NP-MRD: Showing NP-Card for (-)-Gallocatechin (NP0044767)

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Record Information

Version

2.0

Created at

2022-02-24 21:15:26 UTC

Updated at

2022-02-24 21:15:26 UTC

NP-MRD ID

NP0044767

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Gallocatechin

Description

2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol, also known as epigallocatechin, 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. A hydroxyflavan that is 3,4-dihydro-2H-chromene which is substituted at positions 3, 5, and 7 by hydroxy groups, and at position 2 by a 3,4,5-trihydroxyphenyl group. (-)-Gallocatechin is found in Acacia mearnsii, Vachellia pennatula, Alhagi sparsifolia, Berchemia formosana, Betula pendula, Camellia sinensis, Caragana spinosa, Casuarina equisetifolia, Casuarina equisetifolia L. , Celastrus flagellaris, Chrysophyllum cainito, Cistus incanus, Croton lechleri, Cycas circinalis, Dicranopteris pedata, Diospyros kaki, Distylium racemosum, Ekebergia capensis, Elephantorrhiza goetzei, Entada phaseoloides, Eucalyptus ovata, Eugenia brasiliensis, Eugenia uniflora, Excoecaria agallocha, Gossypium hirsutum, Hippophae rhamnoides, Kandelia candel, Larix kaempferi, Leptarrhena pyrolifolia, Limonium gmelinii, Limonium sinense, Lotus corniculatus, Lotus pedunculatus, Lotus uliginosus, Manilkara zapota, Morella rubra, Phyllanthus amarus, Phyllanthus emblica, Phyllanthus niruri, Phyllanthus reticulatus, Pinus sylvestris, Platanus orientalis, Platycarya strobilacea, Platycodon grandiflorus, Potentilla erecta, Pseudolarix amabilis, Pseudolarix kaempferi Gord. , Psidium guajava, Pteroxygonum giraldii, Quercus acutissima, Quercus dentata, Quercus robur, Rhodiola rosea, Rhodiola semenovii, Rosa amblyotis, Rosa davurica , Rosa gracilipes, Rosa koreana, Rosa maximowicziana, Rosa rugosa , Salacia chinensis, Mallotus nudiflorus, Vicia faba, Vitis vinifera, Ziziphus jujuba and Ziziphus mauritiana. (-)-Gallocatechin was first documented in 2000 (LYFoo, et al.). 2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.8480    1.3046   -2.4073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9532    0.6937   -1.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3176   -0.3979   -0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4264   -1.0261    0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8690   -2.1121    0.8103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1570   -0.5680    0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7589    0.5230   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573    1.1305   -1.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4651    0.9822   -0.3763 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087    0.8333    0.8241 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6409    0.3838    0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2124    1.0679   -0.6826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522    0.7402   -1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9727    1.4576   -2.2533 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1708   -0.3022   -0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4114   -0.6078   -1.1645 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080   -0.9761    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3291   -2.0387    0.9866 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3496   -0.6537    0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3797   -0.0323    1.8123 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3762    0.7556    2.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1460   -1.1660    1.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6219    2.1007   -2.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3393   -0.7687   -0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2869   -2.5918    1.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3285    1.9801   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4404    1.8822    1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6547    1.8852   -1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207    2.2117   -2.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7707   -0.0719   -1.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9295   -2.5592    1.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9559   -1.2180    1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301   -0.4247    2.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0882    1.0778    3.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5405   -1.8128    1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -1.6819    0.4695 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  1
 12 28  1  0
 14 29  1  0
 16 30  1  0
 18 31  1  0
 19 32  1  0
M  END


  Mrv1652308231921592D          

 22 24  0  0  0  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  3  1  0  0  0  0
  9  8  2  0  0  0  0
 10  1  1  0  0  0  0
 11  2  2  0  0  0  0
 12  5  1  0  0  0  0
 13  4  2  0  0  0  0
 13  8  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 14  1  0  0  0  0
 22 13  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044767

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2=C(O)C=C(O)C=C2OC1C1=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

> <INCHI_KEY>
XMOCLSLCDHWDHP-UHFFFAOYSA-N

> <FORMULA>
C15H14O7

> <MOLECULAR_WEIGHT>
306.2675

> <EXACT_MASS>
306.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.351314566613958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
75.98060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epigallocatechin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    6   10                                                       
CONECT    2    6   11                                                       
CONECT    3    7    9                                                       
CONECT    4    7   13                                                       
CONECT    5    8   12                                                       
CONECT    6    1    2   15                                                  
CONECT    7    3    4   16                                                  
CONECT    8    5    9   13                                                  
CONECT    9    3    8   17                                                  
CONECT   10    1   14   18                                                  
CONECT   11    2   14   19                                                  
CONECT   12    5   15   20                                                  
CONECT   13    4    8   22                                                  
CONECT   14   10   11   21                                                  
CONECT   15    6   12   22                                                  
CONECT   16    7                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   14                                                            
CONECT   22   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Gallocatechol, (2S-trans)-isomer	HMDB
Gallocatechol, (2R-trans)-isomer	HMDB
Epigallocatechin	HMDB
Epigallocatechol	HMDB
Gallocatechin	HMDB
Gallocatechol	HMDB
Gallocatechol, (2R-cis)-isomer	HMDB

Chemical Formula

C₁₅H₁₄O₇

Average Mass

306.2675 Da

Monoisotopic Mass

306.07395 Da

IUPAC Name

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

Traditional Name

epigallocatechin

CAS Registry Number

Not Available

SMILES

OC1CC2=C(O)C=C(O)C=C2OC1C1=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

InChI Key

XMOCLSLCDHWDHP-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
Acacia mearnsii	LOTUS Database	35616633
Acacia pennatula	LOTUS Database	35616633
Alhagi sparsifolia	LOTUS Database	35616633
Berchemia formosana	LOTUS Database	35616633
Betula pendula	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Caragana spinosa	LOTUS Database	35616633
Casuarina equisetifolia	LOTUS Database	35616633
Casuarina equisetifolia L.	Plant	KNApSAcK
Celastrus flagellaris	LOTUS Database	35616633
Chrysophyllum cainito	LOTUS Database	35616633
Cistus incanus	LOTUS Database	35616633
Croton lechleri	LOTUS Database	35616633
Cycas circinalis	LOTUS Database	35616633
Dicranopteris pedata	LOTUS Database	35616633
Diospyros kaki	LOTUS Database	35616633
Distylium racemosum	LOTUS Database	35616633
Ekebergia capensis	LOTUS Database	35616633
Elephantorrhiza goetzei	LOTUS Database	35616633
Entada phaseoloides	LOTUS Database	35616633
Eucalyptus ovata	LOTUS Database	35616633
Eugenia brasiliensis	LOTUS Database	35616633
Eugenia uniflora	LOTUS Database	35616633
Excoecaria agallocha	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Hippophae rhamnoides	LOTUS Database	35616633
Kandelia candel	LOTUS Database	35616633
Larix kaempferi	LOTUS Database	35616633
Leptarrhena pyrolifolia	LOTUS Database	35616633
Limonium gmelinii	LOTUS Database	35616633
Limonium sinense	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Lotus pedunculatus	LOTUS Database	35616633
Lotus uliginosus	LOTUS Database	35616633
Manilkara zapota	LOTUS Database	35616633
Morella rubra	LOTUS Database	35616633
Phyllanthus amarus	LOTUS Database	35616633
Phyllanthus emblica	LOTUS Database	35616633
Phyllanthus niruri	LOTUS Database	35616633
Phyllanthus reticulatus	LOTUS Database	35616633
Pinus sylvestris	LOTUS Database	35616633
Platanus orientalis	LOTUS Database	35616633
Platycarya strobilacea	LOTUS Database	35616633
Platycodon grandiflorus	LOTUS Database	35616633
Potentilla erecta	LOTUS Database	35616633
Pseudolarix amabilis	LOTUS Database	35616633
Pseudolarix kaempferi Gord.	Plant	KNApSAcK
Psidium guajava	LOTUS Database	35616633
Pteroxygonum giraldii	LOTUS Database	35616633
Quercus acutissima	LOTUS Database	35616633
Quercus dentata	LOTUS Database	35616633
Quercus robur	LOTUS Database	35616633
Rhodiola rosea	LOTUS Database	35616633
Rhodiola semenovii	LOTUS Database	35616633
Rosa amblyotis	Plant	KNApSAcK
Rosa davurica	Plant	KNApSAcK
Rosa gracilipes	Plant	KNApSAcK
Rosa koreana	Plant	KNApSAcK
Rosa maximowicziana	Plant	KNApSAcK
Rosa rugosa	Plant	KNApSAcK
Salacia chinensis	LOTUS Database	35616633
Trewia nudiflora	LOTUS Database	35616633
Vicia faba	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Ziziphus jujuba	LOTUS Database	35616633
Ziziphus mauritiana	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

secondary alcohol (CHEBI:71224 )
polyphenol (CHEBI:71224 )
hydroxyflavan (CHEBI:71224 )
a 2,3-<i>cis</i>-flavan-3-ol (CPD-10411 )

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	29.35 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

HMDB0141542

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093296

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

1249

PDB ID

Not Available

ChEBI ID

71224

Good Scents ID

Not Available

References

General References

L.Y.Foo, Y.Lu, A.L.Molan, D.R.Woodfield, W.C.McNabb (2000). L.Y.Foo, Y.Lu, A.L.Molan, D.R.Woodfield, W.C.McNabb. The phenols and prodelphinidins of white clover flowers. Phytochemistry 54(5), 1 June 2000, Pages 539-548. 10.1016/S0031-9422(00)00124-2. Phytochemistry.

Showing NP-Card for (-)-Gallocatechin (NP0044767)

MOL for NP0044767 ((-)-Gallocatechin)

3D MOL for NP0044767 ((-)-Gallocatechin)

3D SDF for NP0044767 ((-)-Gallocatechin)

3D-SDF for NP0044767 ((-)-Gallocatechin)

PDB for NP0044767 ((-)-Gallocatechin)

3D PDB for NP0044767 ((-)-Gallocatechin)

SMILES for NP0044767 ((-)-Gallocatechin)

INCHI for NP0044767 ((-)-Gallocatechin)

Structure for NP0044767 ((-)-Gallocatechin)

3D Structure for NP0044767 ((-)-Gallocatechin)