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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:40:00 UTC

Update Date

2022-03-07 02:53:53 UTC

HMDB ID

HMDB0033893

Secondary Accession Numbers

HMDB33893

Metabolite Identification

Common Name

4,5-Dimethoxy-1,2-benzenedicarboxylic acid

Description

4,5-Dimethoxy-1,2-benzenedicarboxylic acid belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. Based on a literature review very few articles have been published on 4,5-Dimethoxy-1,2-benzenedicarboxylic acid.

Structure

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

  Mrv0541 05061307252D          

 16 16  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15  1  1  0  0  0  0
 15  7  1  0  0  0  0
 16  2  1  0  0  0  0
 16  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033893

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C=C(C(O)=O)C(=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O6/c1-15-7-3-5(9(11)12)6(10(13)14)4-8(7)16-2/h3-4H,1-2H3,(H,11,12)(H,13,14)

> <INCHI_KEY>
SKBDLRWFSRLIPP-UHFFFAOYSA-N

> <FORMULA>
C10H10O6

> <MOLECULAR_WEIGHT>
226.1828

> <EXACT_MASS>
226.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
20.948701041728896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5-dimethoxybenzene-1,2-dicarboxylic acid

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
0.9730691006666667

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.5369278047234785

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.979681958669602

> <JCHEM_PKA_STRONGEST_BASIC>
-4.622426955370005

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
53.49680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dimethoxybenzene-1,2-dicarboxylic 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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3    5    7                                                       
CONECT    4    6    8                                                       
CONECT    5    3    6    9                                                  
CONECT    6    4    5   10                                                  
CONECT    7    3    8   15                                                  
CONECT    8    4    7   16                                                  
CONECT    9    5   11   12                                                  
CONECT   10    6   13   14                                                  
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14   10                                                            
CONECT   15    1    7                                                       
CONECT   16    2    8                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0033893
HETATM    1  C1  UNL     1      -2.288  -2.993  -0.022  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.290  -1.599  -0.080  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.098  -0.852  -0.036  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.123  -1.441   0.066  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.308  -0.678   0.109  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.557  -1.396   0.218  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.483  -2.685   0.267  1.00  0.00           O  
HETATM    8  O3  UNL     1       3.832  -0.937   0.280  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.241   0.689   0.048  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.390   1.560   0.084  1.00  0.00           C  
HETATM   11  O4  UNL     1       3.587   1.278   0.172  1.00  0.00           O  
HETATM   12  O5  UNL     1       2.160   2.954   0.012  1.00  0.00           O  
HETATM   13  C8  UNL     1      -0.047   1.273  -0.058  1.00  0.00           C  
HETATM   14  C9  UNL     1      -1.187   0.516  -0.099  1.00  0.00           C  
HETATM   15  O6  UNL     1      -2.418   1.123  -0.202  1.00  0.00           O  
HETATM   16  C10 UNL     1      -2.615   2.508  -0.272  1.00  0.00           C  
HETATM   17  H1  UNL     1      -2.072  -3.414  -1.034  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.338  -3.311   0.231  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.623  -3.410   0.750  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.193  -2.512   0.115  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.599  -1.299  -0.289  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.618   3.596   0.618  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.074   2.356  -0.105  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.580   2.919   0.768  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.619   2.709  -0.700  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.846   3.045  -0.844  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4   14
CONECT    4    5   20
CONECT    5    6    9    9
CONECT    6    7    7    8
CONECT    8   21
CONECT    9   10   13
CONECT   10   11   11   12
CONECT   12   22
CONECT   13   14   14   23
CONECT   14   15
CONECT   15   16
CONECT   16   24   25   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,5-Dimethoxy-1,2-benzenedicarboxylate	Generator
4, 5-Dimethoxy-1,2-benzenedicarboxylic acid	HMDB
4,5-Dimethoxy-phthalic acid	HMDB
4,5-Dimethoxyphthalic acid	HMDB
m-Hemipic acid	HMDB
m-Hemipinic acid	HMDB
Metahemipic acid	HMDB
Veratrole-4,5-dicarboxylic acid	HMDB
4,5-Dimethoxybenzene-1,2-dicarboxylate	Generator

Chemical Formula

C₁₀H₁₀O₆

Average Molecular Weight

226.1828

Monoisotopic Molecular Weight

226.047738052

IUPAC Name

4,5-dimethoxybenzene-1,2-dicarboxylic acid

Traditional Name

4,5-dimethoxybenzene-1,2-dicarboxylic acid

CAS Registry Number

577-68-4

SMILES

COC1=C(OC)C=C(C(O)=O)C(=C1)C(O)=O

InChI Identifier

InChI=1S/C10H10O6/c1-15-7-3-5(9(11)12)6(10(13)14)4-8(7)16-2/h3-4H,1-2H3,(H,11,12)(H,13,14)

InChI Key

SKBDLRWFSRLIPP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

P-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

P-methoxybenzoic acid or derivatives
M-methoxybenzoic acid or derivatives
O-dimethoxybenzene
Dimethoxybenzene
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
Alkyl aryl ether
Dicarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033893)
Cytoplasm (HMDB: HMDB0033893)

Source

Exogenous

Exogenous (HMDB: HMDB0033893)

Food

Food (HMDB: HMDB0033893)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033893)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174 - 175 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.57 g/L	ALOGPS
logP	1.16	ALOGPS
logP	0.97	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	2.98	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	53.5 m³·mol⁻¹	ChemAxon
Polarizability	20.95 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	154.197	31661259
DarkChem	[M-H]-	149.452	31661259
DeepCCS	[M+H]+	147.976	30932474
DeepCCS	[M-H]-	145.618	30932474
DeepCCS	[M-2H]-	179.045	30932474
DeepCCS	[M+Na]+	154.069	30932474
AllCCS	[M+H]+	149.0	32859911
AllCCS	[M+H-H2O]+	145.1	32859911
AllCCS	[M+NH4]+	152.6	32859911
AllCCS	[M+Na]+	153.6	32859911
AllCCS	[M-H]-	146.3	32859911
AllCCS	[M+Na-2H]-	146.6	32859911
AllCCS	[M+HCOO]-	147.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4,5-Dimethoxy-1,2-benzenedicarboxylic acid	COC1=C(OC)C=C(C(O)=O)C(=C1)C(O)=O	3168.3	Standard polar	33892256
4,5-Dimethoxy-1,2-benzenedicarboxylic acid	COC1=C(OC)C=C(C(O)=O)C(=C1)C(O)=O	1823.4	Standard non polar	33892256
4,5-Dimethoxy-1,2-benzenedicarboxylic acid	COC1=C(OC)C=C(C(O)=O)C(=C1)C(O)=O	2148.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4,5-Dimethoxy-1,2-benzenedicarboxylic acid,1TMS,isomer #1	COC1=CC(C(=O)O)=C(C(=O)O[Si](C)(C)C)C=C1OC	2034.0	Semi standard non polar	33892256
4,5-Dimethoxy-1,2-benzenedicarboxylic acid,2TMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C=C1OC	2102.9	Semi standard non polar	33892256
4,5-Dimethoxy-1,2-benzenedicarboxylic acid,1TBDMS,isomer #1	COC1=CC(C(=O)O)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1OC	2301.0	Semi standard non polar	33892256
4,5-Dimethoxy-1,2-benzenedicarboxylic acid,2TBDMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1OC	2557.5	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 - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0560-2970000000-1b8bed387dae5bb189de	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9054000000-784bf01cd33a0dab1216	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-Dimethoxy-1,2-benzenedicarboxylic 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 - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid 10V, Positive-QTOF	splash10-004i-0090000000-0e2f409a57fc2c2b2ae2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid 20V, Positive-QTOF	splash10-004i-0290000000-8dc5242bc07e1f15a094	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid 40V, Positive-QTOF	splash10-0059-0910000000-30117e1cf8d87a81e3c2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid 10V, Negative-QTOF	splash10-004i-0390000000-dfc19af6ee36612dc0fb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid 20V, Negative-QTOF	splash10-0059-0950000000-266875143116075421a9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid 40V, Negative-QTOF	splash10-0kl9-1900000000-6cd880fa0753698c961f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid 10V, Positive-QTOF	splash10-0a6r-0090000000-8de715c1593d4b288724	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid 20V, Positive-QTOF	splash10-056r-0390000000-a9c4942ece7399dc166a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid 40V, Positive-QTOF	splash10-014j-9710000000-6f8aee5850ec7ed6269a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid 10V, Negative-QTOF	splash10-001i-0910000000-bb4488dc60ef1f78e397	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid 20V, Negative-QTOF	splash10-000i-0910000000-a9cb9ed3672903b204f5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dimethoxy-1,2-benzenedicarboxylic acid 40V, Negative-QTOF	splash10-00kr-3900000000-f813e190d865c6b2470d	2021-09-24	Wishart 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

FDB012088

KNApSAcK ID

C00058139

Chemspider ID

256696

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

290988

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 4,5-Dimethoxy-1,2-benzenedicarboxylic acid (HMDB0033893)

MOL for HMDB0033893 (4,5-Dimethoxy-1,2-benzenedicarboxylic acid)

3D MOL for HMDB0033893 (4,5-Dimethoxy-1,2-benzenedicarboxylic acid)

3D SDF for HMDB0033893 (4,5-Dimethoxy-1,2-benzenedicarboxylic acid)

3D-SDF for HMDB0033893 (4,5-Dimethoxy-1,2-benzenedicarboxylic acid)

PDB for HMDB0033893 (4,5-Dimethoxy-1,2-benzenedicarboxylic acid)

3D PDB for HMDB0033893 (4,5-Dimethoxy-1,2-benzenedicarboxylic acid)

SMILES for HMDB0033893 (4,5-Dimethoxy-1,2-benzenedicarboxylic acid)

INCHI for HMDB0033893 (4,5-Dimethoxy-1,2-benzenedicarboxylic acid)

Structure for HMDB0033893 (4,5-Dimethoxy-1,2-benzenedicarboxylic acid)

3D Structure for HMDB0033893 (4,5-Dimethoxy-1,2-benzenedicarboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra