NP-MRD: Showing NP-Card for Proanthocyanidin A-2 (NP0025689)

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Record Information

Version

1.0

Created at

2021-06-19 17:44:57 UTC

Updated at

2021-06-29 23:50:47 UTC

NP-MRD ID

NP0025689

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Proanthocyanidin A-2

Provided By

JEOL Database JEOL Logo

Description

Proanthocyanidin A2, also known as ec-(4b,8)(2b,7)-ec or procyanidin A2, 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''. Proanthocyanidin A2 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, proanthocyanidin A2 has been detected, but not quantified in, several different foods, such as chinese cinnamons, ceylon cinnamons, lingonberries, cinnamons, and peanuts. This could make proanthocyanidin A2 a potential biomarker for the consumption of these foods. Procyanidin A2 is a A type proanthocyanidin. Proanthocyanidin A-2 is found in Aesculus hippocastanum, Apis cerana, Arachis hypogaea, Ceratiola ericoides, Cinchona pubescens, Cinnamomum aromaticum, Cinnamomum bejolghota, Crataegus sinaica, Cupania americana, Cupania latifolia, Dimocarpus longan, Ephedra sp., Garcinia mangostana, Hypericum perforatum, Ixora coccinea, Litchi chinensis, Parameria laevigata MOLDENKE, Paullinia cupana, Pavetta owariensis, Rumex acetosa, Theobroma cacao, Urceola micrantha and Vaccinium vitis-idaea. It was first documented in 1998 (PMID: 23195766). Procyanidin B2 can be converted into procyanidin A2 by radical oxidation using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals under neutral conditions (PMID: 22020306) (PMID: 23268742).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119443D          

 66 72  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 66 72  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192119443D          

 66 72  0  0  0  0            999 V2000
   -2.9697    0.5107    6.1988 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0025689

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(O[C@]3(OC4=C([H])C(O[H])=C5C(O[C@]([H])(C6=C([H])C(O[H])=C(O[H])C([H])=C6[H])[C@]([H])(O[H])C5([H])[H])=C4[C@]2([H])[C@@]3([H])O[H])C2=C([H])C([H])=C(O[H])C(O[H])=C2[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26-,27-,29-,30+/m1/s1

> <INCHI_KEY>
NSEWTSAADLNHNH-LSBOWGMISA-N

> <FORMULA>
C30H24O12

> <MOLECULAR_WEIGHT>
576.51

> <EXACT_MASS>
576.126776213

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
57.366416700238155

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
3.590532096666666

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.10475378074171

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.663185265721914

> <JCHEM_PKA_STRONGEST_BASIC>
-3.877330901014532

> <JCHEM_POLAR_SURFACE_AREA>
209.75999999999996

> <JCHEM_REFRACTIVITY>
144.1963

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 36 60  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.970   0.511   6.199  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.358   0.085   5.057  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.047   0.434   4.763  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.463  -0.026   3.583  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.822   0.384   3.370  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.170  -0.849   2.696  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.500  -1.170   3.009  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.089  -0.713   4.188  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.289  -1.969   2.228  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.783  -2.342   0.924  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.687  -3.505   0.477  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.194  -4.746   0.026  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.061  -5.763  -0.387  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.429  -5.549  -0.355  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.271  -6.544  -0.759  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.944  -4.336   0.083  0.00  0.00           C+0
HETATM   17  O   UNK     0      -7.303  -4.186   0.092  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.090  -3.318   0.493  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.054  -1.309  -0.059  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.062  -0.418  -0.358  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.348   0.493  -1.372  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.393   1.438  -1.737  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.659   2.334  -2.733  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.149   1.495  -1.101  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.138   0.551  -0.102  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.820  -0.398   0.286  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.582  -1.381   1.407  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.275  -2.690   1.012  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.943  -3.735   1.943  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.335   0.530   0.574  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.412   1.172  -0.138  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.674   1.056   0.701  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.750   1.597   1.998  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.913   1.473   2.762  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.004   0.805   2.232  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.140   0.683   2.979  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.950   0.259   0.954  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.062  -0.391   0.494  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.795   0.378   0.185  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.027   2.615  -0.515  0.00  0.00           C+0
HETATM   41  O   UNK     0       1.627   3.398   0.620  0.00  0.00           O+0
HETATM   42  C   UNK     0       0.859   2.547  -1.501  0.00  0.00           C+0
HETATM   43  H   UNK     0      -2.337   1.044   6.709  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.467   1.062   5.432  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.103   0.180   2.460  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.115  -0.977   4.429  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.127  -4.957  -0.011  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.669  -6.717  -0.728  0.00  0.00           H+0
HETATM   49  H   UNK     0      -7.166  -6.167  -0.643  0.00  0.00           H+0
HETATM   50  H   UNK     0      -7.506  -3.305   0.452  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.493  -2.365   0.829  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.316   0.453  -1.863  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.571   2.204  -3.045  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.482  -1.607   1.544  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.894  -3.012   0.033  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.493  -3.611   2.741  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.581   0.598  -1.061  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.903   2.125   2.431  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.963   1.895   3.761  0.00  0.00           H+0
HETATM   60  H   UNK     0       7.757   0.183   2.408  0.00  0.00           H+0
HETATM   61  H   UNK     0       6.874  -0.726  -0.398  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.759  -0.054  -0.811  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.870   3.139  -0.978  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.903   2.922   1.067  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.239   2.288  -2.497  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.369   3.526  -1.555  0.00  0.00           H+0
CONECT    1    2   43                                                       
CONECT    2    3    8    1                                                  
CONECT    3    2    4   44                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4   45                                                       
CONECT    6    4    7   27                                                  
CONECT    7    8    6    9                                                  
CONECT    8    7    2   46                                                  
CONECT    9   10    7                                                       
CONECT   10    9   19   11   28                                             
CONECT   11   10   12   18                                                  
CONECT   12   11   13   47                                                  
CONECT   13   12   14   48                                                  
CONECT   14   13   16   15                                                  
CONECT   15   14   49                                                       
CONECT   16   14   18   17                                                  
CONECT   17   16   50                                                       
CONECT   18   16   11   51                                                  
CONECT   19   10   20                                                       
CONECT   20   21   26   19                                                  
CONECT   21   20   22   52                                                  
CONECT   22   24   21   23                                                  
CONECT   23   22   53                                                       
CONECT   24   25   42   22                                                  
CONECT   25   24   30   26                                                  
CONECT   26   27   20   25                                                  
CONECT   27   26    6   28   54                                             
CONECT   28   29   27   10   55                                             
CONECT   29   28   56                                                       
CONECT   30   25   31                                                       
CONECT   31   30   40   32   57                                             
CONECT   32   33   39   31                                                  
CONECT   33   34   32   58                                                  
CONECT   34   33   35   59                                                  
CONECT   35   37   34   36                                                  
CONECT   36   35   60                                                       
CONECT   37   39   35   38                                                  
CONECT   38   37   61                                                       
CONECT   39   37   32   62                                                  
CONECT   40   31   42   41   63                                             
CONECT   41   40   64                                                       
CONECT   42   24   40   65   66                                             
CONECT   43    1                                                            
CONECT   44    3                                                            
CONECT   45    5                                                            
CONECT   46    8                                                            
CONECT   47   12                                                            
CONECT   48   13                                                            
CONECT   49   15                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   21                                                            
CONECT   53   23                                                            
CONECT   54   27                                                            
CONECT   55   28                                                            
CONECT   56   29                                                            
CONECT   57   31                                                            
CONECT   58   33                                                            
CONECT   59   34                                                            
CONECT   60   36                                                            
CONECT   61   38                                                            
CONECT   62   39                                                            
CONECT   63   40                                                            
CONECT   64   41                                                            
CONECT   65   42                                                            
CONECT   66   42                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  144    0
END

RDKit          3D

66 72  0  0  0  0  0  0  0  0999 V2000
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 36 60  1  0
M  END

View in JSmol

Synonyms

Value	Source
Epicatechin-(2beta->7,4beta->8)-epicatechin	ChEBI
Epicatechin-(2b->7,4b->8)-epicatechin	Generator
Epicatechin-(2β->7,4β->8)-epicatechin	Generator
(+)-Proanthocyanidin a2	HMDB
EC-(4b,8)(2b,7)-ec	HMDB
Proanthocyanidin a-2	HMDB
Procyanidin a2	HMDB
Procyanidin dimer a2	HMDB
Procyanidoepicatechin	HMDB
Procyanidol a2	HMDB

Chemical Formula

C₃₀H₂₄O₁₂

Average Mass

576.5100 Da

Monoisotopic Mass

576.12678 Da

IUPAC Name

(1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

Traditional Name

(1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C2C(O[C@]3(OC4=C([H])C(O[H])=C5C(O[C@]([H])(C6=C([H])C(O[H])=C(O[H])C([H])=C6[H])[C@]([H])(O[H])C5([H])[H])=C4[C@]2([H])[C@@]3([H])O[H])C2=C([H])C([H])=C(O[H])C(O[H])=C2[H])=C1[H]

InChI Identifier

InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26-,27-,29-,30+/m1/s1

InChI Key

NSEWTSAADLNHNH-LSBOWGMISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aesculus hippocastanum	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Arachis hypogaea	LOTUS Database	35616633
Ceratiola ericoides	LOTUS Database	35616633
Cinchona pubescens	LOTUS Database	35616633
Cinnamomum aromaticum	LOTUS Database	35616633
Cinnamomum bejolghota	LOTUS Database	35616633
Crataegus sinaica	LOTUS Database	35616633
Cupania americana	LOTUS Database	35616633
Cupania latifolia	LOTUS Database	35616633
Dimocarpus longan	LOTUS Database	35616633
Ephedra sp.	Plant	KNApSAcK
Garcinia mangostana	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Ixora coccinea	LOTUS Database	35616633
Litchi chinensis	LOTUS Database	35616633
Parameria laevigata	JEOL database	Kamiya, K., et al, Chem. Pharm. Bull. 49, 551 (2001)
Paullinia cupana	LOTUS Database	35616633
Pavetta owariensis	LOTUS Database	35616633
Rumex acetosa	LOTUS Database	35616633
Theobroma cacao	LOTUS Database	35616633
Urceola micrantha	LOTUS Database	35616633
Vaccinium vitis-idaea	LOTUS Database	35616633

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

A-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Catechin
Pyranoflavonoid
Flavan-3-ol
Hydroxyflavonoid
3'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Flavan
Pyranochromene
Chromane
1-benzopyran
Benzopyran
Catechol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Ketal
1-hydroxy-4-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

proanthocyanidin (CHEBI:28472 )
hydroxyflavan (CHEBI:28472 )
Condensed tannins (Proanthocyanidins) (C10237 )

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	2.43	ALOGPS
logP	3.59	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	209.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.2 m³·mol⁻¹	ChemAxon
Polarizability	57.37 Å³	ChemAxon
Number of Rings	7	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

HMDB0037655

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016778

KNApSAcK ID

C00002934

Chemspider ID

Not Available

KEGG Compound ID

C10237

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Proanthocyanidin_A2

METLIN ID

Not Available

PubChem Compound

124025

PDB ID

Not Available

ChEBI ID

28472

Good Scents ID

Not Available

References

General References

Gallina L, Dal Pozzo F, Galligioni V, Bombardelli E, Scagliarini A: Inhibition of viral RNA synthesis in canine distemper virus infection by proanthocyanidin A2. Antiviral Res. 2011 Dec;92(3):447-52. doi: 10.1016/j.antiviral.2011.10.004. Epub 2011 Oct 13. [PubMed:22020306 ]
Shahat AA, Ismail SI, Hammouda FM, Azzam SA, Lemiere G, De Bruyne T, De Swaef S, Pieters L, Vlietinck A: Anti-HIV activity of flavonoids and proanthocyanidins from Crataegus sinaica. Phytomedicine. 1998 Apr;5(2):133-6. doi: 10.1016/S0944-7113(98)80010-X. [PubMed:23195766 ]
Pesca MS, Dal Piaz F, Sanogo R, Vassallo A, Bruzual de Abreu M, Rapisarda A, Germano MP, Certo G, De Falco S, De Tommasi N, Braca A: Bioassay-guided isolation of proanthocyanidins with antiangiogenic activities. J Nat Prod. 2013 Jan 25;76(1):29-35. doi: 10.1021/np300614u. Epub 2012 Dec 26. [PubMed:23268742 ]
Kamiya, K., et al. (2001). Kamiya, K., et al, Chem. Pharm. Bull. 49, 551 (2001). Chem. Pharm. Bull..

Showing NP-Card for Proanthocyanidin A-2 (NP0025689)

MOL for NP0025689 (Proanthocyanidin A-2)

3D MOL for NP0025689 (Proanthocyanidin A-2)

3D SDF for NP0025689 (Proanthocyanidin A-2)

3D-SDF for NP0025689 (Proanthocyanidin A-2)

PDB for NP0025689 (Proanthocyanidin A-2)

3D PDB for NP0025689 (Proanthocyanidin A-2)

SMILES for NP0025689 (Proanthocyanidin A-2)

INCHI for NP0025689 (Proanthocyanidin A-2)

Structure for NP0025689 (Proanthocyanidin A-2)

3D Structure for NP0025689 (Proanthocyanidin A-2)