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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:07 UTC

Update Date

2023-02-21 17:19:41 UTC

HMDB ID

HMDB0030800

Secondary Accession Numbers

HMDB30800

Metabolite Identification

Common Name

3-Methoxy-4,5-methylenedioxybenzoic acid

Description

3-Methoxy-4,5-methylenedioxybenzoic acid, also known as 5-methoxypiperonylic acid or myristicic acid, belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. Based on a literature review very few articles have been published on 3-Methoxy-4,5-methylenedioxybenzoic acid.

Structure

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


  Mrv0541 05061305312D          

 14 15  0  0  0  0            999 V2000
    1.9233   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 12  1  1  0  0  0  0
 12  6  1  0  0  0  0
 13  4  1  0  0  0  0
 13  7  1  0  0  0  0
 14  4  1  0  0  0  0
 14  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030800

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2OCOC2=CC(=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O5/c1-12-6-2-5(9(10)11)3-7-8(6)14-4-13-7/h2-3H,4H2,1H3,(H,10,11)

> <INCHI_KEY>
AOHAPDDBNAPPIN-UHFFFAOYSA-N

> <FORMULA>
C9H8O5

> <MOLECULAR_WEIGHT>
196.1568

> <EXACT_MASS>
196.037173366

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
18.16870351213892

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-2H-1,3-benzodioxole-5-carboxylic acid

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
1.0963909260000002

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.873803107241253

> <JCHEM_PKA_STRONGEST_BASIC>
-4.550956428193338

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
45.54430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-methoxy-2H-1,3-benzodioxole-5-carboxylic 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       3.590  -1.007   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.591   5.923   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       8.925   3.613   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    5    6                                                       
CONECT    3    5    7                                                       
CONECT    4   13   14                                                       
CONECT    5    2    3    9                                                  
CONECT    6    2    8   12                                                  
CONECT    7    3    8   13                                                  
CONECT    8    6    7   14                                                  
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    1    6                                                       
CONECT   13    4    7                                                       
CONECT   14    4    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Methoxy-4,5-methylenedioxybenzoate	Generator
5-Methoxypiperonylic acid	HMDB
Myristicic acid	HMDB
Myristicin acid	HMDB
7-Methoxy-2H-1,3-benzodioxole-5-carboxylate	HMDB

Chemical Formula

C₉H₈O₅

Average Molecular Weight

196.1568

Monoisotopic Molecular Weight

196.037173366

IUPAC Name

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

Traditional Name

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

CAS Registry Number

526-34-1

SMILES

COC1=C2OCOC2=CC(=C1)C(O)=O

InChI Identifier

InChI=1S/C9H8O5/c1-12-6-2-5(9(10)11)3-7-8(6)14-4-13-7/h2-3H,4H2,1H3,(H,10,11)

InChI Key

AOHAPDDBNAPPIN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acid and derivatives

Alternative Parents

Substituents

Gallic acid or derivatives
M-methoxybenzoic acid or derivatives
Benzodioxole
Anisole
Alkyl aryl ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Acetal
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030800)
Cytoplasm (HMDB: HMDB0030800)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030800)

Source

Endogenous

Endogenous (HMDB: HMDB0030800)

Plant

Plant (HMDB: HMDB0030800)

Exogenous

Food

Food (HMDB: HMDB0030800)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	212 °C	Not Available
Boiling Point	351.20 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	866.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.680 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.58 g/L	ALOGPS
logP	1.06	ALOGPS
logP	1.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.54 m³·mol⁻¹	ChemAxon
Polarizability	18.17 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]+	144.771	31661259
DarkChem	[M-H]-	142.827	31661259
DeepCCS	[M+H]+	138.916	30932474
DeepCCS	[M-H]-	135.088	30932474
DeepCCS	[M-2H]-	172.579	30932474
DeepCCS	[M+Na]+	148.118	30932474
AllCCS	[M+H]+	140.7	32859911
AllCCS	[M+H-H2O]+	136.4	32859911
AllCCS	[M+NH4]+	144.7	32859911
AllCCS	[M+Na]+	145.8	32859911
AllCCS	[M-H]-	138.5	32859911
AllCCS	[M+Na-2H]-	138.7	32859911
AllCCS	[M+HCOO]-	139.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methoxy-4,5-methylenedioxybenzoic acid	COC1=C2OCOC2=CC(=C1)C(O)=O	2798.0	Standard polar	33892256
3-Methoxy-4,5-methylenedioxybenzoic acid	COC1=C2OCOC2=CC(=C1)C(O)=O	1628.3	Standard non polar	33892256
3-Methoxy-4,5-methylenedioxybenzoic acid	COC1=C2OCOC2=CC(=C1)C(O)=O	1783.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methoxy-4,5-methylenedioxybenzoic acid,1TMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C)=CC2=C1OCO2	1777.2	Semi standard non polar	33892256
3-Methoxy-4,5-methylenedioxybenzoic acid,1TBDMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC2=C1OCO2	2032.8	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 - 3-Methoxy-4,5-methylenedioxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gdj-2900000000-6f0070fc4dd9674a23bc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-9750000000-49895ffa1b1945c0adcf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxy-4,5-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid 10V, Positive-QTOF	splash10-0002-0900000000-82e80345d5901c0b0b87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid 20V, Positive-QTOF	splash10-0002-0900000000-cbe72e26ab6810993e0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid 40V, Positive-QTOF	splash10-0udj-2900000000-310ea8e074df6df250a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid 10V, Negative-QTOF	splash10-0002-0900000000-e06079d7837b2662d803	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid 20V, Negative-QTOF	splash10-0udj-0900000000-cd7e4b8c7ebf9be6f1b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid 40V, Negative-QTOF	splash10-0fb9-9800000000-54781dadda3fd797a5f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid 10V, Negative-QTOF	splash10-0f6t-0900000000-4fe3eefb9d72e9e937f0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid 20V, Negative-QTOF	splash10-0udi-1900000000-7a0b3052d0af50d2b2e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid 40V, Negative-QTOF	splash10-0fkd-6900000000-8ff2eff2cb759c843fb2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid 10V, Positive-QTOF	splash10-002b-0900000000-9dbe1419cdc39d0ecbbd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid 20V, Positive-QTOF	splash10-0f6t-0900000000-110183596f7ace8836ed	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxy-4,5-methylenedioxybenzoic acid 40V, Positive-QTOF	splash10-0ufs-7900000000-b1b0cb97f475c87fbb7c	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB002741

KNApSAcK ID

C00057423

Chemspider ID

527906

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

607309

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1622261

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 3-Methoxy-4,5-methylenedioxybenzoic acid (HMDB0030800)

MOL for HMDB0030800 (3-Methoxy-4,5-methylenedioxybenzoic acid)

3D MOL for HMDB0030800 (3-Methoxy-4,5-methylenedioxybenzoic acid)

3D SDF for HMDB0030800 (3-Methoxy-4,5-methylenedioxybenzoic acid)

3D-SDF for HMDB0030800 (3-Methoxy-4,5-methylenedioxybenzoic acid)

PDB for HMDB0030800 (3-Methoxy-4,5-methylenedioxybenzoic acid)

3D PDB for HMDB0030800 (3-Methoxy-4,5-methylenedioxybenzoic acid)

SMILES for HMDB0030800 (3-Methoxy-4,5-methylenedioxybenzoic acid)

INCHI for HMDB0030800 (3-Methoxy-4,5-methylenedioxybenzoic acid)

Structure for HMDB0030800 (3-Methoxy-4,5-methylenedioxybenzoic acid)

3D Structure for HMDB0030800 (3-Methoxy-4,5-methylenedioxybenzoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra