Epigallocatechin 3,5-digallate

Details

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Internal ID 17d402ab-e1a0-4ead-944d-26071c90e618
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins > Catechin gallates
IUPAC Name [(2R,3R)-7-hydroxy-5-(3,4,5-trihydroxybenzoyl)oxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
SMILES (Canonical) C1C(C(OC2=C1C(=CC(=C2)O)OC(=O)C3=CC(=C(C(=C3)O)O)O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O
SMILES (Isomeric) C1[C@H]([C@H](OC2=C1C(=CC(=C2)O)OC(=O)C3=CC(=C(C(=C3)O)O)O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O
InChI InChI=1S/C29H22O15/c30-13-7-21-14(22(8-13)43-28(40)11-3-17(33)25(38)18(34)4-11)9-23(27(42-21)10-1-15(31)24(37)16(32)2-10)44-29(41)12-5-19(35)26(39)20(36)6-12/h1-8,23,27,30-39H,9H2/t23-,27-/m1/s1
InChI Key RKUDRJTZBDEGNP-YIXXDRMTSA-N
Popularity 6 references in papers

Physical and Chemical Properties

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Molecular Formula C29H22O15
Molecular Weight 610.50 g/mol
Exact Mass 610.09586999 g/mol
Topological Polar Surface Area (TPSA) 264.00 Ų
XlogP 2.90
Atomic LogP (AlogP) 2.86
H-Bond Acceptor 15
H-Bond Donor 10
Rotatable Bonds 5

Synonyms

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(-)-epigallocatechin 3,5-digallate
Epigallocatechin 3,5,-di-O-gallate
37484-73-4
EGCDG
Spectrum_000198
SpecPlus_000282
Spectrum2_000577
Spectrum3_000681
Spectrum4_001521
Spectrum5_000022
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 3,5-digallate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7543 75.43%
Caco-2 - 0.9184 91.84%
Blood Brain Barrier - 0.8000 80.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.6228 62.28%
OATP2B1 inhibitior - 0.5692 56.92%
OATP1B1 inhibitior + 0.8750 87.50%
OATP1B3 inhibitior + 0.9480 94.80%
MATE1 inhibitior - 0.7400 74.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.7251 72.51%
P-glycoprotein inhibitior + 0.7332 73.32%
P-glycoprotein substrate - 0.7872 78.72%
CYP3A4 substrate + 0.5867 58.67%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7217 72.17%
CYP3A4 inhibition - 0.7506 75.06%
CYP2C9 inhibition - 0.7426 74.26%
CYP2C19 inhibition - 0.8889 88.89%
CYP2D6 inhibition - 0.9493 94.93%
CYP1A2 inhibition - 0.8399 83.99%
CYP2C8 inhibition + 0.7008 70.08%
CYP inhibitory promiscuity - 0.8410 84.10%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6575 65.75%
Eye corrosion - 0.9922 99.22%
Eye irritation - 0.7743 77.43%
Skin irritation - 0.6681 66.81%
Skin corrosion - 0.9455 94.55%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition + 0.9009 90.09%
Micronuclear + 0.8859 88.59%
Hepatotoxicity + 0.7250 72.50%
skin sensitisation - 0.8752 87.52%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity - 0.6639 66.39%
Acute Oral Toxicity (c) II 0.4131 41.31%
Estrogen receptor binding + 0.7856 78.56%
Androgen receptor binding + 0.8194 81.94%
Thyroid receptor binding + 0.5299 52.99%
Glucocorticoid receptor binding + 0.6554 65.54%
Aromatase binding - 0.6268 62.68%
PPAR gamma + 0.6865 68.65%
Honey bee toxicity - 0.7740 77.40%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5601 56.01%
Fish aquatic toxicity + 0.9389 93.89%

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 99.05% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 97.25% 91.49%
CHEMBL3194 P02766 Transthyretin 95.60% 90.71%
CHEMBL4302 P08183 P-glycoprotein 1 92.08% 92.98%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.99% 86.33%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 91.04% 83.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.25% 99.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 89.91% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.33% 89.00%
CHEMBL2535 P11166 Glucose transporter 88.78% 98.75%
CHEMBL245 P20309 Muscarinic acetylcholine receptor M3 88.47% 97.53%
CHEMBL2581 P07339 Cathepsin D 87.62% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.59% 97.09%
CHEMBL3004 P33527 Multidrug resistance-associated protein 1 86.44% 96.37%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.70% 94.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.91% 95.56%
CHEMBL1993 P26358 DNA (cytosine-5)-methyltransferase 1 82.80% 95.44%
CHEMBL340 P08684 Cytochrome P450 3A4 82.64% 91.19%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 82.45% 95.78%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.22% 92.94%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.91% 95.89%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 80.83% 97.21%

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.
Camellia sinensis

Cross-Links

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PubChem 467299
LOTUS LTS0005434
wikiData Q105238878