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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:47 UTC

Update Date

2023-02-21 17:22:29 UTC

HMDB ID

HMDB0032613

Secondary Accession Numbers

HMDB32613

Metabolite Identification

Common Name

3,4-Methylenedioxybenzoic acid

Description

3,4-Methylenedioxybenzoic acid, also known as piperonylic acid or 1,3-benzodioxole-5-carboxylic acid, 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. Based on a literature review very few articles have been published on 3,4-Methylenedioxybenzoic acid.

Structure

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

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       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.122   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    5    7                                                       
CONECT    4   11   12                                                       
CONECT    5    1    3    8                                                  
CONECT    6    2    7   11                                                  
CONECT    7    3    6   12                                                  
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4    6                                                       
CONECT   12    4    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3,4-Methylenedioxybenzoate	Generator
1,3-Benzodioxole-5-carboxylic acid	HMDB
1,3-Benzodioxole-5-carboxylic acid, 9ci	HMDB
3, 4-(Methylenedioxy)benzoic acid	HMDB
3,4-(Methylenedioxy)-benzoic acid	HMDB
3,4-(Methylenedioxy)benzoic acid	HMDB
3,4-Dioxymethylenebenzoic acid	HMDB
3,4-Methylene dioxybenzoic acid	HMDB
5-Benzodioxolecarboxylic acid	HMDB
Heliotropic acid	HMDB
Piperonylic acid	HMDB
Protocatechuic acid methylene ether	HMDB
2H-1,3-Benzodioxole-5-carboxylate	HMDB
Piperonylic acid, sodium salt	HMDB

Chemical Formula

C₈H₆O₄

Average Molecular Weight

166.1308

Monoisotopic Molecular Weight

166.02660868

IUPAC Name

2H-1,3-benzodioxole-5-carboxylic acid

Traditional Name

2H-1,3-benzodioxole-5-carboxylic acid

CAS Registry Number

94-53-1

SMILES

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

InChI Identifier

InChI=1S/C8H6O4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2,(H,9,10)

InChI Key

VDVJGIYXDVPQLP-UHFFFAOYSA-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
Benzenoid
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032613)
Cytoplasm (HMDB: HMDB0032613)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032613)

Source

Endogenous

Endogenous (HMDB: HMDB0032613)

Plant

Plant (HMDB: HMDB0032613)

Exogenous

Food

Food (HMDB: HMDB0032613)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0032613)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	229 °C	Not Available
Boiling Point	324.59 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1424 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.810 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	124.452	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001125

Predicted Molecular Properties

Property	Value	Source
Water Solubility	13.2 g/L	ALOGPS
logP	1.26	ALOGPS
logP	1.25	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-4.8	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	1	ChemAxon
Refractivity	39.08 m³·mol⁻¹	ChemAxon
Polarizability	15.25 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
DarkChem	[M+H]+	136.142	31661259
DarkChem	[M-H]-	131.072	31661259
DeepCCS	[M+H]+	132.519	30932474
DeepCCS	[M-H]-	129.807	30932474
DeepCCS	[M-2H]-	165.901	30932474
DeepCCS	[M+Na]+	140.921	30932474
AllCCS	[M+H]+	134.1	32859911
AllCCS	[M+H-H2O]+	129.6	32859911
AllCCS	[M+NH4]+	138.4	32859911
AllCCS	[M+Na]+	139.6	32859911
AllCCS	[M-H]-	130.9	32859911
AllCCS	[M+Na-2H]-	131.4	32859911
AllCCS	[M+HCOO]-	132.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Methylenedioxybenzoic acid	OC(=O)C1=CC2=C(OCO2)C=C1	2561.8	Standard polar	33892256
3,4-Methylenedioxybenzoic acid	OC(=O)C1=CC2=C(OCO2)C=C1	1425.3	Standard non polar	33892256
3,4-Methylenedioxybenzoic acid	OC(=O)C1=CC2=C(OCO2)C=C1	1557.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Methylenedioxybenzoic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C2OCOC2=C1	1588.0	Semi standard non polar	33892256
3,4-Methylenedioxybenzoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C2OCOC2=C1	1847.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)	splash10-014i-4900000000-70cd469c29d2482d95f0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)	splash10-014i-2900000000-4390b1bdc5917c5f26fc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)	splash10-014i-0900000000-7a656232e76ad9e209c7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)	splash10-014i-4900000000-cef5628d095e3f32ecfd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)	splash10-014i-4900000000-70cd469c29d2482d95f0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)	splash10-014i-2900000000-4390b1bdc5917c5f26fc	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)	splash10-014i-0900000000-7a656232e76ad9e209c7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Methylenedioxybenzoic acid EI-B (Non-derivatized)	splash10-014i-4900000000-cef5628d095e3f32ecfd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Methylenedioxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kb-5900000000-5c0de1857ad6317b0e43	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Methylenedioxybenzoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9830000000-33cb18ddb487b6122ed3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Methylenedioxybenzoic 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid Linear Ion Trap , negative-QTOF	splash10-00di-0900000000-6fae03ddbf68a91dbc9a	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 10V, Positive-QTOF	splash10-014i-0900000000-fdf0ce1dbf59e0357420	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 20V, Positive-QTOF	splash10-014i-0900000000-11f8683efcfb6c539620	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 40V, Positive-QTOF	splash10-00di-5900000000-a19edf4a7090e8d4839d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 10V, Negative-QTOF	splash10-014i-0900000000-4d8e4f3c34640b43c05b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 20V, Negative-QTOF	splash10-00xr-0900000000-10b8d66e451092b3d8eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 40V, Negative-QTOF	splash10-006t-9700000000-e2645b4317d232203b0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 10V, Negative-QTOF	splash10-014i-0900000000-81c3cd21eb6448e5cdfb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 20V, Negative-QTOF	splash10-00di-1900000000-266fcca288a86551c6bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 40V, Negative-QTOF	splash10-014l-8900000000-a37f990c1ac7d5aff64a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 10V, Positive-QTOF	splash10-01ba-0900000000-bfc9a42adac7578d6645	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 20V, Positive-QTOF	splash10-01b9-0900000000-6d30ef91858166da4109	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzoic acid 40V, Positive-QTOF	splash10-05fs-4900000000-aa22ba71b3141948e23f	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB010554

KNApSAcK ID

C00031034

Chemspider ID

6928

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7196

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1275031

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

3,4-Methylenedioxybenzoic acid → 6-(2H-1,3-benzodioxole-5-carbonyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

2. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Reactions

3,4-Methylenedioxybenzoic acid → 2-{[(2H-1,3-benzodioxol-5-yl)(hydroxy)methylidene]amino}acetic acid	details

Showing metabocard for 3,4-Methylenedioxybenzoic acid (HMDB0032613)

MOL for HMDB0032613 (3,4-Methylenedioxybenzoic acid)

3D MOL for HMDB0032613 (3,4-Methylenedioxybenzoic acid)

3D SDF for HMDB0032613 (3,4-Methylenedioxybenzoic acid)

3D-SDF for HMDB0032613 (3,4-Methylenedioxybenzoic acid)

PDB for HMDB0032613 (3,4-Methylenedioxybenzoic acid)

3D PDB for HMDB0032613 (3,4-Methylenedioxybenzoic acid)

SMILES for HMDB0032613 (3,4-Methylenedioxybenzoic acid)

INCHI for HMDB0032613 (3,4-Methylenedioxybenzoic acid)

Structure for HMDB0032613 (3,4-Methylenedioxybenzoic acid)

3D Structure for HMDB0032613 (3,4-Methylenedioxybenzoic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions