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(˗)epigallocatechin
- Family: Plantae - Cistaceae
- Kingdom: Plantae
- Class: Flavonoid
| Canonical Smiles | Oc1cc2O[C@H](c3cc(O)c(c(c3)O)O)[C@@H](Cc2c(c1)O) |
|---|---|
| InChI | InChI=1S/C15H13O6/c16-8-5-10(17)9-1-2-13(21-14(9)6-8)7-3-11(18)15(20)12(19)4-7/h2-6,13,16-20H,1H2/t13-/m0/s1 |
| InChIKey | STTCSONHDOMVJH-ZDUSSCGKSA-N |
| Formula | C15H13O6 |
| HBA | 6 |
| HBD | 5 |
| MW | 289.26 |
| Rotatable Bonds | 1 |
| TPSA | 110.38 |
| LogP | 2.1 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.13 |
| Exact Mass | 289.07 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Helianthemum sessiliflorum | Cistaceae | Plantae | 2650562 |
Showing of synonyms
(˗)epigallocatechin
(-)-Epigallocatechin
Epigallocatechin
970-74-1
Epigallocatechol
L-Epigallocatechin
Epi-Gallocatechin
Antiscurvy factor C2
(-)-Epigallocatechol
L-Epigallocatechol
Galloepicatechin
3,3',4',5,5',7-Flavanhexol
(-)-epi-Gallocatechin
Sunphenon EGC
Factor C2 (antiscurvy)
(-)-3,3',4',5,5',7-Flavanhexol
2,3-cis-epigallocatechin
(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Antiscurvy factor C(sub 2)
CCRIS 5441
EGC
UNII-7Z197MG6QL
7Z197MG6QL
CHEBI:42255
1-epi-3',4',5,5',7-Pentahydroxy-3-Flavan
NSC 674039
NSC-674039
DTXSID40891550
2H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-, (2R-cis)-
2H-1-BENZOPYRAN-3,5,7-TRIOL, 3,4-DIHYDRO-2-(3,4,5-TRIHYDROXYPHENYL)-, (2R,3R)-
DTXCID501030643
(2R,3R)-2-(3,4,5-trihydroxyphenyl)chroman-3,5,7-triol
Cis-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol
(-)-EPIGALLOCATECHIN(EGC) (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT)
(2R,3R)-2-(3,4,5-trihydroxyphenyl)chromane-3,5,7-triol
MFCD00075939
(2R,3R)-3,4-Dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol
CHEMBL47386
(-)-EGC
(-)-cis-3,3',4',5,5',7-Hexahydroxyflavane
2-(3,4,5-TRIHYDROXY-PHENYL)-CHROMAN-3,5,7-TRIOL
(-)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol
(-)EPIGALLOCATECHIN
124107-38-6
3beta-Hydroxy-5alpha-pregnan-20-one Sulfate Pyridine Salt
NSC674039
(-) epigallocatechin
Epigallocatechin-(-)
Epigallocatechin (egc)
Spectrum_000806
SpecPlus_000269
Spectrum2_000703
Spectrum3_000248
Spectrum4_000950
Spectrum5_000889
(-)-Epigallocatechin/EGC
(-)-Epigallocatechin(EGC)
SCHEMBL19553
BSPBio_001636
KBioGR_001540
KBioSS_001286
SPECTRUM205113
DivK1c_006365
SPBio_000885
BCBcMAP01_000207
GTPL12461
HY-N0225R
KBio1_001309
KBio2_001286
KBio2_003854
KBio2_006422
KBio3_001136
(-)-Epigallocatechin (Standard)
GLXC-13576
EGC, (-)-EPIGALLOCATECHIN
HY-N0225
MSK40119
AC-394
BDBM50187665
CCG-38353
LMPK12020004
S3922
AKOS015965244
CS-3762
DB03823
DS-5807
FE22729
SDCCGMLS-0066479.P001
SMP1_000114
NCGC00179131-01
NCGC00179131-02
(-)-Epigallocatechin, analytical standard
NCI60_026204
(3,3',4',5,5',7-Hexahydroxyflavan)
E1084
NS00014558
(-)-cis-3,3',4',5,5',7-Hexahydroxyflavan
Epigallocatechin 1000 microg/mL in Acetonitrile
SR-05000002564
Q3044728
SR-05000002564-1
Q51617505
(-)-Epigallocatechin, >=95% (HPLC), from green tea
C24E9F59-8F06-44E2-B2DE-FF132A8774F3
Epigallocatechin, primary pharmaceutical reference standard
Rel-(2R,3R)-2-(3,4,5-Trihydroxyphenyl)chromane-3,5,7-triol
(-)cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
2H-1-Benzopyran-3,7-triol, 3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-, (2R-cis)-
3,3?,4?,5,5?,7-flavanhexol
5,7-triol,3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-2h-1-benzopyran-(2r-cis
L-Gallocatecholl
188819-07-0
- Benabdelaziz I, Haba H, et al. (2015). Lignans and other constituents from Helianthemum sessiliflorum Pers.. Records of Natural Products,2015,9(3),342-348. [View]
Pubchem:
72277
Cas:
970-74-1
Gnps:
CCMSLIB00004684090
Zinc:
ZINC000003870336
Kegg Ligand:
C12136
Chebi:
42255
Nmrshiftdb2:
60021305
Metabolights:
MTBLC42255
Chembl:
CHEMBL47386
Comptox:
DTXSID40891550
Drugbank:
DB03823
Pdb Ligand:
EGT
Bindingdb:
50187665
CPRiL:
3433
SMILES: c1cccc(c12)OC(CC2)c3ccccc3
Level: 1
Mol. Weight: 289.26 g/mol
SMILES: C1CCOc(c12)cccc2
Level: 0
Mol. Weight: 289.26 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 289.26 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.96
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.120
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.17
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.620
- Plasma Protein Binding
- 82.31
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 15.220
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.160
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.630
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.490
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 2.950
- Rat (Acute)
- 2.070
- Rat (Chronic Oral)
- 2.540
- Fathead Minnow
- 4.070
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 462.980
- Hydration Free Energy
- -12.850
- Log(D) at pH=7.4
- 1.270
- Log(P)
- 0.47
- Log S
- -2.06
- Log(Vapor Pressure)
- -8.96
- Melting Point
- 238.81
- pKa Acid
- 7.5
- pKa Basic
- 8.16
No predicted protein targets found for this compound.