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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:32:28 UTC

Update Date

2022-03-07 02:53:51 UTC

HMDB ID

HMDB0033779

Secondary Accession Numbers

HMDB33779

Metabolite Identification

Common Name

Piperic acid

Description

Piperic acid, also known as piperate, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Piperic acid has been detected, but not quantified in, herbs and spices and pepper (spice). This could make piperic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Piperic acid.

Structure

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


  Mrv0541 05061307212D          

 16 17  0  0  0  0            999 V2000
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  5  2  0  0  0  0
  9  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12  4  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16  8  1  0  0  0  0
 16 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033779

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)\C=C\C=C/C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O4/c13-12(14)4-2-1-3-9-5-6-10-11(7-9)16-8-15-10/h1-7H,8H2,(H,13,14)/b3-1-,4-2+

> <INCHI_KEY>
RHBGITBPARBDPH-HSFFGMMNSA-N

> <FORMULA>
C12H10O4

> <MOLECULAR_WEIGHT>
218.2054

> <EXACT_MASS>
218.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
21.474786156036856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4Z)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.286535400999999

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.816675999041073

> <JCHEM_PKA_STRONGEST_BASIC>
-4.741141031886499

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
59.14540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4Z)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      10.122   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.122   4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      12.789   4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    9                                                       
CONECT    4    2   12                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    9   11                                                       
CONECT    8   15   16                                                       
CONECT    9    3    5    7                                                  
CONECT   10    6   11   15                                                  
CONECT   11    7   10   16                                                  
CONECT   12    4   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    8   10                                                       
CONECT   16    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0033779
HETATM    1  O1  UNL     1       3.564  -1.486   1.673  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.309  -0.677   1.069  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.670  -0.783   1.258  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.693   0.318   0.212  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.367   0.390   0.054  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.753   1.365  -0.788  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.497   1.505  -0.957  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.554   0.744  -0.341  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.552   0.076   0.842  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.618  -0.721   1.269  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.750  -0.881   0.519  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.790  -0.215  -0.687  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.746   0.560  -1.100  1.00  0.00           C  
HETATM   14  O3  UNL     1      -4.042  -0.551  -1.235  1.00  0.00           O  
HETATM   15  C12 UNL     1      -4.900  -1.059  -0.229  1.00  0.00           C  
HETATM   16  O4  UNL     1      -3.936  -1.586   0.675  1.00  0.00           O  
HETATM   17  H1  UNL     1       6.249  -0.027   0.882  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.287   1.033  -0.327  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.842  -0.387   0.569  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.485   2.037  -1.319  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.205   2.325  -1.673  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.282   0.221   1.534  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.534  -1.213   2.210  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.790   1.075  -2.041  1.00  0.00           H  
HETATM   25  H9  UNL     1      -5.412  -0.225   0.274  1.00  0.00           H  
HETATM   26  H10 UNL     1      -5.580  -1.838  -0.609  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5    5   18
CONECT    5    6   19
CONECT    6    7    7   20
CONECT    7    8   21
CONECT    8    9    9   13
CONECT    9   10   22
CONECT   10   11   11   23
CONECT   11   12   16
CONECT   12   13   13   14
CONECT   13   24
CONECT   14   15
CONECT   15   16   25   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Piperate	Generator
2,4-Pentadienoic acid, 5-(1,3-benzodioxol-5-yl)- (9ci)	HMDB
5-(1,3-Benzenedioxol-5-yl)-2,4-pentadienoic acid, 9ci	HMDB
5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoic acid	HMDB
5-(1,3-Benzodioxol-5-yl)penta-2,4-dienoic acid	HMDB
Piperic acid (8ci)	HMDB
Piperic acid, 8ci	HMDB
Piperinic acid	HMDB
Piperonic acid	HMDB
(2E,4Z)-5-(2H-1,3-Benzodioxol-5-yl)penta-2,4-dienoate	Generator

Chemical Formula

C₁₂H₁₀O₄

Average Molecular Weight

218.2054

Monoisotopic Molecular Weight

218.057908808

IUPAC Name

(2E,4Z)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid

Traditional Name

(2E,4Z)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid

CAS Registry Number

5285-18-7

SMILES

OC(=O)\C=C\C=C/C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C12H10O4/c13-12(14)4-2-1-3-9-5-6-10-11(7-9)16-8-15-10/h1-7H,8H2,(H,13,14)/b3-1-,4-2+

InChI Key

RHBGITBPARBDPH-HSFFGMMNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Styrene
Medium-chain fatty acid
Heterocyclic fatty acid
Unsaturated fatty acid
Benzenoid
Fatty acid
Fatty acyl
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033779)
Cell membrane (HMDB: HMDB0033779)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033779)

Source

Exogenous

Exogenous (HMDB: HMDB0033779)

Food

Food (HMDB: HMDB0033779)

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033779)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033779)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	215 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	291.7 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	0.31 g/L	ALOGPS
logP	2.79	ALOGPS
logP	2.29	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.82	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.15 m³·mol⁻¹	ChemAxon
Polarizability	21.47 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
DarkChem	[M+H]+	151.362	31661259
DarkChem	[M-H]-	152.057	31661259
DeepCCS	[M+H]+	147.921	30932474
DeepCCS	[M-H]-	145.526	30932474
DeepCCS	[M-2H]-	178.813	30932474
DeepCCS	[M+Na]+	153.834	30932474
AllCCS	[M+H]+	147.4	32859911
AllCCS	[M+H-H2O]+	143.3	32859911
AllCCS	[M+NH4]+	151.2	32859911
AllCCS	[M+Na]+	152.3	32859911
AllCCS	[M-H]-	148.5	32859911
AllCCS	[M+Na-2H]-	148.4	32859911
AllCCS	[M+HCOO]-	148.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piperic acid	OC(=O)\C=C\C=C/C1=CC2=C(OCO2)C=C1	3601.6	Standard polar	33892256
Piperic acid	OC(=O)\C=C\C=C/C1=CC2=C(OCO2)C=C1	1895.6	Standard non polar	33892256
Piperic acid	OC(=O)\C=C\C=C/C1=CC2=C(OCO2)C=C1	2160.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Piperic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C/C=C\C1=CC=C2OCOC2=C1	2209.0	Semi standard non polar	33892256
Piperic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C=C\C1=CC=C2OCOC2=C1	2444.4	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 - Piperic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1930000000-b89f6f6e141be7a35250	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-6590000000-00f335d6958aff048805	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperic 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 - Piperic acid 10V, Positive-QTOF	splash10-0gb9-0290000000-754ab183d5924e215f42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperic acid 20V, Positive-QTOF	splash10-0fk9-2970000000-98c9a65a7364bbc669a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperic acid 40V, Positive-QTOF	splash10-0fi0-5900000000-842d5fe0cc2f2f0aa750	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperic acid 10V, Negative-QTOF	splash10-014i-0290000000-fdd952a8dad85ffb328a	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperic acid 20V, Negative-QTOF	splash10-01b9-0970000000-272641c3b38064a63a3a	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperic acid 40V, Negative-QTOF	splash10-006w-2900000000-e5ab3b143eac4f82ef30	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperic acid 10V, Positive-QTOF	splash10-014i-0390000000-aef6c9f063a6b9f37700	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperic acid 20V, Positive-QTOF	splash10-00di-0920000000-f090f170a98649ab1f98	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperic acid 40V, Positive-QTOF	splash10-0fba-4900000000-a77706a23c99f84076bc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperic acid 10V, Negative-QTOF	splash10-014i-0290000000-8744f4a258d60b707067	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperic acid 20V, Negative-QTOF	splash10-014i-0890000000-9d48d134708fdf43617b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperic acid 40V, Negative-QTOF	splash10-0604-3900000000-bebf3e031317e4fa216a	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

Not Available

FooDB ID

FDB011933

KNApSAcK ID

C00054825

Chemspider ID

22902400

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piperic acid

METLIN ID

Not Available

PubChem Compound

13001421

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1838361

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Piperic acid (HMDB0033779)

MOL for HMDB0033779 (Piperic acid)

3D MOL for HMDB0033779 (Piperic acid)

3D SDF for HMDB0033779 (Piperic acid)

3D-SDF for HMDB0033779 (Piperic acid)

PDB for HMDB0033779 (Piperic acid)

3D PDB for HMDB0033779 (Piperic acid)

SMILES for HMDB0033779 (Piperic acid)

INCHI for HMDB0033779 (Piperic acid)

Structure for HMDB0033779 (Piperic acid)

3D Structure for HMDB0033779 (Piperic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra