Np mrd loader

Showing NP-Card for Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin (NP0049249)

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Record Information
Version2.0
Created at2022-03-17 21:09:27 UTC
Updated at2022-03-17 21:09:27 UTC
NP-MRD IDNP0049249
Secondary Accession NumbersNone
Natural Product Identification
Common NameEpicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin
DescriptionEpicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin has been detected, but not quantified in, fruits and lingonberries. Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin is found in Aesculus hippocastanum . This could make epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0049249 (Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin)


  Mrv0541 02241210512D          

 63 72  0  0  0  0            999 V2000
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   -4.0896    0.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3751    0.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

3D MOL for NP0049249 (Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin)

Download
3D SDF for NP0049249 (Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin)

  Mrv0541 02241210512D          

 63 72  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0049249

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C1=C(O[C@@]3(OC4=C([C@H]1[C@H]3O)C(O)=CC(O)=C4[C@@H]1[C@@H](O)[C@H](OC3=C1C(O)=CC(O)=C3)C1=CC(O)=C(O)C=C1)C1=CC(O)=C(O)C=C1)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)60-41(16-2-5-21(48)25(52)8-16)39(58)37(33)34-28(55)13-29(56)35-38-36-32(62-45(44(38)59,63-43(34)35)17-3-6-22(49)26(53)9-17)14-23(50)19-12-30(57)40(61-42(19)36)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38+,39+,40+,41+,44+,45+/m0/s1

> <INCHI_KEY>
SRWJAXVAWDYXPA-ACNGEOCHSA-N

> <FORMULA>
C45H36O18

> <MOLECULAR_WEIGHT>
864.7565

> <EXACT_MASS>
864.190164348

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
85.10027344102136

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5R,6S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
4.911170094999999

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.035333800176245

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.620945529900164

> <JCHEM_PKA_STRONGEST_BASIC>
-5.1979426554856305

> <JCHEM_POLAR_SURFACE_AREA>
320.14

> <JCHEM_REFRACTIVITY>
216.70460000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049249 (Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin)
Download
PDB for NP0049249 (Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.634   2.625   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.634   1.085   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.300   0.315   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.967   1.085   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.967   2.625   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.300   3.395   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.300   4.935   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.633   3.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.633   4.935   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.967   5.705   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.967   7.245   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.300   9.555   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.300   8.015   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.633   8.015   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.633   9.555   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.967  10.325   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.967  11.865   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.633   0.315   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -7.634  10.325   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.299   5.705   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.341   0.260   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.675  -0.510   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.009   0.260   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.008   1.800   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.675   2.570   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.675   4.110   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.342   2.570   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.342   4.110   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.008   4.880   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.008   6.420   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.675   8.730   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.675   7.190   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.342   7.190   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.342   8.730   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.008   9.500   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.008  11.040   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       4.342  -0.510   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.341   9.500   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       5.676   4.880   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.341   1.800   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.377   7.036   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.710   7.806   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      11.044   7.036   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      11.044   5.496   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       9.710   4.726   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       9.710   3.186   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      12.378   4.726   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      12.378   3.186   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      11.044   2.416   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      11.044   0.876   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       9.710  -1.434   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       9.710   0.106   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      12.378   0.106   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      12.378  -1.434   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      11.044  -2.204   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      11.044  -3.744   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      12.378   7.806   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      13.711   2.416   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      13.711  -2.204   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       6.889   7.435   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0       8.377   5.496   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      -0.993  -0.510   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      -8.968   0.315   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   63                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    8    6                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   40                                                  
CONECT    9    8   10   20                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16   19                                                  
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   12   15   17                                                  
CONECT   17   16                                                            
CONECT   18    4                                                            
CONECT   19   12                                                            
CONECT   20    9                                                            
CONECT   21   40   22   62                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   27   25                                                  
CONECT   25   40   24   26                                                  
CONECT   26   25   29                                                       
CONECT   27   24   28   61                                                  
CONECT   28   27   29   39                                                  
CONECT   29   26   28   30   60                                             
CONECT   30   29   32   33                                                  
CONECT   31   32   35   38                                                  
CONECT   32   30   31                                                       
CONECT   33   30   34                                                       
CONECT   34   33   35                                                       
CONECT   35   31   34   36                                                  
CONECT   36   35                                                            
CONECT   37   23                                                            
CONECT   38   31                                                            
CONECT   39   28                                                            
CONECT   40   21   25    8                                                  
CONECT   41   61   60   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   57                                                  
CONECT   44   43   47   45                                                  
CONECT   45   61   44   46                                                  
CONECT   46   45   49                                                       
CONECT   47   44   48                                                       
CONECT   48   47   49   58                                                  
CONECT   49   46   48   50                                                  
CONECT   50   49   52   53                                                  
CONECT   51   52   55                                                       
CONECT   52   50   51                                                       
CONECT   53   50   54                                                       
CONECT   54   53   55   59                                                  
CONECT   55   51   54   56                                                  
CONECT   56   55                                                            
CONECT   57   43                                                            
CONECT   58   48                                                            
CONECT   59   54                                                            
CONECT   60   41   29                                                       
CONECT   61   41   45   27                                                  
CONECT   62   21                                                            
CONECT   63    2                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  144    0
END

Download
3D PDB for NP0049249 (Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin)
Download
SMILES for NP0049249 (Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin)
O[C@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C1=C(O[C@@]3(OC4=C([C@H]1[C@H]3O)C(O)=CC(O)=C4[C@@H]1[C@@H](O)[C@H](OC3=C1C(O)=CC(O)=C3)C1=CC(O)=C(O)C=C1)C1=CC(O)=C(O)C=C1)C=C2O
Download
INCHI for NP0049249 (Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin)
InChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)60-41(16-2-5-21(48)25(52)8-16)39(58)37(33)34-28(55)13-29(56)35-38-36-32(62-45(44(38)59,63-43(34)35)17-3-6-22(49)26(53)9-17)14-23(50)19-12-30(57)40(61-42(19)36)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38+,39+,40+,41+,44+,45+/m0/s1
Download
View in JSmol
Synonyms
ValueSource
Epicatechin-(4b->8)-epicatechin-(2b->7,4b->8)-catechinGenerator
Epicatechin-(4β->8)-epicatechin-(2β->7,4β->8)-catechinGenerator
Chemical FormulaC45H36O18
Average Mass864.7565 Da
Monoisotopic Mass864.19016 Da
IUPAC Name(1R,5R,6S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol
Traditional Name(1R,5R,6S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol
CAS Registry Number114637-81-9
SMILES
O[C@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C1=C(O[C@@]3(OC4=C([C@H]1[C@H]3O)C(O)=CC(O)=C4[C@@H]1[C@@H](O)[C@H](OC3=C1C(O)=CC(O)=C3)C1=CC(O)=C(O)C=C1)C1=CC(O)=C(O)C=C1)C=C2O
InChI Identifier
InChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)60-41(16-2-5-21(48)25(52)8-16)39(58)37(33)34-28(55)13-29(56)35-38-36-32(62-45(44(38)59,63-43(34)35)17-3-6-22(49)26(53)9-17)14-23(50)19-12-30(57)40(61-42(19)36)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38+,39+,40+,41+,44+,45+/m0/s1
InChI KeySRWJAXVAWDYXPA-ACNGEOCHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aesculus hippocastanumPlant
Vaccinium vitis-idaeaFooDB
Chemical Taxonomy
DescriptionThis compound 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
  • B-type proanthocyanidin
    • 

  • A-type proanthocyanidin
    • 

  • Bi- and polyflavonoid skeleton
    • 

  • Proanthocyanidin
    • 

  • Catechin
    • 

  • Pyranoflavonoid
    • 

  • 3'-hydroxyflavonoid
    • 

  • Flavan-3-ol
    • 

  • 3-hydroxyflavonoid
    • 

  • 4'-hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Hydroxyflavonoid
    • 

  • Flavan
    • 

  • Pyranochromene
    • 

  • 1-benzopyran
    • 

  • Benzopyran
    • 

  • Chromane
    • 

  • Catechol
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Ketal
    • 

  • Phenol
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Secondary alcohol
    • 

  • Polyol
    • 

  • Acetal
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Organooxygen 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
logP3.54ALOGPS
logP4.91ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.62ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area320.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity216.7 m³·mol⁻¹ChemAxon
Polarizability85.1 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038857  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018296  
KNApSAcK IDC00009299  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10350652  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available