NP-MRD: Showing NP-Card for Epicatechin 3-O-(3-O-methylgallate) (NP0056106)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 01:59:08 UTC

Updated at

2022-04-28 01:59:09 UTC

NP-MRD ID

NP0056106

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epicatechin 3-O-(3-O-methylgallate)

Description

Epicatechin 3-O-(3-O-methylgallate), also known as 3-O-(3-methylgalloyl)epicatechin, belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Epicatechin 3-O-(3-O-methylgallate) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Epicatechin 3-O-(3-O-methylgallate) is found, on average, in the highest concentration within tea. This could make epicatechin 3-O-(3-O-methylgallate) a potential biomarker for the consumption of these foods. Epicatechin 3-O-(3-O-methylgallate) is found in Camellia sinensis . Epicatechin 3-O-(3-O-methylgallate) was first documented in 2009 (PMID: 19353533). A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 10221201552D          

 33 36  0  0  0  0            999 V2000
   -3.0054    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7198   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7198   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0054   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2909   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2909   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8620   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8620   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1475    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9959    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4343    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0054   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8620   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9959   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 18  1  0  0  0  0
  4 19  1  0  0  0  0
 12 20  1  0  0  0  0
  9 32  1  6  0  0  0
 21 22  2  0  0  0  0
 21 26  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 23 27  1  0  0  0  0
 24 28  1  0  0  0  0
 25 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    6.3736   -2.0623    1.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3950   -0.6754    1.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2370   -0.0052    0.8274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0566   -0.7066    0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9130   -0.0328    0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6491   -0.7508    0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6669   -1.9941    0.4983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849   -0.0611   -0.0026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7032   -0.7697   -0.1051 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2496   -0.7616   -1.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3667   -1.7264   -1.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6667   -2.3977   -2.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626   -2.2231   -3.9159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7218   -3.3111   -2.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4695   -3.5474   -1.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5360   -4.4660   -1.6364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1431   -2.8572   -0.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0955   -1.9418   -0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8236   -1.2780    0.7789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7488   -0.3651    0.8998 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1821    1.0308    0.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1100    1.4677   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5125    2.8013   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9948    3.7262    0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3881    5.0782    0.6834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0716    3.3098    1.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5564    4.2546    2.5134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721    1.9761    1.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9193    1.3524    0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0924    2.0525    0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1423    3.4454    0.1123 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2433    1.3622    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4312    2.0668    0.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7306   -2.3617    2.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9279   -2.5461    0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3990   -2.4427    1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0073   -1.7852    0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5027   -1.8430    0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    0.2460   -1.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3956   -1.0924   -2.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1830   -1.5835   -3.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9475   -3.8338   -3.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2647   -5.4216   -1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7067   -3.0154    0.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2867   -0.6089    1.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5662    0.7995   -0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2423    3.1475   -0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0160    5.7514    1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720    4.0574    3.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472    1.7147    2.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0012    1.8489   -0.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2701    3.9172   -0.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4646    3.0613    0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32 33  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 28  2  0
 28 26  1  0
 26 27  1  0
 26 24  2  0
 24 25  1  0
 24 23  1  0
 23 22  2  0
 18 17  1  0
 17 15  2  0
 15 16  1  0
 15 14  1  0
 14 12  2  0
 12 13  1  0
 32  3  1  0
 20  9  1  0
 22 21  1  0
 12 11  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
 29 51  1  0
 31 52  1  0
 33 53  1  0
  9 38  1  1
 10 39  1  0
 10 40  1  0
 20 45  1  1
 28 50  1  0
 27 49  1  0
 25 48  1  0
 23 47  1  0
 22 46  1  0
 17 44  1  0
 16 43  1  0
 14 42  1  0
 13 41  1  0
M  END


  Mrv0541 10221201552D          

 33 36  0  0  0  0            999 V2000
   -3.0054    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7198   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7198   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0054   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2909   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2909   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8620   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8620   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1475    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9959    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4343    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0054   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8620   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9959   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 18  1  0  0  0  0
  4 19  1  0  0  0  0
 12 20  1  0  0  0  0
  9 32  1  6  0  0  0
 21 22  2  0  0  0  0
 21 26  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 23 27  1  0  0  0  0
 24 28  1  0  0  0  0
 25 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056106

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C=C(O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O10/c1-31-19-6-11(5-17(28)21(19)29)23(30)33-20-9-13-15(26)7-12(24)8-18(13)32-22(20)10-2-3-14(25)16(27)4-10/h2-8,20,22,24-29H,9H2,1H3/t20-,22-/m1/s1

> <INCHI_KEY>
XGTBMCGGGJLOPS-IFMALSPDSA-N

> <FORMULA>
C23H20O10

> <MOLECULAR_WEIGHT>
456.3989

> <EXACT_MASS>
456.10564686

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
44.06461171728609

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4-dihydroxy-5-methoxybenzoate

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
3.525604955

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.09250288083612

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.611649936311222

> <JCHEM_PKA_STRONGEST_BASIC>
-4.617233962664017

> <JCHEM_POLAR_SURFACE_AREA>
166.14

> <JCHEM_REFRACTIVITY>
114.2467

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4-dihydroxy-5-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-OCT-12         0                                  
HETATM    1  C   UNK     0      -5.610   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.944  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.944  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.610  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.276  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.276  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.943   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.943  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.609  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.609  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.275   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.058   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.275   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.058  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.392   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.392   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.726   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -8.277   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -5.610  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.058   3.850   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.058  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.275  -6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.275  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.058  -8.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.392  -7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.392  -6.160   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.609  -8.470   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.058 -10.010   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       3.726  -8.470   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.058  -3.850   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.392  -3.080   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -0.275  -3.080   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.059  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   32                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16   20                                                  
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   12   15   17                                                  
CONECT   17   16                                                            
CONECT   18    2                                                            
CONECT   19    4                                                            
CONECT   20   12                                                            
CONECT   21   22   26   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26   29                                                  
CONECT   26   21   25                                                       
CONECT   27   23                                                            
CONECT   28   24                                                            
CONECT   29   25   33                                                       
CONECT   30   21   31   32                                                  
CONECT   31   30                                                            
CONECT   32    9   30                                                       
CONECT   33   29                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(-)-Epicatechin 3-(3'-O-methylgallate)	ChEBI
(-)-Epicatechin 3-O-(3'-O-methylgallate)	ChEBI
Epicatechin 3-(3'-O-methylgallate)	ChEBI
(-)-Epicatechin 3-(3'-O-methylgallic acid)	Generator
(-)-Epicatechin 3-O-(3'-O-methylgallic acid)	Generator
Epicatechin 3-(3'-O-methylgallic acid)	Generator
Epicatechin 3-O-(3-O-methylgallic acid)	Generator
3-O-(3-Methylgalloyl)epicatechin	HMDB
Epicatechin 3-(3-O-methylgallate)	HMDB
Epicatechin 3-O-(3-O-methylgallate)	ChEBI
Epicatechin 3-(3-methylgallic acid)	Generator

Chemical Formula

C₂₃H₂₀O₁₀

Average Mass

456.3989 Da

Monoisotopic Mass

456.10565 Da

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4-dihydroxy-5-methoxybenzoate

Traditional Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4-dihydroxy-5-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C=C(O)C=C2O

InChI Identifier

InChI=1S/C23H20O10/c1-31-19-6-11(5-17(28)21(19)29)23(30)33-20-9-13-15(26)7-12(24)8-18(13)32-22(20)10-2-3-14(25)16(27)4-10/h2-8,20,22,24-29H,9H2,1H3/t20-,22-/m1/s1

InChI Key

XGTBMCGGGJLOPS-IFMALSPDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Camellia sinensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid-5-o-glycoside
Flavonoid o-glycoside
Catechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Catechol
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Oxacycle
Polyol
Acetal
Ether
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.86	ALOGPS
logP	3.53	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.61	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114.25 m³·mol⁻¹	ChemAxon
Polarizability	44.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037945

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017115

KNApSAcK ID

C00008869

Chemspider ID

20019468

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21146793

PDB ID

Not Available

ChEBI ID

136553

Good Scents ID

Not Available

References

General References

Iijima T, Mohri Y, Hattori Y, Kashima A, Kamo T, Hirota M, Kiyota H, Makabe H: Synthesis of (-)-epicatechin 3-(3-O-methylgallate) and (+)-catechin 3-(3-O-methylgallate), and their anti-inflammatory activity. Chem Biodivers. 2009 Apr;6(4):520-6. doi: 10.1002/cbdv.200800224. [PubMed:19353533 ]

Showing NP-Card for Epicatechin 3-O-(3-O-methylgallate) (NP0056106)

MOL for NP0056106 (Epicatechin 3-O-(3-O-methylgallate))

3D MOL for NP0056106 (Epicatechin 3-O-(3-O-methylgallate))

3D SDF for NP0056106 (Epicatechin 3-O-(3-O-methylgallate))

3D-SDF for NP0056106 (Epicatechin 3-O-(3-O-methylgallate))

PDB for NP0056106 (Epicatechin 3-O-(3-O-methylgallate))

3D PDB for NP0056106 (Epicatechin 3-O-(3-O-methylgallate))

SMILES for NP0056106 (Epicatechin 3-O-(3-O-methylgallate))

INCHI for NP0056106 (Epicatechin 3-O-(3-O-methylgallate))

Structure for NP0056106 (Epicatechin 3-O-(3-O-methylgallate))

3D Structure for NP0056106 (Epicatechin 3-O-(3-O-methylgallate))