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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:14:15 UTC

Update Date

2022-03-07 02:55:34 UTC

HMDB ID

HMDB0037967

Secondary Accession Numbers

HMDB37967

Metabolite Identification

Common Name

3,3'-Digalloylprocyanidin B2

Description

3,3'-Digalloylprocyanidin B2 belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. 3,3'-Digalloylprocyanidin B2 has been detected, but not quantified in, several different foods, such as green tea, herbal tea, green vegetables, red tea, and common grapes (Vitis vinifera). This could make 3,3'-digalloylprocyanidin B2 a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,3'-Digalloylprocyanidin B2.

Structure

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


  Mrv0541 02241217162D          

 64 71  0  0  0  0            999 V2000
   -3.2031   -1.1593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4881   -1.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4881   -2.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7745   -2.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7745   -3.6344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6387    2.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9251    1.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9251    0.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2031    0.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4881    0.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7745    0.4631    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7745   -1.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0595   -1.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0595   -2.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3444   -2.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692   -2.3968    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0842   -2.8094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2031    2.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4881    1.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7745    2.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0595    1.7007    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0595    0.8757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3526    0.4631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2031   -0.3618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692    4.1757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692    3.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3526    2.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3526    2.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692    1.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0842    2.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0842    2.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910    3.3507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3444   -1.1593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692   -1.5718    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0842   -1.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992   -1.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5128   -1.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5128   -0.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2278    0.0782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0842   -0.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992    0.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992    0.9032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7827   -3.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7827   -4.1981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4977   -2.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4977   -2.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2113   -1.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9237   -2.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9237   -2.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2113   -3.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6387   -1.7231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6387   -3.3731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2113   -0.8981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476    1.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476    0.3944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5626    1.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5626    2.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2763    2.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886    2.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886    1.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2763    1.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037    2.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037    1.2194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2763    3.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 14  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 24  1  0  0  0  0
 10 11  1  0  0  0  0
 10 19  1  0  0  0  0
 11 22  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 33  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 34  1  0  0  0  0
 17 43  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 28  1  6  0  0  0
 22 23  1  6  0  0  0
 23 54  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 31  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  2  0  0  0  0
 35 40  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 41  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 50  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 53  1  0  0  0  0
 48 49  1  0  0  0  0
 48 51  1  0  0  0  0
 49 50  2  0  0  0  0
 49 52  1  0  0  0  0
 54 55  2  0  0  0  0
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 56 57  2  0  0  0  0
 56 61  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 58 64  1  0  0  0  0
 59 60  1  0  0  0  0
 59 62  1  0  0  0  0
 60 61  2  0  0  0  0
 60 63  1  0  0  0  0
M  END

HMDB0037967
     RDKit          3D
3,3'-Digalloylprocyanidin B2
 98105  0  0  0  0  0  0  0  0999 V2000
    6.0536   -0.7588   -1.9764 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6194   -0.3459   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3822    0.2262   -0.8043 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5093    0.3901   -1.9373 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2061    1.8211   -2.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8251    2.1573   -2.3877 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5378    3.3485   -3.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5537    4.1874   -3.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2214    3.5996   -3.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8168    2.7856   -3.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1283    3.0811   -3.3713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5222    1.5987   -2.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5991    0.7160   -1.9830 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2200   -0.2024   -0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8266   -1.4826   -1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7237   -2.0110   -2.4113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5008   -2.3234   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5721   -1.8801    1.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -2.6980    2.3216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9834   -0.5616    1.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3004    0.2581    0.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7232    1.5807    0.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704    2.3739   -0.3014 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4843    3.1614    0.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4403    3.6822    1.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4789    4.4556    2.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6012    4.7637    1.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6249    5.5522    1.7738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6515    4.2579   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7862    4.5522   -0.7828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6208    3.4759   -0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332    1.4327   -1.3682 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5174    0.3694   -0.7337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7746   -0.0553   -0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5467    0.5764   -1.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3061   -1.1977   -0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5980   -1.5980   -0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1074   -2.7206    0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4936   -2.9980    0.3919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2422   -3.5271    1.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6849   -4.6978    1.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8872   -3.2055    1.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540   -4.0810    1.8629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4171   -2.0868    0.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7983    1.3076   -2.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1755    0.1685   -1.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269   -0.5562   -1.7306 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6907   -1.5606   -0.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9668   -2.8548   -0.9935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3398   -3.8034   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4416   -3.4207    1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8156   -4.3326    2.2019 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1708   -2.0944    1.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -1.7529    2.9426 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -1.2019    0.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4352   -0.4757    0.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6163   -1.1029    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3607   -1.2138    1.5930 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5881   -1.8637    1.6274 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8645   -0.6725    2.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5470   -0.7438    3.9757 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -0.0107    2.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1439    0.5288    3.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9272    0.0753    1.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844    0.0340   -2.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9400    2.2522   -2.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4116    2.3171   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135    4.0804   -3.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    4.5175   -3.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3367    3.9457   -3.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    0.1647   -2.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -2.9629   -2.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897   -3.3348   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0460   -3.2363    2.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290   -0.2450    2.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6250    3.1122   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938    3.4680    2.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4391    4.8666    3.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4628    5.9135    2.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8530    4.1767   -1.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7739    3.1417   -1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4807    1.8303   -2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3223   -0.9517   -0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0593   -2.3583   -0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6654   -4.8882    1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4252   -4.8972    2.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3832   -1.8107    0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406   -1.0715   -2.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8805   -3.1855   -2.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372   -4.8043   -0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241217162D          

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M  END
> <DATABASE_ID>
HMDB0037967

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(O)=C2[C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1)C1=C2O[C@@H]([C@@H](CC2=C(O)C=C1O)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C44H34O20/c45-19-11-26(51)34-32(12-19)61-40(16-2-4-22(47)25(50)6-16)42(64-44(60)18-9-30(55)38(58)31(56)10-18)36(34)35-27(52)14-23(48)20-13-33(62-43(59)17-7-28(53)37(57)29(54)8-17)39(63-41(20)35)15-1-3-21(46)24(49)5-15/h1-12,14,33,36,39-40,42,45-58H,13H2/t33-,36-,39-,40-,42-/m1/s1

> <INCHI_KEY>
KTLUHRSHFRODPS-RIQPQZJCSA-N

> <FORMULA>
C44H34O20

> <MOLECULAR_WEIGHT>
882.7288

> <EXACT_MASS>
882.164343528

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
83.51169670903147

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
6.284952780999999

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.321955795340456

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.7725819856569

> <JCHEM_PKA_STRONGEST_BASIC>
-5.485687933076162

> <JCHEM_POLAR_SURFACE_AREA>
354.28000000000003

> <JCHEM_REFRACTIVITY>
218.03740000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037967
     RDKit          3D
3,3'-Digalloylprocyanidin B2
 98105  0  0  0  0  0  0  0  0999 V2000
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    3.2061    1.8211   -2.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8251    2.1573   -2.3877 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8156   -4.3326    2.2019 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1708   -2.0944    1.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -1.7529    2.9426 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4352   -0.4757    0.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3607   -1.2138    1.5930 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5881   -1.8637    1.6274 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5470   -0.7438    3.9757 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -0.0107    2.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1439    0.5288    3.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9272    0.0753    1.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844    0.0340   -2.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9400    2.2522   -2.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5135    4.0804   -3.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1897   -3.3348   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0460   -3.2363    2.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6250    3.1122   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938    3.4680    2.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4391    4.8666    3.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4628    5.9135    2.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8530    4.1767   -1.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7739    3.1417   -1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4807    1.8303   -2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3223   -0.9517   -0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0593   -2.3583   -0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6654   -4.8882    1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4252   -4.8972    2.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3832   -1.8107    0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406   -1.0715   -2.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8805   -3.1855   -2.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372   -4.8043   -0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0392   -5.2868    2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5303   -2.4438    3.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5801   -0.1636    0.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0769   -1.5633   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9395   -2.2752    0.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1053   -0.3173    4.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403    1.0129    3.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9843    0.5717    1.5014 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
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M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -5.979  -2.164   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.644  -2.934   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.644  -4.474   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.312  -5.244   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.312  -6.784   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -8.659   3.945   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -7.327   3.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.327   1.635   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.979   0.864   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.644   1.635   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.312   0.864   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.312  -2.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.978  -2.934   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.978  -4.474   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.643  -5.244   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.689  -4.474   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.024  -5.244   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.979   3.945   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.644   3.175   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.312   3.945   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.978   3.175   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.978   1.635   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.658   0.864   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.979  -0.675   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.689   7.795   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.689   6.255   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.658   5.485   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.658   3.945   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.689   3.175   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.024   3.945   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.024   5.485   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.343   6.255   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.643  -2.164   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.689  -2.934   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.024  -2.164   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.359  -2.934   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.691  -2.164   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.691  -0.624   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.025   0.146   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.024  -0.624   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.359   0.146   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       3.359   1.686   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       3.328  -6.296   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       3.328  -7.836   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       4.662  -5.526   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       4.662  -3.986   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.994  -3.216   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       7.324  -3.986   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.324  -5.526   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.994  -6.296   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       8.659  -3.216   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       8.659  -6.296   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       5.994  -1.676   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       1.582   2.276   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       1.582   0.736   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       2.917   3.046   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       2.917   4.586   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       4.249   5.356   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       5.579   4.586   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       5.579   3.046   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       4.249   2.276   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       6.914   5.356   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0       6.914   2.276   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       4.249   6.896   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   24                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   22   12                                                  
CONECT   12    2   11   13                                                  
CONECT   13   12   14   33                                                  
CONECT   14    4   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16   43                                                       
CONECT   18    7   19                                                       
CONECT   19   10   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   11   21   23                                                  
CONECT   23   22   54                                                       
CONECT   24    9                                                            
CONECT   25   26                                                            
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   21   27   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   26   30   32                                                  
CONECT   32   31                                                            
CONECT   33   13   34                                                       
CONECT   34   16   33   35                                                  
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38                                                            
CONECT   40   35   41                                                       
CONECT   41   38   40   42                                                  
CONECT   42   41                                                            
CONECT   43   17   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   50                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   53                                                  
CONECT   48   47   49   51                                                  
CONECT   49   48   50   52                                                  
CONECT   50   45   49                                                       
CONECT   51   48                                                            
CONECT   52   49                                                            
CONECT   53   47                                                            
CONECT   54   23   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57   61                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59   64                                                  
CONECT   59   58   60   62                                                  
CONECT   60   59   61   63                                                  
CONECT   61   56   60                                                       
CONECT   62   59                                                            
CONECT   63   60                                                            
CONECT   64   58                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  142    0
END

COMPND    HMDB0037967
HETATM    1  O1  UNL     1       6.054  -0.759  -1.976  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.619  -0.346  -0.875  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.382   0.226  -0.804  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.509   0.390  -1.937  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.206   1.821  -2.047  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.825   2.157  -2.388  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.538   3.349  -3.078  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.554   4.187  -3.415  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.221   3.600  -3.373  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.817   2.786  -3.048  1.00  0.00           C  
HETATM   11  O4  UNL     1      -2.128   3.081  -3.371  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.522   1.599  -2.356  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.599   0.716  -1.983  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.220  -0.202  -0.886  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.827  -1.483  -1.137  1.00  0.00           C  
HETATM   16  O5  UNL     1      -0.724  -2.011  -2.411  1.00  0.00           O  
HETATM   17  C12 UNL     1      -0.501  -2.323  -0.051  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.572  -1.880   1.254  1.00  0.00           C  
HETATM   19  O6  UNL     1      -0.256  -2.698   2.322  1.00  0.00           O  
HETATM   20  C14 UNL     1      -0.983  -0.562   1.459  1.00  0.00           C  
HETATM   21  C15 UNL     1      -1.300   0.258   0.410  1.00  0.00           C  
HETATM   22  O7  UNL     1      -1.723   1.581   0.685  1.00  0.00           O  
HETATM   23  C16 UNL     1      -2.370   2.374  -0.301  1.00  0.00           C  
HETATM   24  C17 UNL     1      -3.484   3.161   0.248  1.00  0.00           C  
HETATM   25  C18 UNL     1      -3.440   3.682   1.539  1.00  0.00           C  
HETATM   26  C19 UNL     1      -4.479   4.456   2.005  1.00  0.00           C  
HETATM   27  C20 UNL     1      -5.601   4.764   1.259  1.00  0.00           C  
HETATM   28  O8  UNL     1      -6.625   5.552   1.774  1.00  0.00           O  
HETATM   29  C21 UNL     1      -5.652   4.258  -0.001  1.00  0.00           C  
HETATM   30  O9  UNL     1      -6.786   4.552  -0.783  1.00  0.00           O  
HETATM   31  C22 UNL     1      -4.621   3.476  -0.497  1.00  0.00           C  
HETATM   32  C23 UNL     1      -2.833   1.433  -1.368  1.00  0.00           C  
HETATM   33  O10 UNL     1      -3.517   0.369  -0.734  1.00  0.00           O  
HETATM   34  C24 UNL     1      -4.775  -0.055  -0.863  1.00  0.00           C  
HETATM   35  O11 UNL     1      -5.547   0.576  -1.647  1.00  0.00           O  
HETATM   36  C25 UNL     1      -5.306  -1.198  -0.160  1.00  0.00           C  
HETATM   37  C26 UNL     1      -6.598  -1.598  -0.143  1.00  0.00           C  
HETATM   38  C27 UNL     1      -7.107  -2.721   0.467  1.00  0.00           C  
HETATM   39  O12 UNL     1      -8.494  -2.998   0.392  1.00  0.00           O  
HETATM   40  C28 UNL     1      -6.242  -3.527   1.126  1.00  0.00           C  
HETATM   41  O13 UNL     1      -6.685  -4.698   1.776  1.00  0.00           O  
HETATM   42  C29 UNL     1      -4.887  -3.205   1.169  1.00  0.00           C  
HETATM   43  O14 UNL     1      -4.054  -4.081   1.863  1.00  0.00           O  
HETATM   44  C30 UNL     1      -4.417  -2.087   0.555  1.00  0.00           C  
HETATM   45  C31 UNL     1       0.798   1.308  -2.040  1.00  0.00           C  
HETATM   46  O15 UNL     1       1.175   0.168  -1.365  1.00  0.00           O  
HETATM   47  C32 UNL     1       2.327  -0.556  -1.731  1.00  0.00           C  
HETATM   48  C33 UNL     1       2.691  -1.561  -0.692  1.00  0.00           C  
HETATM   49  C34 UNL     1       2.967  -2.855  -0.994  1.00  0.00           C  
HETATM   50  C35 UNL     1       3.340  -3.803  -0.064  1.00  0.00           C  
HETATM   51  C36 UNL     1       3.442  -3.421   1.242  1.00  0.00           C  
HETATM   52  O16 UNL     1       3.816  -4.333   2.202  1.00  0.00           O  
HETATM   53  C37 UNL     1       3.171  -2.094   1.624  1.00  0.00           C  
HETATM   54  O17 UNL     1       3.279  -1.753   2.943  1.00  0.00           O  
HETATM   55  C38 UNL     1       2.802  -1.202   0.642  1.00  0.00           C  
HETATM   56  C39 UNL     1       6.435  -0.476   0.376  1.00  0.00           C  
HETATM   57  C40 UNL     1       7.616  -1.103   0.387  1.00  0.00           C  
HETATM   58  C41 UNL     1       8.361  -1.214   1.593  1.00  0.00           C  
HETATM   59  O18 UNL     1       9.588  -1.864   1.627  1.00  0.00           O  
HETATM   60  C42 UNL     1       7.865  -0.673   2.749  1.00  0.00           C  
HETATM   61  O19 UNL     1       8.547  -0.744   3.976  1.00  0.00           O  
HETATM   62  C43 UNL     1       6.618  -0.011   2.730  1.00  0.00           C  
HETATM   63  O20 UNL     1       6.144   0.529   3.940  1.00  0.00           O  
HETATM   64  C44 UNL     1       5.927   0.075   1.543  1.00  0.00           C  
HETATM   65  H1  UNL     1       4.084   0.034  -2.831  1.00  0.00           H  
HETATM   66  H2  UNL     1       3.940   2.252  -2.799  1.00  0.00           H  
HETATM   67  H3  UNL     1       3.412   2.317  -1.046  1.00  0.00           H  
HETATM   68  H4  UNL     1       3.513   4.080  -3.214  1.00  0.00           H  
HETATM   69  H5  UNL     1       0.010   4.517  -3.904  1.00  0.00           H  
HETATM   70  H6  UNL     1      -2.337   3.946  -3.899  1.00  0.00           H  
HETATM   71  H7  UNL     1      -2.026   0.165  -2.860  1.00  0.00           H  
HETATM   72  H8  UNL     1      -0.426  -2.963  -2.522  1.00  0.00           H  
HETATM   73  H9  UNL     1      -0.190  -3.335  -0.251  1.00  0.00           H  
HETATM   74  H10 UNL     1      -1.046  -3.236   2.720  1.00  0.00           H  
HETATM   75  H11 UNL     1      -1.029  -0.245   2.499  1.00  0.00           H  
HETATM   76  H12 UNL     1      -1.625   3.112  -0.668  1.00  0.00           H  
HETATM   77  H13 UNL     1      -2.594   3.468   2.159  1.00  0.00           H  
HETATM   78  H14 UNL     1      -4.439   4.867   3.025  1.00  0.00           H  
HETATM   79  H15 UNL     1      -6.463   5.913   2.732  1.00  0.00           H  
HETATM   80  H16 UNL     1      -6.853   4.177  -1.731  1.00  0.00           H  
HETATM   81  H17 UNL     1      -4.774   3.142  -1.515  1.00  0.00           H  
HETATM   82  H18 UNL     1      -3.481   1.830  -2.113  1.00  0.00           H  
HETATM   83  H19 UNL     1      -7.322  -0.952  -0.682  1.00  0.00           H  
HETATM   84  H20 UNL     1      -9.059  -2.358  -0.108  1.00  0.00           H  
HETATM   85  H21 UNL     1      -7.665  -4.888   1.731  1.00  0.00           H  
HETATM   86  H22 UNL     1      -4.425  -4.897   2.307  1.00  0.00           H  
HETATM   87  H23 UNL     1      -3.383  -1.811   0.561  1.00  0.00           H  
HETATM   88  H24 UNL     1       2.141  -1.072  -2.669  1.00  0.00           H  
HETATM   89  H25 UNL     1       2.881  -3.185  -2.041  1.00  0.00           H  
HETATM   90  H26 UNL     1       3.537  -4.804  -0.403  1.00  0.00           H  
HETATM   91  H27 UNL     1       4.039  -5.287   2.018  1.00  0.00           H  
HETATM   92  H28 UNL     1       3.530  -2.444   3.633  1.00  0.00           H  
HETATM   93  H29 UNL     1       2.580  -0.164   0.881  1.00  0.00           H  
HETATM   94  H30 UNL     1       8.077  -1.563  -0.496  1.00  0.00           H  
HETATM   95  H31 UNL     1       9.939  -2.275   0.786  1.00  0.00           H  
HETATM   96  H32 UNL     1       8.105  -0.317   4.807  1.00  0.00           H  
HETATM   97  H33 UNL     1       5.240   1.013   3.960  1.00  0.00           H  
HETATM   98  H34 UNL     1       4.984   0.572   1.501  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   56
CONECT    3    4
CONECT    4    5   47   65
CONECT    5    6   66   67
CONECT    6    7    7   45
CONECT    7    8    9
CONECT    8   68
CONECT    9   10   10   69
CONECT   10   11   12
CONECT   11   70
CONECT   12   13   45   45
CONECT   13   14   32   71
CONECT   14   15   15   21
CONECT   15   16   17
CONECT   16   72
CONECT   17   18   18   73
CONECT   18   19   20
CONECT   19   74
CONECT   20   21   21   75
CONECT   21   22
CONECT   22   23
CONECT   23   24   32   76
CONECT   24   25   25   31
CONECT   25   26   77
CONECT   26   27   27   78
CONECT   27   28   29
CONECT   28   79
CONECT   29   30   31   31
CONECT   30   80
CONECT   31   81
CONECT   32   33   82
CONECT   33   34
CONECT   34   35   35   36
CONECT   36   37   37   44
CONECT   37   38   83
CONECT   38   39   40   40
CONECT   39   84
CONECT   40   41   42
CONECT   41   85
CONECT   42   43   44   44
CONECT   43   86
CONECT   44   87
CONECT   45   46
CONECT   46   47
CONECT   47   48   88
CONECT   48   49   49   55
CONECT   49   50   89
CONECT   50   51   51   90
CONECT   51   52   53
CONECT   52   91
CONECT   53   54   55   55
CONECT   54   92
CONECT   55   93
CONECT   56   57   57   64
CONECT   57   58   94
CONECT   58   59   60   60
CONECT   59   95
CONECT   60   61   62
CONECT   61   96
CONECT   62   63   64   64
CONECT   63   97
CONECT   64   98
END

HMDB0037967
     RDKit          3D
3,3'-Digalloylprocyanidin B2
 98105  0  0  0  0  0  0  0  0999 V2000
    6.0536   -0.7588   -1.9764 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6194   -0.3459   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3822    0.2262   -0.8043 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5093    0.3901   -1.9373 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2061    1.8211   -2.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8251    2.1573   -2.3877 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5378    3.3485   -3.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5537    4.1874   -3.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2214    3.5996   -3.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8168    2.7856   -3.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1283    3.0811   -3.3713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5222    1.5987   -2.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5991    0.7160   -1.9830 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2200   -0.2024   -0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8266   -1.4826   -1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7237   -2.0110   -2.4113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5008   -2.3234   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5721   -1.8801    1.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -2.6980    2.3216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9834   -0.5616    1.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3004    0.2581    0.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7232    1.5807    0.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704    2.3739   -0.3014 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4843    3.1614    0.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4403    3.6822    1.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4789    4.4556    2.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6012    4.7637    1.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6249    5.5522    1.7738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6515    4.2579   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7862    4.5522   -0.7828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6208    3.4759   -0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332    1.4327   -1.3682 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5174    0.3694   -0.7337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7746   -0.0553   -0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5467    0.5764   -1.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3061   -1.1977   -0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5980   -1.5980   -0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1074   -2.7206    0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4936   -2.9980    0.3919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2422   -3.5271    1.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6849   -4.6978    1.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8872   -3.2055    1.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540   -4.0810    1.8629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4171   -2.0868    0.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7983    1.3076   -2.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1755    0.1685   -1.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269   -0.5562   -1.7306 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6907   -1.5606   -0.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9668   -2.8548   -0.9935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3398   -3.8034   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4416   -3.4207    1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8156   -4.3326    2.2019 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1708   -2.0944    1.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -1.7529    2.9426 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -1.2019    0.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4352   -0.4757    0.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6163   -1.1029    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3607   -1.2138    1.5930 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5881   -1.8637    1.6274 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8645   -0.6725    2.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5470   -0.7438    3.9757 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -0.0107    2.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1439    0.5288    3.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9272    0.0753    1.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844    0.0340   -2.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9400    2.2522   -2.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4116    2.3171   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135    4.0804   -3.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    4.5175   -3.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3367    3.9457   -3.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    0.1647   -2.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -2.9629   -2.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897   -3.3348   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0460   -3.2363    2.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290   -0.2450    2.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6250    3.1122   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938    3.4680    2.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4391    4.8666    3.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4628    5.9135    2.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8530    4.1767   -1.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7739    3.1417   -1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4807    1.8303   -2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3223   -0.9517   -0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0593   -2.3583   -0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6654   -4.8882    1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4252   -4.8972    2.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3832   -1.8107    0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406   -1.0715   -2.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8805   -3.1855   -2.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372   -4.8043   -0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0392   -5.2868    2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5303   -2.4438    3.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5801   -0.1636    0.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0769   -1.5633   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9395   -2.2752    0.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1053   -0.3173    4.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403    1.0129    3.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9843    0.5717    1.5014 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
 23 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  1  0
 38 40  2  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
 42 44  2  0
 12 45  2  0
 45 46  1  0
 46 47  1  0
 47 48  1  0
 48 49  2  0
 49 50  1  0
 50 51  2  0
 51 52  1  0
 51 53  1  0
 53 54  1  0
 53 55  2  0
  2 56  1  0
 56 57  2  0
 57 58  1  0
 58 59  1  0
 58 60  2  0
 60 61  1  0
 60 62  1  0
 62 63  1  0
 62 64  2  0
 47  4  1  0
 55 48  1  0
 64 56  1  0
 45  6  1  0
 32 13  1  0
 44 36  1  0
 21 14  1  0
 31 24  1  0
  4 65  1  6
  5 66  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-O-Galloylepicatechin-(4beta->8)-epicatechin-3-O-gallate	HMDB
Proanthocyanidin b2 3,3'-O-gallate	HMDB
Procyanidin b2 3,3'-di-O-gallate	HMDB
Procyanidin b2-3,3'-di-O-gallate	MeSH, HMDB
(2R,3R)-2-(3,4-Dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acid	Generator
Proanthocyanidin b2 3,3'-digallic acid	Generator

Chemical Formula

C₄₄H₃₄O₂₀

Average Molecular Weight

882.7288

Monoisotopic Molecular Weight

882.164343528

IUPAC Name

(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

Traditional Name

CAS Registry Number

79907-44-1

SMILES

OC1=CC(O)=C2[C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1)C1=C2O[C@@H]([C@@H](CC2=C(O)C=C1O)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C44H34O20/c45-19-11-26(51)34-32(12-19)61-40(16-2-4-22(47)25(50)6-16)42(64-44(60)18-9-30(55)38(58)31(56)10-18)36(34)35-27(52)14-23(48)20-13-33(62-43(59)17-7-28(53)37(57)29(54)8-17)39(63-41(20)35)15-1-3-21(46)24(49)5-15/h1-12,14,33,36,39-40,42,45-58H,13H2/t33-,36-,39-,40-,42-/m1/s1

InChI Key

KTLUHRSHFRODPS-RIQPQZJCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

B-type proanthocyanidin
Proanthocyanidin
Bi- and polyflavonoid skeleton
Catechin gallate
Catechin
Hydroxyflavonoid
Flavan-3-ol
3'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Flavan
Galloyl ester
Gallic acid or derivatives
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
P-hydroxybenzoic acid alkyl ester
Benzoate ester
Chromane
Benzopyran
1-benzopyran
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoyl
Catechol
Alkyl aryl ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Dicarboxylic acid or derivatives
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Polyol
Ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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: HMDB0037967)
Cell membrane (HMDB: HMDB0037967)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037967)

Source

Exogenous

Exogenous (HMDB: HMDB0037967)

Food

Food (HMDB: HMDB0037967)

Tea

Fruit

Berry

Common grape (FooDB: FOOD00204)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0037967)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037967)

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
Water Solubility	0.11 g/L	ALOGPS
logP	3.9	ALOGPS
logP	6.28	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.77	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	354.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	218.04 m³·mol⁻¹	ChemAxon
Polarizability	83.51 Å³	ChemAxon
Number of Rings	8	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]+	265.257	30932474
DeepCCS	[M-H]-	263.533	30932474
DeepCCS	[M-2H]-	297.566	30932474
DeepCCS	[M+Na]+	271.428	30932474
AllCCS	[M+H]+	281.3	32859911
AllCCS	[M+H-H2O]+	281.3	32859911
AllCCS	[M+NH4]+	281.3	32859911
AllCCS	[M+Na]+	281.3	32859911
AllCCS	[M-H]-	270.1	32859911
AllCCS	[M+Na-2H]-	274.1	32859911
AllCCS	[M+HCOO]-	278.5	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 - 3,3'-Digalloylprocyanidin B2 10V, Positive-QTOF	splash10-0h0r-0510090450-397db369cb5854acd45f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 20V, Positive-QTOF	splash10-0f6x-0941260210-03ac03f6d42738a5f198	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 40V, Positive-QTOF	splash10-0zfr-0981110010-928d1c64ced9334e4260	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 10V, Negative-QTOF	splash10-001i-0300000390-b8be6162d05537078f36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 20V, Negative-QTOF	splash10-0gdi-0903100430-a69a03fb5779753ab28e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 40V, Negative-QTOF	splash10-016r-0900001000-34b545b4afc98d2d4ec1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 10V, Negative-QTOF	splash10-0043-0090600580-bda7af02a32c22ca6e1e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 20V, Negative-QTOF	splash10-03di-0200000690-3409a8495fb4fdaf7304	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 40V, Negative-QTOF	splash10-004i-1900000360-9b9ea0ecf9a2af888ffc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 10V, Positive-QTOF	splash10-02ai-0100003980-43ce8ef4caabdf963579	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 20V, Positive-QTOF	splash10-003u-0210311390-530307e1a46cd4e3d7c4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Digalloylprocyanidin B2 40V, Positive-QTOF	splash10-05rr-0400040590-7b1370f207f6cbff3c2c	2021-09-22	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

FDB017141

KNApSAcK ID

C00009213

Chemspider ID

110532

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124016

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3,3'-Digalloylprocyanidin B2 (HMDB0037967)

MOL for HMDB0037967 (3,3'-Digalloylprocyanidin B2)

3D MOL for HMDB0037967 (3,3'-Digalloylprocyanidin B2)

3D SDF for HMDB0037967 (3,3'-Digalloylprocyanidin B2)

3D-SDF for HMDB0037967 (3,3'-Digalloylprocyanidin B2)

PDB for HMDB0037967 (3,3'-Digalloylprocyanidin B2)

3D PDB for HMDB0037967 (3,3'-Digalloylprocyanidin B2)

SMILES for HMDB0037967 (3,3'-Digalloylprocyanidin B2)

INCHI for HMDB0037967 (3,3'-Digalloylprocyanidin B2)

Structure for HMDB0037967 (3,3'-Digalloylprocyanidin B2)

3D Structure for HMDB0037967 (3,3'-Digalloylprocyanidin B2)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra