| Common Name |
Homoveratric acid
| Description |
Homoveratric acid is the main metabolite of 3,4-dimethoxyphenylethylamine (DMPEA) in urine. It has been suggested that DMPEA and other amines are in higher concentrations in drug-free schizophrenics than in normal subjects. DMPEA is a the di-methylated metabolite of L-DOPA, the major treatment for Parkinsons disease (PD). (PMID 7059639 , 14311254 , 588645 , 10834300 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(3,4-Dimethoxyphenyl)acetateHMDB
(3,4-Dimethoxyphenyl)acetic acidHMDB
3,4-DimethoxybenzeneacetateHMDB
3,4-Dimethoxybenzeneacetic acidHMDB
3,4-DimethoxyphenylacetateHMDB
3,4-Dimethoxyphenylacetic acidHMDB
HomoveratrateHMDB
| Chemical Formlia |
C10H12O4
| Average Molecliar Weight |
196.1999
| Monoisotopic Molecliar Weight |
196.073558872
| IUPAC Name |
2-(3,4-dimethoxyphenyl)acetic acid
| Traditional Name |
3,4-dimethoxyphenylacetic acid
| CAS Registry Number |
93-40-3
| SMILES |
COC1=CC=C(CC(O)=O)C=C1OC
| InChI Identifier |
InChI=1S/C10H12O4/c1-13-8-4-3-7(6-10(11)12)5-9(8)14-2/h3-5H,6H2,1-2H3,(H,11,12)
| InChI Key |
WUAXWQRULBZETB-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Benzenoids
| Sub Class |
Benzene and substituted derivatives
| Direct Parent |
Dimethoxybenzenes
| Alternative Parents |
Phenoxy compounds
Anisoles
Alkyl aryl ethers
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
O-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Phenol ether
Alkyl aryl ether
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound
| Molecliar Framework |
Aromatic homomonocyclic compounds
| External Descriptors |
monocarboxylic acid (CHEBI:86655 )
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point96 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility1.21 mg/mLALOGPS
logP1.58ALOGPS
logP1.3ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.86ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.29 m3·mol-1ChemAxon
Polarizability19.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0900000000-2a12c40170fec46f4a14View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Negative (Annotated)splash10-00di-0900000000-5debb25eef3cd12b8c67View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Negative (Annotated)splash10-00dl-9800000000-dcdcc653f9617b708e09View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – EI-B (HITACHI M-52) , Positivesplash10-0006-1900000000-b8fad1a07cec70a67baaView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified0.687 +/- 0.175 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified0.5 +/- 0.155 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified0.691 +/- 0.164 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified0.908 +/- 0.314 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified0.645 +/- 0.129 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified0.904 +/- 0.193 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified0.594 +/- 0.174 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified2.613 +/- 2.137 uMAdlit (>18 years old)Male
Normal
19812218
details
UrineDetected and Quantified0.072 +/- 0.01 umol/mmol creatinineAdlit (>18 years old)Male
Normal
19812218
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
575
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000317
| KNApSAcK ID |
Not Available
| Chemspider ID |
6872
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00434
| Metagene Link |
HMDB00434
| METLIN ID |
5423
| PubChem Compound |
7139
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: UNC3866
References |
| Synthesis Reference |
Aboulezz, A. F.; Quelet, R. Derivatives of veratrole. Synthesis of homoveratric acid and some substituted diphenylmethane and fluorenone derivatives. Journal of Chemistry of the United Arab Republic (1962), 5(2), 137-46. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Hempel K, Ullrich H, Philippu G: Quantitative investigation on the urinary excretion and metabolism of 3,4-dimethoxyphenylethylamine in schizophrenics and normal individuals. Biol Psychiatry. 1982 Jan;17(1):49-59. [PubMed:7059639 ]
- PROENCA J, WENNER J: [ON THE EFFECT OF NIKETHAMIDE AND HOMOVERATRIC ACID DIMETHYLAMIDE ON RESPIRATION IN INFANTS]. Monatsschr Kinderheilkd. 1965 Apr;113:341-3. [PubMed:14311254 ]
- Friedhoff AJ, Park S, Schweitzer JW, Burdock EI, Armour M: Excretion of 3,4-dimethoxyphenethylamine (DMPEA) by acute schizophrenics and controls. Biol Psychiatry. 1977 Oct;12(5):643-54. [PubMed:588645 ]
- Charlton CG, Crowell B Jr: Effects of dopamine metabolites on locomotor activities and on the binding of dopamine: relevance to the side effects of L-dopa. Life Sci. 2000 Apr 21;66(22):2159-71. [PubMed:10834300 ]
|
PMID: 19479584