NP-MRD: Showing NP-Card for Homoveratric acid (NP0001178)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-03 04:22:19 UTC

NP-MRD ID

NP0001178

Natural Product DOI

https://doi.org/10.57994/2817

Secondary Accession Numbers

None

Natural Product Identification

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 Parkinson's disease (PD). (PMID 7059639 , 14311254 , 588645 , 10834300 ).

Structure

MOL SDF PDB SMILES InChI

3,4-Dimethoxyphenylacetic acid.mol
  Mrv1652305271900152D          

 14 14  0  0  0  0            999 V2000
    1.7862   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  2  0  0  0  0
  2  5  1  0  0  0  0
 11 12  1  0  0  0  0
  8 11  1  0  0  0  0
 13 14  1  0  0  0  0
  7 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001178

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.1999

> <EXACT_MASS>
196.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.73541977781273

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)acetic acid

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.2956515739999999

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.861393687418164

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5925778261371315

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
50.292

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dimethoxyphenylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3,4-Dimethoxyphenylacetic acid.mol                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       3.334  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.334   0.000   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.668  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.667  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.001  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.001   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.667   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.334   0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.668  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    6   10    2                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11   12    8                                                       
CONECT   12   11                                                            
CONECT   13   14    7                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dimethoxyphenyl)acetic acid	ChEBI
2-(3,4-Dimethoxyphenyl)ethanoic acid	ChEBI
3,4-Dimethoxybenzeneacetic acid	ChEBI
3,4-Dimethoxyphenylacetic acid	ChEBI
Homoveratrumic acid	ChEBI
2-(3,4-Dimethoxyphenyl)acetate	Generator
2-(3,4-Dimethoxyphenyl)ethanoate	Generator
3,4-Dimethoxybenzeneacetate	Generator
3,4-Dimethoxyphenylacetate	Generator
Homoveratrumate	Generator
Homoveratrate	Generator
(3,4-Dimethoxyphenyl)acetate	HMDB
(3,4-Dimethoxyphenyl)acetic acid	HMDB

Chemical Formula

C₁₀H₁₂O₄

Average Mass

196.1999 Da

Monoisotopic Mass

196.07356 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-14	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-14	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos		FooDB
Anatidae		FooDB
Anser anser		FooDB
Bison bison		FooDB
Bos taurus		FooDB
Bos taurus X Bison bison		FooDB
Bubalus bubalis		FooDB
Capra aegagrus hircus		FooDB
Cervidae		FooDB
Cervus canadensis		FooDB
Columba		FooDB
Columbidae		FooDB
Dromaius novaehollandiae		FooDB
Equus caballus		FooDB
Gallus gallus		FooDB
Lagopus muta		FooDB
Leporidae		FooDB
Lepus timidus		FooDB
Melanitta fusca		FooDB
Meleagris gallopavo		FooDB
Numida meleagris		FooDB
Odocoileus		FooDB
Olea europaea	FooDB	PHENOL EXPLORER
Oryctolagus		FooDB
Ovis aries		FooDB
Phasianidae		FooDB
Phasianus colchicus		FooDB
Struthio camelus		FooDB
Sus scrofa		FooDB
Sus scrofa domestica		FooDB
Zingiber officinale		LOTUS database

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Methoxybenzenes

Direct Parent

Dimethoxybenzenes

Alternative Parents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:86655 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	96 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.21 g/L	ALOGPS
logP	1.58	ALOGPS
logP	1.3	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	-4.6	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	4	ChemAxon
Refractivity	50.29 m³·mol⁻¹	ChemAxon
Polarizability	19.74 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000434

DrugBank ID

Not Available

Phenol Explorer Compound ID

575

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

METLIN ID

5423

PubChem Compound

7139

PDB ID

Not Available

ChEBI ID

86655

Good Scents ID

Not Available

References

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 ]

Showing NP-Card for Homoveratric acid (NP0001178)

MOL for NP0001178 (Homoveratric acid)

3D MOL for NP0001178 (Homoveratric acid)

3D SDF for NP0001178 (Homoveratric acid)

3D-SDF for NP0001178 (Homoveratric acid)

PDB for NP0001178 (Homoveratric acid)

3D PDB for NP0001178 (Homoveratric acid)

SMILES for NP0001178 (Homoveratric acid)

INCHI for NP0001178 (Homoveratric acid)

Structure for NP0001178 (Homoveratric acid)

3D Structure for NP0001178 (Homoveratric acid)