NP-MRD: Showing NP-Card for cinnamtannin D1 (NP0036149)

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Record Information

Version

2.0

Created at

2021-06-20 19:23:58 UTC

Updated at

2021-06-30 00:07:39 UTC

NP-MRD ID

NP0036149

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cinnamtannin D1

Provided By

JEOL Database JEOL Logo

Description

Cinnamtannin D1 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''. Cinnamtannin D1 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cinnamtannin D1 has been detected, but not quantified in, fruits and lingonberries. This could make cinnamtannin D1 a potential biomarker for the consumption of these foods. cinnamtannin D1 is found in Cinnamomum cassia, Cinnamomum burmannii, Cinnamomum philippinense, Lindera umbellata and Parameria laevigata. cinnamtannin D1 was first documented in 2011 (PMID: 21875098). A proanthocyanidin found in Cinnamomum cassia.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121243D          

 99108  0  0  0  0            999 V2000
   -0.2961    7.8521    1.5205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0504    6.5311    1.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7274    5.8368    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4483    4.4861    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1673    3.8716   -0.8987 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5234    3.8246    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1822    4.5452    1.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    5.8947    2.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454    4.0081    2.6749 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3475    2.5862    2.5640 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7261    2.2306    3.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7253    3.1989    3.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9873    2.8372    3.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2607    1.4999    4.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4773    1.0817    4.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2878    0.5322    3.8968 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5702   -0.7904    4.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296    0.8843    3.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3987    1.8921    3.4130 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3190    1.3076    2.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4794    0.5165    3.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762   -0.1441    3.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747   -0.9051    3.8938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865   -0.0419    1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0863    0.7821    0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0133    1.4641    1.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8868    2.3739    0.6257 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3195    2.1167    1.0843 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2524    2.7793    0.2144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3415    1.0101   -0.4064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871   -0.0301   -1.0648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1823    0.3630   -2.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3736    0.2822   -3.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000    0.6115   -4.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0091    0.7845   -3.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4001   -0.3130   -0.3115 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2315    0.8655   -0.2770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0831   -0.7689    1.1329 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0662   -2.3024    1.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4476   -2.2216    1.4443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3689   -4.3414    1.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2069   -5.0976    1.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3686   -6.4431    1.6645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9652   -4.5009    1.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028   -3.0978    1.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7273   -2.4531    0.8075 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820   -3.1664    1.1018 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6568   -2.3801    0.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5951   -1.8410   -0.7757 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1538   -1.5211    1.3225 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8559   -2.2643    1.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4464   -4.5807    0.5005 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6377   -5.3269    0.7710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220   -5.3361    1.1175 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9719    8.1531    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4761    6.3196   -0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2697    2.9221   -0.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178    6.4483    2.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5285    4.2495    3.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7331    3.6095    4.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0416    1.8664    4.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4775   -0.7774    4.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2841    0.1077    3.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0834   -0.8047    4.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5318    1.0438    1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1467    2.5123    0.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792   -0.9427   -1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3078   -0.0260   -2.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3260    0.5506   -5.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3464    1.6253   -6.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7585    1.7348   -4.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0741    0.8484   -2.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9827   -1.0774   -0.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0278    0.6373    0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9135   -0.4226    1.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1860   -2.8083    1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3166   -4.8440    1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5053   -6.8721    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6005   -3.2064    2.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852   -1.9309   -1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6534   -0.7978   -2.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6730   -0.6273   -0.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0211   -1.6379    2.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9313   -2.6898    2.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3060   -4.5365   -0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3549   -4.9236    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4487   -5.6946    2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095   -6.2271    0.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  9  1  0  0  0  0
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M  END

     RDKit          3D

 99108  0  0  0  0  0  0  0  0999 V2000
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   -0.0504    6.5311    1.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7274    5.8368    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4483    4.4861    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5234    3.8246    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1822    4.5452    1.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    5.8947    2.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454    4.0081    2.6749 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3475    2.5862    2.5640 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.7253    3.1989    3.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9873    2.8372    3.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2607    1.4999    4.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202121243D          

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M  END
> <DATABASE_ID>
NP0036149

> <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])[C@@]5([H])C5=C(O[H])C([H])=C(O[H])C6=C5O[C@]([H])(C5=C([H])C(O[H])=C(O[H])C([H])=C5[H])[C@@]([H])(O[H])C6([H])[H])=C4[C@]2([H])[C@@]3([H])O[H])C2=C([H])C(O[H])=C(O[H])C([H])=C2[H])=C1[H]

> <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/t30-,37-,38+,39+,40+,41+,44+,45-/m0/s1

> <INCHI_KEY>
BYSRPHRKESMCPO-HMQYECKYSA-N

> <FORMULA>
C45H36O18

> <MOLECULAR_WEIGHT>
864.765

> <EXACT_MASS>
864.190164319

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
84.57628903872651

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-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>
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>
216.70460000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-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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M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0      -0.296   7.852   1.521  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.050   6.531   1.285  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.727   5.837   0.290  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.448   4.486   0.087  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.167   3.872  -0.899  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.523   3.825   0.850  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.182   4.545   1.860  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.899   5.895   2.073  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.145   4.008   2.675  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.348   2.586   2.564  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.726   2.231   3.151  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.725   3.199   3.370  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.987   2.837   3.859  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.261   1.500   4.116  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.477   1.082   4.577  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.288   0.532   3.897  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.570  -0.790   4.104  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.030   0.884   3.435  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.399   1.892   3.413  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.319   1.308   2.813  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.479   0.517   3.631  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.576  -0.144   3.086  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.375  -0.905   3.894  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.887  -0.042   1.721  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.086   0.782   0.919  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.013   1.464   1.458  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.887   2.374   0.626  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.320   2.117   1.084  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.252   2.779   0.214  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.341   1.010  -0.406  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.087  -0.030  -1.065  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.182   0.363  -2.538  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.374   0.282  -3.282  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.400   0.612  -4.641  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.235   1.027  -5.264  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.263   1.350  -6.590  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.047   1.123  -4.551  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.065   1.556  -5.217  0.00  0.00           O+0
HETATM   39  C   UNK     0      -1.009   0.785  -3.202  0.00  0.00           C+0
HETATM   40  C   UNK     0      -3.400  -0.313  -0.312  0.00  0.00           C+0
HETATM   41  O   UNK     0      -4.231   0.866  -0.277  0.00  0.00           O+0
HETATM   42  C   UNK     0      -3.083  -0.769   1.133  0.00  0.00           C+0
HETATM   43  C   UNK     0      -3.066  -2.302   1.216  0.00  0.00           C+0
HETATM   44  C   UNK     0      -4.294  -2.961   1.411  0.00  0.00           C+0
HETATM   45  O   UNK     0      -5.448  -2.222   1.444  0.00  0.00           O+0
HETATM   46  C   UNK     0      -4.369  -4.341   1.554  0.00  0.00           C+0
HETATM   47  C   UNK     0      -3.207  -5.098   1.484  0.00  0.00           C+0
HETATM   48  O   UNK     0      -3.369  -6.443   1.665  0.00  0.00           O+0
HETATM   49  C   UNK     0      -1.965  -4.501   1.230  0.00  0.00           C+0
HETATM   50  C   UNK     0      -1.903  -3.098   1.103  0.00  0.00           C+0
HETATM   51  O   UNK     0      -0.727  -2.453   0.808  0.00  0.00           O+0
HETATM   52  C   UNK     0       0.482  -3.166   1.102  0.00  0.00           C+0
HETATM   53  C   UNK     0       1.657  -2.380   0.525  0.00  0.00           C+0
HETATM   54  C   UNK     0       1.595  -1.841  -0.776  0.00  0.00           C+0
HETATM   55  C   UNK     0       2.702  -1.206  -1.342  0.00  0.00           C+0
HETATM   56  C   UNK     0       3.876  -1.122  -0.613  0.00  0.00           C+0
HETATM   57  O   UNK     0       4.966  -0.516  -1.168  0.00  0.00           O+0
HETATM   58  C   UNK     0       3.956  -1.642   0.676  0.00  0.00           C+0
HETATM   59  O   UNK     0       5.154  -1.521   1.323  0.00  0.00           O+0
HETATM   60  C   UNK     0       2.856  -2.264   1.256  0.00  0.00           C+0
HETATM   61  C   UNK     0       0.446  -4.581   0.500  0.00  0.00           C+0
HETATM   62  O   UNK     0       1.638  -5.327   0.771  0.00  0.00           O+0
HETATM   63  C   UNK     0      -0.722  -5.336   1.117  0.00  0.00           C+0
HETATM   64  H   UNK     0      -0.972   8.153   0.890  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.476   6.320  -0.330  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.270   2.922  -0.693  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.418   6.448   2.850  0.00  0.00           H+0
HETATM   68  H   UNK     0       4.529   4.250   3.158  0.00  0.00           H+0
HETATM   69  H   UNK     0       6.733   3.610   4.021  0.00  0.00           H+0
HETATM   70  H   UNK     0       8.042   1.866   4.693  0.00  0.00           H+0
HETATM   71  H   UNK     0       6.478  -0.777   4.478  0.00  0.00           H+0
HETATM   72  H   UNK     0       3.284   0.108   3.285  0.00  0.00           H+0
HETATM   73  H   UNK     0      -0.233   0.426   4.684  0.00  0.00           H+0
HETATM   74  H   UNK     0      -2.083  -0.805   4.815  0.00  0.00           H+0
HETATM   75  H   UNK     0       0.837   2.139  -0.444  0.00  0.00           H+0
HETATM   76  H   UNK     0       2.532   1.044   1.008  0.00  0.00           H+0
HETATM   77  H   UNK     0       4.147   2.512   0.493  0.00  0.00           H+0
HETATM   78  H   UNK     0      -1.479  -0.943  -1.067  0.00  0.00           H+0
HETATM   79  H   UNK     0      -4.308  -0.026  -2.820  0.00  0.00           H+0
HETATM   80  H   UNK     0      -4.326   0.551  -5.205  0.00  0.00           H+0
HETATM   81  H   UNK     0      -1.346   1.625  -6.790  0.00  0.00           H+0
HETATM   82  H   UNK     0       0.759   1.735  -4.558  0.00  0.00           H+0
HETATM   83  H   UNK     0      -0.074   0.848  -2.652  0.00  0.00           H+0
HETATM   84  H   UNK     0      -3.983  -1.077  -0.839  0.00  0.00           H+0
HETATM   85  H   UNK     0      -5.028   0.637   0.235  0.00  0.00           H+0
HETATM   86  H   UNK     0      -3.914  -0.423   1.766  0.00  0.00           H+0
HETATM   87  H   UNK     0      -6.186  -2.808   1.683  0.00  0.00           H+0
HETATM   88  H   UNK     0      -5.317  -4.844   1.720  0.00  0.00           H+0
HETATM   89  H   UNK     0      -2.505  -6.872   1.773  0.00  0.00           H+0
HETATM   90  H   UNK     0       0.601  -3.206   2.194  0.00  0.00           H+0
HETATM   91  H   UNK     0       0.685  -1.931  -1.365  0.00  0.00           H+0
HETATM   92  H   UNK     0       2.653  -0.798  -2.346  0.00  0.00           H+0
HETATM   93  H   UNK     0       5.673  -0.627  -0.500  0.00  0.00           H+0
HETATM   94  H   UNK     0       5.021  -1.638   2.285  0.00  0.00           H+0
HETATM   95  H   UNK     0       2.931  -2.690   2.253  0.00  0.00           H+0
HETATM   96  H   UNK     0       0.306  -4.537  -0.588  0.00  0.00           H+0
HETATM   97  H   UNK     0       2.355  -4.924   0.247  0.00  0.00           H+0
HETATM   98  H   UNK     0      -0.449  -5.695   2.119  0.00  0.00           H+0
HETATM   99  H   UNK     0      -0.910  -6.227   0.505  0.00  0.00           H+0
CONECT    1    2   64                                                       
CONECT    2    1    3    8                                                  
CONECT    3    4    2   65                                                  
CONECT    4    5    6    3                                                  
CONECT    5    4   66                                                       
CONECT    6   27    4    7                                                  
CONECT    7    9    8    6                                                  
CONECT    8    2    7   67                                                  
CONECT    9    7   10                                                       
CONECT   10   28    9   11   19                                             
CONECT   11   10   18   12                                                  
CONECT   12   13   11   68                                                  
CONECT   13   14   12   69                                                  
CONECT   14   16   13   15                                                  
CONECT   15   14   70                                                       
CONECT   16   18   14   17                                                  
CONECT   17   16   71                                                       
CONECT   18   11   16   72                                                  
CONECT   19   10   20                                                       
CONECT   20   21   26   19                                                  
CONECT   21   22   20   73                                                  
CONECT   22   24   21   23                                                  
CONECT   23   22   74                                                       
CONECT   24   22   25   42                                                  
CONECT   25   26   24   30                                                  
CONECT   26   27   20   25                                                  
CONECT   27    6   28   26   75                                             
CONECT   28   27   10   29   76                                             
CONECT   29   28   77                                                       
CONECT   30   25   31                                                       
CONECT   31   40   30   32   78                                             
CONECT   32   31   39   33                                                  
CONECT   33   34   32   79                                                  
CONECT   34   35   33   80                                                  
CONECT   35   37   34   36                                                  
CONECT   36   35   81                                                       
CONECT   37   39   35   38                                                  
CONECT   38   37   82                                                       
CONECT   39   32   37   83                                                  
CONECT   40   42   31   41   84                                             
CONECT   41   40   85                                                       
CONECT   42   43   24   40   86                                             
CONECT   43   44   50   42                                                  
CONECT   44   43   45   46                                                  
CONECT   45   44   87                                                       
CONECT   46   47   44   88                                                  
CONECT   47   48   46   49                                                  
CONECT   48   47   89                                                       
CONECT   49   63   50   47                                                  
CONECT   50   43   51   49                                                  
CONECT   51   50   52                                                       
CONECT   52   61   51   53   90                                             
CONECT   53   54   60   52                                                  
CONECT   54   55   53   91                                                  
CONECT   55   54   56   92                                                  
CONECT   56   57   58   55                                                  
CONECT   57   56   93                                                       
CONECT   58   59   60   56                                                  
CONECT   59   58   94                                                       
CONECT   60   53   58   95                                                  
CONECT   61   63   62   52   96                                             
CONECT   62   61   97                                                       
CONECT   63   49   61   98   99                                             
CONECT   64    1                                                            
CONECT   65    3                                                            
CONECT   66    5                                                            
CONECT   67    8                                                            
CONECT   68   12                                                            
CONECT   69   13                                                            
CONECT   70   15                                                            
CONECT   71   17                                                            
CONECT   72   18                                                            
CONECT   73   21                                                            
CONECT   74   23                                                            
CONECT   75   27                                                            
CONECT   76   28                                                            
CONECT   77   29                                                            
CONECT   78   31                                                            
CONECT   79   33                                                            
CONECT   80   34                                                            
CONECT   81   36                                                            
CONECT   82   38                                                            
CONECT   83   39                                                            
CONECT   84   40                                                            
CONECT   85   41                                                            
CONECT   86   42                                                            
CONECT   87   45                                                            
CONECT   88   46                                                            
CONECT   89   48                                                            
CONECT   90   52                                                            
CONECT   91   54                                                            
CONECT   92   55                                                            
CONECT   93   57                                                            
CONECT   94   59                                                            
CONECT   95   60                                                            
CONECT   96   61                                                            
CONECT   97   62                                                            
CONECT   98   63                                                            
CONECT   99   63                                                            
MASTER        0    0    0    0    0    0    0    0   99    0  216    0
END

RDKit          3D

99108  0  0  0  0  0  0  0  0999 V2000
   -0.2961    7.8521    1.5205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0504    6.5311    1.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7274    5.8368    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4483    4.4861    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1673    3.8716   -0.8987 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5234    3.8246    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1822    4.5452    1.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    5.8947    2.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454    4.0081    2.6749 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3475    2.5862    2.5640 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7261    2.2306    3.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7253    3.1989    3.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9873    2.8372    3.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2607    1.4999    4.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4773    1.0817    4.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2878    0.5322    3.8968 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5702   -0.7904    4.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296    0.8843    3.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3987    1.8921    3.4130 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3190    1.3076    2.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4794    0.5165    3.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762   -0.1441    3.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747   -0.9051    3.8938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865   -0.0419    1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0863    0.7821    0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0133    1.4641    1.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8868    2.3739    0.6257 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3195    2.1167    1.0843 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2524    2.7793    0.2144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3415    1.0101   -0.4064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871   -0.0301   -1.0648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1823    0.3630   -2.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3736    0.2822   -3.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000    0.6115   -4.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2353    1.0270   -5.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634    1.3502   -6.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0472    1.1225   -4.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0653    1.5563   -5.2174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0091    0.7845   -3.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4001   -0.3130   -0.3115 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2315    0.8655   -0.2770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0831   -0.7689    1.1329 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0662   -2.3024    1.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2943   -2.9612    1.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4476   -2.2216    1.4443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3689   -4.3414    1.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2069   -5.0976    1.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3686   -6.4431    1.6645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9652   -4.5009    1.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028   -3.0978    1.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7273   -2.4531    0.8075 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820   -3.1664    1.1018 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6568   -2.3801    0.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5951   -1.8410   -0.7757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7016   -1.2062   -1.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8759   -1.1220   -0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9658   -0.5159   -1.1679 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9562   -1.6419    0.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1538   -1.5211    1.3225 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8559   -2.2643    1.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4464   -4.5807    0.5005 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6377   -5.3269    0.7710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220   -5.3361    1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9719    8.1531    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4761    6.3196   -0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2697    2.9221   -0.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178    6.4483    2.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5285    4.2495    3.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7331    3.6095    4.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0416    1.8664    4.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4775   -0.7774    4.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2841    0.1077    3.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325    0.4259    4.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8367    2.1394   -0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5318    1.0438    1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3078   -0.0260   -2.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3260    0.5506   -5.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1860   -2.8083    1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3166   -4.8440    1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5053   -6.8721    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6005   -3.2064    2.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852   -1.9309   -1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6534   -0.7978   -2.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6730   -0.6273   -0.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0211   -1.6379    2.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9313   -2.6898    2.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3060   -4.5365   -0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3549   -4.9236    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4487   -5.6946    2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095   -6.2271    0.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  9  1  0
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 41 85  1  0
M  END

View in JSmol

Synonyms

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

Chemical Formula

C₄₅H₃₆O₁₈

Average Mass

864.7650 Da

Monoisotopic Mass

864.19016 Da

IUPAC Name

(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-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

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])[C@@]5([H])C5=C(O[H])C([H])=C(O[H])C6=C5O[C@]([H])(C5=C([H])C(O[H])=C(O[H])C([H])=C5[H])[C@@]([H])(O[H])C6([H])[H])=C4[C@]2([H])[C@@]3([H])O[H])C2=C([H])C(O[H])=C(O[H])C([H])=C2[H])=C1[H]

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/t30-,37-,38+,39+,40+,41+,44+,45-/m0/s1

InChI Key

BYSRPHRKESMCPO-HMQYECKYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD at 298K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD at 298K, 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
Cinnamomum aromaticum	JEOL database	Killday, K. B., et al, J. Nat. Prod. 74, 1833 (2011)
Cinnamomum burmanni	LOTUS Database	35616633
Cinnamomum philippinense	LOTUS Database	35616633
Lindera umbellata	LOTUS Database	35616633
Parameria laevigata	LOTUS Database	35616633
Vaccinium vitis-idaea	FooDB	KNAPSACK

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	84.58 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

HMDB0037673

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46173958

PDB ID

Not Available

ChEBI ID

69305

Good Scents ID

Not Available

References

General References

Killday KB, Davey MH, Glinski JA, Duan P, Veluri R, Proni G, Daugherty FJ, Tempesta MS: Bioactive A-type proanthocyanidins from Cinnamomum cassia. J Nat Prod. 2011 Sep 23;74(9):1833-41. doi: 10.1021/np1007944. Epub 2011 Aug 29. [PubMed:21875098 ]
Killday, K. B., et al. (2011). Killday, K. B., et al, J. Nat. Prod. 74, 1833 (2011). J. Nat. Prod..

Showing NP-Card for cinnamtannin D1 (NP0036149)

MOL for NP0036149 (cinnamtannin D1)

3D MOL for NP0036149 (cinnamtannin D1)

3D SDF for NP0036149 (cinnamtannin D1)

3D-SDF for NP0036149 (cinnamtannin D1)

PDB for NP0036149 (cinnamtannin D1)

3D PDB for NP0036149 (cinnamtannin D1)

SMILES for NP0036149 (cinnamtannin D1)

INCHI for NP0036149 (cinnamtannin D1)

Structure for NP0036149 (cinnamtannin D1)

3D Structure for NP0036149 (cinnamtannin D1)