Epigallocatechin

Details

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Internal ID 394db82e-1e5d-4d7a-9ca5-1967c4e2cb90
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins > Epigallocatechins
IUPAC Name (2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
SMILES (Canonical) C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)O
SMILES (Isomeric) C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)O
InChI 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
Popularity 3,472 references in papers

Physical and Chemical Properties

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Molecular Formula C15H14O7
Molecular Weight 306.27 g/mol
Exact Mass 306.07395278 g/mol
Topological Polar Surface Area (TPSA) 131.00 Ų
XlogP 0.00
Atomic LogP (AlogP) 1.25
H-Bond Acceptor 7
H-Bond Donor 6
Rotatable Bonds 1

Synonyms

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Epigallocatechin
970-74-1
Epigallocatechol
L-Epigallocatechin
epi-Gallocatechin
Antiscurvy factor C2
(-)-Epigallocatechol
l-Epigallocatechol
Galloepicatechin
3,3',4',5,5',7-Flavanhexol
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Epigallocatechin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8922 89.22%
Caco-2 - 0.9372 93.72%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.4440 44.40%
OATP2B1 inhibitior - 0.5692 56.92%
OATP1B1 inhibitior + 0.8361 83.61%
OATP1B3 inhibitior + 0.9480 94.80%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.9141 91.41%
P-glycoprotein inhibitior - 0.9207 92.07%
P-glycoprotein substrate - 0.9341 93.41%
CYP3A4 substrate - 0.5690 56.90%
CYP2C9 substrate - 0.8006 80.06%
CYP2D6 substrate + 0.5322 53.22%
CYP3A4 inhibition - 0.8309 83.09%
CYP2C9 inhibition - 0.9071 90.71%
CYP2C19 inhibition - 0.9041 90.41%
CYP2D6 inhibition - 0.9231 92.31%
CYP1A2 inhibition - 0.9046 90.46%
CYP2C8 inhibition - 0.5715 57.15%
CYP inhibitory promiscuity - 0.8170 81.70%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5825 58.25%
Eye corrosion - 0.9901 99.01%
Eye irritation + 0.9262 92.62%
Skin irritation - 0.5859 58.59%
Skin corrosion - 0.9251 92.51%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4416 44.16%
Micronuclear + 0.8059 80.59%
Hepatotoxicity + 0.6427 64.27%
skin sensitisation - 0.7452 74.52%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity - 0.7385 73.85%
Acute Oral Toxicity (c) IV 0.6433 64.33%
Estrogen receptor binding - 0.5682 56.82%
Androgen receptor binding + 0.7015 70.15%
Thyroid receptor binding + 0.7673 76.73%
Glucocorticoid receptor binding + 0.7692 76.92%
Aromatase binding + 0.6130 61.30%
PPAR gamma + 0.7283 72.83%
Honey bee toxicity - 0.8908 89.08%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.7342 73.42%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.55% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.08% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.78% 97.09%
CHEMBL1951 P21397 Monoamine oxidase A 87.30% 91.49%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.60% 89.00%
CHEMBL3194 P02766 Transthyretin 86.03% 90.71%
CHEMBL1929 P47989 Xanthine dehydrogenase 84.25% 96.12%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.45% 95.56%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 82.94% 99.15%
CHEMBL3401 O75469 Pregnane X receptor 82.34% 94.73%
CHEMBL3004 P33527 Multidrug resistance-associated protein 1 81.55% 96.37%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.20% 86.33%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Acacia baileyana
Acacia dealbata
Acanthospermum glabratum
Actiniopteris radiata
Adenopeltis serrata
Aglaia elaeagnoidea
Aglaia laxiflora
Aldama linearis
Aldama oblongifolia
Alhagi maurorum
Alhagi sparsifolia
Alyxia reinwardtii
Angelica lucida
Apocynum venetum
Artemisia absinthium
Artemisia carvifolia
Artemisia schimperi
Arum cylindraceum
Averrhoa carambola
Azadirachta indica
Bituminaria bituminosa
Brocchia cinerea
Bryum argenteum
Cajanus trinervius
Callicarpa japonica
Callicarpa maingayi
Camellia sinensis
Capnoides sempervirens
Caragana spinosa
Castanea sativa
Centaurea linifolia
Centaurea seridis
Cephalaria uralensis
Ceriscoides turgida
Chrozophora tinctoria
Chrysophyllum cainito
Cneoridium dumosum
Cneorum pulverulentum
Combretum quadrangulare
Coniogramme japonica
Coprosma areolata
Crataegus pinnatifida
Crotalaria aegyptiaca
Croton draconoides
Croton lechleri
Cyanostegia microphylla
Cycas circinalis
Dalbergia stipulacea
Daphniphyllum paxianum
Dasiphora fruticosa
Delphinium ajacis
Dicoma capensis
Dicranopteris pedata
Digitalis isabelliana
Diospyros kaki
Distylium racemosum
Elaeagnus commutata
Elaeagnus glabra
Elephantopus hirtiflorus
Elephantopus mollis
Elymus repens
Entada phaseoloides
Ephedra sinica
Ericameria parryi
Eschweilera coriacea
Esenbeckia grandiflora
Eucalyptus flocktoniae
Euphorbia amygdaloides
Euphorbia leuconeura
Euphorbia turczaninowii
Euryops algoensis
Flindersia brayleyana
Gardenia jasminoides
Geranium sylvaticum
Geranium thunbergii
Ginkgo biloba
Gmelina asiatica
Gomortega keule
Gossypium hirsutum
Gymnosporia senegalensis
Haplophyllum ferganicum
Helichrysum cephaloideum
Heracleum sphondylium
Hesperis matronalis
Hippophae rhamnoides
Hymenoxys insignis
Hypericum balearicum
Hypericum perforatum
Iris ensata
Isocoma pluriflora
Jackiella javanica
Jatropha macrorhiza
Jungermannia obovata
Kummerowia striata
Lavandula dentata
Leptarrhena pyrolifolia
Lespedeza bicolor
Leuzea centauroides
Ligularia cymbulifera
Lilium philadelphicum
Limonium gmelinii
Limonium sinense
Lindera aggregata
Litsea pungens
Lotus corniculatus
Lotus pedunculatus
Lycoris radiata
Machilus glaucescens
Magnolia montana
Mascarenhasia arborescens
Maytenus aquifolium
Maytenus cuzcoina
Meconopsis napaulensis
Mentzelia decapetala
Merremia umbellata
Microtropis fokienensis
Millettia conraui
Mimusops caffra
Morus alba
Myrica rubra
Myrtus communis
Nematolepis phebalioides
Neonauclea sessilifolia
Nerine bowdenii
Nuphar lutea
Onobrychis viciifolia
Palafoxia rosea
Pangium edule
Parkia biglobosa
Pedicularis condensata
Perityle vaseyi
Petasites hybridus
Phoebe formosana
Phoenix loureiroi
Phyllanthus emblica
Phyllanthus niruri
Phyllanthus reticulatus
Picea mariana
Piloselloides hirsuta
Piptocarpha oblonga
Pistacia vera
Platanus orientalis
Platycarya strobilacea
Platyosprion platycarpum
Plectranthus garckeanus
Porella swartziana
Prunus armeniaca
Prunus persica
Pteroxygonum giraldii
Pyrus ussuriensis
Quercus glauca
Quercus mongolica
Quercus robur
Ranunculus sceleratus
Rheum webbianum
Rhodiola rosea
Rhodiola semenovii
Rhus glabra
Ribes nigrum
Salacia chinensis
Salacia reticulata
Salvia coulteri
Salvia parryi
Satureja cuneifolia
Scopolia carniolica
Searsia pyroides
Sedum yvesi
Sempervivum tectorum
Senecio adenophyllus
Senecio flavus
Senegalia catechu
Senegalia polyacantha
Sesbania bispinosa
Sida cordifolia
Solanum nigrum
Solanum sisymbriifolium
Solidago flexicaulis
Solidago serotina
Sonchus ortunoi
Sorbaria sorbifolia
Spatholobus suberectus
Staphylea ternata
Sterculia foetida
Stereospermum cylindricum
Strophanthus kombe
Stryphnodendron adstringens
Styrax ferrugineus
Syzygium samarangense
Tectaria subtriphylla
Thalictrum longistylum
Thymbra spicata
Thymus vulgaris
Trifolium repens
Tripterygium wilfordii
Trollius chinensis
Turraeanthus mannii
Uncaria guianensis
Vaccinium vitis-idaea
Vachellia karroo
Vachellia nilotica subsp. tomentosa
Vachellia pachyphloia
Vachellia pennatula
Valeriana wolgensis
Veronica arvensis
Viburnum urceolatum
Vicia faba
Vigna mungo
Vincetoxicum hirundinaria
Vitellaria paradoxa
Vitis vinifera
Xanthoceras sorbifolium
Xyris pterygoblephara
Ziziphus jujuba
Ziziphus mauritiana
Ziziphus spina-christi

Cross-Links

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PubChem 72277
NPASS NPC220825
ChEMBL CHEMBL47386
LOTUS LTS0043940
wikiData Q105033633