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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:29:23 UTC

Update Date

2022-03-07 02:52:06 UTC

HMDB ID

HMDB0029277

Secondary Accession Numbers

HMDB29277

Metabolite Identification

Common Name

8-8'-Dehydrodiferulic acid

Description

8-8'-Dehydrodiferulic acid belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Based on a literature review very few articles have been published on 8-8'-Dehydrodiferulic acid.

Structure

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


  Mrv0541 05061304432D          

 28 29  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  4  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  2  0  0  0  0
 14  8  2  0  0  0  0
 14 13  1  0  0  0  0
 15  5  1  0  0  0  0
 16  6  1  0  0  0  0
 17  9  1  0  0  0  0
 17 15  2  0  0  0  0
 18 10  1  0  0  0  0
 18 16  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  1  0  0  0  0
 23 19  2  0  0  0  0
 24 19  1  0  0  0  0
 25 20  2  0  0  0  0
 26 20  1  0  0  0  0
 27  1  1  0  0  0  0
 27 17  1  0  0  0  0
 28  2  1  0  0  0  0
 28 18  1  0  0  0  0
M  END

HMDB0029277
     RDKit          3D
8-8'-Dehydrodiferulic acid
 46 47  0  0  0  0  0  0  0  0999 V2000
   -5.5974    1.4836   -1.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7456    0.2812   -0.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6612   -0.1154    0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4806    0.6016    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4168    0.1900    1.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255    0.9999    1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204    0.7070    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0038   -0.5025   -0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872   -1.1504   -0.6797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2595   -1.2067   -0.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862    1.5069    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710    1.4648    0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650    0.6872   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3720    0.8149   -1.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9519    0.0586   -2.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9458   -0.8660   -2.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215   -1.6232   -3.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550   -1.0135   -1.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3419   -1.9235   -0.9628 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8494   -2.1766    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7670   -0.2492   -0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9507    2.4442    2.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9601    3.1310    2.5963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2216    2.5367    2.9095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5766   -1.0021    1.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7527   -1.7059    1.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8127   -1.2958    0.9229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0071   -2.0209    0.8508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2498    2.3280   -0.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5743    1.7108   -1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8584    1.3682   -2.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3948    1.5149   -0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4193    1.9355    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6053   -1.0665   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0297    2.1789    1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6066    1.5282   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6554    0.1486   -3.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2377   -2.2811   -3.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6849   -1.4860    0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995   -2.0886    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2951   -3.2030    0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0920   -0.3723    0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244    3.3342    3.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224   -1.2970    2.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8413   -2.6165    2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7539   -1.6920    0.2836 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
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 11 22  1  0
 22 23  2  0
 22 24  1  0
  5 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27  3  1  0
 21 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  6 33  1  0
 10 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 24 43  1  0
 25 44  1  0
 26 45  1  0
 28 46  1  0
M  END


  Mrv0541 05061304432D          

 28 29  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  4  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  2  0  0  0  0
 14  8  2  0  0  0  0
 14 13  1  0  0  0  0
 15  5  1  0  0  0  0
 16  6  1  0  0  0  0
 17  9  1  0  0  0  0
 17 15  2  0  0  0  0
 18 10  1  0  0  0  0
 18 16  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  1  0  0  0  0
 23 19  2  0  0  0  0
 24 19  1  0  0  0  0
 25 20  2  0  0  0  0
 26 20  1  0  0  0  0
 27  1  1  0  0  0  0
 27 17  1  0  0  0  0
 28  2  1  0  0  0  0
 28 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029277

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C(\C(O)=O)/C(=C/C2=CC(OC)=C(O)C=C2)/C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O8/c1-27-17-9-11(3-5-15(17)21)7-13(19(23)24)14(20(25)26)8-12-4-6-16(22)18(10-12)28-2/h3-10,21-22H,1-2H3,(H,23,24)(H,25,26)/b13-7-,14-8+

> <INCHI_KEY>
SPKZMOSDXTYXLK-MFUUIURDSA-N

> <FORMULA>
C20H18O8

> <MOLECULAR_WEIGHT>
386.3521

> <EXACT_MASS>
386.100167552

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
37.13218245857849

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,3E)-bis[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioic acid

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
2.7879370913333332

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.6403447784729437

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.79245485615123

> <JCHEM_PKA_STRONGEST_BASIC>
-4.59306972465365

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
100.71799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,3E)-bis[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029277
     RDKit          3D
8-8'-Dehydrodiferulic acid
 46 47  0  0  0  0  0  0  0  0999 V2000
   -5.5974    1.4836   -1.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7456    0.2812   -0.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6612   -0.1154    0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4806    0.6016    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4168    0.1900    1.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255    0.9999    1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204    0.7070    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0038   -0.5025   -0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872   -1.1504   -0.6797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2595   -1.2067   -0.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862    1.5069    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710    1.4648    0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650    0.6872   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3720    0.8149   -1.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9519    0.0586   -2.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9458   -0.8660   -2.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215   -1.6232   -3.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550   -1.0135   -1.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3419   -1.9235   -0.9628 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8494   -2.1766    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7670   -0.2492   -0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9507    2.4442    2.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9601    3.1310    2.5963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2216    2.5367    2.9095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5766   -1.0021    1.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7527   -1.7059    1.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8127   -1.2958    0.9229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0071   -2.0209    0.8508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2498    2.3280   -0.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5743    1.7108   -1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8584    1.3682   -2.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3948    1.5149   -0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4193    1.9355    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6053   -1.0665   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0297    2.1789    1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6066    1.5282   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6554    0.1486   -3.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2377   -2.2811   -3.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6849   -1.4860    0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995   -2.0886    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2951   -3.2030    0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0920   -0.3723    0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244    3.3342    3.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224   -1.2970    2.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8413   -2.6165    2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7539   -1.6920    0.2836 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
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 11 22  1  0
 22 23  2  0
 22 24  1  0
  5 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27  3  1  0
 21 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  6 33  1  0
 10 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 24 43  1  0
 25 44  1  0
 26 45  1  0
 28 46  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
CONECT    1   27                                                            
CONECT    2   28                                                            
CONECT    3    5   11                                                       
CONECT    4    6   12                                                       
CONECT    5    3   15                                                       
CONECT    6    4   16                                                       
CONECT    7   11   13                                                       
CONECT    8   12   14                                                       
CONECT    9   11   17                                                       
CONECT   10   12   18                                                       
CONECT   11    3    7    9                                                  
CONECT   12    4    8   10                                                  
CONECT   13    7   14   19                                                  
CONECT   14    8   13   20                                                  
CONECT   15    5   17   21                                                  
CONECT   16    6   18   22                                                  
CONECT   17    9   15   27                                                  
CONECT   18   10   16   28                                                  
CONECT   19   13   23   24                                                  
CONECT   20   14   25   26                                                  
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23   19                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
CONECT   26   20                                                            
CONECT   27    1   17                                                       
CONECT   28    2   18                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0029277
HETATM    1  C1  UNL     1      -5.597   1.484  -1.301  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.746   0.281  -0.566  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.661  -0.115   0.205  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.481   0.602   0.276  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.417   0.190   1.047  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.226   1.000   1.173  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.020   0.707   0.638  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.004  -0.502  -0.115  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.887  -1.150  -0.680  1.00  0.00           O  
HETATM   10  O3  UNL     1      -1.260  -1.207  -0.332  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.086   1.507   1.051  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.271   1.465   0.523  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.765   0.687  -0.548  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.372   0.815  -1.891  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.952   0.059  -2.863  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.946  -0.866  -2.594  1.00  0.00           C  
HETATM   17  O4  UNL     1       4.521  -1.623  -3.590  1.00  0.00           O  
HETATM   18  C14 UNL     1       4.355  -1.013  -1.272  1.00  0.00           C  
HETATM   19  O5  UNL     1       5.342  -1.923  -0.963  1.00  0.00           O  
HETATM   20  C15 UNL     1       5.849  -2.177   0.323  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.767  -0.249  -0.301  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.951   2.444   2.241  1.00  0.00           C  
HETATM   23  O6  UNL     1       1.960   3.131   2.596  1.00  0.00           O  
HETATM   24  O7  UNL     1      -0.222   2.537   2.909  1.00  0.00           O  
HETATM   25  C18 UNL     1      -2.577  -1.002   1.769  1.00  0.00           C  
HETATM   26  C19 UNL     1      -3.753  -1.706   1.691  1.00  0.00           C  
HETATM   27  C20 UNL     1      -4.813  -1.296   0.923  1.00  0.00           C  
HETATM   28  O8  UNL     1      -6.007  -2.021   0.851  1.00  0.00           O  
HETATM   29  H1  UNL     1      -5.250   2.328  -0.684  1.00  0.00           H  
HETATM   30  H2  UNL     1      -6.574   1.711  -1.797  1.00  0.00           H  
HETATM   31  H3  UNL     1      -4.858   1.368  -2.125  1.00  0.00           H  
HETATM   32  H4  UNL     1      -3.395   1.515  -0.296  1.00  0.00           H  
HETATM   33  H5  UNL     1      -1.419   1.935   1.706  1.00  0.00           H  
HETATM   34  H6  UNL     1      -1.605  -1.066  -1.276  1.00  0.00           H  
HETATM   35  H7  UNL     1       3.030   2.179   1.014  1.00  0.00           H  
HETATM   36  H8  UNL     1       1.607   1.528  -2.090  1.00  0.00           H  
HETATM   37  H9  UNL     1       2.655   0.149  -3.916  1.00  0.00           H  
HETATM   38  H10 UNL     1       5.238  -2.281  -3.350  1.00  0.00           H  
HETATM   39  H11 UNL     1       6.685  -1.486   0.571  1.00  0.00           H  
HETATM   40  H12 UNL     1       5.099  -2.089   1.117  1.00  0.00           H  
HETATM   41  H13 UNL     1       6.295  -3.203   0.340  1.00  0.00           H  
HETATM   42  H14 UNL     1       4.092  -0.372   0.714  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.524   3.334   3.427  1.00  0.00           H  
HETATM   44  H16 UNL     1      -1.722  -1.297   2.366  1.00  0.00           H  
HETATM   45  H17 UNL     1      -3.841  -2.617   2.257  1.00  0.00           H  
HETATM   46  H18 UNL     1      -6.754  -1.692   0.284  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   25   25
CONECT    6    7    7   33
CONECT    7    8   11
CONECT    8    9    9   10
CONECT   10   34
CONECT   11   12   12   22
CONECT   12   13   35
CONECT   13   14   14   21
CONECT   14   15   36
CONECT   15   16   16   37
CONECT   16   17   18
CONECT   17   38
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   39   40   41
CONECT   21   42
CONECT   22   23   23   24
CONECT   24   43
CONECT   25   26   44
CONECT   26   27   27   45
CONECT   27   28
CONECT   28   46
END

HMDB0029277
     RDKit          3D
8-8'-Dehydrodiferulic acid
 46 47  0  0  0  0  0  0  0  0999 V2000
   -5.5974    1.4836   -1.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7456    0.2812   -0.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6612   -0.1154    0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4806    0.6016    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4168    0.1900    1.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255    0.9999    1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204    0.7070    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0038   -0.5025   -0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872   -1.1504   -0.6797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2595   -1.2067   -0.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862    1.5069    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710    1.4648    0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650    0.6872   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3720    0.8149   -1.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9519    0.0586   -2.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9458   -0.8660   -2.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215   -1.6232   -3.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550   -1.0135   -1.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3419   -1.9235   -0.9628 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8494   -2.1766    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7670   -0.2492   -0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9507    2.4442    2.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9601    3.1310    2.5963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2216    2.5367    2.9095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5766   -1.0021    1.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7527   -1.7059    1.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8127   -1.2958    0.9229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0071   -2.0209    0.8508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2498    2.3280   -0.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5743    1.7108   -1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8584    1.3682   -2.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3948    1.5149   -0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4193    1.9355    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6053   -1.0665   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0297    2.1789    1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6066    1.5282   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6554    0.1486   -3.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2377   -2.2811   -3.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6849   -1.4860    0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995   -2.0886    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2951   -3.2030    0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0920   -0.3723    0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244    3.3342    3.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224   -1.2970    2.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8413   -2.6165    2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7539   -1.6920    0.2836 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
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 11 22  1  0
 22 23  2  0
 22 24  1  0
  5 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27  3  1  0
 21 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  6 33  1  0
 10 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 24 43  1  0
 25 44  1  0
 26 45  1  0
 28 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-8'-Dehydrodiferulate	Generator
(2E)-Bis[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioate	HMDB

Chemical Formula

C₂₀H₁₈O₈

Average Molecular Weight

386.3521

Monoisotopic Molecular Weight

386.100167552

IUPAC Name

(2Z,3E)-bis[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioic acid

Traditional Name

(2Z,3E)-bis[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioic acid

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(\C=C(\C(O)=O)/C(=C/C2=CC(OC)=C(O)C=C2)/C(O)=O)=C1

InChI Identifier

InChI=1S/C20H18O8/c1-27-17-9-11(3-5-15(17)21)7-13(19(23)24)14(20(25)26)8-12-4-6-16(22)18(10-12)28-2/h3-10,21-22H,1-2H3,(H,23,24)(H,25,26)/b13-7-,14-8+

InChI Key

SPKZMOSDXTYXLK-MFUUIURDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Norlignan skeleton
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Hydroxycinnamic acid
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Ether
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029277)
Cell membrane (HMDB: HMDB0029277)

Source

Endogenous

Endogenous (HMDB: HMDB0029277)

Exogenous

Food

Food (HMDB: HMDB0029277)

Exogenous (HMDB: HMDB0029277)

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	0.029 g/L	ALOGPS
logP	3.24	ALOGPS
logP	2.79	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	2.79	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	100.72 m³·mol⁻¹	ChemAxon
Polarizability	37.13 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
DeepCCS	[M+H]+	200.099	30932474
DeepCCS	[M-H]-	197.724	30932474
DeepCCS	[M-2H]-	230.609	30932474
DeepCCS	[M+Na]+	206.175	30932474
AllCCS	[M+H]+	191.7	32859911
AllCCS	[M+H-H2O]+	188.6	32859911
AllCCS	[M+NH4]+	194.5	32859911
AllCCS	[M+Na]+	195.3	32859911
AllCCS	[M-H]-	189.5	32859911
AllCCS	[M+Na-2H]-	189.5	32859911
AllCCS	[M+HCOO]-	189.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.99 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4197 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.77 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1957.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	206.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	150.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	96.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	512.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	390.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	135.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	991.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	446.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1186.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	391.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	362.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	206.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	106.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-8'-Dehydrodiferulic acid	COC1=C(O)C=CC(\C=C(\C(O)=O)/C(=C/C2=CC(OC)=C(O)C=C2)/C(O)=O)=C1	6253.5	Standard polar	33892256
8-8'-Dehydrodiferulic acid	COC1=C(O)C=CC(\C=C(\C(O)=O)/C(=C/C2=CC(OC)=C(O)C=C2)/C(O)=O)=C1	3327.4	Standard non polar	33892256
8-8'-Dehydrodiferulic acid	COC1=C(O)C=CC(\C=C(\C(O)=O)/C(=C/C2=CC(OC)=C(O)C=C2)/C(O)=O)=C1	3605.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-8'-Dehydrodiferulic acid,1TMS,isomer #1	COC1=CC(/C=C(C(=O)O)/C(=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)C(=O)O)=CC=C1O	3685.8	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,1TMS,isomer #2	COC1=CC(/C=C(C(=O)O)/C(=C\C2=CC=C(O)C(OC)=C2)C(=O)O[Si](C)(C)C)=CC=C1O	3599.0	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,1TMS,isomer #3	COC1=CC(/C=C(C(=O)O)\C(=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)C(=O)O)=CC=C1O	3685.8	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,1TMS,isomer #4	COC1=CC(/C=C(C(=O)O[Si](C)(C)C)/C(=C\C2=CC=C(O)C(OC)=C2)C(=O)O)=CC=C1O	3599.0	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,2TMS,isomer #1	COC1=CC(/C=C(C(=O)O[Si](C)(C)C)/C(=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)C(=O)O)=CC=C1O	3531.9	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,2TMS,isomer #2	COC1=CC(/C=C(C(=O)O)/C(=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)C(=O)O[Si](C)(C)C)=CC=C1O	3531.9	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,2TMS,isomer #3	COC1=CC(/C=C(C(=O)O)/C(=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)C(=O)O)=CC=C1O[Si](C)(C)C	3596.9	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,2TMS,isomer #4	COC1=CC(/C=C(C(=O)O[Si](C)(C)C)/C(=C\C2=CC=C(O)C(OC)=C2)C(=O)O[Si](C)(C)C)=CC=C1O	3440.2	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,2TMS,isomer #5	COC1=CC(/C=C(C(=O)O[Si](C)(C)C)\C(=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)C(=O)O)=CC=C1O	3531.9	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,2TMS,isomer #6	COC1=CC(/C=C(C(=O)O)\C(=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)C(=O)O[Si](C)(C)C)=CC=C1O	3531.9	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,3TMS,isomer #1	COC1=CC(/C=C(C(=O)O[Si](C)(C)C)/C(=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)C(=O)O[Si](C)(C)C)=CC=C1O	3436.8	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,3TMS,isomer #2	COC1=CC(/C=C(C(=O)O[Si](C)(C)C)/C(=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)C(=O)O)=CC=C1O[Si](C)(C)C	3506.3	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,3TMS,isomer #3	COC1=CC(/C=C(C(=O)O)/C(=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3506.3	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,3TMS,isomer #4	COC1=CC(/C=C(C(=O)O[Si](C)(C)C)\C(=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)C(=O)O[Si](C)(C)C)=CC=C1O	3436.8	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,4TMS,isomer #1	COC1=CC(/C=C(C(=O)O[Si](C)(C)C)/C(=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3472.6	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,1TBDMS,isomer #1	COC1=CC(/C=C(C(=O)O)/C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C(=O)O)=CC=C1O	3977.4	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,1TBDMS,isomer #2	COC1=CC(/C=C(C(=O)O)/C(=C\C2=CC=C(O)C(OC)=C2)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	3928.3	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,1TBDMS,isomer #3	COC1=CC(/C=C(C(=O)O)\C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C(=O)O)=CC=C1O	3977.4	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,1TBDMS,isomer #4	COC1=CC(/C=C(C(=O)O[Si](C)(C)C(C)(C)C)/C(=C\C2=CC=C(O)C(OC)=C2)C(=O)O)=CC=C1O	3928.3	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,2TBDMS,isomer #1	COC1=CC(/C=C(C(=O)O[Si](C)(C)C(C)(C)C)/C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C(=O)O)=CC=C1O	4110.6	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,2TBDMS,isomer #2	COC1=CC(/C=C(C(=O)O)/C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	4111.9	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,2TBDMS,isomer #3	COC1=CC(/C=C(C(=O)O)/C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	4176.2	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,2TBDMS,isomer #4	COC1=CC(/C=C(C(=O)O[Si](C)(C)C(C)(C)C)/C(=C\C2=CC=C(O)C(OC)=C2)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	4041.9	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,2TBDMS,isomer #5	COC1=CC(/C=C(C(=O)O[Si](C)(C)C(C)(C)C)\C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C(=O)O)=CC=C1O	4110.6	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,2TBDMS,isomer #6	COC1=CC(/C=C(C(=O)O)\C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	4111.9	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,3TBDMS,isomer #1	COC1=CC(/C=C(C(=O)O[Si](C)(C)C(C)(C)C)/C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	4243.9	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,3TBDMS,isomer #2	COC1=CC(/C=C(C(=O)O[Si](C)(C)C(C)(C)C)/C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	4291.1	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,3TBDMS,isomer #3	COC1=CC(/C=C(C(=O)O)/C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4291.1	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,3TBDMS,isomer #4	COC1=CC(/C=C(C(=O)O[Si](C)(C)C(C)(C)C)\C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	4243.9	Semi standard non polar	33892256
8-8'-Dehydrodiferulic acid,4TBDMS,isomer #1	COC1=CC(/C=C(C(=O)O[Si](C)(C)C(C)(C)C)/C(=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4428.7	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 - 8-8'-Dehydrodiferulic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ko-0409000000-73deae33c335e184e345	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-8'-Dehydrodiferulic acid GC-MS (4 TMS) - 70eV, Positive	splash10-0bt9-3000029000-fffb0377a23ea253dd4e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-8'-Dehydrodiferulic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-8'-Dehydrodiferulic acid 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 - 8-8'-Dehydrodiferulic acid 10V, Positive-QTOF	splash10-000i-0109000000-9c7609ea8cc607bde9d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-8'-Dehydrodiferulic acid 20V, Positive-QTOF	splash10-00ko-0229000000-2925758ef7b4b0f5d02c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-8'-Dehydrodiferulic acid 40V, Positive-QTOF	splash10-052k-0694000000-2f7413d682542540c85d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-8'-Dehydrodiferulic acid 10V, Negative-QTOF	splash10-000i-0009000000-d891ff7c770d199a2495	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-8'-Dehydrodiferulic acid 20V, Negative-QTOF	splash10-000l-0329000000-46cba6d908bc2a00a765	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-8'-Dehydrodiferulic acid 40V, Negative-QTOF	splash10-004l-0904000000-16d0f7babfe6c40538db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-8'-Dehydrodiferulic acid 10V, Negative-QTOF	splash10-000b-0059000000-2afdeabfedfeb460ca2b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-8'-Dehydrodiferulic acid 20V, Negative-QTOF	splash10-004i-0049000000-f517195a4935f779254d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-8'-Dehydrodiferulic acid 40V, Negative-QTOF	splash10-003r-0169000000-923f6f6b34faa93da1f1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-8'-Dehydrodiferulic acid 10V, Positive-QTOF	splash10-00kr-0209000000-db1ab7cae585ebe0c389	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-8'-Dehydrodiferulic acid 20V, Positive-QTOF	splash10-0adi-1719000000-8f6f8555e16bde401fa8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-8'-Dehydrodiferulic acid 40V, Positive-QTOF	splash10-0a4i-2879000000-51984780b51828710be4	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

517

FooDB ID

FDB000272

KNApSAcK ID

Not Available

Chemspider ID

29336462

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750840

PDB ID

Not Available

ChEBI ID

175914

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 8-8'-Dehydrodiferulic acid (HMDB0029277)

MOL for HMDB0029277 (8-8'-Dehydrodiferulic acid)

3D MOL for HMDB0029277 (8-8'-Dehydrodiferulic acid)

3D SDF for HMDB0029277 (8-8'-Dehydrodiferulic acid)

3D-SDF for HMDB0029277 (8-8'-Dehydrodiferulic acid)

PDB for HMDB0029277 (8-8'-Dehydrodiferulic acid)

3D PDB for HMDB0029277 (8-8'-Dehydrodiferulic acid)

SMILES for HMDB0029277 (8-8'-Dehydrodiferulic acid)

INCHI for HMDB0029277 (8-8'-Dehydrodiferulic acid)

Structure for HMDB0029277 (8-8'-Dehydrodiferulic acid)

3D Structure for HMDB0029277 (8-8'-Dehydrodiferulic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra