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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:29:28 UTC

Update Date

2022-03-07 02:52:06 UTC

HMDB ID

HMDB0029291

Secondary Accession Numbers

HMDB29291

Metabolite Identification

Common Name

3,4-Dicaffeoyl-1,5-quinolactone

Description

3,4-Dicaffeoyl-1,5-quinolactone belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Based on a literature review very few articles have been published on 3,4-Dicaffeoyl-1,5-quinolactone.

Structure

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

Structure #1
  Mrv0541 02241212092D          

 36 39  0  0  1  0            999 V2000
   -0.0292   -5.0213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0292   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -3.7838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3998   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998   -5.0213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6853   -5.4338    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2549   -3.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689   -2.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2713   -4.2552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550   -3.1518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7437   -5.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -6.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3324   -6.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1262   -6.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274   -5.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7160   -6.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109   -6.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0996   -6.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946   -6.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1008   -5.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8956   -5.4855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5119   -5.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7171   -5.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4833   -7.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0912   -6.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161   -6.9846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6721   -7.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781   -8.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6591   -9.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0650   -9.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6459  -10.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1790  -10.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5982  -11.2485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5850   -9.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1660   -9.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0518  -11.2638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 11  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  1  0  0  0
  3 10  1  6  0  0  0
  4  5  1  0  0  0  0
  5  9  1  1  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 23  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 19 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  2  0  0  0  0
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 29 35  1  0  0  0  0
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 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 31 36  1  0  0  0  0
M  END

HMDB0029291
     RDKit          3D
3,4-Dicaffeoyl-1,5-quinolactone
 58 61  0  0  0  0  0  0  0  0999 V2000
    3.5013   -1.4706    2.4860 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029   -1.2540    1.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4504   -0.9289    0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859   -0.6867   -0.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4134   -0.3588   -2.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7725   -0.2757   -2.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3265    0.0471   -3.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5168    0.2866   -4.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0463    0.6077   -5.9191 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1557    0.2107   -4.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501    0.4568   -5.6313 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180   -0.1085   -3.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4274   -1.3427    1.6343 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8359   -1.6593    2.8737 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1597   -3.0115    2.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4866   -3.2392    4.2119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8014   -4.5306    4.4917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6512   -2.2693    4.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -0.9839    4.5499 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0416   -1.3714    5.6008 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -2.6187    5.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4740   -3.2328    5.6241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470   -0.5597    3.3846 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7657    0.1394    2.4078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6483    1.4496    2.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019    2.1146    2.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749    2.0680    1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3742    1.3830    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2091    1.9562   -0.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1344    1.1105   -1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9708    1.5420   -2.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9343    2.8631   -2.7346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7765    3.3152   -3.7363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0204    3.6893   -2.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9439    5.0040   -2.5079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1639    3.2434   -1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5247   -0.8820    0.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020   -0.7453   -0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4462   -0.4580   -1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4008    0.1098   -3.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4611    0.7840   -6.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3485    0.3965   -5.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5450   -0.1704   -3.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913   -1.7933    3.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9185   -3.8114    2.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5907   -3.1426    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4635   -5.1838    3.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376   -2.5019    5.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2817   -2.2671    3.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5713   -0.1609    4.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6305    0.2145    3.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3279    3.0952    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4790    0.3209    0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973    0.0630   -1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6935    0.8933   -2.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8075    4.2517   -4.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4742    5.4761   -3.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4645    3.9270   -0.6463 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  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  2  0
 12  5  1  0
 23 14  1  0
 36 29  1  0
 21 16  1  0
  3 37  1  0
  4 38  1  0
  6 39  1  0
  7 40  1  0
  9 41  1  0
 11 42  1  0
 12 43  1  0
 14 44  1  1
 15 45  1  0
 15 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  1
 23 51  1  1
 27 52  1  0
 28 53  1  0
 30 54  1  0
 31 55  1  0
 33 56  1  0
 35 57  1  0
 36 58  1  0
M  END

Structure #1
  Mrv0541 02241212092D          

 36 39  0  0  1  0            999 V2000
   -0.0292   -5.0213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0292   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -3.7838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3998   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998   -5.0213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6853   -5.4338    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2549   -3.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689   -2.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2713   -4.2552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550   -3.1518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7437   -5.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -6.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3324   -6.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1262   -6.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274   -5.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7160   -6.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109   -6.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0996   -6.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946   -6.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1008   -5.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8956   -5.4855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5119   -5.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7171   -5.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4833   -7.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0912   -6.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161   -6.9846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6721   -7.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781   -8.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6591   -9.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0650   -9.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6459  -10.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1790  -10.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5982  -11.2485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5850   -9.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1660   -9.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0518  -11.2638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 11  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  1  0  0  0
  3 10  1  6  0  0  0
  4  5  1  0  0  0  0
  5  9  1  1  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 23  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 19 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 35  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 31 36  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029291

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(O)C=C(\C=C\C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H22O11/c26-15-5-1-13(9-17(15)28)3-7-21(30)34-19-11-25(33)12-20(35-24(25)32)23(19)36-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,33H,11-12H2/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1

> <INCHI_KEY>
ZLYIWYCHNAZAQI-PSEXTPKNSA-N

> <FORMULA>
C25H22O11

> <MOLECULAR_WEIGHT>
498.4356

> <EXACT_MASS>
498.116211546

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
48.10906938959519

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,4R,5R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
2.822701441333333

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.508609186495999

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.907349366856145

> <JCHEM_PKA_STRONGEST_BASIC>
-4.030319513747339

> <JCHEM_POLAR_SURFACE_AREA>
180.04999999999998

> <JCHEM_REFRACTIVITY>
123.272

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,4R,5R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029291
     RDKit          3D
3,4-Dicaffeoyl-1,5-quinolactone
 58 61  0  0  0  0  0  0  0  0999 V2000
    3.5013   -1.4706    2.4860 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029   -1.2540    1.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4504   -0.9289    0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859   -0.6867   -0.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4134   -0.3588   -2.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7725   -0.2757   -2.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3265    0.0471   -3.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5168    0.2866   -4.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0463    0.6077   -5.9191 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1557    0.2107   -4.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501    0.4568   -5.6313 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180   -0.1085   -3.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4274   -1.3427    1.6343 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8359   -1.6593    2.8737 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1597   -3.0115    2.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4866   -3.2392    4.2119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8014   -4.5306    4.4917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6512   -2.2693    4.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -0.9839    4.5499 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0416   -1.3714    5.6008 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -2.6187    5.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4740   -3.2328    5.6241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470   -0.5597    3.3846 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7657    0.1394    2.4078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6483    1.4496    2.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019    2.1146    2.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749    2.0680    1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3742    1.3830    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2091    1.9562   -0.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1344    1.1105   -1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9708    1.5420   -2.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9343    2.8631   -2.7346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7765    3.3152   -3.7363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0204    3.6893   -2.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9439    5.0040   -2.5079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1639    3.2434   -1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5247   -0.8820    0.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020   -0.7453   -0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4462   -0.4580   -1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4008    0.1098   -3.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4611    0.7840   -6.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3485    0.3965   -5.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5450   -0.1704   -3.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913   -1.7933    3.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9185   -3.8114    2.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5907   -3.1426    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4635   -5.1838    3.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376   -2.5019    5.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2817   -2.2671    3.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5713   -0.1609    4.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6305    0.2145    3.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3279    3.0952    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4790    0.3209    0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973    0.0630   -1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6935    0.8933   -2.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8075    4.2517   -4.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4742    5.4761   -3.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4645    3.9270   -0.6463 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  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  2  0
 12  5  1  0
 23 14  1  0
 36 29  1  0
 21 16  1  0
  3 37  1  0
  4 38  1  0
  6 39  1  0
  7 40  1  0
  9 41  1  0
 11 42  1  0
 12 43  1  0
 14 44  1  1
 15 45  1  0
 15 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  1
 23 51  1  1
 27 52  1  0
 28 53  1  0
 30 54  1  0
 31 55  1  0
 33 56  1  0
 35 57  1  0
 36 58  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.055  -9.373   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.055  -7.833   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.279  -7.063   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.613  -7.833   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.613  -9.373   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.279 -10.143   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.342  -5.883   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.555  -4.800   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.240  -7.943   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.289  -5.883   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.388 -10.143   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.279 -11.683   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.487 -11.222   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.102 -12.713   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.971 -10.810   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.070 -11.889   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.554 -11.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.653 -12.555   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.137 -12.143   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.521 -10.652   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -11.005 -10.240   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.422  -9.573   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.939  -9.985   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -10.235 -13.222   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.037 -13.024   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.577 -13.038   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.255 -14.350   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.012 -15.691   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.230 -17.018   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.988 -18.358   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.206 -19.685   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.334 -19.671   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.117 -20.997   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.092 -18.330   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.310 -17.003   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.963 -21.026   0.000  0.00  0.00           O+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7   10                                             
CONECT    4    3    5                                                       
CONECT    5    4    9    6                                                  
CONECT    6    1    5   12                                                  
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    5    7                                                       
CONECT   10    3                                                            
CONECT   11    1   13                                                       
CONECT   12    6   25                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   17   22                                                       
CONECT   24   19                                                            
CONECT   25   12   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   29   34                                                       
CONECT   36   31                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

COMPND    HMDB0029291
HETATM    1  O1  UNL     1       3.501  -1.471   2.486  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.803  -1.254   1.472  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.450  -0.929   0.210  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.786  -0.687  -0.902  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.413  -0.359  -2.179  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.773  -0.276  -2.353  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.326   0.047  -3.601  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.517   0.287  -4.675  1.00  0.00           C  
HETATM    9  O2  UNL     1       5.046   0.608  -5.919  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.156   0.211  -4.532  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.350   0.457  -5.631  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.618  -0.109  -3.296  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.427  -1.343   1.634  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.836  -1.659   2.874  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.160  -3.012   2.862  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.487  -3.239   4.212  1.00  0.00           C  
HETATM   17  O5  UNL     1      -0.801  -4.531   4.492  1.00  0.00           O  
HETATM   18  C13 UNL     1      -1.651  -2.269   4.291  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.910  -0.984   4.550  1.00  0.00           C  
HETATM   20  O6  UNL     1      -0.042  -1.371   5.601  1.00  0.00           O  
HETATM   21  C15 UNL     1       0.436  -2.619   5.230  1.00  0.00           C  
HETATM   22  O7  UNL     1       1.474  -3.233   5.624  1.00  0.00           O  
HETATM   23  C16 UNL     1      -0.047  -0.560   3.385  1.00  0.00           C  
HETATM   24  O8  UNL     1      -0.766   0.139   2.408  1.00  0.00           O  
HETATM   25  C17 UNL     1      -0.648   1.450   2.061  1.00  0.00           C  
HETATM   26  O9  UNL     1       0.202   2.115   2.681  1.00  0.00           O  
HETATM   27  C18 UNL     1      -1.475   2.068   1.011  1.00  0.00           C  
HETATM   28  C19 UNL     1      -2.374   1.383   0.352  1.00  0.00           C  
HETATM   29  C20 UNL     1      -3.209   1.956  -0.689  1.00  0.00           C  
HETATM   30  C21 UNL     1      -4.134   1.110  -1.312  1.00  0.00           C  
HETATM   31  C22 UNL     1      -4.971   1.542  -2.301  1.00  0.00           C  
HETATM   32  C23 UNL     1      -4.934   2.863  -2.735  1.00  0.00           C  
HETATM   33  O10 UNL     1      -5.776   3.315  -3.736  1.00  0.00           O  
HETATM   34  C24 UNL     1      -4.020   3.689  -2.116  1.00  0.00           C  
HETATM   35  O11 UNL     1      -3.944   5.004  -2.508  1.00  0.00           O  
HETATM   36  C25 UNL     1      -3.164   3.243  -1.102  1.00  0.00           C  
HETATM   37  H1  UNL     1       4.525  -0.882   0.171  1.00  0.00           H  
HETATM   38  H2  UNL     1       1.702  -0.745  -0.820  1.00  0.00           H  
HETATM   39  H3  UNL     1       5.446  -0.458  -1.532  1.00  0.00           H  
HETATM   40  H4  UNL     1       6.401   0.110  -3.725  1.00  0.00           H  
HETATM   41  H5  UNL     1       4.461   0.784  -6.707  1.00  0.00           H  
HETATM   42  H6  UNL     1       1.349   0.397  -5.508  1.00  0.00           H  
HETATM   43  H7  UNL     1       1.545  -0.170  -3.173  1.00  0.00           H  
HETATM   44  H8  UNL     1       1.691  -1.793   3.592  1.00  0.00           H  
HETATM   45  H9  UNL     1       0.919  -3.811   2.736  1.00  0.00           H  
HETATM   46  H10 UNL     1      -0.591  -3.143   2.092  1.00  0.00           H  
HETATM   47  H11 UNL     1      -0.463  -5.184   3.830  1.00  0.00           H  
HETATM   48  H12 UNL     1      -2.238  -2.502   5.201  1.00  0.00           H  
HETATM   49  H13 UNL     1      -2.282  -2.267   3.408  1.00  0.00           H  
HETATM   50  H14 UNL     1      -1.571  -0.161   4.825  1.00  0.00           H  
HETATM   51  H15 UNL     1       0.631   0.214   3.814  1.00  0.00           H  
HETATM   52  H16 UNL     1      -1.328   3.095   0.791  1.00  0.00           H  
HETATM   53  H17 UNL     1      -2.479   0.321   0.624  1.00  0.00           H  
HETATM   54  H18 UNL     1      -4.197   0.063  -1.001  1.00  0.00           H  
HETATM   55  H19 UNL     1      -5.694   0.893  -2.791  1.00  0.00           H  
HETATM   56  H20 UNL     1      -5.807   4.252  -4.101  1.00  0.00           H  
HETATM   57  H21 UNL     1      -4.474   5.476  -3.201  1.00  0.00           H  
HETATM   58  H22 UNL     1      -2.464   3.927  -0.646  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   37
CONECT    4    5   38
CONECT    5    6    6   12
CONECT    6    7   39
CONECT    7    8    8   40
CONECT    8    9   10
CONECT    9   41
CONECT   10   11   12   12
CONECT   11   42
CONECT   12   43
CONECT   13   14
CONECT   14   15   23   44
CONECT   15   16   45   46
CONECT   16   17   18   21
CONECT   17   47
CONECT   18   19   48   49
CONECT   19   20   23   50
CONECT   20   21
CONECT   21   22   22
CONECT   23   24   51
CONECT   24   25
CONECT   25   26   26   27
CONECT   27   28   28   52
CONECT   28   29   53
CONECT   29   30   30   36
CONECT   30   31   54
CONECT   31   32   32   55
CONECT   32   33   34
CONECT   33   56
CONECT   34   35   36   36
CONECT   35   57
CONECT   36   58
END

HMDB0029291
     RDKit          3D
3,4-Dicaffeoyl-1,5-quinolactone
 58 61  0  0  0  0  0  0  0  0999 V2000
    3.5013   -1.4706    2.4860 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029   -1.2540    1.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4504   -0.9289    0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859   -0.6867   -0.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4134   -0.3588   -2.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7725   -0.2757   -2.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3265    0.0471   -3.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5168    0.2866   -4.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0463    0.6077   -5.9191 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1557    0.2107   -4.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501    0.4568   -5.6313 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180   -0.1085   -3.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4274   -1.3427    1.6343 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8359   -1.6593    2.8737 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1597   -3.0115    2.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4866   -3.2392    4.2119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8014   -4.5306    4.4917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6512   -2.2693    4.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -0.9839    4.5499 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0416   -1.3714    5.6008 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -2.6187    5.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4740   -3.2328    5.6241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470   -0.5597    3.3846 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7657    0.1394    2.4078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6483    1.4496    2.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019    2.1146    2.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749    2.0680    1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3742    1.3830    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2091    1.9562   -0.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1344    1.1105   -1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9708    1.5420   -2.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9343    2.8631   -2.7346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7765    3.3152   -3.7363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0204    3.6893   -2.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9439    5.0040   -2.5079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1639    3.2434   -1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5247   -0.8820    0.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020   -0.7453   -0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4462   -0.4580   -1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4008    0.1098   -3.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4611    0.7840   -6.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3485    0.3965   -5.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5450   -0.1704   -3.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913   -1.7933    3.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9185   -3.8114    2.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5907   -3.1426    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4635   -5.1838    3.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376   -2.5019    5.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2817   -2.2671    3.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5713   -0.1609    4.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6305    0.2145    3.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3279    3.0952    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4790    0.3209    0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973    0.0630   -1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6935    0.8933   -2.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8075    4.2517   -4.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4742    5.4761   -3.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4645    3.9270   -0.6463 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  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  2  0
 12  5  1  0
 23 14  1  0
 36 29  1  0
 21 16  1  0
  3 37  1  0
  4 38  1  0
  6 39  1  0
  7 40  1  0
  9 41  1  0
 11 42  1  0
 12 43  1  0
 14 44  1  1
 15 45  1  0
 15 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  1
 23 51  1  1
 27 52  1  0
 28 53  1  0
 30 54  1  0
 31 55  1  0
 33 56  1  0
 35 57  1  0
 36 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4-Dicaffeoyl-1,5-quinide	HMDB
3,4-Dicaffeoylquinic acid lactone	HMDB
3,4-Dicaffeoylquinic-1,5-lactone	HMDB
(1R,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	HMDB

Chemical Formula

C₂₅H₂₂O₁₁

Average Molecular Weight

498.4356

Monoisotopic Molecular Weight

498.116211546

IUPAC Name

(1R,3R,4R,5R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(1R,3R,4R,5R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC1=C(O)C=C(\C=C\C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C=C1

InChI Identifier

InChI=1S/C25H22O11/c26-15-5-1-13(9-17(15)28)3-7-21(30)34-19-11-25(33)12-20(35-24(25)32)23(19)36-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,33H,11-12H2/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1

InChI Key

ZLYIWYCHNAZAQI-PSEXTPKNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Tricarboxylic acid or derivatives
Caprolactone
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxepane
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0029291)

Cellular substructure

Membrane (HMDB: HMDB0029291)

Source

Endogenous

Endogenous (HMDB: HMDB0029291)

Plant

Plant (HMDB: HMDB0029291)

Exogenous

Food

Food (HMDB: HMDB0029291)

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
Water Solubility	0.047 g/L	ALOGPS
logP	2.58	ALOGPS
logP	2.82	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.91	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.05 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	123.27 m³·mol⁻¹	ChemAxon
Polarizability	48.11 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	208.222	30932474
DeepCCS	[M-H]-	206.398	30932474
DeepCCS	[M-2H]-	239.64	30932474
DeepCCS	[M+Na]+	213.828	30932474
AllCCS	[M+H]+	212.1	32859911
AllCCS	[M+H-H2O]+	210.3	32859911
AllCCS	[M+NH4]+	213.7	32859911
AllCCS	[M+Na]+	214.2	32859911
AllCCS	[M-H]-	206.4	32859911
AllCCS	[M+Na-2H]-	207.0	32859911
AllCCS	[M+HCOO]-	207.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dicaffeoyl-1,5-quinolactone	OC1=C(O)C=C(\C=C\C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C=C1	7188.7	Standard polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone	OC1=C(O)C=C(\C=C\C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C=C1	4457.3	Standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone	OC1=C(O)C=C(\C=C\C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C=C1	4914.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dicaffeoyl-1,5-quinolactone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C=C1O	4508.3	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,1TMS,isomer #2	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O)=C2)=CC=C1O	4507.3	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,1TMS,isomer #3	C[Si](C)(C)O[C@@]12C[C@@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)[C@@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)[C@@H](C1)OC2=O	4628.2	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,1TMS,isomer #4	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)C[C@]3(O)C[C@H]2OC3=O)=CC=C1O	4507.0	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,1TMS,isomer #5	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)C[C@]3(O)C[C@H]2OC3=O)C=C1O	4507.9	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C=C1O	4472.4	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TMS,isomer #10	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)C[C@]3(O)C[C@H]2OC3=O)C=C1O[Si](C)(C)C	4450.8	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O)=C2)C=C1O	4459.7	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)C=C1O	4478.8	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C=C1O[Si](C)(C)C	4450.8	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TMS,isomer #5	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O)=C2)=CC=C1O	4476.0	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O[Si](C)(C)C)=C3)C[C@]3(O)C[C@H]2OC3=O)C=C1O	4478.8	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TMS,isomer #7	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)=CC=C1O	4490.9	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TMS,isomer #8	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)C[C@]3(O[Si](C)(C)C)C[C@H]2OC3=O)C=C1O	4472.3	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TMS,isomer #9	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)C[C@]3(O[Si](C)(C)C)C[C@H]2OC3=O)=CC=C1O	4476.4	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O)=C2)C=C1O	4494.9	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TMS,isomer #10	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)C[C@]3(O[Si](C)(C)C)C[C@H]2OC3=O)C=C1O[Si](C)(C)C	4454.7	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)C=C1O	4511.5	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C=C1O[Si](C)(C)C	4454.6	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C1O	4474.7	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TMS,isomer #5	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)C[C@]3(O)C[C@H]2OC3=O)C=C1O	4474.6	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TMS,isomer #6	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)C[C@]3(O)C[C@H]2OC3=O)=CC=C1O	4485.4	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TMS,isomer #7	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O[Si](C)(C)C)=C3)C[C@]3(O[Si](C)(C)C)C[C@H]2OC3=O)C=C1O	4511.5	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TMS,isomer #8	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)=CC=C1O	4518.5	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TMS,isomer #9	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)=CC=C1O	4485.3	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C1O	4515.5	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,4TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)C[C@]3(O[Si](C)(C)C)C[C@H]2OC3=O)C=C1O	4515.1	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,4TMS,isomer #3	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)C[C@]3(O[Si](C)(C)C)C[C@H]2OC3=O)=CC=C1O	4520.3	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,4TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C1O[Si](C)(C)C	4497.1	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,4TMS,isomer #5	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)=CC=C1O	4520.8	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,5TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C1O[Si](C)(C)C	4542.6	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C=C1O	4762.7	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O)=C2)=CC=C1O	4770.2	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@]12C[C@@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)[C@@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)[C@@H](C1)OC2=O	4879.7	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)C[C@]3(O)C[C@H]2OC3=O)=CC=C1O	4770.4	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)C[C@]3(O)C[C@H]2OC3=O)C=C1O	4762.5	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C(C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C=C1O	4978.3	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)C[C@]3(O)C[C@H]2OC3=O)C=C1O[Si](C)(C)C(C)(C)C	4934.3	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C=C1O	4968.9	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C=C1O	4988.2	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C=C1O[Si](C)(C)C(C)(C)C	4934.5	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C(C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O)=C2)=CC=C1O	4981.2	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)C[C@]3(O)C[C@H]2OC3=O)C=C1O	4988.4	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)=CC=C1O	5003.3	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)C[C@]3(O[Si](C)(C)C(C)(C)C)C[C@H]2OC3=O)C=C1O	4978.0	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)C[C@]3(O[Si](C)(C)C(C)(C)C)C[C@H]2OC3=O)=CC=C1O	4981.3	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C(C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C=C1O	5273.2	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O)=C3)C[C@]3(O[Si](C)(C)C(C)(C)C)C[C@H]2OC3=O)C=C1O[Si](C)(C)C(C)(C)C	5168.0	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C(C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C=C1O	5280.2	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C(C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C=C1O[Si](C)(C)C(C)(C)C	5168.0	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C=C1O	5173.3	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)C[C@]3(O)C[C@H]2OC3=O)C=C1O	5173.1	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)C[C@]3(O)C[C@H]2OC3=O)=CC=C1O	5182.8	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](OC(=O)/C=C/C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)C[C@]3(O[Si](C)(C)C(C)(C)C)C[C@H]2OC3=O)C=C1O	5279.9	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2C[C@]3(O[Si](C)(C)C(C)(C)C)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)=CC=C1O	5280.1	Semi standard non polar	33892256
3,4-Dicaffeoyl-1,5-quinolactone,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H]2C[C@]3(O)C[C@@H](OC3=O)[C@@H]2OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)=CC=C1O	5182.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01vo-9886600000-f63379f6c628fe9e2eb3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone GC-MS (2 TMS) - 70eV, Positive	splash10-000l-6096073000-7c82421b740aed29f171	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone 10V, Positive-QTOF	splash10-0292-0708900000-e6f217eb974a0032e5f8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone 20V, Positive-QTOF	splash10-03dr-0914200000-cd74afade849797056d6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone 40V, Positive-QTOF	splash10-0c00-0910100000-a668107115b07c936ed6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone 10V, Negative-QTOF	splash10-000b-0416900000-8817bcea9538bac25ef9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone 20V, Negative-QTOF	splash10-01ri-0917200000-0dc1af2813663e52ca90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone 40V, Negative-QTOF	splash10-0200-0911000000-442d25617b079d65470e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone 10V, Negative-QTOF	splash10-0002-0004900000-1b5b25f4a5675746ddb2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone 20V, Negative-QTOF	splash10-000j-0719600000-9a13788665d3fc134261	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone 40V, Negative-QTOF	splash10-000i-0912200000-eee176d30072009e3c8e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone 10V, Positive-QTOF	splash10-0002-0302900000-d9376b1ff360ad2018ee	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone 20V, Positive-QTOF	splash10-03di-0901100000-04a727b1050a51ae1e0a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dicaffeoyl-1,5-quinolactone 40V, Positive-QTOF	splash10-06fs-1900300000-30b2fc0a63435c68e286	2021-09-24	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

546

FooDB ID

FDB000295

KNApSAcK ID

Not Available

Chemspider ID

30776762

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102177109

PDB ID

Not Available

ChEBI ID

169847

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

Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Showing metabocard for 3,4-Dicaffeoyl-1,5-quinolactone (HMDB0029291)

MOL for HMDB0029291 (3,4-Dicaffeoyl-1,5-quinolactone)

3D MOL for HMDB0029291 (3,4-Dicaffeoyl-1,5-quinolactone)

3D SDF for HMDB0029291 (3,4-Dicaffeoyl-1,5-quinolactone)

3D-SDF for HMDB0029291 (3,4-Dicaffeoyl-1,5-quinolactone)

PDB for HMDB0029291 (3,4-Dicaffeoyl-1,5-quinolactone)

3D PDB for HMDB0029291 (3,4-Dicaffeoyl-1,5-quinolactone)

SMILES for HMDB0029291 (3,4-Dicaffeoyl-1,5-quinolactone)

INCHI for HMDB0029291 (3,4-Dicaffeoyl-1,5-quinolactone)

Structure for HMDB0029291 (3,4-Dicaffeoyl-1,5-quinolactone)

3D Structure for HMDB0029291 (3,4-Dicaffeoyl-1,5-quinolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra