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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 06:59:21 UTC

Update Date

2021-09-26 23:01:12 UTC

HMDB ID

HMDB0250017

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Picroside I

Description

Picroside I belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Based on a literature review a significant number of articles have been published on Picroside I. This compound has been identified in human blood as reported by (PMID: 31557052 ). Picroside i is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Picroside I is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

  Mrv1533004161504492D          

 35 39  0  0  0  0            999 V2000
    3.0815    1.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3547    1.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1467    0.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415   -0.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0118   -0.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0727   -1.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3103   -0.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5182   -0.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0776    0.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186    0.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107    1.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1070    2.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111    2.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074    3.3871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115    3.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078    4.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2881    5.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0918    6.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7003    6.3616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6876    6.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4914    7.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0872    8.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8793    7.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4752    8.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2789    9.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4868    9.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910    8.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    3.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2764    4.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8768    2.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    2.6950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810    2.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772    1.5537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    0.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  4  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  0  0  0  0
 12 35  1  0  0  0  0
  3 35  1  0  0  0  0
  8 35  1  0  0  0  0
M  END

HMDB0250017
     RDKit          3D
Picroside I
 63 67  0  0  0  0  0  0  0  0999 V2000
    3.1876    1.5504   -0.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4683    0.7221    0.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865    0.4617    1.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501    1.0434    0.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2337    0.8020    0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1972    1.4780    0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5520    1.3083    0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9690    0.4199    1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0518   -0.2650    1.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6766   -0.0717    1.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4493    0.1134    1.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730    0.3593    1.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -0.4672    2.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403   -0.2246    1.9993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260   -0.7281    0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9731   -0.4079    0.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3704    0.3798   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613    1.6202    0.2547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436    2.0516    0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0148    1.3543   -0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8164    0.1155   -0.8265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5192    0.1878   -2.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9167    1.4250   -2.5527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6162   -0.6013   -3.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5458   -0.5659   -3.7339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3255    0.1119   -2.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9376    1.4888   -2.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7957    2.2774   -3.6408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3910   -0.2455   -1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3886   -2.2202    0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -2.8547    1.8619 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0867   -2.5374    0.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240   -2.0541   -0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5768   -1.9087    2.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9355   -2.1182    2.4037 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1078   -0.2544    1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5562    1.7581   -0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8552    2.1827   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2838    1.8433   -0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0319    0.2658    1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3804   -0.9656    2.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9856   -0.6341    2.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8755    0.2198    0.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9154    1.4512    1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879   -0.1259    3.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0562   -0.3049   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4693    0.5789   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2481    2.9652    0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0447    1.7092    0.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2357   -0.7325   -0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4843   -0.3967   -2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8819    1.6062   -2.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6831   -1.6952   -2.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5272    2.0708   -2.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0207    1.4052   -3.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7864    3.2238   -3.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2774   -1.3684   -1.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7511   -2.6738   -0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463   -3.1695    1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2035   -3.6563    0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7569   -2.7786   -0.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660   -2.4759    3.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1059   -2.0485    3.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 15 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 10  5  1  0
 34 13  1  0
 29 17  1  0
 29 21  1  0
 26 24  1  0
  3 36  1  0
  4 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 15 46  1  0
 17 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
 30 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  0
M  END

  Mrv1533004161504492D          

 35 39  0  0  0  0            999 V2000
    3.0815    1.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3547    1.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1467    0.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415   -0.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0118   -0.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0727   -1.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3103   -0.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5182   -0.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0776    0.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186    0.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107    1.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1070    2.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111    2.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074    3.3871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115    3.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078    4.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2881    5.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0918    6.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7003    6.3616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6876    6.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4914    7.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0872    8.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8793    7.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4752    8.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2789    9.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4868    9.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910    8.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    3.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2764    4.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8768    2.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    2.6950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810    2.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772    1.5537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    0.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  4  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  0  0  0  0
 12 35  1  0  0  0  0
  3 35  1  0  0  0  0
  8 35  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250017

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC12OC1C(O)C1C=COC(OC3OC(COC(=O)C=CC4=CC=CC=C4)C(O)C(O)C3O)C21

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O11/c25-11-24-16-13(17(27)21(24)35-24)8-9-31-22(16)34-23-20(30)19(29)18(28)14(33-23)10-32-15(26)7-6-12-4-2-1-3-5-12/h1-9,13-14,16-23,25,27-30H,10-11H2

> <INCHI_KEY>
XZGPUOQGERGURE-UHFFFAOYSA-N

> <FORMULA>
C24H28O11

> <MOLECULAR_WEIGHT>
492.477

> <EXACT_MASS>
492.163161722

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.87721392821013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-phenylprop-2-enoate

> <ALOGPS_LOGP>
-0.06

> <JCHEM_LOGP>
-0.39791289166666716

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.09247924037918

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.193155090836859

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1218025089548433

> <JCHEM_POLAR_SURFACE_AREA>
167.67000000000002

> <JCHEM_REFRACTIVITY>
116.75920000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250017
     RDKit          3D
Picroside I
 63 67  0  0  0  0  0  0  0  0999 V2000
    3.1876    1.5504   -0.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4683    0.7221    0.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865    0.4617    1.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501    1.0434    0.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2337    0.8020    0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1972    1.4780    0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5520    1.3083    0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9690    0.4199    1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0518   -0.2650    1.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6766   -0.0717    1.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4493    0.1134    1.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730    0.3593    1.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -0.4672    2.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403   -0.2246    1.9993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260   -0.7281    0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9731   -0.4079    0.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3704    0.3798   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613    1.6202    0.2547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436    2.0516    0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0148    1.3543   -0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8164    0.1155   -0.8265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5192    0.1878   -2.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9167    1.4250   -2.5527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6162   -0.6013   -3.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5458   -0.5659   -3.7339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3255    0.1119   -2.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9376    1.4888   -2.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7957    2.2774   -3.6408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3910   -0.2455   -1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3886   -2.2202    0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -2.8547    1.8619 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0867   -2.5374    0.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240   -2.0541   -0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5768   -1.9087    2.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9355   -2.1182    2.4037 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1078   -0.2544    1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5562    1.7581   -0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8552    2.1827   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2838    1.8433   -0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0319    0.2658    1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3804   -0.9656    2.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9856   -0.6341    2.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8755    0.2198    0.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9154    1.4512    1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879   -0.1259    3.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0562   -0.3049   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4693    0.5789   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2481    2.9652    0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0447    1.7092    0.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2357   -0.7325   -0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4843   -0.3967   -2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8819    1.6062   -2.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6831   -1.6952   -2.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5272    2.0708   -2.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0207    1.4052   -3.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7864    3.2238   -3.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2774   -1.3684   -1.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7511   -2.6738   -0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463   -3.1695    1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2035   -3.6563    0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7569   -2.7786   -0.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660   -2.4759    3.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1059   -2.0485    3.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 15 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 10  5  1  0
 34 13  1  0
 29 17  1  0
 29 21  1  0
 26 24  1  0
  3 36  1  0
  4 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 15 46  1  0
 17 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
 30 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0       5.752   3.582   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.395   2.854   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.348   1.314   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.874   1.107   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.931  -0.111   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.755  -1.106   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.869  -2.642   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.446  -0.295   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.967  -0.726   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.145   0.339   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.221   1.835   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.700   2.266   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.066   3.762   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.954   4.827   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.320   6.323   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.208   7.388   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.575   8.883   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.538   9.949   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.171  11.444   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.307  11.875   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.284  12.510   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.917  14.005   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.029  15.071   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.508  14.640   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.620  15.705   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.254  17.201   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.775  17.631   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.663  16.566   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.270   6.957   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.383   8.022   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.637   5.461   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.115   5.031   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.524   4.396   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.891   2.900   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.812   1.201   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   35                                             
CONECT    4    3    5                                                       
CONECT    5    4    3    6                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   35                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   35                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   33                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   16   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   14   34                                                  
CONECT   34   33                                                            
CONECT   35   12    3    8                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

COMPND    HMDB0250017
HETATM    1  O1  UNL     1       3.188   1.550  -0.002  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.468   0.722   0.897  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.886   0.462   1.164  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.850   1.043   0.521  1.00  0.00           C  
HETATM    5  C4  UNL     1       7.234   0.802   0.768  1.00  0.00           C  
HETATM    6  C5  UNL     1       8.197   1.478   0.023  1.00  0.00           C  
HETATM    7  C6  UNL     1       9.552   1.308   0.197  1.00  0.00           C  
HETATM    8  C7  UNL     1       9.969   0.420   1.163  1.00  0.00           C  
HETATM    9  C8  UNL     1       9.052  -0.265   1.918  1.00  0.00           C  
HETATM   10  C9  UNL     1       7.677  -0.072   1.718  1.00  0.00           C  
HETATM   11  O2  UNL     1       2.449   0.113   1.573  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.073   0.359   1.324  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.196  -0.467   2.237  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.140  -0.225   1.999  1.00  0.00           O  
HETATM   15  C12 UNL     1      -1.626  -0.728   0.800  1.00  0.00           C  
HETATM   16  O4  UNL     1      -2.973  -0.408   0.769  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.370   0.380  -0.288  1.00  0.00           C  
HETATM   18  O5  UNL     1      -3.761   1.620   0.255  1.00  0.00           O  
HETATM   19  C14 UNL     1      -5.044   2.052   0.394  1.00  0.00           C  
HETATM   20  C15 UNL     1      -6.015   1.354  -0.109  1.00  0.00           C  
HETATM   21  C16 UNL     1      -5.816   0.116  -0.827  1.00  0.00           C  
HETATM   22  C17 UNL     1      -6.519   0.188  -2.198  1.00  0.00           C  
HETATM   23  O6  UNL     1      -6.917   1.425  -2.553  1.00  0.00           O  
HETATM   24  C18 UNL     1      -5.616  -0.601  -3.001  1.00  0.00           C  
HETATM   25  O7  UNL     1      -4.546  -0.566  -3.734  1.00  0.00           O  
HETATM   26  C19 UNL     1      -4.325   0.112  -2.608  1.00  0.00           C  
HETATM   27  C20 UNL     1      -3.938   1.489  -2.910  1.00  0.00           C  
HETATM   28  O8  UNL     1      -4.796   2.277  -3.641  1.00  0.00           O  
HETATM   29  C21 UNL     1      -4.391  -0.246  -1.175  1.00  0.00           C  
HETATM   30  C22 UNL     1      -1.389  -2.220   0.810  1.00  0.00           C  
HETATM   31  O9  UNL     1      -2.032  -2.855   1.862  1.00  0.00           O  
HETATM   32  C23 UNL     1       0.087  -2.537   0.928  1.00  0.00           C  
HETATM   33  O10 UNL     1       0.724  -2.054  -0.204  1.00  0.00           O  
HETATM   34  C24 UNL     1       0.577  -1.909   2.211  1.00  0.00           C  
HETATM   35  O11 UNL     1       1.935  -2.118   2.404  1.00  0.00           O  
HETATM   36  H1  UNL     1       5.108  -0.254   1.940  1.00  0.00           H  
HETATM   37  H2  UNL     1       5.556   1.758  -0.254  1.00  0.00           H  
HETATM   38  H3  UNL     1       7.855   2.183  -0.744  1.00  0.00           H  
HETATM   39  H4  UNL     1      10.284   1.843  -0.393  1.00  0.00           H  
HETATM   40  H5  UNL     1      11.032   0.266   1.323  1.00  0.00           H  
HETATM   41  H6  UNL     1       9.380  -0.966   2.681  1.00  0.00           H  
HETATM   42  H7  UNL     1       6.986  -0.634   2.337  1.00  0.00           H  
HETATM   43  H8  UNL     1       0.876   0.220   0.265  1.00  0.00           H  
HETATM   44  H9  UNL     1       0.915   1.451   1.570  1.00  0.00           H  
HETATM   45  H10 UNL     1       0.388  -0.126   3.305  1.00  0.00           H  
HETATM   46  H11 UNL     1      -1.056  -0.305  -0.031  1.00  0.00           H  
HETATM   47  H12 UNL     1      -2.469   0.579  -0.905  1.00  0.00           H  
HETATM   48  H13 UNL     1      -5.248   2.965   0.918  1.00  0.00           H  
HETATM   49  H14 UNL     1      -7.045   1.709   0.008  1.00  0.00           H  
HETATM   50  H15 UNL     1      -6.236  -0.732  -0.215  1.00  0.00           H  
HETATM   51  H16 UNL     1      -7.484  -0.397  -2.021  1.00  0.00           H  
HETATM   52  H17 UNL     1      -7.882   1.606  -2.535  1.00  0.00           H  
HETATM   53  H18 UNL     1      -5.683  -1.695  -2.601  1.00  0.00           H  
HETATM   54  H19 UNL     1      -3.527   2.071  -2.054  1.00  0.00           H  
HETATM   55  H20 UNL     1      -3.021   1.405  -3.584  1.00  0.00           H  
HETATM   56  H21 UNL     1      -4.786   3.224  -3.413  1.00  0.00           H  
HETATM   57  H22 UNL     1      -4.277  -1.368  -1.111  1.00  0.00           H  
HETATM   58  H23 UNL     1      -1.751  -2.674  -0.126  1.00  0.00           H  
HETATM   59  H24 UNL     1      -2.946  -3.169   1.631  1.00  0.00           H  
HETATM   60  H25 UNL     1       0.204  -3.656   0.967  1.00  0.00           H  
HETATM   61  H26 UNL     1       0.757  -2.779  -0.877  1.00  0.00           H  
HETATM   62  H27 UNL     1       0.066  -2.476   3.037  1.00  0.00           H  
HETATM   63  H28 UNL     1       2.106  -2.049   3.384  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4   36
CONECT    4    5   37
CONECT    5    6    6   10
CONECT    6    7   38
CONECT    7    8    8   39
CONECT    8    9   40
CONECT    9   10   10   41
CONECT   10   42
CONECT   11   12
CONECT   12   13   43   44
CONECT   13   14   34   45
CONECT   14   15
CONECT   15   16   30   46
CONECT   16   17
CONECT   17   18   29   47
CONECT   18   19
CONECT   19   20   20   48
CONECT   20   21   49
CONECT   21   22   29   50
CONECT   22   23   24   51
CONECT   23   52
CONECT   24   25   26   53
CONECT   25   26
CONECT   26   27   29
CONECT   27   28   54   55
CONECT   28   56
CONECT   29   57
CONECT   30   31   32   58
CONECT   31   59
CONECT   32   33   34   60
CONECT   33   61
CONECT   34   35   62
CONECT   35   63
END

HMDB0250017
     RDKit          3D
Picroside I
 63 67  0  0  0  0  0  0  0  0999 V2000
    3.1876    1.5504   -0.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4683    0.7221    0.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865    0.4617    1.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501    1.0434    0.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2337    0.8020    0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1972    1.4780    0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5520    1.3083    0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9690    0.4199    1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0518   -0.2650    1.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6766   -0.0717    1.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4493    0.1134    1.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730    0.3593    1.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -0.4672    2.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403   -0.2246    1.9993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260   -0.7281    0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9731   -0.4079    0.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3704    0.3798   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613    1.6202    0.2547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436    2.0516    0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0148    1.3543   -0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8164    0.1155   -0.8265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5192    0.1878   -2.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9167    1.4250   -2.5527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6162   -0.6013   -3.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5458   -0.5659   -3.7339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3255    0.1119   -2.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9376    1.4888   -2.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7957    2.2774   -3.6408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3910   -0.2455   -1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3886   -2.2202    0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -2.8547    1.8619 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0867   -2.5374    0.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240   -2.0541   -0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5768   -1.9087    2.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9355   -2.1182    2.4037 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1078   -0.2544    1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5562    1.7581   -0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8552    2.1827   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2838    1.8433   -0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0319    0.2658    1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3804   -0.9656    2.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9856   -0.6341    2.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8755    0.2198    0.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9154    1.4512    1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879   -0.1259    3.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0562   -0.3049   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4693    0.5789   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2481    2.9652    0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0447    1.7092    0.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2357   -0.7325   -0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4843   -0.3967   -2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8819    1.6062   -2.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6831   -1.6952   -2.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5272    2.0708   -2.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0207    1.4052   -3.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7864    3.2238   -3.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2774   -1.3684   -1.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7511   -2.6738   -0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463   -3.1695    1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2035   -3.6563    0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7569   -2.7786   -0.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660   -2.4759    3.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1059   -2.0485    3.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 15 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 10  5  1  0
 34 13  1  0
 29 17  1  0
 29 21  1  0
 26 24  1  0
  3 36  1  0
  4 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 15 46  1  0
 17 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
 30 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3,4,5-Trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0,]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-phenylprop-2-enoic acid	HMDB
(3,4,5-Trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-phenylprop-2-enoic acid	HMDB

Chemical Formula

C₂₄H₂₈O₁₁

Average Molecular Weight

492.477

Monoisotopic Molecular Weight

492.163161722

IUPAC Name

(3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-phenylprop-2-enoate

Traditional Name

(3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

OCC12OC1C(O)C1C=COC(OC3OC(COC(=O)C=CC4=CC=CC=C4)C(O)C(O)C3O)C21

InChI Identifier

InChI=1S/C24H28O11/c25-11-24-16-13(17(27)21(24)35-24)8-9-31-22(16)34-23-20(30)19(29)18(28)14(33-23)10-32-15(26)7-6-12-4-2-1-3-5-12/h1-9,13-14,16-23,25,27-30H,10-11H2

InChI Key

XZGPUOQGERGURE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Styrene
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Monosaccharide
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.06	ALOGPS
logP	-0.4	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	167.67 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	116.76 m³·mol⁻¹	ChemAxon
Polarizability	48.88 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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-2H]-	243.067	30932474
DeepCCS	[M+Na]+	218.301	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Picroside I	OCC12OC1C(O)C1C=COC(OC3OC(COC(=O)C=CC4=CC=CC=C4)C(O)C(O)C3O)C21	4855.9	Standard polar	33892256
Picroside I	OCC12OC1C(O)C1C=COC(OC3OC(COC(=O)C=CC4=CC=CC=C4)C(O)C(O)C3O)C21	3767.8	Standard non polar	33892256
Picroside I	OCC12OC1C(O)C1C=COC(OC3OC(COC(=O)C=CC4=CC=CC=C4)C(O)C(O)C3O)C21	4254.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Picroside I,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OCC12OC1C(O)C1C=COC(OC3OC(COC(=O)C=CC4=CC=CC=C4)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)C12	4432.9	Semi standard non polar	33892256
Picroside I,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OCC12OC1C(O)C1C=COC(OC3OC(COC(=O)C=CC4=CC=CC=C4)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)C12	4546.9	Standard non polar	33892256
Picroside I,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OCC12OC1C(O)C1C=COC(OC3OC(COC(=O)C=CC4=CC=CC=C4)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)C12	5227.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (Non-derivatized) - 70eV, Positive	splash10-02h9-3323900000-2b461ae20fb3242ec204	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picroside I GC-MS (TMS_3_8) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picroside I 10V, Positive-QTOF	splash10-000x-0900700000-ebbe2f9f21be79bc2ebe	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picroside I 20V, Positive-QTOF	splash10-001i-0901200000-bc5c96d9704702c9434d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picroside I 40V, Positive-QTOF	splash10-0udi-0900200000-0d949c4d88bcd5ae7db0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picroside I 10V, Negative-QTOF	splash10-0006-0402900000-ab7f508018895615e70e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picroside I 20V, Negative-QTOF	splash10-0006-0209700000-f492264801d89d54701a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picroside I 40V, Negative-QTOF	splash10-0fb9-9500100000-959246a30876ce5b505c	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74029789

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Picroside I (HMDB0250017)

MOL for HMDB0250017 (Picroside I)

3D MOL for HMDB0250017 (Picroside I)

3D SDF for HMDB0250017 (Picroside I)

3D-SDF for HMDB0250017 (Picroside I)

PDB for HMDB0250017 (Picroside I)

3D PDB for HMDB0250017 (Picroside I)

SMILES for HMDB0250017 (Picroside I)

INCHI for HMDB0250017 (Picroside I)

Structure for HMDB0250017 (Picroside I)

3D Structure for HMDB0250017 (Picroside I)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra