NP-MRD: Showing NP-Card for 5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol (NP0160387)

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Record Information

Version

2.0

Created at

2022-09-02 18:20:07 UTC

Updated at

2022-09-02 18:20:07 UTC

NP-MRD ID

NP0160387

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

Description

Pavetannin B6, also known as cinnamtannin D-1, 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''. Pavetannin B6 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, pavetannin B6 has been detected, but not quantified in, herbs and spices. 5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol is found in Aesculus hippocastanum, Cinnamomum burmannii, Cinnamomum philippinense, Cinnamomum verum, Cryptocarya obovata, Dicranopteris pedata, Guioa crenulata, Ixora coccinea, Kandelia candel, Lindera aggregata, Parameria laevigata, Pavetta owariensis, Rumex acetosa and Vaccinium vitis-idaea. This could make pavetannin B6 a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 05061309562D          

 63 72  0  0  0  0            999 V2000
    2.4171   -2.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2104   -2.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8033   -2.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6030   -1.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8097   -1.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168   -1.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242   -3.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0310   -3.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380   -3.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6384   -4.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316   -4.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0245   -4.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1959   -0.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9956   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2023    0.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6094   -0.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0454   -4.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4107   -3.6857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4288   -0.6028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2226   -0.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8161   -0.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6153    0.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8215    0.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2303    0.1973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1652   -1.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0337   -1.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602   -2.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3531   -2.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5520   -1.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9580   -0.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2086    1.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0089    1.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2150    2.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6226    1.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9470   -2.8932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217   -1.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0578    3.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2241    2.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3040    1.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1156    1.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3974    2.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8694    3.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4731    3.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1911    4.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7207    5.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    5.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8170    4.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2861    3.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462    1.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586    1.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7404    2.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2097    2.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0646    5.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6115    2.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9891   -1.1645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0020    0.8895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0059    1.3266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3645    0.4753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5528    2.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6287    4.1204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3448   -1.2919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6320   -5.4066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015    2.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5 16  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 11 12  2  0  0  0  0
 11 62  1  0  0  0  0
 13 14  2  0  0  0  0
 13 55  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 56  1  0  0  0  0
 16 21  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  0  0  0  0
 19 25  1  0  0  0  0
 20 21  1  0  0  0  0
 20 36  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 31  1  0  0  0  0
 23 24  1  0  0  0  0
 23 34  1  0  0  0  0
 25 26  2  0  0  0  0
 25 30  1  0  0  0  0
 26 27  1  0  0  0  0
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 28 29  1  0  0  0  0
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 31 32  2  0  0  0  0
 31 57  1  0  0  0  0
 32 33  1  0  0  0  0
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 34 39  1  0  0  0  0
 37 38  1  0  0  0  0
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 37 43  1  0  0  0  0
 38 39  1  0  0  0  0
 38 54  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 49  1  0  0  0  0
 41 42  1  0  0  0  0
 41 52  1  0  0  0  0
 43 44  2  0  0  0  0
 43 48  1  0  0  0  0
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 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 46 53  1  0  0  0  0
 47 48  2  0  0  0  0
 47 60  1  0  0  0  0
 49 50  2  0  0  0  0
 49 58  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 51 59  1  0  0  0  0
 33 63  1  0  0  0  0
 63 37  1  0  0  0  0
M  END

     RDKit          3D

 99108  0  0  0  0  0  0  0  0999 V2000
    5.8393    3.3525   -4.7931 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3087    2.4795   -3.8665 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2643    1.6767   -4.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7118    0.7829   -3.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6761    0.0336   -3.7997 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2201    0.7085   -2.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2951    1.5313   -1.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7993    2.3911   -2.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8458    1.4877   -0.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614    0.9334    0.6314 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6672    0.9539    1.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9615    2.1926    2.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6497    2.3306    3.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0695    1.2184    4.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7719    1.3240    5.5459 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7734   -0.0199    3.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1821   -1.1657    4.4635 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0820   -0.1546    2.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8249    1.7806    0.7299 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5432    1.3062    0.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4519    1.8114    1.2132 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2020    1.2744    0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849    1.8123    1.6727 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1235   -0.2813   -0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3677    0.2660   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5771   -0.2349   -1.0470 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5829   -0.4081    0.1115 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6866   -1.1463   -0.3121 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591   -1.3298   -1.4373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461   -1.2643   -2.1978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5389   -2.5349   -2.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8362   -2.5213   -4.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286   -3.6558   -5.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9120   -4.8813   -4.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117   -6.0096   -5.1993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6143   -4.9413   -3.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5022   -6.1543   -2.4474 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1030    3.1875    1.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9486   -0.0018    2.0891 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.4526    4.2822   -4.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8462    1.7235   -5.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8436   -1.1250    2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5832    2.6416    1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7863    2.5608    2.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

  Mrv0541 05061309562D          

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M  END
> <DATABASE_ID>
NP0160387

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2=C(OC1C1=CC=C(O)C(O)=C1)C(C1C(O)C(OC3=C1C(O)=CC1=C3C3C(O)C(OC4=C3C(O)=CC(O)=C4)(O1)C1=CC=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1)=C(O)C=C2O

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

> <INCHI_KEY>
BYSRPHRKESMCPO-UHFFFAOYSA-N

> <FORMULA>
C45H36O18

> <MOLECULAR_WEIGHT>
864.7565

> <EXACT_MASS>
864.190164348

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
84.27467780666458

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-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>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.014707025187052

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.597961065379815

> <JCHEM_PKA_STRONGEST_BASIC>
-5.217533055260987

> <JCHEM_POLAR_SURFACE_AREA>
320.14

> <JCHEM_REFRACTIVITY>
216.70460000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-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

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.512  -4.963   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.993  -5.386   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.099  -4.315   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.726  -2.821   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.245  -2.398   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.138  -3.469   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.405  -6.034   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.925  -5.611   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.818  -6.682   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.192  -8.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.672  -8.598   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.779  -7.528   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.832  -1.751   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.458  -0.257   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.978   0.167   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.871  -0.904   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.085  -9.246   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.367  -6.880   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.800  -1.125   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.282  -1.551   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.390  -0.481   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.015   1.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.533   1.435   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.430   0.368   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.308  -2.194   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.063  -3.689   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.046  -4.758   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.526  -4.332   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.897  -2.837   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.788  -1.768   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.123   2.076   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.750   3.569   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.268   3.994   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.162   2.926   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.634  -5.401   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       2.654  -3.047   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -0.108   5.871   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.418   4.423   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.567   3.242   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.082   3.514   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.608   4.961   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -1.623   6.135   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       0.883   7.047   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.357   8.498   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       1.345   9.676   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       2.876   9.412   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       3.392   7.964   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       2.401   6.785   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -3.073   2.335   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -4.589   2.603   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -5.115   4.050   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -4.125   5.229   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       3.854  10.596   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      -1.141   4.719   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       9.313  -2.174   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       5.604   1.660   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       5.611   2.476   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      -2.547   0.887   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      -6.632   4.319   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       4.907   7.691   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      -4.377  -2.412   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0       3.046 -10.092   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0       1.869   5.482   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   16                                                  
CONECT    6    1    5                                                       
CONECT    7    1    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   62                                                  
CONECT   12    7   11                                                       
CONECT   13    4   14   55                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   56                                                  
CONECT   16    5   15   21                                                  
CONECT   17   10                                                            
CONECT   18    2                                                            
CONECT   19   20   24   25                                                  
CONECT   20   19   21   36                                                  
CONECT   21   16   20   22                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24   34                                                  
CONECT   24   19   23                                                       
CONECT   25   19   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30   61                                                  
CONECT   30   25   29                                                       
CONECT   31   22   32   57                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   63                                                  
CONECT   34   23   33   39                                                  
CONECT   35   28                                                            
CONECT   36   20                                                            
CONECT   37   38   42   43   63                                             
CONECT   38   37   39   54                                                  
CONECT   39   34   38   40                                                  
CONECT   40   39   41   49                                                  
CONECT   41   40   42   52                                                  
CONECT   42   37   41                                                       
CONECT   43   37   44   48                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   53                                                  
CONECT   47   46   48   60                                                  
CONECT   48   43   47                                                       
CONECT   49   40   50   58                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   59                                                  
CONECT   52   41   51                                                       
CONECT   53   46                                                            
CONECT   54   38                                                            
CONECT   55   13                                                            
CONECT   56   15                                                            
CONECT   57   31                                                            
CONECT   58   49                                                            
CONECT   59   51                                                            
CONECT   60   47                                                            
CONECT   61   29                                                            
CONECT   62   11                                                            
CONECT   63   33   37                                                       
MASTER        0    0    0    0    0    0    0    0   63    0  144    0
END

View in JSmol

Synonyms

Value	Source
Catechin(2b->7,4b->8)-ent-epicatechin(4a->8)catechin	HMDB
Cinnamtannin D-1	HMDB

Chemical Formula

C₄₅H₃₆O₁₈

Average Mass

864.7565 Da

Monoisotopic Mass

864.19016 Da

IUPAC Name

5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-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

CAS Registry Number

Not Available

SMILES

OC1CC2=C(OC1C1=CC=C(O)C(O)=C1)C(C1C(O)C(OC3=C1C(O)=CC1=C3C3C(O)C(OC4=C3C(O)=CC(O)=C4)(O1)C1=CC=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1)=C(O)C=C2O

InChI Identifier

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

InChI Key

BYSRPHRKESMCPO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aesculus hippocastanum	LOTUS Database	35616633
Cinnamomum burmanni	LOTUS Database	35616633
Cinnamomum philippinense	LOTUS Database	35616633
Cinnamomum verum	LOTUS Database	35616633
Cryptocarya obovata	LOTUS Database	35616633
Dicranopteris pedata	LOTUS Database	35616633
Guioa crenulata	LOTUS Database	35616633
Ixora coccinea	LOTUS Database	35616633
Kandelia candel	LOTUS Database	35616633
Lindera aggregata	LOTUS Database	35616633
Parameria laevigata	LOTUS Database	35616633
Pavetta owariensis	LOTUS Database	35616633
Rumex acetosa	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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	3.54	ALOGPS
logP	4.91	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.6	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	320.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	216.7 m³·mol⁻¹	ChemAxon
Polarizability	84.27 Å³	ChemAxon
Number of Rings	10	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

HMDB0037674

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016801

KNApSAcK ID

Not Available

Chemspider ID

22370090

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13990885

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol (NP0160387)

MOL for NP0160387 (5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D MOL for NP0160387 (5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D SDF for NP0160387 (5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D-SDF for NP0160387 (5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

PDB for NP0160387 (5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D PDB for NP0160387 (5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

SMILES for NP0160387 (5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

INCHI for NP0160387 (5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

Structure for NP0160387 (5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D Structure for NP0160387 (5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)