(-)-Epigallocatechin 3-O-gallate
precursor
Showing entry for (-)-Epigallocatechin 3-O-gallate
Identification
- PhytoHub ID
- PHUB000265
- Name
- (-)-Epigallocatechin 3-O-gallate
- Systematic Name
- (−)-Epigallocatechin-3-O-gallate
- Synonyms
- EGCG
- CAS Number
- Not Available
- Average Mass
- 458.375
- Monoisotopic Mass
- 458.0849114
- Chemical Formula
- C22H18O11
- IUPAC Name
- (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
- InChI Key
- WMBWREPUVVBILR-PUUMMNGONA-N
- InChI Identifier
InChI=1/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-/s2
- SMILES
OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC(O)=C(O)C(O)=C1
- Structure
Calculated Properties
- Solubility (ALOGPS)
- 7.28e-02 g/l
- LogS (ALOGPS)
- -3.80
- LogP (ALOGPS)
- 2.38
- Hydrogen Acceptors
- 10
- Hydrogen Donors
- 8
- Rotatable Bond Count
- 4
- Polar Surface Area
- 197.36999999999998
- Refractivity
- 111.74529999999999
- Polarizability
- 42.62355309481916
- Formal Charge
- 0
- Physiological Charge
- 0
- pKa (strongest basic)
- -5.423934990004845
- pKa (strongest acidic)
- 7.992993558286566
- Number of Rings
- 4
- Rule of Five
- No
- Bioavailability
- Yes
- Ghose Filter
- Yes
- Veber's Rule
- No
- MDDR-like Rule
- No
External Links
No external links
Taxonomy as Food Phytochemical
- Family
- Polyphenols
- Class
- Flavonoids
- Sub-class
- Flavanols
Spectra from Online Resources
Record ID | Source | Description | View |
---|---|---|---|
TY000083 | MassBank | LC-ESI-ITTOF Spectrum - -, [M+H]+ | View Spectra |
Food Sources
Name | Group | |||
---|---|---|---|---|
Black tea | Teas and herbal teas | Publications | Show | |
Green tea | Teas and herbal teas | Publications | Show |
Role as Biomarker of intake
No roles as Biomarker of intake found
Metabolism
Food Phytochemical | Metabolite | Species | Biofluids | Origin | TMax | CMax | Urinary Excretion | Formula | Monoisotopic mass | ||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
(-)-Epigallocatechin 3-O-gallate | (-)-Epigallocatechin 3-O-gallate | Not Available | Not Available | Not Available | Not Available | Not Available | Not Available | C22H18O11 | 458.0849114 | Detailed Intervention Studies | |||
(-)-Epigallocatechin 3-O-gallate | (Epi)gallocatechin-3-O-gallate O-sulfate | human | ileal fluid, plasma | Not Available | Not Available | Not Available | Not Available | C22H18O14S | 538.4410395 | Publications | |||
(-)-Epigallocatechin 3-O-gallate | O-Methyl(epi)gallocatechin-3-O-gallate O-sulfate | human | ileal fluid | Not Available | Not Available | Not Available | Not Available | C23H20O14S | 552.4680283 | Publications | |||
(-)-Epigallocatechin 3-O-gallate | 5-(3’,4’,5’-trihydroxyphenyl)-gamma-valerolactone | human | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C11H12O5 | 224.068473486 | Publications | |||
(-)-Epigallocatechin 3-O-gallate | 5-(Phenyl)-γ-valerolactone-sulfate-glucuronide | human | plasma, urine | host-gut microbiota co-metabolite | 3h-5h | <20 nmol/L | <1% | Publications | |||||
Red Wine Flavan-3-ols | (-)-Epigallocatechin 3-O-gallate | human | plasma | unchanged | 1h-3h | 0.5-2µmol/L | Not Available | C22H18O11 | 458.0849114 | Publications |
Inter-Individual Variations in Metabolism
Food Phytochemical | Metabolite | Effect | Value | |||
---|---|---|---|---|---|---|
(-)-Epigallocatechin 3-O-gallate | 5-(Phenyl)-γ-valerolactone-sulfate-glucuronide | Microbiota | Effect, clusters | Publications | ||
Red Wine Flavan-3-ols | (-)-Epigallocatechin 3-O-gallate | Genotype | No effect | Publications |