    1.8123    2.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    2.3803    1.5058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5143    1.3908    2.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2587    3.1128    0.3352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3536   -0.6149   -4.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4045    2.2288   -4.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1476    3.9125   -2.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130   -0.4317   -2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6639    2.5244    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6939   -0.6345    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -2.1551    3.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3709   -1.3234    5.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655    1.3539    4.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9691    2.7705    2.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    3.0849    2.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6739    0.7601    1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7504    4.0711    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3116    3.3071    0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
 10 11  1  0  0  0  0
  4  3  1  0  0  0  0
 11 12  2  0  0  0  0
  6  4  2  0  0  0  0
 12 13  1  0  0  0  0
  3  2  2  0  0  0  0
 13 15  2  0  0  0  0
 15 17  1  0  0  0  0
  2  8  1  0  0  0  0
 17 19  2  0  0  0  0
 19 11  1  0  0  0  0
  8  7  2  0  0  0  0
  2  1  1  0  0  0  0
  7  9  1  0  0  0  0
  4  5  1  0  0  0  0
  6 22  1  0  0  0  0
 20 21  1  0  0  0  0
 22 20  1  0  0  0  0
 15 16  1  0  0  0  0
 20 10  1  0  0  0  0
 13 14  1  0  0  0  0
 10  9  1  0  0  0  0
 17 18  1  0  0  0  0
  3 24  1  0  0  0  0
  8 26  1  0  0  0  0
 22 35  1  0  0  0  0
 22 36  1  0  0  0  0
 20 33  1  1  0  0  0
 10 27  1  6  0  0  0
 12 28  1  0  0  0  0
 19 32  1  0  0  0  0
  1 23  1  0  0  0  0
  5 25  1  0  0  0  0
 21 34  1  0  0  0  0
 16 30  1  0  0  0  0
 14 29  1  0  0  0  0
 18 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031142

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(O[C@]([H])(C3=C([H])C(O[H])=C(O[H])C(O[H])=C3[H])[C@]([H])(O[H])C2([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1

> <INCHI_KEY>
XMOCLSLCDHWDHP-IUODEOHRSA-N

> <FORMULA>
C15H14O7

> <MOLECULAR_WEIGHT>
306.2675

> <EXACT_MASS>
306.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.137041688986052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
1.4915416936666661

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.513028720443094

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.728532640650023

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2949984309607405

> <JCHEM_POLAR_SURFACE_AREA>
130.61

> <JCHEM_REFRACTIVITY>
75.9806

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epigallocatechin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -2.9748    0.1261   -4.4757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0132    0.8271   -3.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322    1.9486   -3.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003    2.6855   -2.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6974    3.7932   -1.9979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628    2.3140   -0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225    1.1951   -1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587    0.4400   -2.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518    0.7451    0.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2854    1.7514    1.0049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4648    1.1319    2.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8195   -0.1061    2.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0553   -0.6409    3.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3679   -1.8349    4.3190 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605    0.0395    4.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179   -0.4799    5.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174    1.2593    3.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5120    1.9290    4.1098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6660    1.8123    2.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    2.3803    1.5058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5143    1.3908    2.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2587    3.1128    0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3536   -0.6149   -4.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4045    2.2288   -4.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1476    3.9125   -2.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130   -0.4317   -2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6639    2.5244    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6939   -0.6345    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -2.1551    3.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3709   -1.3234    5.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655    1.3539    4.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9691    2.7705    2.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    3.0849    2.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6739    0.7601    1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7504    4.0711    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3116    3.3071    0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
 10 11  1  0
  4  3  1  0
 11 12  2  0
  6  4  2  0
 12 13  1  0
  3  2  2  0
 13 15  2  0
 15 17  1  0
  2  8  1  0
 17 19  2  0
 19 11  1  0
  8  7  2  0
  2  1  1  0
  7  9  1  0
  4  5  1  0
  6 22  1  0
 20 21  1  0
 22 20  1  0
 15 16  1  0
 20 10  1  0
 13 14  1  0
 10  9  1  0
 17 18  1  0
  3 24  1  0
  8 26  1  0
 22 35  1  0
 22 36  1  0
 20 33  1  1
 10 27  1  6
 12 28  1  0
 19 32  1  0
  1 23  1  0
  5 25  1  0
 21 34  1  0
 16 30  1  0
 14 29  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.975   0.126  -4.476  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.013   0.827  -3.306  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.832   1.949  -3.253  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.900   2.686  -2.072  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.697   3.793  -1.998  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.163   2.314  -0.942  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.322   1.195  -1.032  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.259   0.440  -2.205  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.552   0.745   0.010  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.285   1.751   1.005  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.465   1.132   2.124  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.820  -0.106   2.697  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.055  -0.641   3.731  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.368  -1.835   4.319  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.061   0.040   4.200  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.818  -0.480   5.215  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.417   1.259   3.645  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.512   1.929   4.110  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.666   1.812   2.616  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.600   2.380   1.506  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.514   1.391   2.012  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.259   3.113   0.335  0.00  0.00           C+0
HETATM   23  H   UNK     0      -2.354  -0.615  -4.376  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.404   2.229  -4.131  0.00  0.00           H+0
HETATM   25  H   UNK     0      -5.148   3.913  -2.851  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.613  -0.432  -2.241  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.664   2.524   0.529  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.694  -0.635   2.327  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.197  -2.155   3.921  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.371  -1.323   5.434  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.865   1.354   4.819  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.969   2.771   2.202  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.416   3.085   2.324  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.674   0.760   1.286  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.750   4.071   0.173  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.312   3.307   0.571  0.00  0.00           H+0
CONECT    1    2   23                                                       
CONECT    2    3    8    1                                                  
CONECT    3    4    2   24                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4   25                                                       
CONECT    6    7    4   22                                                  
CONECT    7    6    8    9                                                  
CONECT    8    2    7   26                                                  
CONECT    9    7   10                                                       
CONECT   10   11   20    9   27                                             
CONECT   11   10   12   19                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12   15   14                                                  
CONECT   14   13   29                                                       
CONECT   15   13   17   16                                                  
CONECT   16   15   30                                                       
CONECT   17   15   19   18                                                  
CONECT   18   17   31                                                       
CONECT   19   17   11   32                                                  
CONECT   20   21   22   10   33                                             
CONECT   21   20   34                                                       
CONECT   22    6   20   35   36                                             
CONECT   23    1                                                            
CONECT   24    3                                                            
CONECT   25    5                                                            
CONECT   26    8                                                            
CONECT   27   10                                                            
CONECT   28   12                                                            
CONECT   29   14                                                            
CONECT   30   16                                                            
CONECT   31   18                                                            
CONECT   32   19                                                            
CONECT   33   20                                                            
CONECT   34   21                                                            
CONECT   35   22                                                            
CONECT   36   22                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

RDKit          3D

36 38  0  0  0  0  0  0  0  0999 V2000
   -2.9748    0.1261   -4.4757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0132    0.8271   -3.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322    1.9486   -3.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003    2.6855   -2.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6974    3.7932   -1.9979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628    2.3140   -0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225    1.1951   -1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587    0.4400   -2.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518    0.7451    0.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2854    1.7514    1.0049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4648    1.1319    2.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8195   -0.1061    2.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0553   -0.6409    3.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3679   -1.8349    4.3190 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605    0.0395    4.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179   -0.4799    5.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174    1.2593    3.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5120    1.9290    4.1098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6660    1.8123    2.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999    2.3803    1.5058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5143    1.3908    2.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2587    3.1128    0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3536   -0.6149   -4.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4045    2.2288   -4.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1476    3.9125   -2.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130   -0.4317   -2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6639    2.5244    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6939   -0.6345    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -2.1551    3.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3709   -1.3234    5.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655    1.3539    4.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9691    2.7705    2.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    3.0849    2.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6739    0.7601    1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7504    4.0711    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3116    3.3071    0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
 10 11  1  0
  4  3  1  0
 11 12  2  0
  6  4  2  0
 12 13  1  0
  3  2  2  0
 13 15  2  0
 15 17  1  0
  2  8  1  0
 17 19  2  0
 19 11  1  0
  8  7  2  0
  2  1  1  0
  7  9  1  0
  4  5  1  0
  6 22  1  0
 20 21  1  0
 22 20  1  0
 15 16  1  0
 20 10  1  0
 13 14  1  0
 10  9  1  0
 17 18  1  0
  3 24  1  0
  8 26  1  0
 22 35  1  0
 22 36  1  0
 20 33  1  1
 10 27  1  6
 12 28  1  0
 19 32  1  0
  1 23  1  0
  5 25  1  0
 21 34  1  0
 16 30  1  0
 14 29  1  0
 18 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
(-)-3,3',4',5,5',7-Flavanhexol	ChEBI
(2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol	ChEBI
2,3-cis-Epigallocatechin	ChEBI
Epigallocatechol	ChEBI
L-Epigallocatechin	ChEBI
(-)-cis-3,3',4',5,5',7-Hexahydroxyflavan	HMDB
(-)-cis-3,3',4',5,5',7-Hexahydroxyflavane	HMDB
(-)-Epigallocatechol	HMDB
Antiscurvy factor C2	HMDB
EGC	HMDB
Epigallocatechin	HMDB
L-Epigallocatechol	HMDB
Gallocatechol, (2R-trans)-isomer	HMDB
Gallocatechol	HMDB
Gallocatechol, (2R-cis)-isomer	HMDB
Gallocatechin	HMDB
(-)-3,3’,4’,5,5’,7-flavanhexol	HMDB
(-)-Epi-gallocatechin	HMDB
(2R,3R)-3,4-Dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol	HMDB
1-Epi-3',4',5',5,7-pentahydroxy-3-flavanol	HMDB
1-Epi-3’,4’,5’,5,7-pentahydroxy-3-flavanol	HMDB
3,3',4',5,5',7-Flavanhexol	HMDB
3,3’,4’,5,5’,7-flavanhexol	HMDB
Galloepicatechin	HMDB
Epi-gallocatechin	HMDB
(-)-Epigallocatechin	HMDB
(2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,5,7-trihydroxychroman	HMDB

Chemical Formula

C₁₅H₁₄O₇

Average Mass

306.2675 Da

Monoisotopic Mass

306.07395 Da

IUPAC Name

(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

epigallocatechin

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C2C(O[C@]([H])(C3=C([H])C(O[H])=C(O[H])C(O[H])=C3[H])[C@]([H])(O[H])C2([H])[H])=C1[H]

InChI Identifier

InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1

InChI Key

XMOCLSLCDHWDHP-IUODEOHRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Acetone-d6, 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
Acacia binervia	LOTUS Database	35616633
Acacia karoo	LOTUS Database	35616633
Acacia melanoxylon	LOTUS Database	35616633
Acacia nilotica	KNApSAcK Database	22123792
Acacia pennatula	LOTUS Database	35616633
Acacia polyacantha	LOTUS Database	35616633
Actinidia chinensis	FooDB	PHENOL EXPLORER
Agaricus bisporus	FooDB	USDA
Alhagi maurorum	LOTUS Database	35616633
Alhagi sparsifolia	LOTUS Database	35616633
Allium ampeloprasum	FooDB	USDA
Allium cepa L.	FooDB	USDA
Anacardium occidentale	FooDB	PHENOL EXPLORER
Ananas comosus	FooDB	PHENOL EXPLORER
Annona reticulata	FooDB	PHENOL EXPLORER
Apis cerana	LOTUS Database	35616633
Apium graveolens	FooDB	USDA
Apocynum venetum	LOTUS Database	35616633
Arachis hypogaea	FooDB	PHENOL EXPLORER
Averrhoa carambola	FooDB	KNAPSACK
Averrhoa carambola L.	KNApSAcK Database	22123792
Azadirachta indica	LOTUS Database	35616633
Bertholletia excelsa	FooDB	PHENOL EXPLORER
Beta vulgaris	FooDB	USDA
Brassica oleracea	FooDB	PHENOL EXPLORER
Brassica oleracea var. botrytis	FooDB	PHENOL EXPLORER
Brassica oleracea var. gemmifera	FooDB	PHENOL EXPLORER
Brassica oleracea var. italica	FooDB	PHENOL EXPLORER
Brassica rapa	FooDB	USDA
Brassica ruvo	FooDB	USDA
Camellia sinensis	KNApSAcK Database	22123792
Capsicum annuum	FooDB	PHENOL EXPLORER
Caragana spinosa	LOTUS Database	35616633
Carya illinoinensis	FooDB	PHENOL EXPLORER
Castanea	FooDB	PHENOL EXPLORER
Castanea sativa	FooDB	USDA
Chrysophyllum cainito	LOTUS Database	35616633
Cicer arietinum	FooDB	PHENOL EXPLORER
Cichorium endivia	FooDB	USDA
Cichorium intybus	FooDB	USDA
Cistus salviifolius	KNApSAcK Database	22123792
Citrullus lanatus	FooDB	USDA
Citrus paradisi	FooDB	USDA
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	PHENOL EXPLORER
Coffea arabica L.	FooDB	PHENOL EXPLORER
Coffea canephora	FooDB	PHENOL EXPLORER
Combretum quadrangulare	KNApSAcK Database	22123792
Corylus	FooDB	USDA
Corylus avellana	FooDB	PHENOL EXPLORER
Croton draconoides	LOTUS Database	35616633
Croton lechleri	KNApSAcK Database	22123792
Cucumis melo	FooDB	PHENOL EXPLORER
Cucumis sativus L.	FooDB	PHENOL EXPLORER
Cucurbita	FooDB	PHENOL EXPLORER
Cycas circinalis	LOTUS Database	35616633
Cydonia oblonga	FooDB	PHENOL EXPLORER
Cynara scolymus	FooDB	USDA
Daucus carota ssp. sativus	FooDB	PHENOL EXPLORER
Dicranopteris pedata	LOTUS Database	35616633
Diospyros kaki	FooDB	PHENOL EXPLORER
Diospyros virginiana	FooDB	USDA
Distylium racemosum	LOTUS Database	35616633
Elaeagnus glabra	LOTUS Database	35616633
Entada phaseoloides	LOTUS Database	35616633
Ephedra sinica	LOTUS Database	35616633
Eschweilera coriacea	LOTUS Database	35616633
Esenbeckia grandiflora	LOTUS Database	35616633
Ficus carica	FooDB	PHENOL EXPLORER
Fragaria x ananassa	FooDB	PHENOL EXPLORER
Geranium thunbergii	LOTUS Database	35616633
Ginkgo biloba	KNApSAcK Database	22123792
Gossypium	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gossypium hirsutum	LOTUS Database	35616633
Guazuma ulmifolia	KNApSAcK Database	22123792
Gymnosporia montana	LOTUS Database	35616633
Helianthemum glomeratum	LOTUS Database	35616633
Hippophae rhamnoides	LOTUS Database	35616633
Juglans regia	FooDB	PHENOL EXPLORER
Koenigia coriaria	LOTUS Database	35616633
Lactuca sativa	FooDB	PHENOL EXPLORER
Laurus nobilis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lens culinaris	FooDB	PHENOL EXPLORER
Leptarrhena pyrolifolia	LOTUS Database	35616633
Limonium gmelinii	LOTUS Database	35616633
Limonium sinense	LOTUS Database	35616633
Lindera aggregata	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Lotus pedunculatus	LOTUS Database	35616633
Macadamia	FooDB	USDA
Macadamia tetraphylla	FooDB	PHENOL EXPLORER
Malus pumila	FooDB	PHENOL EXPLORER
Mangifera indica	FooDB	PHENOL EXPLORER
Matricaria chamomilla	LOTUS Database	35616633
Matricaria recutita	FooDB	PHENOL EXPLORER
Maytenus senegalensis	LOTUS Database	35616633
Medicago truncatula	KNApSAcK Database	22123792
Mentha x piperita	FooDB	PHENOL EXPLORER
Mespilus germanica	FooDB	PHENOL EXPLORER
Morella rubra	LOTUS Database	35616633
Morus alba	LOTUS Database	35616633
Musa acuminata	FooDB	PHENOL EXPLORER
Myrica rubra	KNApSAcK Database	22123792
Myrtus communis	LOTUS Database	35616633
Olea europaea	FooDB	PHENOL EXPLORER
Onobrychis viciifolia	LOTUS Database	35616633
Oryza sativa	FooDB	USDA
Parkia biglobosa	LOTUS Database	35616633
Pelargonium sidoides	KNApSAcK Database	22123792
Persea americana	FooDB	PHENOL EXPLORER
Phaseolus vulgaris	FooDB	PHENOL EXPLORER
Phoenix dactylifera	FooDB	USDA
Phyllanthus emblica	KNApSAcK Database	22123792
Phyllanthus niruri	LOTUS Database	35616633
Phyllanthus reticulatus	LOTUS Database	35616633
Pinus	FooDB	PHENOL EXPLORER
Pinus edulis	FooDB	USDA
Pinus sibirica	KNApSAcK Database	22123792
Pistacia vera	FooDB	PHENOL EXPLORER
Pisum sativum	FooDB	PHENOL EXPLORER
Platanus orientalis	LOTUS Database	35616633
Platycarya strobilacea	LOTUS Database	35616633
Potentilla fruticosa	LOTUS Database	35616633
Prunus armeniaca	FooDB	PHENOL EXPLORER
Prunus avium	FooDB	PHENOL EXPLORER
Prunus avium L.	FooDB	USDA
Prunus domestica	FooDB	PHENOL EXPLORER
Prunus dulcis	FooDB	PHENOL EXPLORER
Prunus persica	FooDB	USDA
Prunus persica var. nucipersica	FooDB	PHENOL EXPLORER
Prunus persica var. persica	FooDB	PHENOL EXPLORER
Pteroxygonum giraldii	LOTUS Database	35616633
Punica granatum	KNApSAcK Database	22123792
Pyrus communis	FooDB	PHENOL EXPLORER
Quercus glauca	LOTUS Database	35616633
Quercus robur	LOTUS Database	35616633
Raphanus sativus	FooDB	USDA
Rheum rhabarbarum	FooDB	PHENOL EXPLORER
Rhodiola rosea	LOTUS Database	35616633
Rhodiola sachalinensis	KNApSAcK Database	22123792
Rhodiola semenovii	LOTUS Database	35616633
Rhododendron brachycarpum ssp.brachycarpum	KNApSAcK Database	22123792
Rhododendron catawbiense	KNApSAcK Database	22123792
Rhododendron Cunningham's white	KNApSAcK Database	22123792
Rhododendron dichroanthum ssp.scyphocalyx	KNApSAcK Database	22123792
Rhododendron micranthum	KNApSAcK Database	22123792
Rhododendron oreotrephes	KNApSAcK Database	22123792
Rhododendron praevernum	KNApSAcK Database	22123792
Rhododendron smirnowii	KNApSAcK Database	22123792
Rhododendron ungernii	KNApSAcK Database	22123792
Rhus glabra	LOTUS Database	35616633
Rhus typhina	LOTUS Database	35616633
Ribes nigrum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ribes rubrum	FooDB	PHENOL EXPLORER
Ribes uva-crispa	FooDB	PHENOL EXPLORER
Rubus idaeus	FooDB	PHENOL EXPLORER
Salacia chinensis	LOTUS Database	35616633
Salacia prinoides	KNApSAcK Database	22123792
Salacia reticulata	LOTUS Database	35616633
Sempervivum tectorum	LOTUS Database	35616633
Solanum lycopersicum	FooDB	USDA
Solanum lycopersicum var. lycopersicum	FooDB	PHENOL EXPLORER
Solanum melongena	FooDB	PHENOL EXPLORER
Solanum tuberosum	FooDB	PHENOL EXPLORER
Stryphnodendron adstringens	KNApSAcK Database	22123792
Syzygium aqueum	LOTUS Database	35616633
Syzygium spp.	KNApSAcK Database	22123792
Taxus fuana	KNApSAcK Database	22123792
Taxus yunnanensis	KNApSAcK Database	22123792
Tectaria subtriphylla	LOTUS Database	35616633
Theobroma cacao	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Trifolium repens	LOTUS Database	35616633
Tripterygium hypoglaucum	KNApSAcK Database	22123792
Triticum aestivum	FooDB	PHENOL EXPLORER
Uncaria guianensis	LOTUS Database	35616633
Vaccinium	FooDB	USDA
Vaccinium corymbosum	FooDB	PHENOL EXPLORER
Vaccinium macrocarpon	FooDB	USDA
Vaccinium myrtillus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium oxycoccos	FooDB	PHENOL EXPLORER
Vaccinium vitis-idaea	KNApSAcK Database	22123792
Vicia faba	KNApSAcK Database	22123792
Vitellaria paradoxa	LOTUS Database	35616633
Vitis	FooDB	USDA
Vitis rotundifolia	FooDB	USDA
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Xanthoceras sorbifolia	KNApSAcK Database	22123792
Xanthoceras sorbifolium	LOTUS Database	35616633
Zea mays L.	FooDB	PHENOL EXPLORER
Ziziphus jujuba	LOTUS Database	35616633
Ziziphus spina-christi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Epigallocatechins

Alternative Parents

Substituents

Epigallocatechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
1-benzopyran
Chromane
Benzopyran
Pyrogallol derivative
Benzenetriol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

catechin (CHEBI:42255 )
flavan-3,3',4',5,5',7-hexol (CHEBI:42255 )
Flavans, Flavanols and Leucoanthocyanidins (C12136 )
Flavan 3-ols (C12136 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020004 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	685.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	15450 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.100 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	0.71	ALOGPS
logP	1.49	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.73	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	130.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.98 m³·mol⁻¹	ChemAxon
Polarizability	29.14 Å³	ChemAxon
Number of Rings	3	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

HMDB0038361

DrugBank ID

DB03823

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

PDB ID

ChEBI ID

Good Scents ID

References

General References

Cooper R, Morre DJ, Morre DM: Medicinal benefits of green tea: part II. review of anticancer properties. J Altern Complement Med. 2005 Aug;11(4):639-52. doi: 10.1089/acm.2005.11.639. [PubMed:16131288 ]
Lin SC, Wang CP, Chen YM, Lu SY, Fann MJ, Liu CJ, Kao SY, Chang KW: Regulation of IGFBP-5 expression during tumourigenesis and differentiation of oral keratinocytes. J Pathol. 2002 Nov;198(3):317-25. doi: 10.1002/path.1220. [PubMed:12375264 ]
Davies SL, Bozzo J: Spotlight on tNOX: a tumor-selective target for cancer therapies. Drug News Perspect. 2006 May;19(4):223-5. doi: 10.1358/dnp.2006.19.4.1007077. [PubMed:16823496 ]
Zhu N, Huang TC, Yu Y, LaVoie EJ, Yang CS, Ho CT: Identification of oxidation products of (-)-epigallocatechin gallate and (-)-epigallocatechin with H(2)O(2). J Agric Food Chem. 2000 Apr;48(4):979-81. doi: 10.1021/jf991188c. [PubMed:10775337 ]
Ko CH, Lau KM, Choy WY, Leung PC: Effects of tea catechins, epigallocatechin, gallocatechin, and gallocatechin gallate, on bone metabolism. J Agric Food Chem. 2009 Aug 26;57(16):7293-7. doi: 10.1021/jf901545u. [PubMed:19653629 ]
Davis, A. L., et al. (1996). Davis, A. L., et al, Magn. Reson. Chem. 34, 887 (1996). Mag. Reson. Chem..

Showing NP-Card for epigallocatechin (NP0031142)

MOL for NP0031142 (epigallocatechin)

3D MOL for NP0031142 (epigallocatechin)

3D SDF for NP0031142 (epigallocatechin)

3D-SDF for NP0031142 (epigallocatechin)

PDB for NP0031142 (epigallocatechin)

3D PDB for NP0031142 (epigallocatechin)

SMILES for NP0031142 (epigallocatechin)

INCHI for NP0031142 (epigallocatechin)

Structure for NP0031142 (epigallocatechin)

3D Structure for NP0031142 (epigallocatechin)