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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:33:45 UTC

Update Date

2022-03-07 02:52:22 UTC

HMDB ID

HMDB0029950

Secondary Accession Numbers

HMDB29950

Metabolite Identification

Common Name

Punicafolin

Description

Punicafolin belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Punicafolin has been detected, but not quantified in, fruits and pomegranates (Punica granatum). This could make punicafolin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Punicafolin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061304562D          

 67 73  0  0  0  0            999 V2000
    2.2982    1.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7039    1.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0926   -2.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8939   -0.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3289    1.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2951    2.4280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6378   -3.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0061    0.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0752    1.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1516   -1.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542    1.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9587   -2.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1499    2.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5555    2.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7757   -2.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5769   -1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4470    2.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1354   -3.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3229    0.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7774   -2.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7785    3.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5178   -2.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1301    2.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4486   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9541   -3.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2751   -2.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3820   -0.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -1.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9567   -0.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6979    0.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5315   -0.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0964    1.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4611   -1.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8976    0.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4329    2.8124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1842    3.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166   -3.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191   -1.0681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7542    1.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5061    3.6112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7187    0.4223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8145   -4.4886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6302    3.8962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009   -2.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8724    2.6860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2588   -1.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4518   -4.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786   -2.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0938   -2.7646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3770    1.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723   -0.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7795    1.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8971   -1.2271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4768   -0.9462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482    0.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5807    0.5244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2736   -1.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1554    0.4220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3884   -1.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777    0.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 14  8  2  0  0  0  0
 15  1  1  0  0  0  0
 16  2  2  0  0  0  0
 17  3  1  0  0  0  0
 18  4  2  0  0  0  0
 19  5  1  0  0  0  0
 20  6  2  0  0  0  0
 21  7  1  0  0  0  0
 22  8  1  0  0  0  0
 23  9  1  0  0  0  0
 24 13  1  0  0  0  0
 25 14  1  0  0  0  0
 25 24  1  0  0  0  0
 26 15  2  0  0  0  0
 26 16  1  0  0  0  0
 27 17  2  0  0  0  0
 27 18  1  0  0  0  0
 28 19  2  0  0  0  0
 28 20  1  0  0  0  0
 29 21  2  0  0  0  0
 30 22  2  0  0  0  0
 31 24  2  0  0  0  0
 31 29  1  0  0  0  0
 32 25  2  0  0  0  0
 32 30  1  0  0  0  0
 33 23  1  0  0  0  0
 34 33  1  0  0  0  0
 35 34  1  0  0  0  0
 36 10  1  0  0  0  0
 37 11  1  0  0  0  0
 38 12  1  0  0  0  0
 39 13  1  0  0  0  0
 40 14  1  0  0  0  0
 41 35  1  0  0  0  0
 42 15  1  0  0  0  0
 43 16  1  0  0  0  0
 44 17  1  0  0  0  0
 45 18  1  0  0  0  0
 46 19  1  0  0  0  0
 47 20  1  0  0  0  0
 48 21  1  0  0  0  0
 49 22  1  0  0  0  0
 50 26  1  0  0  0  0
 51 27  1  0  0  0  0
 52 28  1  0  0  0  0
 53 29  1  0  0  0  0
 54 30  1  0  0  0  0
 55 31  1  0  0  0  0
 56 32  1  0  0  0  0
 57 36  2  0  0  0  0
 58 37  2  0  0  0  0
 59 38  2  0  0  0  0
 60 39  2  0  0  0  0
 61 40  2  0  0  0  0
 62  9  1  0  0  0  0
 62 39  1  0  0  0  0
 63 23  1  0  0  0  0
 63 41  1  0  0  0  0
 64 35  1  0  0  0  0
 64 37  1  0  0  0  0
 65 38  1  0  0  0  0
 65 41  1  0  0  0  0
 40 66  1  0  0  0  0
 66 34  1  0  0  0  0
 33 67  1  0  0  0  0
 67 36  1  0  0  0  0
M  END

HMDB0029950
     RDKit          3D
Punicafolin
 97103  0  0  0  0  0  0  0  0999 V2000
    2.1285   -3.7129   -0.9076 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1873   -3.0475   -1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1638   -1.6784   -1.3514 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8675   -1.0564   -1.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6547   -0.5575   -2.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475    0.2452   -2.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7546   -0.5288   -2.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7171    0.4097   -2.1931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0978    0.3193   -2.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575    1.1683   -3.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0087   -0.5532   -1.5323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7425   -1.3827   -2.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7009   -2.2565   -1.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3858   -3.0493   -2.9264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9582   -2.3281   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9503   -3.2333   -0.2121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2800   -1.5485    0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6336   -1.7099    1.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2725   -0.6279   -0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7154    0.1164    0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4257    0.1615    1.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2085    0.9116    2.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2200    1.5753    3.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9642    2.3042    4.4726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4912    1.5352    2.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4766    2.2351    3.5016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7403    0.8224    1.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0569    0.8690    1.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1989   -0.4757    1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -1.4055    1.8677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4504   -0.2410   -0.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5389    0.7392   -0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5368    1.3559   -1.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4642    2.3232   -1.8981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1730    3.6582   -2.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0505    3.9351   -2.2648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1655    4.7030   -2.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5241    4.5172   -2.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4519    5.5414   -2.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8114    5.3130   -2.3138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9998    6.8058   -2.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8809    7.8708   -2.9224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6422    7.0217   -2.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874    8.3153   -3.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567    5.9842   -2.6537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9003    0.0465   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2976   -0.3223    0.9787 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3929    0.1611    1.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1087    1.0044    1.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6514   -0.3497    2.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7507    0.1335    3.6843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0279   -0.3295    4.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1328    0.1651    5.6299 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2034   -1.2722    5.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4961   -1.7230    6.8066 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1040   -1.7693    4.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196   -2.7115    5.5083 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8476   -1.2918    3.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4584   -3.7943   -1.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6376   -3.1246   -1.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8665   -3.7422   -1.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0595   -3.0875   -1.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8870   -5.1054   -1.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0676   -5.8340   -1.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7296   -5.8148   -0.9685 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7673   -7.1775   -0.7512 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5031   -5.1484   -0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0627   -1.8038   -1.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6321    0.7183   -3.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9036   -0.9108   -3.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6995   -1.4480   -2.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5990   -1.3398   -3.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0900   -3.7079   -2.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4821   -3.8269   -0.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3389   -2.3561    1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2447    0.9665    3.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7067    2.7906    4.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4122    2.2012    3.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5018    0.4976    0.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893    1.6121    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5592    1.8474   -1.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8851    3.5340   -2.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4374    6.0897   -2.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4862    8.7728   -3.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1920    8.4421   -3.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2951    6.2012   -2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6384    0.8088   -0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3964    0.8705    3.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3171   -0.1867    6.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9293   -2.4112    7.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061304562D          

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M  END
> <DATABASE_ID>
HMDB0029950

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(=CC(O)=C1O)C(=O)OC1OC2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC(C2OC(=O)C2=CC(O)=C(O)C(O)=C2)C1OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C41H30O26/c42-15-1-10(2-16(43)26(15)50)36(57)64-33-23-9-62-39(60)13-7-21(48)29(53)31(55)24(13)25-14(8-22(49)30(54)32(25)56)40(61)65-34(33)35(66-37(58)11-3-17(44)27(51)18(45)4-11)41(63-23)67-38(59)12-5-19(46)28(52)20(47)6-12/h1-8,23,33-35,41-56H,9H2

> <INCHI_KEY>
DPBVYZVSXAZMAY-UHFFFAOYSA-N

> <FORMULA>
C41H30O26

> <MOLECULAR_WEIGHT>
938.6613

> <EXACT_MASS>
938.102531132

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
83.38652933834237

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
15

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,7,8,11,12,13-hexahydroxy-3,16-dioxo-22,23-bis(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
4.264459746333333

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.713248422866321

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.291757998000738

> <JCHEM_PKA_STRONGEST_BASIC>
-6.053696234918747

> <JCHEM_POLAR_SURFACE_AREA>
444.18000000000006

> <JCHEM_REFRACTIVITY>
213.82510000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7,8,11,12,13-hexahydroxy-3,16-dioxo-22,23-bis(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029950
     RDKit          3D
Punicafolin
 97103  0  0  0  0  0  0  0  0999 V2000
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    1.6547   -0.5575   -2.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4961   -1.7230    6.8066 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3196   -2.7115    5.5083 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4584   -3.7943   -1.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6376   -3.1246   -1.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8665   -3.7422   -1.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0676   -5.8340   -1.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7673   -7.1775   -0.7512 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6321    0.7183   -3.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9036   -0.9108   -3.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0900   -3.7079   -2.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3389   -2.3561    1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7067    2.7906    4.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4122    2.2012    3.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4893    1.6121    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5592    1.8474   -1.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8851    3.5340   -2.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4374    6.0897   -2.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4862    8.7728   -3.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1920    8.4421   -3.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2951    6.2012   -2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6384    0.8088   -0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3964    0.8705    3.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3171   -0.1867    6.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9293   -2.4112    7.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069   -3.0697    5.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9901   -1.6526    3.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5803   -2.0600   -1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1427   -2.1065   -1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9233   -5.3268   -1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9692   -7.7487   -0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5755   -5.6739   -0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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M  END

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       4.290   3.246   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.914   3.726   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.173  -4.011   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.669  -1.803   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.614   2.133   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.551   4.532   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.888  -0.085   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.657  -5.732   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.478   1.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.740   2.728   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.283  -2.475   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.661   2.996   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.880  -1.249   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.256  -4.313   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.013   4.761   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.637   5.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.448  -4.875   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.944  -2.666   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.999   2.805   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.834   5.205   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.400  -0.376   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.586  -6.960   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.203   0.306   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.384  -2.704   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.784  -4.123   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.187   5.758   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.833  -4.202   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.110   4.341   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.904  -1.831   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.114  -6.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.896  -2.995   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.714  -5.351   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.313  -1.230   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.038  -2.093   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.653  -1.421   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.903   1.830   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.992  -1.612   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.047   2.324   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.367  -0.958   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.327  -3.085   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.542   0.115   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.675   5.250   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       7.811   6.238   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -1.338  -6.411   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -4.329  -1.994   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -3.275   1.942   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -0.945   6.741   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      14.408   0.788   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       8.987  -8.379   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       4.910   7.273   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -4.108  -5.066   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -3.495   5.014   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      15.416  -2.122   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      12.043  -7.998   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      13.400  -4.450   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      13.242  -5.161   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       8.170   2.704   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       0.882  -0.076   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       3.322   3.187   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       9.141  -2.291   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0       8.357  -1.766   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0       8.863   0.497   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0       4.817   0.979   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       2.377  -2.284   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       2.157   0.788   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0       6.325  -3.410   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0       7.425   0.110   0.000  0.00  0.00           O+0
CONECT    1   10   15                                                       
CONECT    2   10   16                                                       
CONECT    3   11   17                                                       
CONECT    4   11   18                                                       
CONECT    5   12   19                                                       
CONECT    6   12   20                                                       
CONECT    7   13   21                                                       
CONECT    8   14   22                                                       
CONECT    9   23   62                                                       
CONECT   10    1    2   36                                                  
CONECT   11    3    4   37                                                  
CONECT   12    5    6   38                                                  
CONECT   13    7   24   39                                                  
CONECT   14    8   25   40                                                  
CONECT   15    1   26   42                                                  
CONECT   16    2   26   43                                                  
CONECT   17    3   27   44                                                  
CONECT   18    4   27   45                                                  
CONECT   19    5   28   46                                                  
CONECT   20    6   28   47                                                  
CONECT   21    7   29   48                                                  
CONECT   22    8   30   49                                                  
CONECT   23    9   33   63                                                  
CONECT   24   13   25   31                                                  
CONECT   25   14   24   32                                                  
CONECT   26   15   16   50                                                  
CONECT   27   17   18   51                                                  
CONECT   28   19   20   52                                                  
CONECT   29   21   31   53                                                  
CONECT   30   22   32   54                                                  
CONECT   31   24   29   55                                                  
CONECT   32   25   30   56                                                  
CONECT   33   23   34   67                                                  
CONECT   34   33   35   66                                                  
CONECT   35   34   41   64                                                  
CONECT   36   10   57   67                                                  
CONECT   37   11   58   64                                                  
CONECT   38   12   59   65                                                  
CONECT   39   13   60   62                                                  
CONECT   40   14   61   66                                                  
CONECT   41   35   63   65                                                  
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   26                                                            
CONECT   51   27                                                            
CONECT   52   28                                                            
CONECT   53   29                                                            
CONECT   54   30                                                            
CONECT   55   31                                                            
CONECT   56   32                                                            
CONECT   57   36                                                            
CONECT   58   37                                                            
CONECT   59   38                                                            
CONECT   60   39                                                            
CONECT   61   40                                                            
CONECT   62    9   39                                                       
CONECT   63   23   41                                                       
CONECT   64   35   37                                                       
CONECT   65   38   41                                                       
CONECT   66   40   34                                                       
CONECT   67   33   36                                                       
MASTER        0    0    0    0    0    0    0    0   67    0  146    0
END

COMPND    HMDB0029950
HETATM    1  O1  UNL     1       2.129  -3.713  -0.908  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.187  -3.048  -1.133  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.164  -1.678  -1.351  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.868  -1.056  -1.308  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.655  -0.558  -2.567  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.547   0.245  -2.723  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.755  -0.529  -2.617  1.00  0.00           C  
HETATM    8  O4  UNL     1      -1.717   0.410  -2.193  1.00  0.00           O  
HETATM    9  C5  UNL     1      -3.098   0.319  -2.251  1.00  0.00           C  
HETATM   10  O5  UNL     1      -3.657   1.168  -3.103  1.00  0.00           O  
HETATM   11  C6  UNL     1      -4.009  -0.553  -1.532  1.00  0.00           C  
HETATM   12  C7  UNL     1      -4.742  -1.383  -2.419  1.00  0.00           C  
HETATM   13  C8  UNL     1      -5.701  -2.256  -1.985  1.00  0.00           C  
HETATM   14  O6  UNL     1      -6.386  -3.049  -2.926  1.00  0.00           O  
HETATM   15  C9  UNL     1      -5.958  -2.328  -0.653  1.00  0.00           C  
HETATM   16  O7  UNL     1      -6.950  -3.233  -0.212  1.00  0.00           O  
HETATM   17  C10 UNL     1      -5.280  -1.549   0.243  1.00  0.00           C  
HETATM   18  O8  UNL     1      -5.634  -1.710   1.569  1.00  0.00           O  
HETATM   19  C11 UNL     1      -4.273  -0.628  -0.179  1.00  0.00           C  
HETATM   20  C12 UNL     1      -3.715   0.116   0.956  1.00  0.00           C  
HETATM   21  C13 UNL     1      -2.426   0.162   1.464  1.00  0.00           C  
HETATM   22  C14 UNL     1      -2.208   0.912   2.659  1.00  0.00           C  
HETATM   23  C15 UNL     1      -3.220   1.575   3.299  1.00  0.00           C  
HETATM   24  O9  UNL     1      -2.964   2.304   4.473  1.00  0.00           O  
HETATM   25  C16 UNL     1      -4.491   1.535   2.800  1.00  0.00           C  
HETATM   26  O10 UNL     1      -5.477   2.235   3.502  1.00  0.00           O  
HETATM   27  C17 UNL     1      -4.740   0.822   1.652  1.00  0.00           C  
HETATM   28  O11 UNL     1      -6.057   0.869   1.258  1.00  0.00           O  
HETATM   29  C18 UNL     1      -1.199  -0.476   1.024  1.00  0.00           C  
HETATM   30  O12 UNL     1      -0.749  -1.406   1.868  1.00  0.00           O  
HETATM   31  O13 UNL     1      -0.450  -0.241  -0.139  1.00  0.00           O  
HETATM   32  C19 UNL     1       0.539   0.739  -0.349  1.00  0.00           C  
HETATM   33  C20 UNL     1       0.537   1.356  -1.728  1.00  0.00           C  
HETATM   34  O14 UNL     1      -0.464   2.323  -1.898  1.00  0.00           O  
HETATM   35  C21 UNL     1      -0.173   3.658  -2.173  1.00  0.00           C  
HETATM   36  O15 UNL     1       1.051   3.935  -2.265  1.00  0.00           O  
HETATM   37  C22 UNL     1      -1.165   4.703  -2.352  1.00  0.00           C  
HETATM   38  C23 UNL     1      -2.524   4.517  -2.246  1.00  0.00           C  
HETATM   39  C24 UNL     1      -3.452   5.541  -2.429  1.00  0.00           C  
HETATM   40  O16 UNL     1      -4.811   5.313  -2.314  1.00  0.00           O  
HETATM   41  C25 UNL     1      -3.000   6.806  -2.729  1.00  0.00           C  
HETATM   42  O17 UNL     1      -3.881   7.871  -2.922  1.00  0.00           O  
HETATM   43  C26 UNL     1      -1.642   7.022  -2.841  1.00  0.00           C  
HETATM   44  O18 UNL     1      -1.187   8.315  -3.148  1.00  0.00           O  
HETATM   45  C27 UNL     1      -0.757   5.984  -2.654  1.00  0.00           C  
HETATM   46  C28 UNL     1       1.900   0.047  -0.297  1.00  0.00           C  
HETATM   47  O19 UNL     1       2.298  -0.322   0.979  1.00  0.00           O  
HETATM   48  C29 UNL     1       3.393   0.161   1.659  1.00  0.00           C  
HETATM   49  O20 UNL     1       4.109   1.004   1.107  1.00  0.00           O  
HETATM   50  C30 UNL     1       3.651  -0.350   2.998  1.00  0.00           C  
HETATM   51  C31 UNL     1       4.751   0.134   3.684  1.00  0.00           C  
HETATM   52  C32 UNL     1       5.028  -0.329   4.957  1.00  0.00           C  
HETATM   53  O21 UNL     1       6.133   0.165   5.630  1.00  0.00           O  
HETATM   54  C33 UNL     1       4.203  -1.272   5.534  1.00  0.00           C  
HETATM   55  O22 UNL     1       4.496  -1.723   6.807  1.00  0.00           O  
HETATM   56  C34 UNL     1       3.104  -1.769   4.874  1.00  0.00           C  
HETATM   57  O23 UNL     1       2.320  -2.712   5.508  1.00  0.00           O  
HETATM   58  C35 UNL     1       2.848  -1.292   3.604  1.00  0.00           C  
HETATM   59  C36 UNL     1       4.458  -3.794  -1.154  1.00  0.00           C  
HETATM   60  C37 UNL     1       5.638  -3.125  -1.395  1.00  0.00           C  
HETATM   61  C38 UNL     1       6.867  -3.742  -1.433  1.00  0.00           C  
HETATM   62  O24 UNL     1       8.060  -3.087  -1.673  1.00  0.00           O  
HETATM   63  C39 UNL     1       6.887  -5.105  -1.214  1.00  0.00           C  
HETATM   64  O25 UNL     1       8.068  -5.834  -1.228  1.00  0.00           O  
HETATM   65  C40 UNL     1       5.730  -5.815  -0.968  1.00  0.00           C  
HETATM   66  O26 UNL     1       5.767  -7.178  -0.751  1.00  0.00           O  
HETATM   67  C41 UNL     1       4.503  -5.148  -0.939  1.00  0.00           C  
HETATM   68  H1  UNL     1       1.063  -1.804  -1.099  1.00  0.00           H  
HETATM   69  H2  UNL     1       0.632   0.718  -3.732  1.00  0.00           H  
HETATM   70  H3  UNL     1      -0.904  -0.911  -3.673  1.00  0.00           H  
HETATM   71  H4  UNL     1      -0.699  -1.448  -2.033  1.00  0.00           H  
HETATM   72  H5  UNL     1      -4.599  -1.340  -3.507  1.00  0.00           H  
HETATM   73  H6  UNL     1      -7.090  -3.708  -2.731  1.00  0.00           H  
HETATM   74  H7  UNL     1      -7.482  -3.827  -0.784  1.00  0.00           H  
HETATM   75  H8  UNL     1      -6.339  -2.356   1.833  1.00  0.00           H  
HETATM   76  H9  UNL     1      -1.245   0.967   3.148  1.00  0.00           H  
HETATM   77  H10 UNL     1      -3.707   2.791   4.940  1.00  0.00           H  
HETATM   78  H11 UNL     1      -6.412   2.201   3.127  1.00  0.00           H  
HETATM   79  H12 UNL     1      -6.502   0.498   0.464  1.00  0.00           H  
HETATM   80  H13 UNL     1       0.489   1.612   0.335  1.00  0.00           H  
HETATM   81  H14 UNL     1       1.559   1.847  -1.837  1.00  0.00           H  
HETATM   82  H15 UNL     1      -2.885   3.534  -2.008  1.00  0.00           H  
HETATM   83  H16 UNL     1      -5.437   6.090  -2.455  1.00  0.00           H  
HETATM   84  H17 UNL     1      -3.486   8.773  -3.140  1.00  0.00           H  
HETATM   85  H18 UNL     1      -0.192   8.442  -3.223  1.00  0.00           H  
HETATM   86  H19 UNL     1       0.295   6.201  -2.751  1.00  0.00           H  
HETATM   87  H20 UNL     1       2.638   0.809  -0.669  1.00  0.00           H  
HETATM   88  H21 UNL     1       5.396   0.870   3.235  1.00  0.00           H  
HETATM   89  H22 UNL     1       6.317  -0.187   6.559  1.00  0.00           H  
HETATM   90  H23 UNL     1       3.929  -2.411   7.278  1.00  0.00           H  
HETATM   91  H24 UNL     1       1.507  -3.070   5.003  1.00  0.00           H  
HETATM   92  H25 UNL     1       1.990  -1.653   3.039  1.00  0.00           H  
HETATM   93  H26 UNL     1       5.580  -2.060  -1.562  1.00  0.00           H  
HETATM   94  H27 UNL     1       8.143  -2.107  -1.842  1.00  0.00           H  
HETATM   95  H28 UNL     1       8.923  -5.327  -1.406  1.00  0.00           H  
HETATM   96  H29 UNL     1       4.969  -7.749  -0.569  1.00  0.00           H  
HETATM   97  H30 UNL     1       3.576  -5.674  -0.750  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   59
CONECT    3    4
CONECT    4    5   46   68
CONECT    5    6
CONECT    6    7   33   69
CONECT    7    8   70   71
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   19
CONECT   12   13   72
CONECT   13   14   15   15
CONECT   14   73
CONECT   15   16   17
CONECT   16   74
CONECT   17   18   19   19
CONECT   18   75
CONECT   19   20
CONECT   20   21   21   27
CONECT   21   22   29
CONECT   22   23   23   76
CONECT   23   24   25
CONECT   24   77
CONECT   25   26   27   27
CONECT   26   78
CONECT   27   28
CONECT   28   79
CONECT   29   30   30   31
CONECT   31   32
CONECT   32   33   46   80
CONECT   33   34   81
CONECT   34   35
CONECT   35   36   36   37
CONECT   37   38   38   45
CONECT   38   39   82
CONECT   39   40   41   41
CONECT   40   83
CONECT   41   42   43
CONECT   42   84
CONECT   43   44   45   45
CONECT   44   85
CONECT   45   86
CONECT   46   47   87
CONECT   47   48
CONECT   48   49   49   50
CONECT   50   51   51   58
CONECT   51   52   88
CONECT   52   53   54   54
CONECT   53   89
CONECT   54   55   56
CONECT   55   90
CONECT   56   57   58   58
CONECT   57   91
CONECT   58   92
CONECT   59   60   60   67
CONECT   60   61   93
CONECT   61   62   63   63
CONECT   62   94
CONECT   63   64   65
CONECT   64   95
CONECT   65   66   67   67
CONECT   66   96
CONECT   67   97
END

HMDB0029950
     RDKit          3D
Punicafolin
 97103  0  0  0  0  0  0  0  0999 V2000
    2.1285   -3.7129   -0.9076 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1873   -3.0475   -1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1638   -1.6784   -1.3514 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8675   -1.0564   -1.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6547   -0.5575   -2.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475    0.2452   -2.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7546   -0.5288   -2.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7171    0.4097   -2.1931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0978    0.3193   -2.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575    1.1683   -3.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0087   -0.5532   -1.5323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7425   -1.3827   -2.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7009   -2.2565   -1.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3858   -3.0493   -2.9264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9582   -2.3281   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9503   -3.2333   -0.2121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2800   -1.5485    0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6336   -1.7099    1.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2725   -0.6279   -0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7154    0.1164    0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4257    0.1615    1.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2085    0.9116    2.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2200    1.5753    3.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9642    2.3042    4.4726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4912    1.5352    2.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4766    2.2351    3.5016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7403    0.8224    1.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0569    0.8690    1.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1989   -0.4757    1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -1.4055    1.8677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4504   -0.2410   -0.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5389    0.7392   -0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5368    1.3559   -1.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4642    2.3232   -1.8981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1730    3.6582   -2.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0505    3.9351   -2.2648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1655    4.7030   -2.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5241    4.5172   -2.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4519    5.5414   -2.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8114    5.3130   -2.3138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9998    6.8058   -2.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8809    7.8708   -2.9224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6422    7.0217   -2.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874    8.3153   -3.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567    5.9842   -2.6537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9003    0.0465   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2976   -0.3223    0.9787 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3929    0.1611    1.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1087    1.0044    1.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6514   -0.3497    2.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7507    0.1335    3.6843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0279   -0.3295    4.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1328    0.1651    5.6299 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2034   -1.2722    5.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4961   -1.7230    6.8066 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1040   -1.7693    4.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196   -2.7115    5.5083 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8476   -1.2918    3.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4584   -3.7943   -1.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6376   -3.1246   -1.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8665   -3.7422   -1.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0595   -3.0875   -1.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8870   -5.1054   -1.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0676   -5.8340   -1.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7296   -5.8148   -0.9685 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7673   -7.1775   -0.7512 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5031   -5.1484   -0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0627   -1.8038   -1.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6321    0.7183   -3.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9036   -0.9108   -3.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6995   -1.4480   -2.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5990   -1.3398   -3.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0900   -3.7079   -2.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4821   -3.8269   -0.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3389   -2.3561    1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2447    0.9665    3.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7067    2.7906    4.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4122    2.2012    3.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5018    0.4976    0.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893    1.6121    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5592    1.8474   -1.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8851    3.5340   -2.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4374    6.0897   -2.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4862    8.7728   -3.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1920    8.4421   -3.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2951    6.2012   -2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6384    0.8088   -0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3964    0.8705    3.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3171   -0.1867    6.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9293   -2.4112    7.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069   -3.0697    5.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9901   -1.6526    3.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5803   -2.0600   -1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1427   -2.1065   -1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9233   -5.3268   -1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9692   -7.7487   -0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5755   -5.6739   -0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 21 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  0
 39 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  1  0
 43 45  2  0
 32 46  1  0
 46 47  1  0
 47 48  1  0
 48 49  2  0
 48 50  1  0
 50 51  2  0
 51 52  1  0
 52 53  1  0
 52 54  2  0
 54 55  1  0
 54 56  1  0
 56 57  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2,4-Tri-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-b-D-glucopyranose	HMDB
6,7,8,11,12,13-Hexahydroxy-3,16-dioxo-21,22-bis(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,6,8,10,12,14-hexaen-23-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₄₁H₃₀O₂₆

Average Molecular Weight

938.6613

Monoisotopic Molecular Weight

938.102531132

IUPAC Name

6,7,8,11,12,13-hexahydroxy-3,16-dioxo-22,23-bis(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate

Traditional Name

6,7,8,11,12,13-hexahydroxy-3,16-dioxo-22,23-bis(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

88847-11-4

SMILES

OC1=CC(=CC(O)=C1O)C(=O)OC1OC2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC(C2OC(=O)C2=CC(O)=C(O)C(O)=C2)C1OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C41H30O26/c42-15-1-10(2-16(43)26(15)50)36(57)64-33-23-9-62-39(60)13-7-21(48)29(53)31(55)24(13)25-14(8-22(49)30(54)32(25)56)40(61)65-34(33)35(66-37(58)11-3-17(44)27(51)18(45)4-11)41(63-23)67-38(59)12-5-19(46)28(52)20(47)6-12/h1-8,23,33-35,41-56H,9H2

InChI Key

DPBVYZVSXAZMAY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Pentacarboxylic acid or derivatives
Macrolide
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Carboxylic acid ester
Lactone
Polyol
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029950)
Cell membrane (HMDB: HMDB0029950)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029950)

Source

Endogenous

Endogenous (HMDB: HMDB0029950)

Plant

Plant (HMDB: HMDB0029950)

Exogenous

Food

Food (HMDB: HMDB0029950)

Fruit

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0029950)

Not Available

Topoisomerase-II inhibitor (HMDB: HMDB0029950)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	235 - 237 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.12 g/L	ALOGPS
logP	3.32	ALOGPS
logP	4.26	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.29	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	444.18 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	213.83 m³·mol⁻¹	ChemAxon
Polarizability	83.39 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	283.431	30932474
DeepCCS	[M-H]-	281.536	30932474
DeepCCS	[M-2H]-	315.502	30932474
DeepCCS	[M+Na]+	289.521	30932474
AllCCS	[M+H]+	274.0	32859911
AllCCS	[M+H-H2O]+	274.4	32859911
AllCCS	[M+NH4]+	273.6	32859911
AllCCS	[M+Na]+	273.5	32859911
AllCCS	[M-H]-	279.1	32859911
AllCCS	[M+Na-2H]-	282.7	32859911
AllCCS	[M+HCOO]-	286.6	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicafolin 10V, Positive-QTOF	splash10-0uy0-0704516905-5080ee8668e635d06d54	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicafolin 20V, Positive-QTOF	splash10-0uk9-0921001603-62fcd0a40a80d44731f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicafolin 40V, Positive-QTOF	splash10-0ul0-0931500100-e7988b38d5eccc4c32bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicafolin 10V, Negative-QTOF	splash10-00kr-0300000926-9d0cec2910cddb7b2ddb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicafolin 20V, Negative-QTOF	splash10-014i-0901022511-6ec3cdc428cbd79b5fe8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicafolin 40V, Negative-QTOF	splash10-014i-0900000000-1ee4d37707a6fa76ee52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicafolin 10V, Positive-QTOF	splash10-00ri-0100020419-2f5d14d9f65c7e598c53	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicafolin 20V, Positive-QTOF	splash10-0far-1900010484-badb2f12c5a33ccc17fd	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicafolin 40V, Positive-QTOF	splash10-0uxr-2900121241-beda1774d8eb11fc603d	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicafolin 10V, Negative-QTOF	splash10-00kr-0300000609-626aeac928729fec02d6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicafolin 20V, Negative-QTOF	splash10-0gbi-0901000225-09273f8bc5778fa89e36	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Punicafolin 40V, Negative-QTOF	splash10-016r-3900001171-16d7ed4b35f00fccb3ea	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001230

KNApSAcK ID

Not Available

Chemspider ID

417252

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Punicafolin

METLIN ID

Not Available

PubChem Compound

475273

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1812441

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
(). Takashi Tanaka, Gen-Ichiro Nonaka, and Itsuo Nishioka: Punicafolin, an ellagitannin from the leaves of Punica granatum. Phytochemistry 24, no. 9 (1985): 2075-2078. [Isolation]. .

Enzymes

Enzyme Details

1. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Reactions

Punicafolin → Tercatain	details

Showing metabocard for Punicafolin (HMDB0029950)

MOL for HMDB0029950 (Punicafolin)

3D MOL for HMDB0029950 (Punicafolin)

3D SDF for HMDB0029950 (Punicafolin)

3D-SDF for HMDB0029950 (Punicafolin)

PDB for HMDB0029950 (Punicafolin)

3D PDB for HMDB0029950 (Punicafolin)

SMILES for HMDB0029950 (Punicafolin)

INCHI for HMDB0029950 (Punicafolin)

Structure for HMDB0029950 (Punicafolin)

3D Structure for HMDB0029950 (Punicafolin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra

Enzymes

Reactions