Compound Summary
Compound Information
(-)-Epigallocatechin gallate
Compound Name: | (-)-Epigallocatechin gallate |
Compound CID: | 65064 |
Synonyms: | (-)-Epigallocatechin gallate EGCG Epigallocatechin gallate 989-51-5 Epigallocatechin 3-gallate More... |
Iupac Name: | [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate |
InChI: | InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1 |
InChIKey: | WMBWREPUVVBILR-WIYYLYMNSA-N |
Canonical Smiles: | C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O |
Isomeric Smiles: | C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O |
Molecular Weight: | 458.4 |
Molecular Formula: | C22H18O11 |
Compound Structure
2D Structure:
3D Structure:
Computed Properties
(-)-Epigallocatechin gallate
Molecular Weight: | 458.4 |
Molecular Formula: | C22H18O11 |
Hydrogen Bond Donor Count: | 8 |
Hydrogen Bond Acceptor Count: | 11 |
Rotatable Bond Count: | 4 |
Heavy Atom Count: | 33 |
Complexity: | 667 |
Synonyms
(-)-Epigallocatechin gallate
| (-)-Epigallocatechin gallate | (-)-Epigallocatechin gallate |
|---|---|
(-)-Epigallocatechin gallate |
EGCG |
Epigallocatechin gallate |
989-51-5 |
Epigallocatechin 3-gallate |
Epigallocatechin-3-gallate |
Tea catechin |
(-)-Epigallocatechin-3-o-gallate |
Epigallocatechin-3-monogallate |
Teavigo |
(-)-Epigallocatechol gallate |
(-)-epigallocatechin 3-gallate |
Catechin deriv. |
UNII-BQM438CTEL |
Green tea extract |
(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate |
BQM438CTEL |
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate |
CHEBI:4806 |
CHEMBL297453 |
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate |
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate |
DSSTox_CID_567 |
C22H18O11 |
DSSTox_RID_78830 |
DSSTox_GSID_29889 |
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate |
TEA polyphenol |
(-)-cis-3,3,4,5,5,7-Hexahydroxy-flavane-3-gallate |
(-)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate |
CAS-989-51-5 |
SMR000449288 |
CCRIS 3729 |
SR-01000759328 |
L-Epigallocatechin gallate |
PF-EGCg 90 |
Epigallocate |
EPIGALOCATECHIN GALLATE |
NVP-XAA 723 |
(-)-EGCG |
Epigallocic acid |
Teavigo; |
Teatannin II |
2kdh |
3oob |
4awm |
(-)-epigallocatechin 3-O-gallate |
KDH |
Epigallocatechol, 3-gallate, (-)- |
(-)-Epigallocatechin gallate (EGCG) |
Epigallocatcchin Gallate |
Epigallocatechol Gallate |
Spectrum_000316 |
SpecPlus_000277 |
Spectrum2_000168 |
Spectrum3_000244 |
Spectrum4_001541 |
Spectrum5_000102 |
Galloyl-L-epigallocatechol |
3-O-Galloylepigallocatechin |
(-)-Epigallocatechin gallat |
(-)-Epigallocatehin gallate |
SCHEMBL35258 |
BSPBio_001628 |
epigallocatechin-gallate-(-) |
KBioGR_002002 |
KBioSS_000796 |
SPECTRUM210239 |
cid_65064 |
MLS000758300 |
MLS001424000 |
DivK1c_006373 |
SPBio_000035 |
Epigallocatechin monogallate, B |
GTPL7002 |
MEGxp0_001166 |
DTXSID1029889 |
ACon1_001054 |
KBio1_001317 |
KBio2_000796 |
KBio2_003364 |
KBio2_005932 |
KBio3_001128 |
AOB2839 |
HMS2051K21 |
HMS3649E08 |
ZINC3870412 |
Tox21_201468 |
Tox21_303457 |
BDBM50070942 |
CCG-38378 |
FR-109 |
LMPK12030005 |
MFCD00075940 |
s2250 |
AKOS015918182 |
ACN-035233 |
CS-1258 |
DB12116 |
DS-9030 |
EBD2138593 |
MCULE-3341525983 |
MCULE-7760530136 |
NC00078 |
SDCCGMLS-0066550.P001 |
(-)-Epigallocatechin gallate, >=95% |
(-)-Epigallocatechin-3-gallate; EGCG |
NCGC00164319-01 |
NCGC00164319-02 |
NCGC00164319-03 |
NCGC00164319-04 |
NCGC00164319-06 |
NCGC00257243-01 |
NCGC00259019-01 |
(-)-Epigallocatechin gallate (85% (-)-epigallocatechin gallate, 10% (-)-epigallocatechin, 5% (-)- epicatechin gallate) |
(2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-12H-benzopyran-3,5,7-triol-3-(3,4,5-trihydroxybenzoate) |
AC-34075 |
BP-30205 |
HY-13653 |
K791 |
ST097428 |
AB0014381 |
E0694 |
N1874 |
SW197458-3 |
C09731 |
M01719 |
(-)-Epigallocatechin gallate, >=97.0% (HPLC) |
(-)-Epigallocatechin gallate, analytical standard |
989E515 |
A845931 |
Gallic acid, 3-ester with epigallocatechol, (-)- |
Q393339 |
SR-01000946601 |
Q-100914 |
SR-01000759328-5 |
SR-01000759328-6 |
SR-01000946601-1 |
Epigallocatechin-3-gallate 1000 microg/mL in Acetonitrile |
UNII-T432289GYZ component WMBWREPUVVBILR-WIYYLYMNSA-N |
(-)-Epigallocatechin gallate, >=80% (HPLC), from green tea |
Epigallocatechin gallate, primary pharmaceutical reference standard |
(-)-Epigallocatechin-3-O-gallate, United States Pharmacopeia (USP) Reference Standard |
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxyb enzoate |
5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 2,3,4-trihydroxybenzoate |
Epigallocatechin gallate, Pharmaceutical Secondary Standard; Certified Reference Material |
(-)-cis-3,4-Dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1(2H)-benzopyran-3-yl Gallate |
(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl-3,4,5-trihydroxybenzoate |
3,4,5-Trihydroxybenzoic acid (2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester |
3,4-Dihydro-5,7-dihydroxy-2R-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3R-yl-3,4,5-trihydroxybenzoate |
Benzoic acid, 3,4,5-trihydroxy-, (2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester |
Benzoic acid, 3,4,5-trihydroxy-, 3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester, (2R-cis)- |
Benzoic acid, 3,4,5-trihydroxy-,(2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester |
Experimental Data
(-)-Epigallocatechin gallate
| Species | Dosage | Unit | CG Lifespan(AVG/MED days) | TG Lifespan(AVG/MED days) | Lifespan Change(AVG/MED%) | CG Lifespan(MAX days) | TG Lifespan(MAX days) | Lifespan Change(MAX%) | Significant | Strain | Gender | PubMed | Active Label |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Caenorhabditis elegans | 25 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 25 | ug/mL | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 100 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 10 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 220 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 50 | ug/mL | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 50 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 50 | ug/mL | 21.77 | 23.75 | 0.09 | S | N2 | 32908638 | Active | ||||
| Caenorhabditis elegans | 25 | umol/L | 25.3 | 25.4 | 0 | 35 | 35 | 0 | NS | N2 | 28992589 | Inactive | |
| Caenorhabditis elegans | 0.1 | ug/mL | 13.1 | S | N2 | 31201898 | Active | ||||||
| Caenorhabditis elegans | 10 | umol/L | 25.3 | 25.6 | 0.01 | 35 | 35.1 | 0 | NS | N2 | 28992589 | Inactive | |
| Rattus norvegicus | 25 | mg/kg | 14.1 | S | C57BL/6 | 31201898 | Active | ||||||
| Drosophila melanogaster | 10 | mg/mL | 51 | 59 | 0.16 | S | w1118 | MALES | 26375250 | Active | |||
| Caenorhabditis elegans | 400 | umol/L | 25.3 | 25.3 | 0 | 35 | 34.8 | -0.01 | NS | N2 | 28992589 | Inactive | |
| Caenorhabditis elegans | 300 | umol/L | 25.3 | 27.1 | 0.07 | 35 | 36.4 | 0.04 | S | N2 | 28992589 | Active | |
| Caenorhabditis elegans | 100 | umol/L | 20 | S | N2 | 31201898 | Active | ||||||
| Caenorhabditis elegans | 600 | umol/L | 25.3 | 24.7 | -0.02 | 35 | 34.1 | -0.03 | NS | N2 | 28992589 | Inactive | |
| Caenorhabditis elegans | 200 | umol/L | 25.3 | 29.5 | 0.17 | 35 | 36.1 | 0.03 | S | N2 | 28992589 | Active | |
| Caenorhabditis elegans | 500 | umol/L | 25.3 | 25.2 | 0 | 35 | 34.6 | -0.01 | NS | N2 | 28992589 | Inactive | |
| Mus musculus | 0.25 | % | 30.3 | S | C57BL/6 | 31201898 | Active | ||||||
| Caenorhabditis elegans | 1000 | umol/L | 25.3 | 21.1 | -0.17 | 35 | 30.4 | -0.13 | S | N2 | 28992589 | Inactive | |
| Caenorhabditis elegans | 800 | umol/L | 25.3 | 23.3 | -0.08 | 35 | 31.2 | -0.11 | S | N2 | 28992589 | Inactive | |
| Caenorhabditis elegans | 100 | umol/L | 25.3 | 28.7 | 0.13 | 35 | 35.8 | 0.02 | S | N2 | 28992589 | Active | |
| Caenorhabditis elegans | 50 | umol/L | 25.3 | 26.6 | 0.05 | 35 | 36 | 0.03 | NS | N2 | 28992589 | Inactive | |
| Caenorhabditis elegans | 100 | umol/L | 17.08 | 16.78 | -1.704 | NS | N2 | 33008901 | Inactive | ||||
| Caenorhabditis elegans | 10 | umol/L | 16.74 | 16.98 | 1.42 | NS | N2 | 33008901 | Inactive | ||||
| Caenorhabditis elegans | 25 | umol/L | 12.4 | 13 | 0.05 | 21 | 22 | 0.05 | NS | N2 | 17156833 | Inactive | |
| Caenorhabditis elegans | 220 | umol/L | 24.14 | 26.49 | 0.1 | 34 | 35 | 0.03 | NS | N2 | 19085685 | Inactive | |
| Caenorhabditis elegans | 220 | umol/L | 20.88 | 23.86 | 0.14 | 30 | 34 | 0.13 | S | fem-1(hc17) | 19085685 | Active | |
| Rattus norvegicus | 25 | mg/kg | 647.5 | 735 | 0.14 | S | Wistar | 23834676 | Active | ||||
| Caenorhabditis elegans | 100 | umol/L | 29.5 | 35.4 | 20 | 47 | 53.3 | 13 | S | 20513639 | Active | ||
| Caenorhabditis elegans | 10 | ug/mL | 1.8 | NS | N2 | 33683565 | Inactive | ||||||
| Caenorhabditis elegans | 1 | ug/mL | 1.7 | NS | N2 | 33683565 | Inactive | ||||||
| Caenorhabditis elegans | 220 | umol/L | 10.14 | S | N2 | 33683565 | Active | ||||||
| Caenorhabditis elegans | 0.1 | ug/mL | -1.8 | NS | N2 | 33683565 | Inactive | ||||||
| Caenorhabditis elegans | 25 | umol/L | 4.8 | 4.76 | NS | N2 | 33683565 | Inactive |
Experimental Data Visualization
(-)-Epigallocatechin gallate
Statistics Data
(-)-Epigallocatechin gallate
| Species | Lifespan Change(AVG/MED%) | Lifespan Change(MAX%) | Count Reference | Count Data point |
|---|---|---|---|---|
| Caenorhabditis elegans | 20 | 13 | 8 | 32 |
| Drosophila melanogaster | 0.16 | 1 | 1 | |
| Mus musculus | 30.3 | 1 | 1 | |
| Rattus norvegicus | 14.1 | 2 | 2 |
Statistics Data Visualization
(-)-Epigallocatechin gallate
