Np mrd loader

Showing NP-Card for Proanthocyanidin B2 3,3'-digallate (NP0048958)

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Record Information
Version2.0
Created at2022-03-17 21:04:52 UTC
Updated at2022-03-17 21:04:52 UTC
NP-MRD IDNP0048958
Secondary Accession NumbersNone
Natural Product Identification
Common NameProanthocyanidin B2 3,3'-digallate
Description3,3'-Digalloylprocyanidin B2, also known as procyanidin B2 3,3'-di-O-gallate, 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''. 3,3'-Digalloylprocyanidin B2 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,3'-Digalloylprocyanidin B2 has been detected, but not quantified in, a few different foods, such as common grapes, green vegetables, and tea. Proanthocyanidin B2 3,3'-digallate is found in Camellia sinensis , Polygonum multiflorum , Pyrola incarnata, Rheum rhizome, Rheum sp., Rhodiola semenovii and Rumex acetosa. This could make 3,3'-digalloylprocyanidin B2 a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048958 (Proanthocyanidin B2 3,3'-digallate)


  Mrv0541 02241217162D          

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M  END
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3D MOL for NP0048958 (Proanthocyanidin B2 3,3'-digallate)

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3D SDF for NP0048958 (Proanthocyanidin B2 3,3'-digallate)

  Mrv0541 02241217162D          

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M  END
> <DATABASE_ID>
NP0048958

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C2[C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1)C1=C2O[C@@H]([C@@H](CC2=C(O)C=C1O)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C44H34O20/c45-19-11-26(51)34-32(12-19)61-40(16-2-4-22(47)25(50)6-16)42(64-44(60)18-9-30(55)38(58)31(56)10-18)36(34)35-27(52)14-23(48)20-13-33(62-43(59)17-7-28(53)37(57)29(54)8-17)39(63-41(20)35)15-1-3-21(46)24(49)5-15/h1-12,14,33,36,39-40,42,45-58H,13H2/t33-,36-,39-,40-,42-/m1/s1

> <INCHI_KEY>
KTLUHRSHFRODPS-RIQPQZJCSA-N

> <FORMULA>
C44H34O20

> <MOLECULAR_WEIGHT>
882.7288

> <EXACT_MASS>
882.164343528

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
83.51169670903147

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
6.284952780999999

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.321955795340456

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.7725819856569

> <JCHEM_PKA_STRONGEST_BASIC>
-5.485687933076162

> <JCHEM_POLAR_SURFACE_AREA>
354.28000000000003

> <JCHEM_REFRACTIVITY>
218.03740000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0048958 (Proanthocyanidin B2 3,3'-digallate)
Download
PDB for NP0048958 (Proanthocyanidin B2 3,3'-digallate)
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  O   UNK     0      -5.979  -2.164   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.644  -2.934   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.644  -4.474   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.312  -5.244   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.312  -6.784   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -8.659   3.945   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -7.327   3.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.327   1.635   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.979   0.864   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.644   1.635   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.312   0.864   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.312  -2.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.978  -2.934   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.978  -4.474   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.643  -5.244   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.689  -4.474   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.024  -5.244   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.979   3.945   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.644   3.175   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.312   3.945   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.978   3.175   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.978   1.635   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.658   0.864   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.979  -0.675   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.689   7.795   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.689   6.255   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.658   5.485   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.658   3.945   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.689   3.175   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.024   3.945   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.024   5.485   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.343   6.255   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.643  -2.164   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.689  -2.934   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.024  -2.164   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.359  -2.934   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.691  -2.164   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.691  -0.624   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.025   0.146   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.024  -0.624   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.359   0.146   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       3.359   1.686   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       3.328  -6.296   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       3.328  -7.836   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       4.662  -5.526   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       4.662  -3.986   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.994  -3.216   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       7.324  -3.986   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.324  -5.526   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.994  -6.296   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       8.659  -3.216   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       8.659  -6.296   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       5.994  -1.676   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       1.582   2.276   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       1.582   0.736   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       2.917   3.046   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       2.917   4.586   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       4.249   5.356   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       5.579   4.586   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       5.579   3.046   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       4.249   2.276   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       6.914   5.356   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0       6.914   2.276   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       4.249   6.896   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   24                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   22   12                                                  
CONECT   12    2   11   13                                                  
CONECT   13   12   14   33                                                  
CONECT   14    4   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16   43                                                       
CONECT   18    7   19                                                       
CONECT   19   10   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   11   21   23                                                  
CONECT   23   22   54                                                       
CONECT   24    9                                                            
CONECT   25   26                                                            
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   21   27   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   26   30   32                                                  
CONECT   32   31                                                            
CONECT   33   13   34                                                       
CONECT   34   16   33   35                                                  
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38                                                            
CONECT   40   35   41                                                       
CONECT   41   38   40   42                                                  
CONECT   42   41                                                            
CONECT   43   17   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   50                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   53                                                  
CONECT   48   47   49   51                                                  
CONECT   49   48   50   52                                                  
CONECT   50   45   49                                                       
CONECT   51   48                                                            
CONECT   52   49                                                            
CONECT   53   47                                                            
CONECT   54   23   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57   61                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59   64                                                  
CONECT   59   58   60   62                                                  
CONECT   60   59   61   63                                                  
CONECT   61   56   60                                                       
CONECT   62   59                                                            
CONECT   63   60                                                            
CONECT   64   58                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  142    0
END

Download
3D PDB for NP0048958 (Proanthocyanidin B2 3,3'-digallate)
Download
SMILES for NP0048958 (Proanthocyanidin B2 3,3'-digallate)
OC1=CC(O)=C2[C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1)C1=C2O[C@@H]([C@@H](CC2=C(O)C=C1O)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1
Download
INCHI for NP0048958 (Proanthocyanidin B2 3,3'-digallate)
InChI=1S/C44H34O20/c45-19-11-26(51)34-32(12-19)61-40(16-2-4-22(47)25(50)6-16)42(64-44(60)18-9-30(55)38(58)31(56)10-18)36(34)35-27(52)14-23(48)20-13-33(62-43(59)17-7-28(53)37(57)29(54)8-17)39(63-41(20)35)15-1-3-21(46)24(49)5-15/h1-12,14,33,36,39-40,42,45-58H,13H2/t33-,36-,39-,40-,42-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
3-O-Galloylepicatechin-(4beta->8)-epicatechin-3-O-gallateHMDB
Proanthocyanidin b2 3,3'-O-gallateHMDB
Procyanidin b2 3,3'-di-O-gallateHMDB
Procyanidin b2-3,3'-di-O-gallateHMDB
(2R,3R)-2-(3,4-Dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acidGenerator
Proanthocyanidin b2 3,3'-digallic acidGenerator
Chemical FormulaC44H34O20
Average Mass882.7288 Da
Monoisotopic Mass882.16434 Da
IUPAC Name(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
CAS Registry Number79907-44-1
SMILES
OC1=CC(O)=C2[C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1)C1=C2O[C@@H]([C@@H](CC2=C(O)C=C1O)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C44H34O20/c45-19-11-26(51)34-32(12-19)61-40(16-2-4-22(47)25(50)6-16)42(64-44(60)18-9-30(55)38(58)31(56)10-18)36(34)35-27(52)14-23(48)20-13-33(62-43(59)17-7-28(53)37(57)29(54)8-17)39(63-41(20)35)15-1-3-21(46)24(49)5-15/h1-12,14,33,36,39-40,42,45-58H,13H2/t33-,36-,39-,40-,42-/m1/s1
InChI KeyKTLUHRSHFRODPS-RIQPQZJCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Camellia sinensisPlant
Polygonum multiflorumPlant
Pyrola incarnataLOTUS Database
Rheum rhizomePlant
Rheum sp.Plant
Rhodiola semenoviiLOTUS Database
Rumex acetosaLOTUS Database
Vitis vinifera L.FooDB
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
  • B-type proanthocyanidin
    • 

  • Proanthocyanidin
    • 

  • Bi- and polyflavonoid skeleton
    • 

  • Catechin gallate
    • 

  • Catechin
    • 

  • Hydroxyflavonoid
    • 

  • Flavan-3-ol
    • 

  • 3'-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • 4'-hydroxyflavonoid
    • 

  • Flavan
    • 

  • Galloyl ester
    • 

  • Gallic acid or derivatives
    • 

  • M-hydroxybenzoic acid ester
    • 

  • P-hydroxybenzoic acid ester
    • 

  • P-hydroxybenzoic acid alkyl ester
    • 

  • Benzoate ester
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Benzenetriol
    • 

  • Benzoic acid or derivatives
    • 

  • Pyrogallol derivative
    • 

  • Benzoyl
    • 

  • Catechol
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Carboxylic acid ester
    • 

  • Polyol
    • 

  • Ether
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP3.9ALOGPS
logP6.28ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.77ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area354.28 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity218.04 m³·mol⁻¹ChemAxon
Polarizability83.51 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0037967  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017141  
KNApSAcK IDC00009213  
Chemspider ID110532  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound124016  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available