NP-MRD: Showing NP-Card for Cinnamtannin III (NP0048868)

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Record Information

Version

2.0

Created at

2022-03-17 21:03:28 UTC

Updated at

2022-03-17 21:03:28 UTC

NP-MRD ID

NP0048868

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cinnamtannin III

Description

Cinnamtannin III 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''. Thus, cinnamtannin III is considered to be a flavonoid lipid molecule. Cinnamtannin III is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Cinnamtannin III has been detected, but not quantified in, chinese cinnamons and herbs and spices. This could make cinnamtannin III a potential biomarker for the consumption of these foods. A proanthocyanidin isolated from Cinnamomum cassia.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241219322D          

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M  END


  Mrv0541 02241219322D          

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M  END
> <DATABASE_ID>
NP0048868

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CC2=C(O)C=C(O)C([C@@H]3[C@@H](O)[C@H](OC4=C([C@@H]5[C@@H](O)[C@H](OC6=C([C@@H]7[C@@H](O)[C@H](OC8=C([C@@H]9[C@@H](O)[C@H](OC%10=C([C@@H]%11[C@@H](O)[C@H](OC%12=CC(O)=CC(O)=C%11%12)C%11=CC=C(O)C(O)=C%11)C(O)=CC(O)=C9%10)C9=CC=C(O)C(O)=C9)C(O)=CC(O)=C78)C7=CC=C(O)C(O)=C7)C(O)=CC(O)=C56)C5=CC=C(O)C(O)=C5)C(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2O[C@@H]1C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C90H74O36/c91-33-19-48(105)60-59(20-33)121-81(28-2-8-36(93)43(100)14-28)75(116)70(60)62-50(107)23-52(109)64-72(77(118)83(123-87(62)64)30-4-10-38(95)45(102)16-30)66-54(111)25-56(113)68-74(79(120)85(125-89(66)68)32-6-12-40(97)47(104)18-32)69-57(114)26-55(112)67-73(78(119)84(126-90(67)69)31-5-11-39(96)46(103)17-31)65-53(110)24-51(108)63-71(76(117)82(124-88(63)65)29-3-9-37(94)44(101)15-29)61-49(106)22-41(98)34-21-58(115)80(122-86(34)61)27-1-7-35(92)42(99)13-27/h1-20,22-26,58,70-85,91-120H,21H2/t58-,70-,71+,72-,73+,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-/m1/s1

> <INCHI_KEY>
UUOWTYGESRVWCF-WKWFDMPLSA-N

> <FORMULA>
C90H74O36

> <MOLECULAR_WEIGHT>
1731.529

> <EXACT_MASS>
1730.39597876

> <JCHEM_ACCEPTOR_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
174.4302318403196

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
30

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.68

> <JCHEM_LOGP>
8.398297007

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
18

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.955136281792809

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.581129036234547

> <JCHEM_PKA_STRONGEST_BASIC>
-5.2146223756239864

> <JCHEM_POLAR_SURFACE_AREA>
662.2800000000003

> <JCHEM_REFRACTIVITY>
436.5411999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.75e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.767  -6.098   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.101  -5.328   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.434  -6.098   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.434  -7.638   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.101  -8.408   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.767  -7.638   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.433  -8.408   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.900  -7.638   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.900  -6.098   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.433  -5.328   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.234  -5.328   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.568  -3.018   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.234  -3.788   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.568  -6.098   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.901  -5.328   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.901  -3.788   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.768  -5.328   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.101  -9.948   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.234  -8.408   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.235  -3.018   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.235  -6.098   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.857 -11.733   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.810 -11.733   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.810 -13.273   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.477 -14.043   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.857 -13.273   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.191 -14.043   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.524 -13.273   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.524 -11.733   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.191 -10.963   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.858 -10.963   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.192  -8.653   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.858  -9.423   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.192 -11.733   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.525 -10.963   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.525  -9.423   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.144 -10.963   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -0.477 -15.583   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       4.858 -14.043   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       8.859  -8.653   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       8.859 -11.733   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.477 -10.963   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.450 -17.276   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.116 -16.506   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.783 -17.276   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       0.783 -18.816   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.116 -19.586   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       3.450 -18.816   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.784 -19.586   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.117 -18.816   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.117 -17.276   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       4.784 -16.506   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       7.451 -16.506   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       8.785 -14.196   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       7.451 -14.966   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       8.785 -17.276   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      10.118 -16.506   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      10.118 -14.966   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -0.551 -16.506   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       2.116 -21.126   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0       7.451 -19.586   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      11.452 -14.196   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      11.452 -17.276   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0       6.074 -22.911   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       3.407 -22.911   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       3.407 -24.451   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       4.741 -25.221   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       6.074 -24.451   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       7.408 -25.221   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0       8.742 -24.451   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0       8.742 -22.911   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0       7.408 -22.141   0.000  0.00  0.00           O+0
HETATM   73  C   UNK     0      10.075 -22.141   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      11.409 -19.831   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      10.075 -20.601   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      11.409 -22.911   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      12.743 -22.141   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      12.743 -20.601   0.000  0.00  0.00           C+0
HETATM   79  O   UNK     0       2.073 -22.141   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0       4.741 -26.761   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0      10.075 -25.221   0.000  0.00  0.00           O+0
HETATM   82  O   UNK     0      14.076 -19.831   0.000  0.00  0.00           O+0
HETATM   83  O   UNK     0      14.076 -22.911   0.000  0.00  0.00           O+0
HETATM   84  C   UNK     0       4.741 -22.141   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0       8.620 -28.386   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0       7.286 -27.616   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0       5.953 -28.386   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0       5.953 -29.926   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0       7.286 -30.696   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0       8.620 -29.926   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0       9.954 -30.696   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      11.287 -29.926   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      11.287 -28.386   0.000  0.00  0.00           C+0
HETATM   94  O   UNK     0       9.954 -27.616   0.000  0.00  0.00           O+0
HETATM   95  C   UNK     0      12.621 -27.616   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      13.955 -25.306   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      12.621 -26.076   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      13.955 -28.386   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      15.288 -27.616   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      15.288 -26.076   0.000  0.00  0.00           C+0
HETATM  101  O   UNK     0       4.619 -27.616   0.000  0.00  0.00           O+0
HETATM  102  O   UNK     0       7.286 -32.236   0.000  0.00  0.00           O+0
HETATM  103  O   UNK     0      12.621 -30.696   0.000  0.00  0.00           O+0
HETATM  104  O   UNK     0      16.622 -25.306   0.000  0.00  0.00           O+0
HETATM  105  O   UNK     0      16.622 -28.386   0.000  0.00  0.00           O+0
HETATM  106  C   UNK     0      11.244 -34.021   0.000  0.00  0.00           C+0
HETATM  107  C   UNK     0       8.577 -34.021   0.000  0.00  0.00           C+0
HETATM  108  C   UNK     0       8.577 -35.561   0.000  0.00  0.00           C+0
HETATM  109  C   UNK     0       9.911 -36.331   0.000  0.00  0.00           C+0
HETATM  110  C   UNK     0      11.244 -35.561   0.000  0.00  0.00           C+0
HETATM  111  C   UNK     0      12.578 -36.331   0.000  0.00  0.00           C+0
HETATM  112  C   UNK     0      13.912 -35.561   0.000  0.00  0.00           C+0
HETATM  113  C   UNK     0      13.912 -34.021   0.000  0.00  0.00           C+0
HETATM  114  O   UNK     0      12.578 -33.251   0.000  0.00  0.00           O+0
HETATM  115  C   UNK     0      15.245 -33.251   0.000  0.00  0.00           C+0
HETATM  116  C   UNK     0      16.579 -30.941   0.000  0.00  0.00           C+0
HETATM  117  C   UNK     0      15.245 -31.711   0.000  0.00  0.00           C+0
HETATM  118  C   UNK     0      16.579 -34.021   0.000  0.00  0.00           C+0
HETATM  119  C   UNK     0      17.913 -33.251   0.000  0.00  0.00           C+0
HETATM  120  C   UNK     0      17.913 -31.711   0.000  0.00  0.00           C+0
HETATM  121  O   UNK     0       7.243 -33.251   0.000  0.00  0.00           O+0
HETATM  122  O   UNK     0       9.911 -37.871   0.000  0.00  0.00           O+0
HETATM  123  O   UNK     0      15.245 -36.331   0.000  0.00  0.00           O+0
HETATM  124  O   UNK     0      19.246 -30.941   0.000  0.00  0.00           O+0
HETATM  125  O   UNK     0      19.246 -34.021   0.000  0.00  0.00           O+0
HETATM  126  C   UNK     0       9.911 -33.251   0.000  0.00  0.00           C+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    1    7                                                  
CONECT    7    8    6   42                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    1                                                       
CONECT   11    9   13   14                                                  
CONECT   12   13   16                                                       
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   12   20                                                  
CONECT   17    3                                                            
CONECT   18    5                                                            
CONECT   19    8                                                            
CONECT   20   16                                                            
CONECT   21   15                                                            
CONECT   22   42   26   30                                                  
CONECT   23   42   24   37                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   38                                                  
CONECT   26   25   22   27                                                  
CONECT   27   28   26   44                                                  
CONECT   28   27   29   39                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   22                                                       
CONECT   31   29   33   34                                                  
CONECT   32   33   36                                                       
CONECT   33   31   32                                                       
CONECT   34   31   35                                                       
CONECT   35   34   36   41                                                  
CONECT   36   35   32   40                                                  
CONECT   37   23                                                            
CONECT   38   25                                                            
CONECT   39   28                                                            
CONECT   40   36                                                            
CONECT   41   35                                                            
CONECT   42   22   23    7                                                  
CONECT   43   44   48   52                                                  
CONECT   44   43   45   27                                                  
CONECT   45   44   46   59                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   60                                                  
CONECT   48   47   43   49                                                  
CONECT   49   50   48   84                                                  
CONECT   50   49   51   61                                                  
CONECT   51   50   52   53                                                  
CONECT   52   51   43                                                       
CONECT   53   51   55   56                                                  
CONECT   54   55   58                                                       
CONECT   55   53   54                                                       
CONECT   56   53   57                                                       
CONECT   57   56   58   63                                                  
CONECT   58   57   54   62                                                  
CONECT   59   45                                                            
CONECT   60   47                                                            
CONECT   61   50                                                            
CONECT   62   58                                                            
CONECT   63   57                                                            
CONECT   64   84   68   72                                                  
CONECT   65   84   66   79                                                  
CONECT   66   65   67                                                       
CONECT   67   66   68   80                                                  
CONECT   68   67   64   69                                                  
CONECT   69   70   68   86                                                  
CONECT   70   69   71   81                                                  
CONECT   71   70   72   73                                                  
CONECT   72   71   64                                                       
CONECT   73   71   75   76                                                  
CONECT   74   75   78                                                       
CONECT   75   73   74                                                       
CONECT   76   73   77                                                       
CONECT   77   76   78   83                                                  
CONECT   78   77   74   82                                                  
CONECT   79   65                                                            
CONECT   80   67                                                            
CONECT   81   70                                                            
CONECT   82   78                                                            
CONECT   83   77                                                            
CONECT   84   64   65   49                                                  
CONECT   85   86   90   94                                                  
CONECT   86   85   87   69                                                  
CONECT   87   86   88  101                                                  
CONECT   88   87   89                                                       
CONECT   89   88   90  102                                                  
CONECT   90   89   85   91                                                  
CONECT   91   92   90  126                                                  
CONECT   92   91   93  103                                                  
CONECT   93   92   94   95                                                  
CONECT   94   93   85                                                       
CONECT   95   93   97   98                                                  
CONECT   96   97  100                                                       
CONECT   97   95   96                                                       
CONECT   98   95   99                                                       
CONECT   99   98  100  105                                                  
CONECT  100   99   96  104                                                  
CONECT  101   87                                                            
CONECT  102   89                                                            
CONECT  103   92                                                            
CONECT  104  100                                                            
CONECT  105   99                                                            
CONECT  106  126  110  114                                                  
CONECT  107  126  108  121                                                  
CONECT  108  107  109                                                       
CONECT  109  108  110  122                                                  
CONECT  110  109  106  111                                                  
CONECT  111  112  110                                                       
CONECT  112  111  113  123                                                  
CONECT  113  112  114  115                                                  
CONECT  114  113  106                                                       
CONECT  115  113  117  118                                                  
CONECT  116  117  120                                                       
CONECT  117  115  116                                                       
CONECT  118  115  119                                                       
CONECT  119  118  120  125                                                  
CONECT  120  119  116  124                                                  
CONECT  121  107                                                            
CONECT  122  109                                                            
CONECT  123  112                                                            
CONECT  124  120                                                            
CONECT  125  119                                                            
CONECT  126  106  107   91                                                  
MASTER        0    0    0    0    0    0    0    0  126    0  286    0
END

View in JSmol

Synonyms

Value	Source
[Epicatechin-(4beta->8)]5-epicatechin	Kegg
[Epicatechin-(4b->8)]5-epicatechin	Generator
[Epicatechin-(4β->8)]5-epicatechin	Generator
Cinnamtannin a4	HMDB
Epicatechin-(4beta->8)5-epicatechin	HMDB
[Epicatechin(4b->8)]5-epicatechin	HMDB

Chemical Formula

C₉₀H₇₄O₃₆

Average Mass

1731.5290 Da

Monoisotopic Mass

1730.39598 Da

IUPAC Name

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

Traditional Name

CAS Registry Number

88847-05-6

SMILES

O[C@@H]1CC2=C(O)C=C(O)C([C@@H]3[C@@H](O)[C@H](OC4=C([C@@H]5[C@@H](O)[C@H](OC6=C([C@@H]7[C@@H](O)[C@H](OC8=C([C@@H]9[C@@H](O)[C@H](OC%10=C([C@@H]%11[C@@H](O)[C@H](OC%12=CC(O)=CC(O)=C%11%12)C%11=CC=C(O)C(O)=C%11)C(O)=CC(O)=C9%10)C9=CC=C(O)C(O)=C9)C(O)=CC(O)=C78)C7=CC=C(O)C(O)=C7)C(O)=CC(O)=C56)C5=CC=C(O)C(O)=C5)C(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2O[C@@H]1C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C90H74O36/c91-33-19-48(105)60-59(20-33)121-81(28-2-8-36(93)43(100)14-28)75(116)70(60)62-50(107)23-52(109)64-72(77(118)83(123-87(62)64)30-4-10-38(95)45(102)16-30)66-54(111)25-56(113)68-74(79(120)85(125-89(66)68)32-6-12-40(97)47(104)18-32)69-57(114)26-55(112)67-73(78(119)84(126-90(67)69)31-5-11-39(96)46(103)17-31)65-53(110)24-51(108)63-71(76(117)82(124-88(63)65)29-3-9-37(94)44(101)15-29)61-49(106)22-41(98)34-21-58(115)80(122-86(34)61)27-1-7-35(92)42(99)13-27/h1-20,22-26,58,70-85,91-120H,21H2/t58-,70-,71+,72-,73+,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-/m1/s1

InChI Key

UUOWTYGESRVWCF-WKWFDMPLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cinnamomum aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Bi- and polyflavonoid skeleton
Proanthocyanidin
Catechin
Flavan-3-ol
Hydroxyflavonoid
3'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Flavan
Chromane
1-benzopyran
Benzopyran
Catechol
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

proanthocyanidin (CHEBI:10150 )
hydroxyflavan (CHEBI:10150 )
Proanthocyanidins (C10222 )
Condensed tannins (Proanthocyanidins) (C10222 )
Proanthocyanidins (LMPK12030007 )

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	4.68	ALOGPS
logP	8.4	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.58	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	36	ChemAxon
Hydrogen Donor Count	30	ChemAxon
Polar Surface Area	662.28 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	436.54 m³·mol⁻¹	ChemAxon
Polarizability	174.43 Å³	ChemAxon
Number of Rings	18	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon