Compound Summary
Compound Information
(-)-Epicatechin
Compound Name: | (-)-Epicatechin |
Compound CID: | 72276 |
Synonyms: | (-)-Epicatechin Epicatechin 490-46-0 L-Epicatechin (-)-Epicatechol More... |
Iupac Name: | (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol |
InChI: | InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 |
InChIKey: | PFTAWBLQPZVEMU-UKRRQHHQSA-N |
Canonical Smiles: | C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O |
Isomeric Smiles: | C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O |
Molecular Weight: | 290.27 |
Molecular Formula: | C15H14O6 |
Compound Structure
2D Structure:
3D Structure:
Computed Properties
(-)-Epicatechin
Molecular Weight: | 290.27 |
Molecular Formula: | C15H14O6 |
Hydrogen Bond Donor Count: | 5 |
Hydrogen Bond Acceptor Count: | 6 |
Rotatable Bond Count: | 1 |
Heavy Atom Count: | 21 |
Complexity: | 364 |
Synonyms
(-)-Epicatechin
| (-)-Epicatechin | (-)-Epicatechin |
|---|---|
(-)-Epicatechin |
Epicatechin |
490-46-0 |
L-Epicatechin |
(-)-Epicatechol |
(2R,3R)-2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol |
Epicatechol |
l-Acacatechin |
l-Epicatechol |
epi-Catechin |
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol |
UNII-34PHS7TU43 |
epi-Catechol |
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol |
CHEBI:90 |
Epicatechol, (-)- |
(2R,3R)-(-)-Epicatechin |
34PHS7TU43 |
NSC81161 |
(-)epicatechin |
(-)-cis-Epicatechin |
NSC 81161 |
2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-cis)- |
DSSTox_CID_25133 |
DSSTox_RID_80694 |
DSSTox_GSID_45133 |
(2R,3R)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol |
Epicatechin-(-) |
(-)-(2R:3R)-5,7,3,4-Tetrahydroxyflavan-3-ol |
CAS-490-46-0 |
SMR000156230 |
CCRIS 7097 |
2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3R)- |
EINECS 207-710-1 |
Acacatechin |
Colatein |
alpha-catechin |
Kakaol |
Teacatechin I |
MFCD00075648 |
NSC-81161 |
.alpha. Catechin |
NCGC00015215-02 |
28E |
L(-)-Epicatechin |
Prestwick_203 |
2,3-cis-epicatechin |
L-Epicatechin ,(S) |
Spectrum_000159 |
SpecPlus_000267 |
2-(3,4-Dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromene |
Spectrum2_000675 |
Spectrum3_000243 |
Spectrum4_000949 |
Spectrum5_000929 |
Lopac-C-1251 |
Oprea1_209947 |
SCHEMBL19412 |
BSPBio_001626 |
KBioGR_001538 |
KBioSS_000639 |
SPECTRUM210206 |
cid_72276 |
MLS001304012 |
MLS001304152 |
DivK1c_006363 |
SPBio_000769 |
CHEMBL583912 |
DTXSID4045133 |
ACon1_001106 |
BCBcMAP01_000224 |
BDBM23417 |
KBio1_001307 |
KBio2_000639 |
KBio2_003207 |
KBio2_005775 |
KBio3_001126 |
HMS1923M05 |
KUC104404N |
ZINC119988 |
HY-N0001 |
Tox21_110101 |
3,3,4,5,7-Pentahydroxyflavane |
CCG-38571 |
LMPK12020003 |
s4723 |
(-)-Epicatechin, analytical standard |
AKOS015895981 |
Tox21_110101_1 |
(-)-Epicatechin, >=90% (HPLC) |
ACN-035300 |
CS-3760 |
DB12039 |
DS-3358 |
EBD2184991 |
KSC-10-144 |
MCULE-8775451204 |
SDCCGMLS-0066927.P001 |
2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-,(2R,3R)- |
SMP1_000115 |
NCGC00015215-01 |
NCGC00016415-01 |
NCGC00016415-02 |
NCGC00016415-03 |
NCGC00016415-04 |
NCGC00017331-08 |
AC-14586 |
BP-30203 |
CAS-154-23-4 |
P692 |
CAS-7295-85-4 |
B4964 |
(-)-Epicatechin 1000 microg/mL in Acetone |
A12043 |
C09727 |
O10053 |
(-)-Epicatechin 1000 microg/mL in Acetonitrile |
490E460 |
A871843 |
(-)-Epicatechin, >=98% (HPLC), from green tea |
Q-200001 |
CF3BA0C2-DE1B-44AB-A4D3-800F017221BA |
Epicatechin, primary pharmaceutical reference standard |
Q23050136 |
UNII-T432289GYZ component PFTAWBLQPZVEMU-UKRRQHHQSA-N |
2-(3,4-dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromene;L-Epicatechin |
(-)-cis-3,3,4,5,7-Pentahydroxyflavane, (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol" |
Experimental Data
(-)-Epicatechin
| 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 | 200 | umol/L | 18.3 | 19.2 | 0.05 | Unclear | N2 | 35968754 | |||||
| Caenorhabditis elegans | 50 | umol/L | 18.3 | 19.1 | 0.04 | Unclear | N2 | 35968754 | |||||
| Caenorhabditis elegans | 100 | umol/L | 18.3 | 19.6 | 0.07 | Unclear | N2 | 35968754 | |||||
| Drosophila melanogaster | 1 | umol/L | 48 | 28 | -0.42 | 82 | 93 | 0.13 | NS | Canton-S | MALES | 28066251 | Inactive |
| Drosophila melanogaster | 0.3 | umol/L | 48 | 49 | 0.02 | 82 | 79 | -0.04 | NS | Canton-S | FEMALES | 28066251 | Inactive |
| Drosophila melanogaster | 0.5 | umol/L | 47 | 47 | 0 | 76 | 68 | -0.11 | NS | Canton-S | MALES | 28066251 | Inactive |
| Drosophila melanogaster | 0.5 | umol/L | 48 | 50 | 0.04 | 82 | 78 | -0.05 | NS | Canton-S | MALES | 28066251 | Inactive |
| Drosophila melanogaster | 0.3 | umol/L | 48 | 35 | -0.27 | 82 | 64 | -0.22 | S | Canton-S | MALES | 28066251 | Inactive |
| Drosophila melanogaster | 0.3 | umol/L | 58 | 54 | -0.07 | 78 | 97 | 0.24 | S | Canton-S | FEMALES | 28066251 | Inactive |
| Drosophila melanogaster | 0.5 | umol/L | 48 | 38 | -0.21 | 82 | 76 | -0.07 | S | Canton-S | FEMALES | 28066251 | Inactive |
| Drosophila melanogaster | 0.3 | umol/L | 47 | 48 | 0.02 | 76 | 72 | -0.05 | NS | Canton-S | MALES | 28066251 | Inactive |
| Drosophila melanogaster | 1 | umol/L | 47 | 42 | -0.11 | 76 | 62 | -0.18 | S | Canton-S | MALES | 28066251 | Inactive |
| Drosophila melanogaster | 0.5 | umol/L | 58 | 64 | 0.1 | 78 | 86 | 0.1 | S | Canton-S | FEMALES | 28066251 | Active |
| Drosophila melanogaster | 1 | umol/L | 48 | 47 | -0.02 | 82 | 93 | 0.13 | S | Canton-S | FEMALES | 28066251 | Inactive |
| Drosophila melanogaster | 1 | umol/L | 58 | 62 | 0.07 | 78 | 89 | 0.14 | NS | Canton-S | FEMALES | 28066251 | Inactive |
| Caenorhabditis elegans | 100 | umol/L | 29.5 | 34 | 15 | 47 | 52 | 11 | S | 20513639 | Active | ||
| Mus musculus | 0.25 | %w/v | 238 | 294 | 0.24 | S | MALES | 30096038 | Active | ||||
| Drosophila melanogaster | 0.1 | mg/mL | 3.7 | Unclear | Oregon-R | MALES | 8326745 | ||||||
| Drosophila melanogaster | 0.01 | mg/mL | 1.8 | Unclear | Oregon-R | MALES | 8326745 | ||||||
| Drosophila melanogaster | 0.1 | mM | 42 | S | Canton-S | 21525262 | Active | ||||||
| Drosophila melanogaster | 1 | mg/mL | 7.4 | Unclear | Oregon-R | MALES | 8326745 | ||||||
| Caenorhabditis elegans | 65 | ug/mL | 19.27 | 19.93 | 3.4 | NS | fem-1(hc17) | 20717869 | Inactive |
Experimental Data Visualization
(-)-Epicatechin
Statistics Data
(-)-Epicatechin
| Species | Lifespan Change(AVG/MED%) | Lifespan Change(MAX%) | Count Reference | Count Data point |
|---|---|---|---|---|
| Caenorhabditis elegans | 15 | 11 | 3 | 5 |
| Drosophila melanogaster | 42 | 0.24 | 3 | 16 |
| Mus musculus | 0.24 | 1 | 1 |
Statistics Data Visualization
(-)-Epicatechin
