NP-MRD: Showing NP-Card for Epigallocatechin 3-O-caffeate (NP0056139)

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Record Information

Version

2.0

Created at

2022-04-28 02:00:22 UTC

Updated at

2022-04-28 02:00:22 UTC

NP-MRD ID

NP0056139

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epigallocatechin 3-O-caffeate

Description

Epigallocatechin 3-caffeate belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Epigallocatechin 3-O-caffeate is found in Camellia sinensis . Epigallocatechin 3-caffeate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241220572D          

 34 37  0  0  0  0            999 V2000
   -8.9837   -2.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6982   -2.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6982   -3.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9837   -3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2692   -3.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2692   -2.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5548   -2.1045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5548   -3.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8403   -3.3419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8403   -2.5169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1258   -2.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4113   -0.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1258   -1.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4113   -2.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6969   -2.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6968   -1.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4125   -2.1045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824   -0.8669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824   -2.5169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9837   -4.5794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4113   -0.0419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3026   -6.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5881   -6.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5881   -7.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3026   -7.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0171   -7.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0171   -6.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3026   -8.6160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8737   -7.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3026   -5.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5881   -4.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5881   -4.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3026   -3.6660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8737   -3.6660    0.0000 O   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
  2 17  1  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
  4 20  1  0  0  0  0
 12 21  1  0  0  0  0
  9 33  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  0  0  0  0
 24 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    1.4732   -1.9441    2.1764 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6287   -1.0350    1.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760   -0.5211    0.9950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1618    0.4239    0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4724    0.9410   -0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5673    1.9556   -1.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7797    2.4978   -1.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9562    2.0579   -0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1725    2.6215   -1.3825 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8806    1.0645   -0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0115    0.5782    0.5604 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6489    0.5122    0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4954   -0.5363    0.7036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784   -1.0280    1.0187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4129   -1.7474   -0.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5256   -2.5417    0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8366   -3.7791   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1640   -4.3791   -1.1263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8960   -4.4506    0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6110   -3.8986    1.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6631   -4.6198    2.1553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795   -2.6511    2.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2330   -1.9735    1.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9135   -0.7229    1.9662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7425   -0.0194    1.5440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1934    0.9939    0.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3991    1.6638    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907    2.6225   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1095    3.2764    0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1373    2.9587   -1.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6562    3.9286   -2.0155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9389    2.3209   -1.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808    2.6449   -2.5365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4679    1.3371   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124   -0.9503    1.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    0.8063   -0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6306    2.2966   -1.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8376    3.2800   -2.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1949    3.3513   -2.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9051    0.9418    0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6257   -0.2649    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7030   -1.8447    1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8452   -1.0542   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571   -2.3721   -0.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3910   -3.9913   -1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1759   -5.4256    0.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5989   -4.4910    1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8526   -2.2532    2.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3484    0.5129    2.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9638    1.3784    1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6155    2.9952    0.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2769    4.3000   -2.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5113    3.3501   -3.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5128    0.8827   -0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 22  2  0
 22 23  1  0
 23 16  2  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 12  2  0
 12 10  1  0
 10 11  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
 14 25  1  0
 25 24  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 24 23  1  0
 34 26  1  0
  6  5  1  0
 21 47  1  0
 22 48  1  0
 15 43  1  0
 15 44  1  0
 14 42  1  1
  3 35  1  0
  4 36  1  0
 12 41  1  0
 11 40  1  0
  9 39  1  0
  7 38  1  0
  6 37  1  0
 25 49  1  1
 27 50  1  0
 29 51  1  0
 31 52  1  0
 33 53  1  0
 34 54  1  0
 18 45  1  0
 19 46  1  0
M  END


  Mrv0541 02241220572D          

 34 37  0  0  0  0            999 V2000
   -8.9837   -2.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6982   -2.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6982   -3.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9837   -3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2692   -3.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2692   -2.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5548   -2.1045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5548   -3.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8403   -3.3419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8403   -2.5169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1258   -2.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4113   -0.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1258   -1.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4113   -2.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6969   -2.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6968   -1.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4125   -2.1045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824   -0.8669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824   -2.5169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9837   -4.5794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4113   -0.0419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3026   -6.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5881   -6.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5881   -7.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3026   -7.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0171   -7.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0171   -6.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3026   -8.6160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8737   -7.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3026   -5.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5881   -4.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5881   -4.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3026   -3.6660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8737   -3.6660    0.0000 O   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
  2 17  1  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
  4 20  1  0  0  0  0
 12 21  1  0  0  0  0
  9 33  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  0  0  0  0
 24 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0056139

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C[C@@H](OC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@H](O2)C2=CC(O)=C(O)C(O)=C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H20O10/c25-13-8-16(27)14-10-21(33-22(31)4-2-11-1-3-15(26)17(28)5-11)24(34-20(14)9-13)12-6-18(29)23(32)19(30)7-12/h1-9,21,24-30,32H,10H2/b4-2+/t21-,24-/m1/s1

> <INCHI_KEY>
BNLVODKLELGOBT-WEDYXYFPSA-N

> <FORMULA>
C24H20O10

> <MOLECULAR_WEIGHT>
468.4096

> <EXACT_MASS>
468.10564686

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
45.70575101197346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
3.9183017683333325

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.039366782066208

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.534046348472804

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9235619173194225

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
119.5101

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epigallocatechin 3-O-caffeate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0     -16.770  -3.928   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -18.103  -4.698   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -18.103  -6.238   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -16.770  -7.008   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -15.436  -6.238   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -15.436  -4.698   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -14.102  -3.928   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -14.102  -7.008   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.769  -6.238   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.769  -4.698   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -11.435  -3.928   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.101  -1.618   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -11.435  -2.388   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.101  -4.698   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.768  -3.928   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.767  -2.388   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -19.437  -3.928   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -7.434  -1.618   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -7.434  -4.698   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0     -16.770  -8.548   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0     -10.101  -0.078   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -11.765 -11.463   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -10.431 -12.233   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.431 -13.773   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.765 -14.543   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -13.099 -13.773   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.099 -12.233   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -11.765 -16.083   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -9.098 -14.543   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -11.765  -9.923   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.431  -9.153   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -10.431  -7.613   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -11.765  -6.843   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -9.098  -6.843   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   33                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16   21                                                  
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   12   15   18                                                  
CONECT   17    2                                                            
CONECT   18   16                                                            
CONECT   19   15                                                            
CONECT   20    4                                                            
CONECT   21   12                                                            
CONECT   22   23   27   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   25                                                            
CONECT   29   24                                                            
CONECT   30   22   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33    9   32                                                       
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Epigallocatechin 3-caffeic acid	Generator

Chemical Formula

C₂₄H₂₀O₁₀

Average Mass

468.4096 Da

Monoisotopic Mass

468.10565 Da

IUPAC Name

(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

epigallocatechin 3-O-caffeate

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C[C@@H](OC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@H](O2)C2=CC(O)=C(O)C(O)=C2)C(O)=C1

InChI Identifier

InChI=1S/C24H20O10/c25-13-8-16(27)14-10-21(33-22(31)4-2-11-1-3-15(26)17(28)5-11)24(34-20(14)9-13)12-6-18(29)23(32)19(30)7-12/h1-9,21,24-30,32H,10H2/b4-2+/t21-,24-/m1/s1

InChI Key

BNLVODKLELGOBT-WEDYXYFPSA-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 fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Disaccharide
Glycosyl compound
O-glycosyl compound
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Heterocyclic fatty acid
Hydroxy fatty acid
Alpha-hydroxy acid
Fatty acid
Hydroxy acid
Oxane
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	2.9	ALOGPS
logP	3.92	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.53	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	119.51 m³·mol⁻¹	ChemAxon
Polarizability	45.71 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001634

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14284598

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Epigallocatechin 3-O-caffeate (NP0056139)

MOL for NP0056139 (Epigallocatechin 3-O-caffeate)

3D MOL for NP0056139 (Epigallocatechin 3-O-caffeate)

3D SDF for NP0056139 (Epigallocatechin 3-O-caffeate)

3D-SDF for NP0056139 (Epigallocatechin 3-O-caffeate)

PDB for NP0056139 (Epigallocatechin 3-O-caffeate)

3D PDB for NP0056139 (Epigallocatechin 3-O-caffeate)

SMILES for NP0056139 (Epigallocatechin 3-O-caffeate)

INCHI for NP0056139 (Epigallocatechin 3-O-caffeate)

Structure for NP0056139 (Epigallocatechin 3-O-caffeate)

3D Structure for NP0056139 (Epigallocatechin 3-O-caffeate)