NP-MRD: Showing NP-Card for [Gallocatechin(4alpha->8)]2-catechin (NP0049087)

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Record Information

Version

1.0

Created at

2022-03-17 21:06:55 UTC

Updated at

2022-03-17 21:06:56 UTC

NP-MRD ID

NP0049087

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[Gallocatechin(4alpha->8)]2-catechin

Description

[Gallocatechin(4alpha->8)]2catechin 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)]2catechin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, [Gallocatechin(4alpha->8)]2catechin has been detected, but not quantified in, barley and cereals and cereal products. [Gallocatechin(4alpha->8)]2-catechin is found in Cistus incanus and Eucalyptus ovata. This could make [gallocatechin(4alpha->8)]2catechin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310242D          

 65 73  0  0  0  0            999 V2000
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M  END


  Mrv0541 05061310242D          

 65 73  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0049087

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C(C1C(O)C(OC3=C(C4C(O)C(OC5=CC(O)=CC(O)=C45)C4=CC(O)=C(O)C(O)=C4)C(O)=CC(O)=C13)C1=CC(O)=C(O)C(O)=C1)=C(O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C45H38O20/c46-16-8-21(50)31-30(9-16)63-42(14-4-25(54)37(59)26(55)5-14)39(61)35(31)33-23(52)12-24(53)34-36(40(62)43(65-45(33)34)15-6-27(56)38(60)28(57)7-15)32-22(51)11-19(48)17-10-29(58)41(64-44(17)32)13-1-2-18(47)20(49)3-13/h1-9,11-12,29,35-36,39-43,46-62H,10H2

> <INCHI_KEY>
RJFFPCHJOFXZQD-UHFFFAOYSA-N

> <FORMULA>
C45H38O20

> <MOLECULAR_WEIGHT>
898.7712

> <EXACT_MASS>
898.195643656

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
85.16744920981586

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
17

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.8292523686666664

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.939212237793026

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.445115272930868

> <JCHEM_PKA_STRONGEST_BASIC>
-5.214622450767423

> <JCHEM_POLAR_SURFACE_AREA>
371.6000000000001

> <JCHEM_REFRACTIVITY>
222.97810000000013

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.60e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -4.199   1.379   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -2.239  -2.016   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       6.240   5.866   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
CONECT    2    1   18                                                       
CONECT    3   13   20                                                       
CONECT    4   14   25                                                       
CONECT    5   14   26                                                       
CONECT    6   15   27                                                       
CONECT    7   15   28                                                       
CONECT    8   16   21                                                       
CONECT    9   16   30                                                       
CONECT   10   17   29                                                       
CONECT   11   19   22                                                       
CONECT   12   23   24                                                       
CONECT   13    1    3   41                                                  
CONECT   14    4    5   42                                                  
CONECT   15    6    7   43                                                  
CONECT   16    8    9   46                                                  
CONECT   17   10   19   44                                                  
CONECT   18    2   20   47                                                  
CONECT   19   11   17   48                                                  
CONECT   20    3   18   49                                                  
CONECT   21    8   31   50                                                  
CONECT   22   11   32   51                                                  
CONECT   23   12   33   52                                                  
CONECT   24   12   34   53                                                  
CONECT   25    4   37   54                                                  
CONECT   26    5   37   55                                                  
CONECT   27    6   38   56                                                  
CONECT   28    7   38   57                                                  
CONECT   29   10   41   58                                                  
CONECT   30    9   31   63                                                  
CONECT   31   21   30   35                                                  
CONECT   32   22   36   44                                                  
CONECT   33   23   35   45                                                  
CONECT   34   24   36   45                                                  
CONECT   35   31   33   39                                                  
CONECT   36   32   34   40                                                  
CONECT   37   25   26   59                                                  
CONECT   38   27   28   60                                                  
CONECT   39   35   42   61                                                  
CONECT   40   36   43   62                                                  
CONECT   41   13   29   64                                                  
CONECT   42   14   39   63                                                  
CONECT   43   15   40   65                                                  
CONECT   44   17   32   64                                                  
CONECT   45   33   34   65                                                  
CONECT   46   16                                                            
CONECT   47   18                                                            
CONECT   48   19                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   23                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   28                                                            
CONECT   58   29                                                            
CONECT   59   37                                                            
CONECT   60   38                                                            
CONECT   61   39                                                            
CONECT   62   40                                                            
CONECT   63   30   42                                                       
CONECT   64   41   44                                                       
CONECT   65   43   45                                                       
MASTER        0    0    0    0    0    0    0    0   65    0  146    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₄₅H₃₈O₂₀

Average Mass

898.7712 Da

Monoisotopic Mass

898.19564 Da

IUPAC Name

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

Traditional Name

CAS Registry Number

79136-97-3

SMILES

OC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C(C1C(O)C(OC3=C(C4C(O)C(OC5=CC(O)=CC(O)=C45)C4=CC(O)=C(O)C(O)=C4)C(O)=CC(O)=C13)C1=CC(O)=C(O)C(O)=C1)=C(O)C=C2O

InChI Identifier

InChI=1S/C45H38O20/c46-16-8-21(50)31-30(9-16)63-42(14-4-25(54)37(59)26(55)5-14)39(61)35(31)33-23(52)12-24(53)34-36(40(62)43(65-45(33)34)15-6-27(56)38(60)28(57)7-15)32-22(51)11-19(48)17-10-29(58)41(64-44(17)32)13-1-2-18(47)20(49)3-13/h1-9,11-12,29,35-36,39-43,46-62H,10H2

InChI Key

RJFFPCHJOFXZQD-UHFFFAOYSA-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
Eucalyptus ovata	LOTUS Database	35616633
Hordeum vulgare	FooDB	KNAPSACK

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
Proanthocyanidin
Bi- and polyflavonoid skeleton
Epigallocatechin
Catechin
Hydroxyflavonoid
Flavan-3-ol
3'-hydroxyflavonoid
3-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Flavan
1-benzopyran
Benzopyran
Chromane
Benzenetriol
Pyrogallol derivative
Catechol
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Polyol
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen 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	3.1	ALOGPS
logP	3.83	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.45	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	17	ChemAxon
Polar Surface Area	371.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	222.98 m³·mol⁻¹	ChemAxon
Polarizability	85.17 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

HMDB0038373

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017716

KNApSAcK ID

C00009120

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

14890508

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)]2-catechin (NP0049087)

MOL for NP0049087 ([Gallocatechin(4alpha->8)]2-catechin)

3D MOL for NP0049087 ([Gallocatechin(4alpha->8)]2-catechin)

3D SDF for NP0049087 ([Gallocatechin(4alpha->8)]2-catechin)

3D-SDF for NP0049087 ([Gallocatechin(4alpha->8)]2-catechin)

PDB for NP0049087 ([Gallocatechin(4alpha->8)]2-catechin)

3D PDB for NP0049087 ([Gallocatechin(4alpha->8)]2-catechin)

SMILES for NP0049087 ([Gallocatechin(4alpha->8)]2-catechin)

INCHI for NP0049087 ([Gallocatechin(4alpha->8)]2-catechin)

Structure for NP0049087 ([Gallocatechin(4alpha->8)]2-catechin)

3D Structure for NP0049087 ([Gallocatechin(4alpha->8)]2-catechin)