NP-MRD: Showing NP-Card for Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin (NP0049626)

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Record Information

Version

2.0

Created at

2022-03-17 21:15:31 UTC

Updated at

2022-03-17 21:15:31 UTC

NP-MRD ID

NP0049626

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin

Description

Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin, also known as [gallocatechin-(4alpha->8)]2-gallocatechin, belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin has been detected, but not quantified in, a few different foods, such as barley, blackcurrants, and cereals and cereal products. Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin is found in Cistus incanus. This could make gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241210382D          

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M  END


  Mrv0541 02241210382D          

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 56 66  1  0  0  0  0
 28 45  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0049626

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C(O)=C1)C([C@H]1[C@H](O)[C@H](OC3=C1C(O)=CC(O)=C3[C@H]1[C@H](O)[C@H](OC3=C1C(O)=CC(O)=C3)C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C(O)=C1)=C(O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C45H38O21/c46-15-7-18(48)30-29(8-15)64-42(13-3-24(54)37(60)25(55)4-13)39(62)34(30)32-20(50)11-21(51)33-35(40(63)43(66-45(32)33)14-5-26(56)38(61)27(57)6-14)31-19(49)10-17(47)16-9-28(58)41(65-44(16)31)12-1-22(52)36(59)23(53)2-12/h1-8,10-11,28,34-35,39-43,46-63H,9H2/t28-,34-,35+,39-,40-,41+,42+,43+/m0/s1

> <INCHI_KEY>
NVTLDVSBUJGIAD-QHBXHTPSSA-N

> <FORMULA>
C45H38O21

> <MOLECULAR_WEIGHT>
914.7706

> <EXACT_MASS>
914.190558278

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
89.38479973546174

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
18

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R)-8-[(2R,3S,4S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
3.5256870469999995

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.852092039900647

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.375079693821142

> <JCHEM_PKA_STRONGEST_BASIC>
-6.011005500432657

> <JCHEM_POLAR_SURFACE_AREA>
391.8300000000001

> <JCHEM_REFRACTIVITY>
224.95900000000012

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R)-8-[(2R,3S,4S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <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                                  
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HETATM    2  C   UNK     0      -7.989   2.805   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.989   1.265   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.655   0.495   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.321   1.265   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.321   2.805   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.988   3.575   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.988   0.495   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.654   1.265   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.654   2.805   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.320   3.575   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.013   5.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.320   5.115   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.013   2.805   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.347   3.575   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.347   5.115   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.655  -0.525   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.320   0.495   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.473   2.909   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.013   7.425   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.973  -1.365   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.307  -2.135   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.307  -3.675   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.973  -4.445   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.639  -3.675   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.639  -2.135   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.306  -1.365   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.306  -4.445   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.028  -3.675   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.028  -2.135   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.362  -1.365   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.695   0.945   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.362   0.175   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.695  -2.135   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.029  -1.365   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.029   0.175   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.640  -1.365   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -3.973  -5.764   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       1.362  -4.445   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       5.363  -2.135   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       5.363   0.945   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       2.681   5.885   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -9.322   3.575   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       2.661   2.139   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -1.221  -6.594   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -2.555  -7.364   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -2.555  -8.904   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -1.221  -9.674   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.112  -8.904   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       0.112  -7.364   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       1.446  -6.594   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       1.446  -9.674   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       2.780  -8.904   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       2.780  -7.364   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       4.113  -6.594   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       5.447  -4.284   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       4.113  -5.054   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       5.447  -7.364   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       6.781  -6.594   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       6.781  -5.054   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      -3.889  -6.594   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      -1.221 -11.214   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0       4.113  -9.674   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       8.114  -7.364   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       8.114  -4.284   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0       5.412  -3.091   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   43                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   21                                                  
CONECT    9    8   10   18                                                  
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   19                                                  
CONECT   16   12   15   42                                                  
CONECT   17    4                                                            
CONECT   18    9                                                            
CONECT   19   15                                                            
CONECT   20   12                                                            
CONECT   21   22   26    8                                                  
CONECT   22   21   23   37                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   38                                                  
CONECT   25   24   26   28                                                  
CONECT   26   21   25   27                                                  
CONECT   27   26   30                                                       
CONECT   28   25   29   45                                                  
CONECT   29   28   30   39                                                  
CONECT   30   27   29   31                                                  
CONECT   31   30   33   34                                                  
CONECT   32   33   36   44                                                  
CONECT   33   31   32                                                       
CONECT   34   31   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   32   35   41                                                  
CONECT   37   22                                                            
CONECT   38   24                                                            
CONECT   39   29                                                            
CONECT   40   35                                                            
CONECT   41   36                                                            
CONECT   42   16                                                            
CONECT   43    2                                                            
CONECT   44   32                                                            
CONECT   45   46   50   28                                                  
CONECT   46   45   47   61                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   62                                                  
CONECT   49   48   50   52                                                  
CONECT   50   45   49   51                                                  
CONECT   51   50   54                                                       
CONECT   52   49   53                                                       
CONECT   53   52   54   63                                                  
CONECT   54   51   53   55                                                  
CONECT   55   54   57   58                                                  
CONECT   56   57   60   66                                                  
CONECT   57   55   56                                                       
CONECT   58   55   59                                                       
CONECT   59   58   60   64                                                  
CONECT   60   56   59   65                                                  
CONECT   61   46                                                            
CONECT   62   48                                                            
CONECT   63   53                                                            
CONECT   64   59                                                            
CONECT   65   60                                                            
CONECT   66   56                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  148    0
END

View in JSmol

Synonyms

Value	Source
Gallocatechin-(4a->8)-gallocatechin-(4a->8)-gallocatechin	Generator
Gallocatechin-(4α->8)-gallocatechin-(4α->8)-gallocatechin	Generator
Gallocatechin(4a->8)gallocatechin(4a->8)gallocatechin	HMDB
[Gallocatechin-(4alpha->8)]2-gallocatechin	HMDB

Chemical Formula

C₄₅H₃₈O₂₁

Average Mass

914.7706 Da

Monoisotopic Mass

914.19056 Da

IUPAC Name

(2R,3S,4R)-8-[(2R,3S,4S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

CAS Registry Number

87402-90-2

SMILES

O[C@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C(O)=C1)C([C@H]1[C@H](O)[C@H](OC3=C1C(O)=CC(O)=C3[C@H]1[C@H](O)[C@H](OC3=C1C(O)=CC(O)=C3)C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C(O)=C1)=C(O)C=C2O

InChI Identifier

InChI=1S/C45H38O21/c46-15-7-18(48)30-29(8-15)64-42(13-3-24(54)37(60)25(55)4-13)39(62)34(30)32-20(50)11-21(51)33-35(40(63)43(66-45(32)33)14-5-26(56)38(61)27(57)6-14)31-19(49)10-17(47)16-9-28(58)41(65-44(16)31)12-1-22(52)36(59)23(53)2-12/h1-8,10-11,28,34-35,39-43,46-63H,9H2/t28-,34-,35+,39-,40-,41+,42+,43+/m0/s1

InChI Key

NVTLDVSBUJGIAD-QHBXHTPSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cistus incanus	Plant	KNApSAcK
Hordeum vulgare	FooDB	KNAPSACK
Ribes nigrum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

C-type proanthocyanidin
B-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Epigallocatechin
Catechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Chromane
Benzopyran
1-benzopyran
Pyrogallol derivative
Benzenetriol
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Ether
Oxacycle
Polyol
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
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	3.03	ALOGPS
logP	3.53	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.38	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	18	ChemAxon
Polar Surface Area	391.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	224.96 m³·mol⁻¹	ChemAxon
Polarizability	89.38 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0040378

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020110

KNApSAcK ID

C00009121

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

71664720

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin (NP0049626)

MOL for NP0049626 (Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin)

3D MOL for NP0049626 (Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin)

3D SDF for NP0049626 (Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin)

3D-SDF for NP0049626 (Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin)

PDB for NP0049626 (Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin)

3D PDB for NP0049626 (Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin)

SMILES for NP0049626 (Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin)

INCHI for NP0049626 (Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin)

Structure for NP0049626 (Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin)

3D Structure for NP0049626 (Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin)