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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:10:55 UTC

Update Date

2022-03-07 02:56:40 UTC

HMDB ID

HMDB0040619

Secondary Accession Numbers

HMDB40619

Metabolite Identification

Common Name

Piperoic acid

Description

Piperoic acid, also known as piperoate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on Piperoic acid.

Structure

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


  Mrv0541 02241210252D          

 26 26  0  0  0  0            999 V2000
    3.8103   -1.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1684   -1.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4464   -1.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4464   -0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0881    0.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7242    0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0824   -0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3602    0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3611   -0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3611   -1.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0824    0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464    0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684   -0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    1.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684    1.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464    1.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8045    1.4840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2544   -1.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5324   -1.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5324   -2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2544    0.2002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5324   -0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5324   -1.0025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684    2.2060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 21  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 24  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 26  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
M  END

HMDB0040619
     RDKit          3D
Piperoic acid
 56 56  0  0  0  0  0  0  0  0999 V2000
   -5.7575    1.8270   -0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2502    0.6236   -0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1450    0.6103   -2.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8929   -0.4320   -0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0057   -0.3980    1.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6148   -0.6211    1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1720   -1.9451    1.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0148   -3.1540    1.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1013   -2.2012    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837   -1.1185    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087   -1.3114    0.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0141   -0.1438    0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5779    1.2198    0.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.3820   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8692    0.7352   -1.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2927    0.7141   -0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405    1.5723    0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0570    1.5293    0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5484    2.4304    1.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7493    2.3858    2.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6690    3.3267    2.4342 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9218    0.6252    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5149   -0.2526   -0.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4212   -1.1440   -1.3148 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1900   -0.1807   -1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7108   -1.0292   -2.1195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6638    1.5674    0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9827    2.2840    0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0862    2.5922   -1.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3866   -0.0944   -2.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1151    0.3289   -2.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8141    1.6272   -2.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5122   -1.3482   -0.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4196    0.5540    1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7039   -1.2005    1.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8030   -0.6500    2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9882    0.2180    1.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4898   -3.4646    0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3006   -3.9421    1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7326   -2.8816    2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8887   -3.2512    0.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5624   -0.1100    0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0429   -1.2895   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2396   -1.3419    1.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872   -2.2643    0.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0189    1.6916   -0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1440    1.1737    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041    1.8734    0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3444   -1.3911   -0.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4591    1.7212   -0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586    0.6501   -2.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0205    2.2680    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8567    4.3135    2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9610    0.5986    0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2078   -1.8000   -2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611   -1.7181   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 25 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 21 53  1  0
 22 54  1  0
 24 55  1  0
 26 56  1  0
M  END


  Mrv0541 02241210252D          

 26 26  0  0  0  0            999 V2000
    3.8103   -1.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1684   -1.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4464   -1.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4464   -0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0881    0.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7242    0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0824   -0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3602    0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3611   -0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3611   -1.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0824    0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464    0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684   -0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    1.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684    1.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464    1.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8045    1.4840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2544   -1.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5324   -1.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5324   -2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2544    0.2002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5324   -0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5324   -1.0025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684    2.2060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 21  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 24  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 26  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040619

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC\C(C)=C/CC\C(C)=C\CC1=CC(=CC(O)=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O4/c1-15(2)7-5-8-16(3)9-6-10-17(4)11-12-18-13-19(22(25)26)14-20(23)21(18)24/h7,9,11,13-14,23-24H,5-6,8,10,12H2,1-4H3,(H,25,26)/b16-9-,17-11+

> <INCHI_KEY>
VWHKYMBCXCSQEZ-KKYJLSSQSA-N

> <FORMULA>
C22H30O4

> <MOLECULAR_WEIGHT>
358.4712

> <EXACT_MASS>
358.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
41.39648012309541

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4-dihydroxy-5-[(2E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzoic acid

> <ALOGPS_LOGP>
5.21

> <JCHEM_LOGP>
6.0716936299999995

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.279265526650002

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.1281674458459845

> <JCHEM_PKA_STRONGEST_BASIC>
-6.349574389344849

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
109.12399999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxy-5-[(2E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040619
     RDKit          3D
Piperoic acid
 56 56  0  0  0  0  0  0  0  0999 V2000
   -5.7575    1.8270   -0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2502    0.6236   -0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1450    0.6103   -2.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8929   -0.4320   -0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0057   -0.3980    1.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6148   -0.6211    1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1720   -1.9451    1.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0148   -3.1540    1.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1013   -2.2012    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837   -1.1185    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087   -1.3114    0.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0141   -0.1438    0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5779    1.2198    0.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.3820   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8692    0.7352   -1.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2927    0.7141   -0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405    1.5723    0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0570    1.5293    0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5484    2.4304    1.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7493    2.3858    2.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6690    3.3267    2.4342 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9218    0.6252    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5149   -0.2526   -0.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4212   -1.1440   -1.3148 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1900   -0.1807   -1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7108   -1.0292   -2.1195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6638    1.5674    0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9827    2.2840    0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0862    2.5922   -1.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3866   -0.0944   -2.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1151    0.3289   -2.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8141    1.6272   -2.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5122   -1.3482   -0.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4196    0.5540    1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7039   -1.2005    1.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8030   -0.6500    2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9882    0.2180    1.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4898   -3.4646    0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3006   -3.9421    1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7326   -2.8816    2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8887   -3.2512    0.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5624   -0.1100    0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0429   -1.2895   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2396   -1.3419    1.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872   -2.2643    0.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0189    1.6916   -0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1440    1.1737    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041    1.8734    0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3444   -1.3911   -0.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4591    1.7212   -0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586    0.6501   -2.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0205    2.2680    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8567    4.3135    2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9610    0.5986    0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2078   -1.8000   -2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611   -1.7181   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 25 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 21 53  1  0
 22 54  1  0
 24 55  1  0
 26 56  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       7.113  -1.871   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.914  -2.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.567  -1.871   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.567  -0.374   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.764   0.524   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.219   0.374   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.020  -0.374   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.672   0.374   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.674  -0.374   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.674  -1.871   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.020   0.374   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.219  -0.374   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.567   0.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.914  -0.374   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.262   0.374   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.262   1.871   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.914   2.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.567   1.871   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.368   2.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.808  -1.871   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.460  -2.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.460  -4.118   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -9.808   0.374   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -8.460  -0.374   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -8.460  -1.871   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -5.914   4.118   0.000  0.00  0.00           O+0
CONECT    1    2   21                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   13   17   19                                                  
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21    1   20   22                                                  
CONECT   22   21                                                            
CONECT   23   24                                                            
CONECT   24   15   23   25                                                  
CONECT   25   24                                                            
CONECT   26   17                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

COMPND    HMDB0040619
HETATM    1  C1  UNL     1      -5.758   1.827  -0.288  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.250   0.624  -0.974  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.145   0.610  -2.448  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.893  -0.432  -0.281  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.006  -0.398   1.201  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.615  -0.621   1.807  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.172  -1.945   1.330  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.015  -3.154   1.693  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.101  -2.201   0.607  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.184  -1.118   0.177  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.209  -1.311   0.746  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.014  -0.144   0.226  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.578   1.220   0.575  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.070  -0.382  -0.515  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.869   0.735  -1.032  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.293   0.714  -0.567  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.740   1.572   0.419  1.00  0.00           C  
HETATM   18  C18 UNL     1       6.057   1.529   0.822  1.00  0.00           C  
HETATM   19  C19 UNL     1       6.548   2.430   1.862  1.00  0.00           C  
HETATM   20  O1  UNL     1       7.749   2.386   2.224  1.00  0.00           O  
HETATM   21  O2  UNL     1       5.669   3.327   2.434  1.00  0.00           O  
HETATM   22  C20 UNL     1       6.922   0.625   0.235  1.00  0.00           C  
HETATM   23  C21 UNL     1       6.515  -0.253  -0.755  1.00  0.00           C  
HETATM   24  O3  UNL     1       7.421  -1.144  -1.315  1.00  0.00           O  
HETATM   25  C22 UNL     1       5.190  -0.181  -1.133  1.00  0.00           C  
HETATM   26  O4  UNL     1       4.711  -1.029  -2.119  1.00  0.00           O  
HETATM   27  H1  UNL     1      -6.664   1.567   0.310  1.00  0.00           H  
HETATM   28  H2  UNL     1      -4.983   2.284   0.388  1.00  0.00           H  
HETATM   29  H3  UNL     1      -6.086   2.592  -1.022  1.00  0.00           H  
HETATM   30  H4  UNL     1      -4.387  -0.094  -2.837  1.00  0.00           H  
HETATM   31  H5  UNL     1      -6.115   0.329  -2.909  1.00  0.00           H  
HETATM   32  H6  UNL     1      -4.814   1.627  -2.774  1.00  0.00           H  
HETATM   33  H7  UNL     1      -4.512  -1.348  -0.718  1.00  0.00           H  
HETATM   34  H8  UNL     1      -5.420   0.554   1.573  1.00  0.00           H  
HETATM   35  H9  UNL     1      -5.704  -1.200   1.536  1.00  0.00           H  
HETATM   36  H10 UNL     1      -3.803  -0.650   2.914  1.00  0.00           H  
HETATM   37  H11 UNL     1      -2.988   0.218   1.515  1.00  0.00           H  
HETATM   38  H12 UNL     1      -4.490  -3.465   0.758  1.00  0.00           H  
HETATM   39  H13 UNL     1      -3.301  -3.942   1.997  1.00  0.00           H  
HETATM   40  H14 UNL     1      -4.733  -2.882   2.489  1.00  0.00           H  
HETATM   41  H15 UNL     1      -1.889  -3.251   0.318  1.00  0.00           H  
HETATM   42  H16 UNL     1      -1.562  -0.110   0.250  1.00  0.00           H  
HETATM   43  H17 UNL     1      -1.043  -1.290  -0.943  1.00  0.00           H  
HETATM   44  H18 UNL     1       0.240  -1.342   1.834  1.00  0.00           H  
HETATM   45  H19 UNL     1       0.587  -2.264   0.335  1.00  0.00           H  
HETATM   46  H20 UNL     1       0.019   1.692  -0.275  1.00  0.00           H  
HETATM   47  H21 UNL     1      -0.144   1.174   1.416  1.00  0.00           H  
HETATM   48  H22 UNL     1       1.404   1.873   0.930  1.00  0.00           H  
HETATM   49  H23 UNL     1       2.344  -1.391  -0.739  1.00  0.00           H  
HETATM   50  H24 UNL     1       2.459   1.721  -0.806  1.00  0.00           H  
HETATM   51  H25 UNL     1       2.859   0.650  -2.158  1.00  0.00           H  
HETATM   52  H26 UNL     1       4.020   2.268   0.851  1.00  0.00           H  
HETATM   53  H27 UNL     1       5.857   4.313   2.373  1.00  0.00           H  
HETATM   54  H28 UNL     1       7.961   0.599   0.559  1.00  0.00           H  
HETATM   55  H29 UNL     1       7.208  -1.800  -2.024  1.00  0.00           H  
HETATM   56  H30 UNL     1       5.261  -1.718  -2.603  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    4    4
CONECT    3   30   31   32
CONECT    4    5   33
CONECT    5    6   34   35
CONECT    6    7   36   37
CONECT    7    8    9    9
CONECT    8   38   39   40
CONECT    9   10   41
CONECT   10   11   42   43
CONECT   11   12   44   45
CONECT   12   13   14   14
CONECT   13   46   47   48
CONECT   14   15   49
CONECT   15   16   50   51
CONECT   16   17   17   25
CONECT   17   18   52
CONECT   18   19   22   22
CONECT   19   20   20   21
CONECT   21   53
CONECT   22   23   54
CONECT   23   24   25   25
CONECT   24   55
CONECT   25   26
CONECT   26   56
END

HMDB0040619
     RDKit          3D
Piperoic acid
 56 56  0  0  0  0  0  0  0  0999 V2000
   -5.7575    1.8270   -0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2502    0.6236   -0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1450    0.6103   -2.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8929   -0.4320   -0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0057   -0.3980    1.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6148   -0.6211    1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1720   -1.9451    1.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0148   -3.1540    1.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1013   -2.2012    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837   -1.1185    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087   -1.3114    0.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0141   -0.1438    0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5779    1.2198    0.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.3820   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8692    0.7352   -1.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2927    0.7141   -0.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405    1.5723    0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0570    1.5293    0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5484    2.4304    1.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7493    2.3858    2.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6690    3.3267    2.4342 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9218    0.6252    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5149   -0.2526   -0.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4212   -1.1440   -1.3148 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1900   -0.1807   -1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7108   -1.0292   -2.1195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6638    1.5674    0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9827    2.2840    0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0862    2.5922   -1.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3866   -0.0944   -2.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1151    0.3289   -2.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8141    1.6272   -2.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5122   -1.3482   -0.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4196    0.5540    1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7039   -1.2005    1.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8030   -0.6500    2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9882    0.2180    1.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4898   -3.4646    0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3006   -3.9421    1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7326   -2.8816    2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8887   -3.2512    0.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5624   -0.1100    0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0429   -1.2895   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2396   -1.3419    1.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872   -2.2643    0.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0189    1.6916   -0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1440    1.1737    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041    1.8734    0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3444   -1.3911   -0.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4591    1.7212   -0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586    0.6501   -2.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0205    2.2680    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8567    4.3135    2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9610    0.5986    0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2078   -1.8000   -2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611   -1.7181   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 25 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 21 53  1  0
 22 54  1  0
 24 55  1  0
 26 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Piperoate	Generator
3,4-Dihydroxy-5-(3,7,11-trimethyl-2,6,10-dodecatrienyl)benzoic acid, 9ci	HMDB
3,4-Dihydroxy-5-[(2E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzoate	Generator

Chemical Formula

C₂₂H₃₀O₄

Average Molecular Weight

358.4712

Monoisotopic Molecular Weight

358.214409448

IUPAC Name

3,4-dihydroxy-5-[(2E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzoic acid

Traditional Name

3,4-dihydroxy-5-[(2E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzoic acid

CAS Registry Number

110979-04-9

SMILES

CC(C)=CCC\C(C)=C/CC\C(C)=C\CC1=CC(=CC(O)=C1O)C(O)=O

InChI Identifier

InChI=1S/C22H30O4/c1-15(2)7-5-8-16(3)9-6-10-17(4)11-12-18-13-19(22(25)26)14-20(23)21(18)24/h7,9,11,13-14,23-24H,5-6,8,10,12H2,1-4H3,(H,25,26)/b16-9-,17-11+

InChI Key

VWHKYMBCXCSQEZ-KKYJLSSQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Dihydroxybenzoic acid
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040619)

Source

Endogenous

Endogenous (HMDB: HMDB0040619)

Plant

Plant (HMDB: HMDB0040619)

Animal

Animal (HMDB: HMDB0040619)

Exogenous

Food

Food (HMDB: HMDB0040619)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0040619)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0040619)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0040619)

Lipid metabolism pathway (HMDB: HMDB0040619)

Cellular process

Cell signaling (HMDB: HMDB0040619)

Biochemical process

Lipid transport (HMDB: HMDB0040619)

Role

Biological role

Energy source (HMDB: HMDB0040619)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040619)

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	0.0041 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0074 g/L	ALOGPS
logP	5.21	ALOGPS
logP	6.07	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	109.12 m³·mol⁻¹	ChemAxon
Polarizability	41.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	189.941	30932474
DeepCCS	[M-H]-	187.312	30932474
DeepCCS	[M-2H]-	222.222	30932474
DeepCCS	[M+Na]+	198.512	30932474
AllCCS	[M+H]+	193.8	32859911
AllCCS	[M+H-H2O]+	191.0	32859911
AllCCS	[M+NH4]+	196.4	32859911
AllCCS	[M+Na]+	197.2	32859911
AllCCS	[M-H]-	190.2	32859911
AllCCS	[M+Na-2H]-	190.9	32859911
AllCCS	[M+HCOO]-	191.7	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.	9.28 minutes	32390414
Predicted by Siyang on May 30, 2022	18.3451 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.1 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3135.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	383.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	218.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	193.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	135.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	815.3 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	788.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1644.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	729.7 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	1357.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	549.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	490.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	220.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	335.1 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	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piperoic acid	CC(C)=CCC\C(C)=C/CC\C(C)=C\CC1=CC(=CC(O)=C1O)C(O)=O	4487.9	Standard polar	33892256
Piperoic acid	CC(C)=CCC\C(C)=C/CC\C(C)=C\CC1=CC(=CC(O)=C1O)C(O)=O	2853.8	Standard non polar	33892256
Piperoic acid	CC(C)=CCC\C(C)=C/CC\C(C)=C\CC1=CC(=CC(O)=C1O)C(O)=O	2986.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Piperoic acid,1TMS,isomer #1	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O)=CC(O[Si](C)(C)C)=C1O	2996.4	Semi standard non polar	33892256
Piperoic acid,1TMS,isomer #2	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O)=CC(O)=C1O[Si](C)(C)C	3012.7	Semi standard non polar	33892256
Piperoic acid,1TMS,isomer #3	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC(O)=C1O	2980.1	Semi standard non polar	33892256
Piperoic acid,2TMS,isomer #1	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O	2912.9	Semi standard non polar	33892256
Piperoic acid,2TMS,isomer #2	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	2963.9	Semi standard non polar	33892256
Piperoic acid,2TMS,isomer #3	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC(O)=C1O[Si](C)(C)C	2892.6	Semi standard non polar	33892256
Piperoic acid,3TMS,isomer #1	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	2888.0	Semi standard non polar	33892256
Piperoic acid,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C1O	3248.4	Semi standard non polar	33892256
Piperoic acid,1TBDMS,isomer #2	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O)=CC(O)=C1O[Si](C)(C)C(C)(C)C	3254.8	Semi standard non polar	33892256
Piperoic acid,1TBDMS,isomer #3	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O)=C1O	3244.1	Semi standard non polar	33892256
Piperoic acid,2TBDMS,isomer #1	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1O	3385.0	Semi standard non polar	33892256
Piperoic acid,2TBDMS,isomer #2	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3428.1	Semi standard non polar	33892256
Piperoic acid,2TBDMS,isomer #3	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O)=C1O[Si](C)(C)C(C)(C)C	3362.6	Semi standard non polar	33892256
Piperoic acid,3TBDMS,isomer #1	CC(C)=CCC/C(C)=C\CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3525.0	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 - Piperoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-052u-4794000000-614f946a414526282fa6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperoic acid GC-MS (3 TMS) - 70eV, Positive	splash10-0bti-3200490000-eb06b56b5bd31050dd8e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperoic 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 - Piperoic acid 10V, Positive-QTOF	splash10-0a4l-0209000000-de9d26ec5270b0ed631c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperoic acid 20V, Positive-QTOF	splash10-07i6-3915000000-f291a2e4d7f9663999d5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperoic acid 40V, Positive-QTOF	splash10-0axr-6971000000-bf23c20da4f866ce9332	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperoic acid 10V, Negative-QTOF	splash10-0a4i-0009000000-7260f36534ba6c117207	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperoic acid 20V, Negative-QTOF	splash10-08fr-0009000000-c255cefe5c508b4f87da	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperoic acid 40V, Negative-QTOF	splash10-0a4j-1693000000-19dc8e37b5b5e30464db	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperoic acid 10V, Negative-QTOF	splash10-0a4i-0009000000-2f03955460468a98f0cb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperoic acid 20V, Negative-QTOF	splash10-0avi-0915000000-485c74686f00f247eddc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperoic acid 40V, Negative-QTOF	splash10-00di-0940000000-af9921e98940f228e995	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperoic acid 10V, Positive-QTOF	splash10-0a4i-1339000000-f04e5ab3471be6946af6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperoic acid 20V, Positive-QTOF	splash10-0gb9-1920000000-7f9af0dc095d3710c8ec	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperoic acid 40V, Positive-QTOF	splash10-06di-0900000000-8f05e1b9ef363780f02a	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020410

KNApSAcK ID

C00056456

Chemspider ID

30777494

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13845942

PDB ID

Not Available

ChEBI ID

174808

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1884791

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Piperoic acid (HMDB0040619)

MOL for HMDB0040619 (Piperoic acid)

3D MOL for HMDB0040619 (Piperoic acid)

3D SDF for HMDB0040619 (Piperoic acid)

3D-SDF for HMDB0040619 (Piperoic acid)

PDB for HMDB0040619 (Piperoic acid)

3D PDB for HMDB0040619 (Piperoic acid)

SMILES for HMDB0040619 (Piperoic acid)

INCHI for HMDB0040619 (Piperoic acid)

Structure for HMDB0040619 (Piperoic acid)

3D Structure for HMDB0040619 (Piperoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra