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

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Record Information
Version2.0
Created at2022-03-17 21:06:55 UTC
Updated at2022-03-17 21:06:56 UTC
NP-MRD IDNP0049087
Secondary Accession NumbersNone
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
Thumb
MOLSDFPDBSMILESInChI

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


  Mrv0541 05061310242D          

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

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

  Mrv0541 05061310242D          

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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

$$$$

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

Download
3D PDB for NP0049087 ([Gallocatechin(4alpha->8)]2-catechin)
Download
SMILES for NP0049087 ([Gallocatechin(4alpha->8)]2-catechin)
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
Download
INCHI for NP0049087 ([Gallocatechin(4alpha->8)]2-catechin)
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
Download
View in JSmol
Synonyms
ValueSource
[Gallocatechin(4a->8)]2catechinGenerator
[Gallocatechin(4α->8)]2catechinGenerator
[Gallocatechin(4a->8)]2-catechinHMDB
[Gallocatechin-(4alpha->8)]2-catechinHMDB
[Gallocatechin(4α->8)]2-catechinGenerator
Chemical FormulaC45H38O20
Average Mass898.7712 Da
Monoisotopic Mass898.19564 Da
IUPAC Name4-[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 Name4-[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
CAS Registry Number79136-97-3
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 KeyRJFFPCHJOFXZQD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cistus incanusPlant
Eucalyptus ovataLOTUS Database
Hordeum vulgareFooDB
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''.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassBiflavonoids and polyflavonoids  
Direct ParentBiflavonoids 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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.1ALOGPS
logP3.83ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.45ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area371.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity222.98 m³·mol⁻¹ChemAxon
Polarizability85.17 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038373  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017716  
KNApSAcK IDC00009120  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14890508  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available