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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 11:18:12 UTC

Update Date

2021-09-24 11:18:12 UTC

HMDB ID

HMDB0304637

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4,5-Dicaffeoylquinic acid

Description

(1R,3R,4R,5S)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. Based on a literature review very few articles have been published on (1R,3R,4R,5S)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid.

Structure

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


  Mrv1652301212022253D          

 37 39  0  0  0  0            999 V2000
    5.0729    1.7190   -1.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4640    2.8721   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    0.8844   -0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250    0.7939   -0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9940    2.6600   -2.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4382    3.8125   -0.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5679    0.9663    0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848    0.7969   -1.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5068    3.0271    0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0822    1.6933    0.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9247   -4.4092    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3829   -3.5135    0.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3036    1.8975   -0.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2541    1.8049   -0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1695    3.7813   -1.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2668    3.6801    0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339    3.9863   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0822    2.6283    1.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0816   -3.6478   -0.7855 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5542   -2.2603    0.5196 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5955   -0.1116    1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3647   -0.2632   -1.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3507   -2.3285   -0.6838 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6844   -5.4648    1.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5360   -4.7669    0.6791 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1243    4.6990   -1.7040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2488    4.6285    0.4464 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6533    5.1373    0.6081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8733    2.4622    2.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6054   -4.3577   -1.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499   -0.0680    2.1271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5544   -0.2761   -2.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641   -6.6220    1.9949 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066   -4.8770    3.1841 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9883   -5.5867   -0.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847   -1.1954    0.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2846   -1.2826   -0.6365 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  1 13  1  0  0  0  0
  2  6  2  0  0  0  0
  2 14  1  0  0  0  0
  3  7  2  0  0  0  0
  3 13  1  0  0  0  0
  4  8  2  0  0  0  0
  4 14  1  0  0  0  0
  5 15  1  0  0  0  0
  6 16  1  0  0  0  0
  7 21  1  0  0  0  0
  8 22  1  0  0  0  0
  9 13  2  0  0  0  0
  9 17  1  0  0  0  0
 10 14  2  0  0  0  0
 10 18  1  0  0  0  0
 11 19  1  0  0  0  0
 11 25  1  0  0  0  0
 12 20  1  0  0  0  0
 12 25  1  0  0  0  0
 15 17  2  0  0  0  0
 15 26  1  0  0  0  0
 16 18  2  0  0  0  0
 16 27  1  0  0  0  0
 17 28  1  0  0  0  0
 18 29  1  0  0  0  0
 19 23  1  0  0  0  0
 19 30  1  0  0  0  0
 20 23  1  0  0  0  0
 20 36  1  0  0  0  0
 21 31  2  0  0  0  0
 21 36  1  0  0  0  0
 22 32  2  0  0  0  0
 22 37  1  0  0  0  0
 23 37  1  0  0  0  0
 24 25  1  0  0  0  0
 24 33  2  0  0  0  0
 24 34  1  0  0  0  0
 25 35  1  0  0  0  0
M  END

HMDB0304637
     RDKit          3D
4,5-Dicaffeoylquinic acid
 61 63  0  0  0  0  0  0  0  0999 V2000
    2.1526    0.0996    1.9376 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1672   -0.3088    0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8142    0.5354   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3626    1.6839    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9982    2.5067   -0.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5649    3.7178   -0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966    4.5818   -1.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883    4.2665   -2.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9278    5.1435   -3.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7386    3.0801   -3.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8181    2.7415   -4.4782 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1011    2.2119   -2.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5726   -1.5261    0.4748 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9562   -2.3151    1.4711 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6748   -3.6306    1.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217   -4.7966    1.0701 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8675   -4.7136   -0.3141 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7059   -6.0259    1.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8848   -6.3045    2.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321   -6.8525    0.4400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4428   -4.9759    1.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9343   -3.6563    2.2091 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2918   -3.6133    2.4476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4859   -2.5938    1.2104 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3074   -1.4356    1.2983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0763   -0.9674    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0599   -1.5946   -0.8183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9065    0.2458    0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6473    0.6955   -0.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4976    1.8827   -0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2219    2.2224   -1.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0495    3.3023   -1.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1756    4.0928   -0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0169    5.1953   -0.6422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4662    3.7718    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6280    4.5953    1.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6216    2.6623    0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8019    0.1436   -1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3174    1.9863    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4886    3.9581    0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269    5.5155   -1.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9973    4.9134   -4.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4124    1.8698   -4.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6732    1.2806   -2.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0577   -1.7673    2.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6331   -3.5534    1.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015   -3.8509    2.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5803   -4.1150   -0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4055   -7.8224    0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3766   -5.6676    2.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514   -5.3393    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4260   -3.3748    3.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247   -3.8050    1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6278   -2.9826    0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9259    0.7886    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5920    0.1046   -1.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1239    1.5967   -2.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5788    3.5030   -2.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1379    5.8021    0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1579    4.4542    2.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0892    2.4375    1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 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  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  2  0
 12  5  1  0
 24 14  1  0
 37 30  1  0
  3 38  1  0
  4 39  1  0
  6 40  1  0
  7 41  1  0
  9 42  1  0
 11 43  1  0
 12 44  1  0
 14 45  1  1
 15 46  1  0
 15 47  1  0
 17 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  1
 23 53  1  0
 24 54  1  6
 28 55  1  0
 29 56  1  0
 31 57  1  0
 32 58  1  0
 34 59  1  0
 36 60  1  0
 37 61  1  0
M  END


  Mrv1652301212022253D          

 37 39  0  0  0  0            999 V2000
    5.0729    1.7190   -1.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4640    2.8721   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    0.8844   -0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250    0.7939   -0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9940    2.6600   -2.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4382    3.8125   -0.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5679    0.9663    0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848    0.7969   -1.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5068    3.0271    0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0822    1.6933    0.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9247   -4.4092    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3829   -3.5135    0.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3036    1.8975   -0.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2541    1.8049   -0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1695    3.7813   -1.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2668    3.6801    0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339    3.9863   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0822    2.6283    1.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0816   -3.6478   -0.7855 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5542   -2.2603    0.5196 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5955   -0.1116    1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3647   -0.2632   -1.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3507   -2.3285   -0.6838 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6844   -5.4648    1.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5360   -4.7669    0.6791 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1243    4.6990   -1.7040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2488    4.6285    0.4464 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6533    5.1373    0.6081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8733    2.4622    2.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6054   -4.3577   -1.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499   -0.0680    2.1271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5544   -0.2761   -2.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641   -6.6220    1.9949 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066   -4.8770    3.1841 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9883   -5.5867   -0.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847   -1.1954    0.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2846   -1.2826   -0.6365 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  1 13  1  0  0  0  0
  2  6  2  0  0  0  0
  2 14  1  0  0  0  0
  3  7  2  0  0  0  0
  3 13  1  0  0  0  0
  4  8  2  0  0  0  0
  4 14  1  0  0  0  0
  5 15  1  0  0  0  0
  6 16  1  0  0  0  0
  7 21  1  0  0  0  0
  8 22  1  0  0  0  0
  9 13  2  0  0  0  0
  9 17  1  0  0  0  0
 10 14  2  0  0  0  0
 10 18  1  0  0  0  0
 11 19  1  0  0  0  0
 11 25  1  0  0  0  0
 12 20  1  0  0  0  0
 12 25  1  0  0  0  0
 15 17  2  0  0  0  0
 15 26  1  0  0  0  0
 16 18  2  0  0  0  0
 16 27  1  0  0  0  0
 17 28  1  0  0  0  0
 18 29  1  0  0  0  0
 19 23  1  0  0  0  0
 19 30  1  0  0  0  0
 20 23  1  0  0  0  0
 20 36  1  0  0  0  0
 21 31  2  0  0  0  0
 21 36  1  0  0  0  0
 22 32  2  0  0  0  0
 22 37  1  0  0  0  0
 23 37  1  0  0  0  0
 24 25  1  0  0  0  0
 24 33  2  0  0  0  0
 24 34  1  0  0  0  0
 25 35  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304637

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H]1OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20+,23+,25+/m0/s1

> <INCHI_KEY>
UFCLZKMFXSILNL-CWIYAZRISA-N

> <FORMULA>
C25H24O12

> <MOLECULAR_WEIGHT>
516.455

> <EXACT_MASS>
516.126776213

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
50.20158702699577

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,4R,5S)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
2.158230316666666

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.907569606355128

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3113236711174387

> <JCHEM_PKA_STRONGEST_BASIC>
-3.246879196378373

> <JCHEM_POLAR_SURFACE_AREA>
211.27999999999994

> <JCHEM_REFRACTIVITY>
126.76419999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,4R,5S)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304637
     RDKit          3D
4,5-Dicaffeoylquinic acid
 61 63  0  0  0  0  0  0  0  0999 V2000
    2.1526    0.0996    1.9376 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1672   -0.3088    0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8142    0.5354   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3626    1.6839    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9982    2.5067   -0.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5649    3.7178   -0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966    4.5818   -1.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883    4.2665   -2.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9278    5.1435   -3.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7386    3.0801   -3.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8181    2.7415   -4.4782 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1011    2.2119   -2.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5726   -1.5261    0.4748 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9562   -2.3151    1.4711 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6748   -3.6306    1.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217   -4.7966    1.0701 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8675   -4.7136   -0.3141 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7059   -6.0259    1.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8848   -6.3045    2.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321   -6.8525    0.4400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4428   -4.9759    1.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9343   -3.6563    2.2091 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2918   -3.6133    2.4476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4859   -2.5938    1.2104 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3074   -1.4356    1.2983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0763   -0.9674    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0599   -1.5946   -0.8183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9065    0.2458    0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6473    0.6955   -0.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4976    1.8827   -0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2219    2.2224   -1.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0495    3.3023   -1.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1756    4.0928   -0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0169    5.1953   -0.6422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4662    3.7718    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6280    4.5953    1.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6216    2.6623    0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8019    0.1436   -1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3174    1.9863    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4886    3.9581    0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269    5.5155   -1.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9973    4.9134   -4.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4124    1.8698   -4.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6732    1.2806   -2.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0577   -1.7673    2.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6331   -3.5534    1.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015   -3.8509    2.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5803   -4.1150   -0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4055   -7.8224    0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3766   -5.6676    2.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514   -5.3393    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4260   -3.3748    3.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247   -3.8050    1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6278   -2.9826    0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9259    0.7886    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5920    0.1046   -1.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1239    1.5967   -2.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5788    3.5030   -2.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1379    5.8021    0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1579    4.4542    2.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0892    2.4375    1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 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  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  2  0
 12  5  1  0
 24 14  1  0
 37 30  1  0
  3 38  1  0
  4 39  1  0
  6 40  1  0
  7 41  1  0
  9 42  1  0
 11 43  1  0
 12 44  1  0
 14 45  1  1
 15 46  1  0
 15 47  1  0
 17 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  1
 23 53  1  0
 24 54  1  6
 28 55  1  0
 29 56  1  0
 31 57  1  0
 32 58  1  0
 34 59  1  0
 36 60  1  0
 37 61  1  0
M  END

HEADER    PROTEIN                                 21-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-20         0                                  
HETATM    1  C   UNK     0       5.073   1.719  -1.743  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.464   2.872  -1.078  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.324   0.884  -0.226  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.225   0.794  -0.440  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.994   2.660  -2.086  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.438   3.813  -0.876  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.568   0.966   0.832  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.385   0.797  -1.441  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.507   3.027   0.182  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.082   1.693   0.853  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.925  -4.409   0.515  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.383  -3.514   0.673  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.304   1.898  -0.580  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.254   1.805  -0.244  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.170   3.781  -1.296  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.267   3.680   0.243  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.434   3.986  -0.153  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.082   2.628   1.091  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.082  -3.648  -0.786  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.554  -2.260   0.520  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.595  -0.112   1.117  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.365  -0.263  -1.576  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.351  -2.329  -0.684  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.684  -5.465   1.974  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.536  -4.767   0.679  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.124   4.699  -1.704  0.00  0.00           O+0
HETATM   27  O   UNK     0      -7.249   4.628   0.446  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.653   5.137   0.608  0.00  0.00           O+0
HETATM   29  O   UNK     0      -6.873   2.462   2.200  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.605  -4.358  -1.868  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.850  -0.068   2.127  0.00  0.00           O+0
HETATM   32  O   UNK     0      -0.554  -0.276  -2.526  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.164  -6.622   1.995  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.307  -4.877   3.184  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.988  -5.587  -0.330  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.485  -1.195   0.277  0.00  0.00           O+0
HETATM   37  O   UNK     0      -1.285  -1.283  -0.637  0.00  0.00           O+0
CONECT    1    5   13                                                       
CONECT    2    6   14                                                       
CONECT    3    7   13                                                       
CONECT    4    8   14                                                       
CONECT    5    1   15                                                       
CONECT    6    2   16                                                       
CONECT    7    3   21                                                       
CONECT    8    4   22                                                       
CONECT    9   13   17                                                       
CONECT   10   14   18                                                       
CONECT   11   19   25                                                       
CONECT   12   20   25                                                       
CONECT   13    1    3    9                                                  
CONECT   14    2    4   10                                                  
CONECT   15    5   17   26                                                  
CONECT   16    6   18   27                                                  
CONECT   17    9   15   28                                                  
CONECT   18   10   16   29                                                  
CONECT   19   11   23   30                                                  
CONECT   20   12   23   36                                                  
CONECT   21    7   31   36                                                  
CONECT   22    8   32   37                                                  
CONECT   23   19   20   37                                                  
CONECT   24   25   33   34                                                  
CONECT   25   11   12   24   35                                             
CONECT   26   15                                                            
CONECT   27   16                                                            
CONECT   28   17                                                            
CONECT   29   18                                                            
CONECT   30   19                                                            
CONECT   31   21                                                            
CONECT   32   22                                                            
CONECT   33   24                                                            
CONECT   34   24                                                            
CONECT   35   25                                                            
CONECT   36   20   21                                                       
CONECT   37   22   23                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

COMPND    HMDB0304637
HETATM    1  O1  UNL     1       2.153   0.100   1.938  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.167  -0.309   0.753  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.814   0.535  -0.249  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.363   1.684   0.079  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.998   2.507  -0.924  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.565   3.718  -0.515  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.197   4.582  -1.387  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.288   4.267  -2.718  1.00  0.00           C  
HETATM    9  O2  UNL     1       5.928   5.144  -3.595  1.00  0.00           O  
HETATM   10  C8  UNL     1       4.739   3.080  -3.146  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.818   2.741  -4.478  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.101   2.212  -2.255  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.573  -1.526   0.475  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.956  -2.315   1.471  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.675  -3.631   1.653  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.922  -4.797   1.070  1.00  0.00           C  
HETATM   17  O5  UNL     1       0.868  -4.714  -0.314  1.00  0.00           O  
HETATM   18  C13 UNL     1       1.706  -6.026   1.408  1.00  0.00           C  
HETATM   19  O6  UNL     1       1.885  -6.305   2.640  1.00  0.00           O  
HETATM   20  O7  UNL     1       2.232  -6.852   0.440  1.00  0.00           O  
HETATM   21  C14 UNL     1      -0.443  -4.976   1.697  1.00  0.00           C  
HETATM   22  C15 UNL     1      -0.934  -3.656   2.209  1.00  0.00           C  
HETATM   23  O8  UNL     1      -2.292  -3.613   2.448  1.00  0.00           O  
HETATM   24  C16 UNL     1      -0.486  -2.594   1.210  1.00  0.00           C  
HETATM   25  O9  UNL     1      -1.307  -1.436   1.298  1.00  0.00           O  
HETATM   26  C17 UNL     1      -2.076  -0.967   0.272  1.00  0.00           C  
HETATM   27  O10 UNL     1      -2.060  -1.595  -0.818  1.00  0.00           O  
HETATM   28  C18 UNL     1      -2.907   0.246   0.438  1.00  0.00           C  
HETATM   29  C19 UNL     1      -3.647   0.696  -0.553  1.00  0.00           C  
HETATM   30  C20 UNL     1      -4.498   1.883  -0.483  1.00  0.00           C  
HETATM   31  C21 UNL     1      -5.222   2.222  -1.632  1.00  0.00           C  
HETATM   32  C22 UNL     1      -6.050   3.302  -1.699  1.00  0.00           C  
HETATM   33  C23 UNL     1      -6.176   4.093  -0.582  1.00  0.00           C  
HETATM   34  O11 UNL     1      -7.017   5.195  -0.642  1.00  0.00           O  
HETATM   35  C24 UNL     1      -5.466   3.772   0.564  1.00  0.00           C  
HETATM   36  O12 UNL     1      -5.628   4.595   1.654  1.00  0.00           O  
HETATM   37  C25 UNL     1      -4.622   2.662   0.620  1.00  0.00           C  
HETATM   38  H1  UNL     1       2.802   0.144  -1.252  1.00  0.00           H  
HETATM   39  H2  UNL     1       3.317   1.986   1.133  1.00  0.00           H  
HETATM   40  H3  UNL     1       4.489   3.958   0.532  1.00  0.00           H  
HETATM   41  H4  UNL     1       5.627   5.516  -1.038  1.00  0.00           H  
HETATM   42  H5  UNL     1       5.997   4.913  -4.579  1.00  0.00           H  
HETATM   43  H6  UNL     1       4.412   1.870  -4.783  1.00  0.00           H  
HETATM   44  H7  UNL     1       3.673   1.281  -2.610  1.00  0.00           H  
HETATM   45  H8  UNL     1       1.058  -1.767   2.435  1.00  0.00           H  
HETATM   46  H9  UNL     1       2.633  -3.553   1.113  1.00  0.00           H  
HETATM   47  H10 UNL     1       1.901  -3.851   2.708  1.00  0.00           H  
HETATM   48  H11 UNL     1       1.580  -4.115  -0.675  1.00  0.00           H  
HETATM   49  H12 UNL     1       2.405  -7.822   0.600  1.00  0.00           H  
HETATM   50  H13 UNL     1      -0.377  -5.668   2.577  1.00  0.00           H  
HETATM   51  H14 UNL     1      -1.151  -5.339   0.927  1.00  0.00           H  
HETATM   52  H15 UNL     1      -0.426  -3.375   3.177  1.00  0.00           H  
HETATM   53  H16 UNL     1      -2.825  -3.805   1.638  1.00  0.00           H  
HETATM   54  H17 UNL     1      -0.628  -2.983   0.166  1.00  0.00           H  
HETATM   55  H18 UNL     1      -2.926   0.789   1.368  1.00  0.00           H  
HETATM   56  H19 UNL     1      -3.592   0.105  -1.483  1.00  0.00           H  
HETATM   57  H20 UNL     1      -5.124   1.597  -2.520  1.00  0.00           H  
HETATM   58  H21 UNL     1      -6.579   3.503  -2.624  1.00  0.00           H  
HETATM   59  H22 UNL     1      -7.138   5.802   0.156  1.00  0.00           H  
HETATM   60  H23 UNL     1      -5.158   4.454   2.542  1.00  0.00           H  
HETATM   61  H24 UNL     1      -4.089   2.437   1.509  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   38
CONECT    4    5   39
CONECT    5    6    6   12
CONECT    6    7   40
CONECT    7    8    8   41
CONECT    8    9   10
CONECT    9   42
CONECT   10   11   12   12
CONECT   11   43
CONECT   12   44
CONECT   13   14
CONECT   14   15   24   45
CONECT   15   16   46   47
CONECT   16   17   18   21
CONECT   17   48
CONECT   18   19   19   20
CONECT   20   49
CONECT   21   22   50   51
CONECT   22   23   24   52
CONECT   23   53
CONECT   24   25   54
CONECT   25   26
CONECT   26   27   27   28
CONECT   28   29   29   55
CONECT   29   30   56
CONECT   30   31   31   37
CONECT   31   32   57
CONECT   32   33   33   58
CONECT   33   34   35
CONECT   34   59
CONECT   35   36   37   37
CONECT   36   60
CONECT   37   61
END

HMDB0304637
     RDKit          3D
4,5-Dicaffeoylquinic acid
 61 63  0  0  0  0  0  0  0  0999 V2000
    2.1526    0.0996    1.9376 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1672   -0.3088    0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8142    0.5354   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3626    1.6839    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9982    2.5067   -0.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5649    3.7178   -0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966    4.5818   -1.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883    4.2665   -2.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9278    5.1435   -3.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7386    3.0801   -3.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8181    2.7415   -4.4782 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1011    2.2119   -2.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5726   -1.5261    0.4748 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9562   -2.3151    1.4711 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6748   -3.6306    1.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217   -4.7966    1.0701 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8675   -4.7136   -0.3141 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7059   -6.0259    1.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8848   -6.3045    2.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321   -6.8525    0.4400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4428   -4.9759    1.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9343   -3.6563    2.2091 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2918   -3.6133    2.4476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4859   -2.5938    1.2104 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3074   -1.4356    1.2983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0763   -0.9674    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0599   -1.5946   -0.8183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9065    0.2458    0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6473    0.6955   -0.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4976    1.8827   -0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2219    2.2224   -1.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0495    3.3023   -1.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1756    4.0928   -0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0169    5.1953   -0.6422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4662    3.7718    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6280    4.5953    1.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6216    2.6623    0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8019    0.1436   -1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3174    1.9863    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4886    3.9581    0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269    5.5155   -1.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9973    4.9134   -4.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4124    1.8698   -4.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6732    1.2806   -2.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0577   -1.7673    2.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6331   -3.5534    1.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015   -3.8509    2.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5803   -4.1150   -0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4055   -7.8224    0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3766   -5.6676    2.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514   -5.3393    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4260   -3.3748    3.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247   -3.8050    1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6278   -2.9826    0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9259    0.7886    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5920    0.1046   -1.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1239    1.5967   -2.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5788    3.5030   -2.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1379    5.8021    0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1579    4.4542    2.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0892    2.4375    1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 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  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  2  0
 12  5  1  0
 24 14  1  0
 37 30  1  0
  3 38  1  0
  4 39  1  0
  6 40  1  0
  7 41  1  0
  9 42  1  0
 11 43  1  0
 12 44  1  0
 14 45  1  1
 15 46  1  0
 15 47  1  0
 17 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  1
 23 53  1  0
 24 54  1  6
 28 55  1  0
 29 56  1  0
 31 57  1  0
 32 58  1  0
 34 59  1  0
 36 60  1  0
 37 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1R,3R,4R,5S)-3,4-Bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylate	Generator

Chemical Formula

C₂₅H₂₄O₁₂

Average Molecular Weight

516.455

Monoisotopic Molecular Weight

516.126776213

IUPAC Name

(1R,3R,4R,5S)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid

Traditional Name

(1R,3R,4R,5S)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H]1OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20+,23+,25+/m0/s1

InChI Key

UFCLZKMFXSILNL-CWIYAZRISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
Tricarboxylic acid or derivatives
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Cyclohexanol
Fatty acyl
Benzenoid
Hydroxy acid
Monocyclic benzene moiety
Alpha-hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Globe artichoke (FooDB: FOOD00071)

Coffee and coffee product

Coffee

Coffee (FooDB: FOOD00058)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

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	2.05	ALOGPS
logP	2.16	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	211.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.76 m³·mol⁻¹	ChemAxon
Polarizability	50.2 Å³	ChemAxon
Number of Rings	3	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
AllCCS	[M+H]+	214.974	32859911
AllCCS	[M+H-H2O]+	213.319	32859911
AllCCS	[M+Na]+	216.903	32859911
AllCCS	[M+NH4]+	216.477	32859911
AllCCS	[M-H]-	209.52	32859911
AllCCS	[M+Na-2H]-	210.534	32859911
AllCCS	[M+HCOO]-	211.795	32859911
DeepCCS	[M+H]+	208.749	30932474
DeepCCS	[M-H]-	206.853	30932474
DeepCCS	[M-2H]-	240.091	30932474
DeepCCS	[M+Na]+	214.399	30932474

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 - 4,5-Dicaffeoylquinic acid 10V, Positive-QTOF	splash10-02ta-0802690000-f6fe8ec973a62b4d6739	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dicaffeoylquinic acid 20V, Positive-QTOF	splash10-03di-0911300000-7afc545cd09156b97277	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dicaffeoylquinic acid 40V, Positive-QTOF	splash10-03ds-0900100000-8c354d9ad36f7ac76746	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dicaffeoylquinic acid 10V, Negative-QTOF	splash10-014i-0401090000-111d25512125ef51b7c0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dicaffeoylquinic acid 20V, Negative-QTOF	splash10-0udr-0709210000-8ff069cd1b756cb80f24	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dicaffeoylquinic acid 40V, Negative-QTOF	splash10-000i-0901300000-da4d885c39d6bdd04ad7	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

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

102170141

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

Not Available

Showing metabocard for 4,5-Dicaffeoylquinic acid (HMDB0304637)

MOL for HMDB0304637 (4,5-Dicaffeoylquinic acid)

3D MOL for HMDB0304637 (4,5-Dicaffeoylquinic acid)

3D SDF for HMDB0304637 (4,5-Dicaffeoylquinic acid)

3D-SDF for HMDB0304637 (4,5-Dicaffeoylquinic acid)

PDB for HMDB0304637 (4,5-Dicaffeoylquinic acid)

3D PDB for HMDB0304637 (4,5-Dicaffeoylquinic acid)

SMILES for HMDB0304637 (4,5-Dicaffeoylquinic acid)

INCHI for HMDB0304637 (4,5-Dicaffeoylquinic acid)

Structure for HMDB0304637 (4,5-Dicaffeoylquinic acid)

3D Structure for HMDB0304637 (4,5-Dicaffeoylquinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra