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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-22 16:36:45 UTC

Update Date

2021-09-22 16:36:45 UTC

HMDB ID

HMDB0301718

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-5'-Dehydrodiferulic acid

Description

5-5'-dehydrodiferulic acid, also known as 8-O-4'-diferulic acid, belongs to biphenyls and derivatives class of compounds. Those are organic compounds containing to benzene rings linked together by a C-C bond. 5-5'-dehydrodiferulic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 5-5'-dehydrodiferulic acid can be found in a number of food items such as corn, common wheat, semolina, and hard wheat, which makes 5-5'-dehydrodiferulic acid a potential biomarker for the consumption of these food products.

Structure

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


  Mrv0541 02241223392D          

 28 29  0  0  0  0            999 V2000
   -0.6813    2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031    1.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031    0.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248    0.5606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031   -1.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031   -0.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248   -0.5606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031    1.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6813    2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397    1.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397    0.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813    0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813   -0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405   -0.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397   -1.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6813   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031   -1.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248   -2.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7664    1.6032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248    2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248    2.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7664   -1.6032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664    1.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0446    2.0844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0446   -2.0844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664   -1.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 11  2  0  0  0  0
  2  3  2  0  0  0  0
  2 26  1  0  0  0  0
  3  4  1  0  0  0  0
  3 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5 16  2  0  0  0  0
  6  7  2  0  0  0  0
  6 27  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  9 10  2  0  0  0  0
  9 22  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0301718
     RDKit          3D
5-5'-Dehydrodiferulic acid
 46 47  0  0  0  0  0  0  0  0999 V2000
    4.7044    2.6744    1.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3053    2.6398    1.7851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6729    1.6771    1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4074    0.7505    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7794   -0.2212   -0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393   -1.1797   -1.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1860   -2.1466   -1.8720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1107   -3.0955   -2.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6252   -3.9962   -3.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -3.0185   -2.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4177   -0.2118   -0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271    0.7329    0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8233    0.6780    0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423   -0.4020    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9054   -0.4799    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291   -1.5947    1.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0472   -2.5905    1.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342   -3.6981    2.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2876   -4.6288    2.8042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2240   -3.7128    2.0616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5508    0.5546   -0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955    1.6317   -0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491    2.6571   -1.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9608    2.5687   -1.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043    1.6770   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8077    2.7492   -1.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125    1.6624    0.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5937    2.6226    1.5959 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0318    3.5618    2.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336    1.7822    2.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1012    2.6732    0.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4848    0.7822    0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7269   -1.1057   -0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1221   -2.2276   -2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8230   -3.1358   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9180   -0.9597   -1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214   -1.1438    1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7248   -1.5880    0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9836   -2.6266    1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902   -4.6293    1.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297    0.4763   -0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4241    2.5021   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1720    1.6601   -2.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2923    3.4906   -2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1935    2.8487   -1.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    3.3394    2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 15 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 12 27  2  0
 27 28  1  0
 27  3  1  0
 25 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  6 33  1  0
  7 34  1  0
 10 35  1  0
 11 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
 21 41  1  0
 24 42  1  0
 24 43  1  0
 24 44  1  0
 26 45  1  0
 28 46  1  0
M  END


  Mrv0541 02241223392D          

 28 29  0  0  0  0            999 V2000
   -0.6813    2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031    1.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031    0.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248    0.5606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031   -1.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031   -0.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248   -0.5606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031    1.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6813    2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397    1.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397    0.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813    0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813   -0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405   -0.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397   -1.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6813   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031   -1.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248   -2.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7664    1.6032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248    2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248    2.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7664   -1.6032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664    1.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0446    2.0844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0446   -2.0844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664   -1.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 11  2  0  0  0  0
  2  3  2  0  0  0  0
  2 26  1  0  0  0  0
  3  4  1  0  0  0  0
  3 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5 16  2  0  0  0  0
  6  7  2  0  0  0  0
  6 27  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  9 10  2  0  0  0  0
  9 22  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301718

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C(=CC(\C=C\C(O)=O)=C1)C1=CC(\C=C\C(O)=O)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O8/c1-27-15-9-11(3-5-17(21)22)7-13(19(15)25)14-8-12(4-6-18(23)24)10-16(28-2)20(14)26/h3-10,25-26H,1-2H3,(H,21,22)(H,23,24)/b5-3+,6-4+

> <INCHI_KEY>
LBQZVWQOPFFQJI-GGWOSOGESA-N

> <FORMULA>
C20H18O8

> <MOLECULAR_WEIGHT>
386.3521

> <EXACT_MASS>
386.100167552

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
39.08654381216658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(3-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxy-3-methoxyphenyl}-4-hydroxy-5-methoxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
3.023678891333333

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.9169799573211455

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.305431780769453

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5967981212061

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
102.08619999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diferulic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301718
     RDKit          3D
5-5'-Dehydrodiferulic acid
 46 47  0  0  0  0  0  0  0  0999 V2000
    4.7044    2.6744    1.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3053    2.6398    1.7851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6729    1.6771    1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4074    0.7505    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7794   -0.2212   -0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393   -1.1797   -1.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1860   -2.1466   -1.8720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1107   -3.0955   -2.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6252   -3.9962   -3.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -3.0185   -2.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4177   -0.2118   -0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271    0.7329    0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8233    0.6780    0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423   -0.4020    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9054   -0.4799    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291   -1.5947    1.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0472   -2.5905    1.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342   -3.6981    2.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2876   -4.6288    2.8042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2240   -3.7128    2.0616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5508    0.5546   -0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955    1.6317   -0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491    2.6571   -1.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9608    2.5687   -1.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043    1.6770   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8077    2.7492   -1.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125    1.6624    0.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5937    2.6226    1.5959 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0318    3.5618    2.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336    1.7822    2.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1012    2.6732    0.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4848    0.7822    0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7269   -1.1057   -0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1221   -2.2276   -2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8230   -3.1358   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9180   -0.9597   -1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214   -1.1438    1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7248   -1.5880    0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9836   -2.6266    1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902   -4.6293    1.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297    0.4763   -0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4241    2.5021   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1720    1.6601   -2.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2923    3.4906   -2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1935    2.8487   -1.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    3.3394    2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 15 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 12 27  2  0
 27 28  1  0
 27  3  1  0
 25 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  6 33  1  0
  7 34  1  0
 10 35  1  0
 11 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
 21 41  1  0
 24 42  1  0
 24 43  1  0
 24 44  1  0
 26 45  1  0
 28 46  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.272   3.741   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.619   3.142   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.619   1.496   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.966   1.046   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.272  -3.741   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.619  -3.142   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.619  -1.496   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.966  -1.046   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.619   2.993   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.272   3.741   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.074   2.993   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.074   1.496   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.272   0.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.272  -0.747   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.076  -1.496   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.074  -2.993   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.272  -3.741   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.619  -2.993   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.966  -3.741   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.966  -5.238   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.164   2.993   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.966   3.741   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.966   5.238   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.164  -2.993   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.164   3.292   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.817   3.891   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -3.817  -3.891   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.164  -3.292   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3   26                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3                                                            
CONECT    5    6   16                                                       
CONECT    6    5    7   27                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7                                                            
CONECT    9   10   22                                                       
CONECT   10    9   11                                                       
CONECT   11    1   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13    3   12   14                                                  
CONECT   14    7   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16    5   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19                                                            
CONECT   21   22                                                            
CONECT   22    9   21   23                                                  
CONECT   23   22                                                            
CONECT   24   19                                                            
CONECT   25   26                                                            
CONECT   26    2   25                                                       
CONECT   27    6   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0301718
HETATM    1  C1  UNL     1       4.704   2.674   1.900  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.305   2.640   1.785  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.673   1.677   1.011  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.407   0.751   0.352  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.779  -0.221  -0.429  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.639  -1.180  -1.099  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.186  -2.147  -1.872  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.111  -3.096  -2.529  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.625  -3.996  -3.256  1.00  0.00           O  
HETATM   10  O3  UNL     1       5.479  -3.018  -2.367  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.418  -0.212  -0.511  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.627   0.733   0.158  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.823   0.678   0.035  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.542  -0.402   0.579  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.905  -0.480   0.470  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.629  -1.595   1.028  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.047  -2.590   1.663  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.834  -3.698   2.209  1.00  0.00           C  
HETATM   19  O4  UNL     1      -3.288  -4.629   2.804  1.00  0.00           O  
HETATM   20  O5  UNL     1      -5.224  -3.713   2.062  1.00  0.00           O  
HETATM   21  C16 UNL     1      -3.551   0.555  -0.202  1.00  0.00           C  
HETATM   22  C17 UNL     1      -2.895   1.632  -0.751  1.00  0.00           C  
HETATM   23  O6  UNL     1      -3.549   2.657  -1.417  1.00  0.00           O  
HETATM   24  C18 UNL     1      -4.961   2.569  -1.523  1.00  0.00           C  
HETATM   25  C19 UNL     1      -1.504   1.677  -0.620  1.00  0.00           C  
HETATM   26  O7  UNL     1      -0.808   2.749  -1.162  1.00  0.00           O  
HETATM   27  C20 UNL     1       1.312   1.662   0.911  1.00  0.00           C  
HETATM   28  O8  UNL     1       0.594   2.623   1.596  1.00  0.00           O  
HETATM   29  H1  UNL     1       5.032   3.562   2.460  1.00  0.00           H  
HETATM   30  H2  UNL     1       5.134   1.782   2.391  1.00  0.00           H  
HETATM   31  H3  UNL     1       5.101   2.673   0.853  1.00  0.00           H  
HETATM   32  H4  UNL     1       4.485   0.782   0.448  1.00  0.00           H  
HETATM   33  H5  UNL     1       4.727  -1.106  -0.961  1.00  0.00           H  
HETATM   34  H6  UNL     1       2.122  -2.228  -2.013  1.00  0.00           H  
HETATM   35  H7  UNL     1       5.823  -3.136  -1.402  1.00  0.00           H  
HETATM   36  H8  UNL     1       0.918  -0.960  -1.114  1.00  0.00           H  
HETATM   37  H9  UNL     1      -0.921  -1.144   1.079  1.00  0.00           H  
HETATM   38  H10 UNL     1      -4.725  -1.588   0.901  1.00  0.00           H  
HETATM   39  H11 UNL     1      -1.984  -2.627   1.801  1.00  0.00           H  
HETATM   40  H12 UNL     1      -5.690  -4.629   1.987  1.00  0.00           H  
HETATM   41  H13 UNL     1      -4.630   0.476  -0.278  1.00  0.00           H  
HETATM   42  H14 UNL     1      -5.424   2.502  -0.516  1.00  0.00           H  
HETATM   43  H15 UNL     1      -5.172   1.660  -2.111  1.00  0.00           H  
HETATM   44  H16 UNL     1      -5.292   3.491  -2.061  1.00  0.00           H  
HETATM   45  H17 UNL     1       0.193   2.849  -1.109  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.004   3.339   2.167  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3
CONECT    3    4    4   27
CONECT    4    5   32
CONECT    5    6   11   11
CONECT    6    7    7   33
CONECT    7    8   34
CONECT    8    9    9   10
CONECT   10   35
CONECT   11   12   36
CONECT   12   13   27   27
CONECT   13   14   14   25
CONECT   14   15   37
CONECT   15   16   21   21
CONECT   16   17   17   38
CONECT   17   18   39
CONECT   18   19   19   20
CONECT   20   40
CONECT   21   22   41
CONECT   22   23   25   25
CONECT   23   24
CONECT   24   42   43   44
CONECT   25   26
CONECT   26   45
CONECT   27   28
CONECT   28   46
END

HMDB0301718
     RDKit          3D
5-5'-Dehydrodiferulic acid
 46 47  0  0  0  0  0  0  0  0999 V2000
    4.7044    2.6744    1.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3053    2.6398    1.7851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6729    1.6771    1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4074    0.7505    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7794   -0.2212   -0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393   -1.1797   -1.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1860   -2.1466   -1.8720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1107   -3.0955   -2.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6252   -3.9962   -3.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -3.0185   -2.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4177   -0.2118   -0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271    0.7329    0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8233    0.6780    0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423   -0.4020    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9054   -0.4799    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291   -1.5947    1.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0472   -2.5905    1.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342   -3.6981    2.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2876   -4.6288    2.8042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2240   -3.7128    2.0616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5508    0.5546   -0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955    1.6317   -0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491    2.6571   -1.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9608    2.5687   -1.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043    1.6770   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8077    2.7492   -1.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125    1.6624    0.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5937    2.6226    1.5959 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0318    3.5618    2.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336    1.7822    2.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1012    2.6732    0.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4848    0.7822    0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7269   -1.1057   -0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1221   -2.2276   -2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8230   -3.1358   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9180   -0.9597   -1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214   -1.1438    1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7248   -1.5880    0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9836   -2.6266    1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902   -4.6293    1.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297    0.4763   -0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4241    2.5021   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1720    1.6601   -2.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2923    3.4906   -2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1935    2.8487   -1.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    3.3394    2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 15 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 12 27  2  0
 27 28  1  0
 27  3  1  0
 25 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  6 33  1  0
  7 34  1  0
 10 35  1  0
 11 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
 21 41  1  0
 24 42  1  0
 24 43  1  0
 24 44  1  0
 26 45  1  0
 28 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E)-3-{5'-[(1E)-2-carboxyeth-1-en-1-yl]-2',6-dihydroxy-3',5-dimethoxy-[1,1'-biphenyl]-3-yl}prop-2-enoate	Generator
5-5'-Dehydrodiferulate	Generator
8-O-4'-Diferulic acid	MeSH
8-5'-Diferulic acid	MeSH
8-5'-b Diferulic acid	MeSH

Chemical Formula

C₂₀H₁₈O₈

Average Molecular Weight

386.3521

Monoisotopic Molecular Weight

386.100167552

IUPAC Name

(2E)-3-(3-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxy-3-methoxyphenyl}-4-hydroxy-5-methoxyphenyl)prop-2-enoic acid

Traditional Name

diferulic acid

CAS Registry Number

Not Available

SMILES

COC1=C(O)C(=CC(\C=C\C(O)=O)=C1)C1=CC(\C=C\C(O)=O)=CC(OC)=C1O

InChI Identifier

InChI=1S/C20H18O8/c1-27-15-9-11(3-5-17(21)22)7-13(19(15)25)14-8-12(4-6-18(23)24)10-16(28-2)20(14)26/h3-10,25-26H,1-2H3,(H,21,22)(H,23,24)/b5-3+,6-4+

InChI Key

LBQZVWQOPFFQJI-GGWOSOGESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Biphenyls and derivatives

Alternative Parents

Substituents

Biphenyl
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid
Hydroxycinnamic acid or derivatives
Methoxyphenol
Anisole
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Phenol
Dicarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ferulic acid (CHEBI:27420 )
Neolignans (C10446 )

Ontology

Not Available

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)
Corn (FooDB: FOOD00205)
Oat (FooDB: FOOD00022)
Rye (FooDB: FOOD00169)
Common wheat (FooDB: FOOD00187)
Hard wheat (FooDB: FOOD00242)

Cereal product

Semolina (FooDB: FOOD00745)

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	2.99	ALOGPS
logP	3.02	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	102.09 m³·mol⁻¹	ChemAxon
Polarizability	39.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	191.708	32859911
AllCCS	[M+H-H2O]+	188.779	32859911
AllCCS	[M+Na]+	195.189	32859911
AllCCS	[M+NH4]+	194.413	32859911
AllCCS	[M-H]-	189.643	32859911
AllCCS	[M+Na-2H]-	189.744	32859911
AllCCS	[M+HCOO]-	190.007	32859911
DeepCCS	[M+H]+	185.917	30932474
DeepCCS	[M-H]-	183.559	30932474
DeepCCS	[M-2H]-	217.278	30932474
DeepCCS	[M+Na]+	192.39	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 - 5-5'-Dehydrodiferulic acid 10V, Positive-QTOF	splash10-00kr-0009000000-d85c9cd7d779cbb13cd5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-5'-Dehydrodiferulic acid 20V, Positive-QTOF	splash10-00to-0019000000-424056ed345e5e27507d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-5'-Dehydrodiferulic acid 40V, Positive-QTOF	splash10-05nb-1092000000-6e6087e1a0fe84a224b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-5'-Dehydrodiferulic acid 10V, Negative-QTOF	splash10-000i-0009000000-53f37140b678ecc22005	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-5'-Dehydrodiferulic acid 20V, Negative-QTOF	splash10-000l-0409000000-8c55934149c7f7d6b5c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-5'-Dehydrodiferulic acid 40V, Negative-QTOF	splash10-004l-2905000000-fc1ef99a4bce98927953	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-5'-Dehydrodiferulic acid 10V, Positive-QTOF	splash10-014r-0009000000-fd497a558934a7ae9a74	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-5'-Dehydrodiferulic acid 20V, Positive-QTOF	splash10-00kr-0009000000-751294a3942fc8914698	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-5'-Dehydrodiferulic acid 40V, Positive-QTOF	splash10-00te-0039000000-9abbf7d297c32e80c804	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-5'-Dehydrodiferulic acid 10V, Negative-QTOF	splash10-002k-0059000000-b0468f7e67b529055b51	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-5'-Dehydrodiferulic acid 20V, Negative-QTOF	splash10-0002-0095000000-3126232d3e36cd932974	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-5'-Dehydrodiferulic acid 40V, Negative-QTOF	splash10-004j-0079000000-21f7ca5e5f2d54b1cbe0	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 5-5'-Dehydrodiferulic acid (HMDB0301718)

MOL for HMDB0301718 (5-5'-Dehydrodiferulic acid)

3D MOL for HMDB0301718 (5-5'-Dehydrodiferulic acid)

3D SDF for HMDB0301718 (5-5'-Dehydrodiferulic acid)

3D-SDF for HMDB0301718 (5-5'-Dehydrodiferulic acid)

PDB for HMDB0301718 (5-5'-Dehydrodiferulic acid)

3D PDB for HMDB0301718 (5-5'-Dehydrodiferulic acid)

SMILES for HMDB0301718 (5-5'-Dehydrodiferulic acid)

INCHI for HMDB0301718 (5-5'-Dehydrodiferulic acid)

Structure for HMDB0301718 (5-5'-Dehydrodiferulic acid)

3D Structure for HMDB0301718 (5-5'-Dehydrodiferulic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra