Compound Summary
(-)-Epigallocatechin gallate
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 | Dose | Unit | Control(Avg days) | Treatment(Avg days) | Avg/Med Lifespan Change(%) | Control(Max days) | Treatment(Max days) | Max Lifespan Change(%) | Significant | Strain | Gender | PubMed | Avg/Med Lifespan Change tab |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Caenorhabditis elegans | 25.000000000000000 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 25.000000000000000 | ug/mL | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 100.000000000000000 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 10.000000000000000 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 220.000000000000000 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 50.000000000000000 | ug/mL | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 50.000000000000000 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 50.000000000000000 | ug/mL | 21.770000000000000 | 23.750000000000000 | 0.090000000000000 | S | N2 | 32908638 | Active | ||||
| Caenorhabditis elegans | 25.000000000000000 | umol/L | 25.300000000000000 | 25.400000000000000 | 0.000000000000000 | 35.000000000000000 | 35.000000000000000 | 0.000000000000000 | NS | N2 | 28992589 | Inactive | |
| Caenorhabditis elegans | 0.100000000000000 | ug/mL | 13.100000000000000 | S | N2 | 31201898 | Active | ||||||
| Caenorhabditis elegans | 10.000000000000000 | umol/L | 25.300000000000000 | 25.600000000000000 | 0.010000000000000 | 35.000000000000000 | 35.100000000000000 | 0.000000000000000 | NS | N2 | 28992589 | Inactive | |
| Rattus norvegicus | 25.000000000000000 | mg/kg | 14.100000000000000 | S | C57BL/6 | 31201898 | Active | ||||||
| Drosophila melanogaster | 10.000000000000000 | mg/mL | 51.000000000000000 | 59.000000000000000 | 0.160000000000000 | S | w1118 | MALES | 26375250 | Active | |||
| Caenorhabditis elegans | 400.000000000000000 | umol/L | 25.300000000000000 | 25.300000000000000 | 0.000000000000000 | 35.000000000000000 | 34.800000000000000 | -0.010000000000000 | NS | N2 | 28992589 | Inactive | |
| Caenorhabditis elegans | 300.000000000000000 | umol/L | 25.300000000000000 | 27.100000000000000 | 0.070000000000000 | 35.000000000000000 | 36.400000000000000 | 0.040000000000000 | S | N2 | 28992589 | Active | |
| Caenorhabditis elegans | 100.000000000000000 | umol/L | 20.000000000000000 | S | N2 | 31201898 | Active | ||||||
| Caenorhabditis elegans | 600.000000000000000 | umol/L | 25.300000000000000 | 24.700000000000000 | -0.020000000000000 | 35.000000000000000 | 34.100000000000000 | -0.030000000000000 | NS | N2 | 28992589 | Inactive | |
| Caenorhabditis elegans | 200.000000000000000 | umol/L | 25.300000000000000 | 29.500000000000000 | 0.170000000000000 | 35.000000000000000 | 36.100000000000000 | 0.030000000000000 | S | N2 | 28992589 | Active | |
| Caenorhabditis elegans | 500.000000000000000 | umol/L | 25.300000000000000 | 25.200000000000000 | 0.000000000000000 | 35.000000000000000 | 34.600000000000000 | -0.010000000000000 | NS | N2 | 28992589 | Inactive | |
| Mus musculus | 0.250000000000000 | % | 30.300000000000000 | S | C57BL/6 | 31201898 | Active | ||||||
| Caenorhabditis elegans | 1000.000000000000000 | umol/L | 25.300000000000000 | 21.100000000000000 | -0.170000000000000 | 35.000000000000000 | 30.400000000000000 | -0.130000000000000 | S | N2 | 28992589 | Inactive | |
| Caenorhabditis elegans | 800.000000000000000 | umol/L | 25.300000000000000 | 23.300000000000000 | -0.080000000000000 | 35.000000000000000 | 31.200000000000000 | -0.110000000000000 | S | N2 | 28992589 | Inactive | |
| Caenorhabditis elegans | 100.000000000000000 | umol/L | 25.300000000000000 | 28.700000000000000 | 0.130000000000000 | 35.000000000000000 | 35.800000000000000 | 0.020000000000000 | S | N2 | 28992589 | Active | |
| Caenorhabditis elegans | 50.000000000000000 | umol/L | 25.300000000000000 | 26.600000000000000 | 0.050000000000000 | 35.000000000000000 | 36.000000000000000 | 0.030000000000000 | NS | N2 | 28992589 | Inactive | |
| Caenorhabditis elegans | 100.000000000000000 | umol/L | 17.080000000000000 | 16.780000000000000 | -1.704000000000000 | NS | N2 | 33008901 | Inactive | ||||
| Caenorhabditis elegans | 10.000000000000000 | umol/L | 16.740000000000000 | 16.980000000000000 | 1.420000000000000 | NS | N2 | 33008901 | Inactive | ||||
| Caenorhabditis elegans | 25.000000000000000 | umol/L | 12.400000000000000 | 13.000000000000000 | 0.050000000000000 | 21.000000000000000 | 22.000000000000000 | 0.050000000000000 | NS | N2 | 17156833 | Inactive | |
| Caenorhabditis elegans | 220.000000000000000 | umol/L | 24.140000000000000 | 26.490000000000000 | 0.100000000000000 | 34.000000000000000 | 35.000000000000000 | 0.030000000000000 | NS | N2 | 19085685 | Inactive | |
| Caenorhabditis elegans | 220.000000000000000 | umol/L | 20.880000000000000 | 23.860000000000000 | 0.140000000000000 | 30.000000000000000 | 34.000000000000000 | 0.130000000000000 | S | fem-1(hc17) | 19085685 | Active | |
| Rattus norvegicus | 25.000000000000000 | mg/kg | 647.500000000000000 | 735.000000000000000 | 0.140000000000000 | S | Wistar | 23834676 | Active | ||||
| Caenorhabditis elegans | 100.000000000000000 | umol/L | 29.500000000000000 | 35.400000000000000 | 20.000000000000000 | 47.000000000000000 | 53.300000000000000 | 13.000000000000000 | S | 20513639 | Active | ||
| Caenorhabditis elegans | 10.000000000000000 | ug/mL | 1.800000000000000 | NS | N2 | 33683565 | Inactive | ||||||
| Caenorhabditis elegans | 1.000000000000000 | ug/mL | 1.700000000000000 | NS | N2 | 33683565 | Inactive | ||||||
| Caenorhabditis elegans | 220.000000000000000 | umol/L | 10.140000000000000 | S | N2 | 33683565 | Active | ||||||
| Caenorhabditis elegans | 0.100000000000000 | ug/mL | -1.800000000000000 | NS | N2 | 33683565 | Inactive | ||||||
| Caenorhabditis elegans | 25.000000000000000 | umol/L | 4.800000000000000 | 4.760000000000000 | NS | N2 | 33683565 | Inactive |
Experimental Data Visualization
(-)-Epigallocatechin gallate
Statistics Data
(-)-Epigallocatechin gallate
| Species | Avg/Med Lifespan Change(%) | Max Lifespan Change(%) | Count Reference | Count Data point |
|---|---|---|---|---|
| Caenorhabditis elegans | 20.000000000000000 | 13.000000000000000 | 8 | 32 |
| Drosophila melanogaster | 0.160000000000000 | 1 | 1 | |
| Mus musculus | 30.300000000000000 | 1 | 1 | |
| Rattus norvegicus | 14.100000000000000 | 2 | 2 |
Statistics Data Visualization
(-)-Epigallocatechin gallate
