NP-MRD: Showing NP-Card for (+)-Gallocatechin (NP0137085)

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Record Information

Version

2.0

Created at

2022-05-30 16:41:14 UTC

Updated at

2022-05-30 16:41:14 UTC

NP-MRD ID

NP0137085

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Gallocatechin

Description

(+)-Gallocatechin, also known as gallocatechol or casuarin, belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety (+)-Gallocatechin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (+)-Gallocatechin is a bitter tasting compound. Outside of the human body, (+)-Gallocatechin is found, on average, in the highest concentration within a few different foods, such as tea, broad beans, and cottonseeds and in a lower concentration in redcurrants, lentils, and grape wines (+)-Gallocatechin has also been detected, but not quantified in, several different foods, such as green bell peppers, cucumbers, guava, apricots, and green beans. (+)-Gallocatechin is found in Acacia mearnsii, Acacia mollifolia, Acacia rigens, Alhagi sparsifolia, Ampelopsis japonica, Apocynum venetum, Atuna racemosa, Azadirachta indica, Berchemia formosana, Betula pendula, Camellia sinensis, Casuarina equisetifolia, Celastrus flagellaris, Chrysophyllum cainito, Cistus creticus, Cistus incanus, Cornus kousa, Croton draconoides, Croton lechleri, Croton urucurana, Cucurbita pepo, Cycas circinalis, Diospyros kaki, Ekebergia capensis, Eucalyptus ovata, Euclea crispa, Eugenia brasiliensis, Eugenia uniflora, Excoecaria agallocha, Ginkgo biloba, Hamamelis virginiana, Hippophae rhamnoides, Hordeum vulgare, Humulus lupulus, Kandelia candel, Laurus nobilis, Leptarrhena pyrolifolia, Limonium gmelinii, Lotus corniculatus, Lotus uliginosus, Mallotus japonicus, Manilkara zapota, Maytenus disticha, Metasequoia glyptostroboides, Morella rubra, Morus alba, Onobrychis cyri, Phyllanthus amarus, Phyllanthus emblica, Phyllanthus niruri, Picea abies, Pinus sylvestris, Platycarya strobilacea, Potentilla anserina, Potentilla erecta, Psidium guajava, Pterocarpus angolensis, Pueraria montana, Punica granatum, Quercus acutissima, Quercus dentata, Quercus glauca, Quercus robur, Rhodiola semenovii, Rhus typhina, Ribes nigrum, Salix sachalinensis, Sanguisorba officinalis, Saxifraga cuneifolia, Stryphnodendron adstringens, Swietenia mahagoni, Tectaria subtriphylla, Thermopsis rhombifolia, Mallotus nudiflorus, Trifolium globosum, Trifolium repens, Vaccinium vitis-idaea, Vitellaria paradoxa, Vitis vinifera, Wisteria brachybotrys, Ziziphus jujuba and Ziziphus spina-christi. (+)-Gallocatechin was first documented in 1998 (PMID: 9741297). This could make (+)-gallocatechin a potential biomarker for the consumption of these foods (PMID: 22430120).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    4.7988    3.2143   -0.0290 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9910    2.1095    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5602    0.9226    0.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8279   -0.2160    0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4564   -1.3870    1.1670 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4330   -0.1625    0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456    0.9979    0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250    2.1189   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623    1.0190    0.0122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1283   -0.1789   -0.4957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5909   -0.0551   -0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1995    1.0997   -1.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5638    1.1805   -1.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1745    2.3371   -1.6143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3627    0.1132   -0.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7446    0.2496   -0.8598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7992   -1.0293   -0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6122   -2.0839    0.0886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007   -1.0878   -0.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976   -1.3788    0.2570 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0778   -2.5448   -0.5229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6652   -1.3834    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4735    4.1155   -0.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6411    0.8389    0.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0210   -2.2580    1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622    3.0317   -0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481   -0.2852   -1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693    1.9089   -1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1777    2.4054   -1.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3492   -0.5203   -0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1591   -2.9204    0.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0416   -2.0506    0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110   -1.5394    1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9028   -2.8020   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2066   -2.2867    0.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881   -1.4924    1.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 22  1  0
 22  6  1  0
  6  4  2  0
  4  5  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2  8  1  0
  8  7  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 10 20  1  0
 19 11  1  0
  7  6  1  0
 21 34  1  0
 20 33  1  1
 22 35  1  0
 22 36  1  0
  5 25  1  0
  3 24  1  0
  1 23  1  0
  8 26  1  0
 10 27  1  6
 12 28  1  0
 14 29  1  0
 16 30  1  0
 18 31  1  0
 19 32  1  0
M  END


  Mrv1652309272007452D          

 22 24  0  0  0  0            999 V2000
   -1.3450    2.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0576    1.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299    2.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6287    1.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0864    0.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0840    2.4834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0588    2.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7733    2.4802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3425    0.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3425    0.0062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990    2.0719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5135    2.4844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135    3.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2280    2.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8002    1.2468    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5147    0.8344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424    3.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6569    3.7219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2280    3.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2280    4.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424    2.4844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6569    2.0719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1  3  2  0  0  0  0
  7  2  2  0  0  0  0
  2  9  1  0  0  0  0
  9  4  2  0  0  0  0
  6  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6 11  1  0  0  0  0
  5 15  1  0  0  0  0
 15 11  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  2  0  0  0  0
 12 14  1  0  0  0  0
 19 13  1  0  0  0  0
 19 17  2  0  0  0  0
 14 21  2  0  0  0  0
 21 17  1  0  0  0  0
 15 16  1  1  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137085

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m0/s1

> <INCHI_KEY>
XMOCLSLCDHWDHP-SWLSCSKDSA-N

> <FORMULA>
C15H14O7

> <MOLECULAR_WEIGHT>
306.27

> <EXACT_MASS>
306.073952791

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.028294552603217

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
1.4915416936666661

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.513028720443094

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.728532640650023

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2949984309607405

> <JCHEM_POLAR_SURFACE_AREA>
130.61

> <JCHEM_REFRACTIVITY>
75.9806

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-gallocatechin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -2.511   4.632   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.841   2.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.176   3.864   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.174   2.323   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.161   1.555   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.157   4.636   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.843   3.860   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.177   4.630   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.506   1.552   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.506   0.012   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.491   3.868   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.825   4.638   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.825   6.178   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.159   3.868   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.494   2.327   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.827   1.558   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.492   6.178   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.826   6.948   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.159   6.948   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.159   8.488   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.492   4.638   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.826   3.868   0.000  0.00  0.00           O+0
CONECT    1    7    3                                                       
CONECT    2    7    9                                                       
CONECT    3    1    6    4                                                  
CONECT    4    9    3    5                                                  
CONECT    5    4   15                                                       
CONECT    6    3   11                                                       
CONECT    7    1    2    8                                                  
CONECT    8    7                                                            
CONECT    9    2    4   10                                                  
CONECT   10    9                                                            
CONECT   11    6   15   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   19                                                       
CONECT   14   12   21                                                       
CONECT   15    5   11   16                                                  
CONECT   16   15                                                            
CONECT   17   19   21   18                                                  
CONECT   18   17                                                            
CONECT   19   13   17   20                                                  
CONECT   20   19                                                            
CONECT   21   14   17   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
(+)-Gallocatechol	ChEBI
(2R,3S)-(+)-Gallocatechin	ChEBI
(2R,3S)-Flavan-3,3',4',5,5',7-hexol	ChEBI
(2R,3S)-Flavan-3,5,7,3',4',5'-hexol	ChEBI
(2R,3S)-Gallocatechin	ChEBI
Gallocatechin	ChEBI
Gallocatechol	Kegg
(+)-trans-3,3',4',5,5',7-Hexahydroxyflavan	HMDB
Casuarin	HMDB
D-Gallocatechin	HMDB
Epigallocatechol	HMDB
Epigallocatechin	HMDB
Gallocatechol, (2S-trans)-isomer	HMDB
Gallocatechol, (2R-cis)-isomer	HMDB
Gallocatechol, (2R-trans)-isomer	HMDB
(2R,3S)-3,4-Dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol	PhytoBank
(+)-Gallocatechin	PhytoBank
NSC 674038	PhytoBank
d-Gallocatechol	PhytoBank

Chemical Formula

C₁₅H₁₄O₇

Average Mass

306.2700 Da

Monoisotopic Mass

306.07395 Da

IUPAC Name

(2R,3S)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

(+)-gallocatechin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m0/s1

InChI Key

XMOCLSLCDHWDHP-SWLSCSKDSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Acacia mearnsii	LOTUS Database	35616633
Acacia mollifolia	LOTUS Database	35616633
Acacia rigens	LOTUS Database	35616633
Alhagi sparsifolia	LOTUS Database	35616633
Ampelopsis japonica	LOTUS Database	35616633
Apocynum venetum	LOTUS Database	35616633
Atuna racemosa	LOTUS Database	35616633
Azadirachta indica	LOTUS Database	35616633
Berchemia formosana	LOTUS Database	35616633
Betula pendula	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Casuarina equisetifolia	LOTUS Database	35616633
Celastrus flagellaris	LOTUS Database	35616633
Chrysophyllum cainito	LOTUS Database	35616633
Cistus creticus	LOTUS Database	35616633
Cistus incanus	LOTUS Database	35616633
Cornus kousa	LOTUS Database	35616633
Croton draconoides	LOTUS Database	35616633
Croton lechleri	LOTUS Database	35616633
Croton urucurana	LOTUS Database	35616633
Cucurbita pepo	LOTUS Database	35616633
Cycas circinalis	LOTUS Database	35616633
Diospyros kaki	LOTUS Database	35616633
Ekebergia capensis	LOTUS Database	35616633
Eucalyptus ovata	LOTUS Database	35616633
Euclea crispa	LOTUS Database	35616633
Eugenia brasiliensis	LOTUS Database	35616633
Eugenia uniflora	LOTUS Database	35616633
Excoecaria agallocha	LOTUS Database	35616633
Ginkgo biloba	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Hippophae rhamnoides	LOTUS Database	35616633
Hordeum vulgare	LOTUS Database	35616633
Humulus lupulus	LOTUS Database	35616633
Kandelia candel	LOTUS Database	35616633
Laurus nobilis	LOTUS Database	35616633
Leptarrhena pyrolifolia	LOTUS Database	35616633
Limonium gmelinii	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Lotus uliginosus	LOTUS Database	35616633
Mallotus japonicus	LOTUS Database	35616633
Manilkara zapota	LOTUS Database	35616633
Maytenus disticha	LOTUS Database	35616633
Metasequoia glyptostroboides	LOTUS Database	35616633
Morella rubra	LOTUS Database	35616633
Morus alba	LOTUS Database	35616633
Onobrychis cyri	LOTUS Database	35616633
Phyllanthus amarus	LOTUS Database	35616633
Phyllanthus emblica	LOTUS Database	35616633
Phyllanthus niruri	LOTUS Database	35616633
Picea abies	LOTUS Database	35616633
Pinus sylvestris	LOTUS Database	35616633
Platycarya strobilacea	LOTUS Database	35616633
Potentilla anserina	LOTUS Database	35616633
Potentilla erecta	LOTUS Database	35616633
Psidium guajava	LOTUS Database	35616633
Pterocarpus angolensis	LOTUS Database	35616633
Pueraria montana	LOTUS Database	35616633
Punica granatum	LOTUS Database	35616633
Quercus acutissima	LOTUS Database	35616633
Quercus dentata	LOTUS Database	35616633
Quercus glauca	LOTUS Database	35616633
Quercus robur	LOTUS Database	35616633
Rhodiola semenovii	LOTUS Database	35616633
Rhus typhina	LOTUS Database	35616633
Ribes nigrum	LOTUS Database	35616633
Salix sachalinensis	LOTUS Database	35616633
Sanguisorba officinalis	LOTUS Database	35616633
Saxifraga cuneifolia	LOTUS Database	35616633
Stryphnodendron adstringens	LOTUS Database	35616633
Swietenia mahagoni	LOTUS Database	35616633
Tectaria subtriphylla	LOTUS Database	35616633
Thermopsis rhombifolia	LOTUS Database	35616633
Trewia nudiflora	LOTUS Database	35616633
Trifolium globosum	LOTUS Database	35616633
Trifolium repens	LOTUS Database	35616633
Vaccinium vitis-idaea	LOTUS Database	35616633
Vitellaria paradoxa	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Wisteria brachybotrys	LOTUS Database	35616633
Ziziphus jujuba	LOTUS Database	35616633
Ziziphus spina-christi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Epigallocatechins

Alternative Parents

Substituents

Epigallocatechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
1-benzopyran
Chromane
Benzopyran
Pyrogallol derivative
Benzenetriol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

catechin (CHEBI:68330 )
flavan-3,3',4',5,5',7-hexol (CHEBI:68330 )
Flavans, Flavanols and Leucoanthocyanidins (C12127 )
Flavan 3-ols (C12127 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020002 )

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	0.71	ALOGPS
logP	1.49	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.73	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	130.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.98 m³·mol⁻¹	ChemAxon
Polarizability	29.03 Å³	ChemAxon
Number of Rings	3	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

HMDB0038365

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65084

PDB ID

Not Available

ChEBI ID

31018

Good Scents ID

Not Available

References

General References

Luo ZM, Ling TJ, Li LX, Zhang ZZ, Zhu HT, Zhang YJ, Wan XC: A new norisoprenoid and other compounds from Fuzhuan brick tea. Molecules. 2012 Mar 19;17(3):3539-46. doi: 10.3390/molecules17033539. [PubMed:22430120 ]
Noreen Y, Serrano G, Perera P, Bohlin L: Flavan-3-ols isolated from some medicinal plants inhibiting COX-1 and COX-2 catalysed prostaglandin biosynthesis. Planta Med. 1998 Aug;64(6):520-4. doi: 10.1055/s-2006-957506. [PubMed:9741297 ]

Showing NP-Card for (+)-Gallocatechin (NP0137085)

MOL for NP0137085 ((+)-Gallocatechin)

3D MOL for NP0137085 ((+)-Gallocatechin)

3D SDF for NP0137085 ((+)-Gallocatechin)

3D-SDF for NP0137085 ((+)-Gallocatechin)

PDB for NP0137085 ((+)-Gallocatechin)

3D PDB for NP0137085 ((+)-Gallocatechin)

SMILES for NP0137085 ((+)-Gallocatechin)

INCHI for NP0137085 ((+)-Gallocatechin)

Structure for NP0137085 ((+)-Gallocatechin)

3D Structure for NP0137085 ((+)-Gallocatechin)