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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:47 UTC
Update Date2019-07-23 06:11:23 UTC
HMDB IDHMDB0032613
Secondary Accession Numbers
  • HMDB32613
Metabolite Identification
Common Name3,4-Methylenedioxybenzoic acid
Description3,4-Methylenedioxybenzoic acid is found in herbs and spices. 3,4-Methylenedioxybenzoic acid is isolated from Piper longum (long pepper
Structure
Data?1563862282
Synonyms
ValueSource
1,3-Benzodioxole-5-carboxylic acidHMDB
1,3-Benzodioxole-5-carboxylic acid, 9ciHMDB
3, 4-(Methylenedioxy)benzoic acidHMDB
3,4-(Methylenedioxy)-benzoic acidHMDB
3,4-(Methylenedioxy)benzoic acidHMDB
3,4-Dioxymethylenebenzoic acidHMDB
3,4-Methylene dioxybenzoic acidHMDB
5-Benzodioxolecarboxylic acidHMDB
Heliotropic acidHMDB
Piperonylic acidHMDB
Protocatechuic acid methylene etherHMDB
Chemical FormulaC8H6O4
Average Molecular Weight166.1308
Monoisotopic Molecular Weight166.02660868
IUPAC Name2H-1,3-benzodioxole-5-carboxylic acid
Traditional Name2H-1,3-benzodioxole-5-carboxylic acid
CAS Registry Number94-53-1
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 KeyVDVJGIYXDVPQLP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Benzoyl
  • Benzenoid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point229 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.2 g/LALOGPS
logP1.26ALOGPS
logP1.25ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.08 m³·mol⁻¹ChemAxon
Polarizability15.25 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-4900000000-70cd469c29d2482d95f0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-2900000000-4390b1bdc5917c5f26fcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0900000000-7a656232e76ad9e209c7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-4900000000-cef5628d095e3f32ecfdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-4900000000-70cd469c29d2482d95f0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-2900000000-4390b1bdc5917c5f26fcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0900000000-7a656232e76ad9e209c7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-4900000000-cef5628d095e3f32ecfdJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kb-5900000000-5c0de1857ad6317b0e43JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9830000000-33cb18ddb487b6122ed3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-6fae03ddbf68a91dbc9aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-fdf0ce1dbf59e0357420JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-11f8683efcfb6c539620JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-5900000000-a19edf4a7090e8d4839dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-4d8e4f3c34640b43c05bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-0900000000-10b8d66e451092b3d8ebJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006t-9700000000-e2645b4317d232203b0bJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010554
KNApSAcK IDC00031034
Chemspider ID6928
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7196
PDB ID0HN
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

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 aciddetails
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 aciddetails