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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:36:46 UTC

Update Date

2022-03-07 02:53:52 UTC

HMDB ID

HMDB0033839

Secondary Accession Numbers

HMDB33839

Metabolite Identification

Common Name

Eudesmic acid

Description

Eudesmic acid, also known as trimethylgallate or eudesmate, 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. Eudesmic acid has been detected, but not quantified in, olives (Olea europaea). This could make eudesmic acid a potential biomarker for the consumption of these foods. Eudesmic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Eudesmic acid.

Structure

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


  Mrv0541 05061307242D          

 15 15  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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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    0.8250    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
    1.4289    0.0000    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   -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
    0.0000    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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  1  1  0  0  0  0
 13  7  1  0  0  0  0
 14  2  1  0  0  0  0
 14  8  1  0  0  0  0
 15  3  1  0  0  0  0
 15  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033839

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O5/c1-13-7-4-6(10(11)12)5-8(14-2)9(7)15-3/h4-5H,1-3H3,(H,11,12)

> <INCHI_KEY>
SJSOFNCYXJUNBT-UHFFFAOYSA-N

> <FORMULA>
C10H12O5

> <MOLECULAR_WEIGHT>
212.1993

> <EXACT_MASS>
212.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
20.78795815083101

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,5-trimethoxybenzoic acid

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.1578149269999998

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9186574758108184

> <JCHEM_PKA_STRONGEST_BASIC>
-4.458577254135112

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
52.703800000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trimethoxybenzoic 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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   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       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4    6    7                                                       
CONECT    5    6    8                                                       
CONECT    6    4    5   10                                                  
CONECT    7    4    9   13                                                  
CONECT    8    5    9   14                                                  
CONECT    9    7    8   15                                                  
CONECT   10    6   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1    7                                                       
CONECT   14    2    8                                                       
CONECT   15    3    9                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0033839
HETATM    1  C1  UNL     1       3.358   1.522   0.275  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.641   0.325   0.347  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.253   0.370   0.239  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.595   1.565   0.064  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.797   1.582  -0.041  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.539   2.799  -0.224  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.935   3.883  -0.293  1.00  0.00           O  
HETATM    8  O3  UNL     1      -2.906   2.791  -0.325  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.488   0.386   0.033  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.840  -0.801   0.207  1.00  0.00           C  
HETATM   11  O4  UNL     1      -1.479  -2.028   0.288  1.00  0.00           O  
HETATM   12  C8  UNL     1      -2.848  -2.236   0.208  1.00  0.00           C  
HETATM   13  C9  UNL     1       0.535  -0.821   0.311  1.00  0.00           C  
HETATM   14  O5  UNL     1       1.243  -2.020   0.490  1.00  0.00           O  
HETATM   15  C10 UNL     1       1.694  -2.760  -0.638  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.423   1.349   0.505  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.318   1.945  -0.757  1.00  0.00           H  
HETATM   18  H3  UNL     1       2.924   2.241   0.985  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.124   2.506   0.005  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.470   2.990   0.483  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.587   0.356  -0.045  1.00  0.00           H  
HETATM   22  H7  UNL     1      -3.310  -2.352   1.231  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.022  -3.242  -0.275  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.420  -1.484  -0.331  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.442  -2.259  -1.591  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.294  -3.776  -0.544  1.00  0.00           H  
HETATM   27  H12 UNL     1       2.799  -2.832  -0.606  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   19
CONECT    5    6    9    9
CONECT    6    7    7    8
CONECT    8   20
CONECT    9   10   21
CONECT   10   11   13   13
CONECT   11   12
CONECT   12   22   23   24
CONECT   13   14
CONECT   14   15
CONECT   15   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Methoxy-veratric acid	ChEBI
Gallic acid trimethyl ether	ChEBI
Tri-O-methylgallic acid	ChEBI
Trimethylgallic acid	ChEBI
5-Methoxy-veratrate	Generator
Gallate trimethyl ether	Generator
Tri-O-methylgallate	Generator
Trimethylgallate	Generator
Eudesmate	Generator
3,4,5-Trimethoxy-benzoic acid	HMDB
3,4,5-Trimethoxybenzoic acid	HMDB
3,4,5-Trimethoxybenzoic acid, potassium salt	MeSH, HMDB
3,4,5-Trimethoxybenzoic acid, sodium salt	MeSH, HMDB
Eudesmic acid	ChEBI
3,4,5-Trimethoxybenzoate	Generator

Chemical Formula

C₁₀H₁₂O₅

Average Molecular Weight

212.1993

Monoisotopic Molecular Weight

212.068473494

IUPAC Name

3,4,5-trimethoxybenzoic acid

Traditional Name

3,4,5-trimethoxybenzoic acid

CAS Registry Number

118-41-2

SMILES

COC1=CC(=CC(OC)=C1OC)C(O)=O

InChI Identifier

InChI=1S/C10H12O5/c1-13-7-4-6(10(11)12)5-8(14-2)9(7)15-3/h4-5H,1-3H3,(H,11,12)

InChI Key

SJSOFNCYXJUNBT-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
P-methoxybenzoic acid or derivatives
Benzoic acid
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Methoxybenzene
Alkyl aryl ether
Ether
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoic acids (CHEBI:454991 )
methoxybenzene (CHEBI:454991 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033839)
Cytoplasm (HMDB: HMDB0033839)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033839)

Source

Exogenous

Food

Food (HMDB: HMDB0033839)

Vegetable

Fruit vegetable

Olive (FooDB: FOOD00121)

Endogenous

Plant

Plant (HMDB: HMDB0033839)

Not Available

Nutrient (HMDB: HMDB0033839)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	171 - 172 °C	Not Available
Boiling Point	376.26 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2482 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.900 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.07 g/L	ALOGPS
logP	1.34	ALOGPS
logP	1.16	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	-4.5	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	4	ChemAxon
Refractivity	52.7 m³·mol⁻¹	ChemAxon
Polarizability	20.79 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]+	150.127	31661259
DarkChem	[M-H]-	148.898	31661259
DeepCCS	[M+H]+	145.353	30932474
DeepCCS	[M-H]-	141.526	30932474
DeepCCS	[M-2H]-	178.705	30932474
DeepCCS	[M+Na]+	154.243	30932474
AllCCS	[M+H]+	146.4	32859911
AllCCS	[M+H-H2O]+	142.4	32859911
AllCCS	[M+NH4]+	150.1	32859911
AllCCS	[M+Na]+	151.2	32859911
AllCCS	[M-H]-	145.4	32859911
AllCCS	[M+Na-2H]-	146.0	32859911
AllCCS	[M+HCOO]-	146.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Eudesmic acid	COC1=CC(=CC(OC)=C1OC)C(O)=O	2868.0	Standard polar	33892256
Eudesmic acid	COC1=CC(=CC(OC)=C1OC)C(O)=O	1738.3	Standard non polar	33892256
Eudesmic acid	COC1=CC(=CC(OC)=C1OC)C(O)=O	1808.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Eudesmic acid,1TMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C)=CC(OC)=C1OC	1817.0	Semi standard non polar	33892256
Eudesmic acid,1TBDMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	2059.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Eudesmic acid EI-B (Non-derivatized)	splash10-03di-2980000000-afb090eb7ad8965361eb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Eudesmic acid EI-B (Non-derivatized)	splash10-03di-2980000000-afb090eb7ad8965361eb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eudesmic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-029t-1910000000-51e01b0aba39ed5d9260	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eudesmic acid GC-MS (1 TMS) - 70eV, Positive	splash10-01b9-9580000000-85aa6d4b7970e0da98b2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eudesmic 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eudesmic acid LC-ESI-qTof , Positive-QTOF	splash10-000i-1900000000-51dd23095eb0a8f6acd9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eudesmic acid , positive-QTOF	splash10-000i-1900000000-51dd23095eb0a8f6acd9	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eudesmic acid 10V, Positive-QTOF	splash10-03di-0090000000-8d2127f2f4f3bed04236	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eudesmic acid 20V, Positive-QTOF	splash10-03di-0290000000-0d99c705c693ea385930	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eudesmic acid 40V, Positive-QTOF	splash10-00lr-4900000000-20972d8d5d3f46ef643c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eudesmic acid 10V, Negative-QTOF	splash10-03di-0390000000-cd0ea5cfdee7f476543e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eudesmic acid 20V, Negative-QTOF	splash10-03xr-0940000000-3e0ef17967c14438cf9c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eudesmic acid 40V, Negative-QTOF	splash10-004i-9600000000-5187cf2706f3f4e4f76b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eudesmic acid 10V, Positive-QTOF	splash10-03di-0590000000-deee1962242fb78f182b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eudesmic acid 20V, Positive-QTOF	splash10-03xr-0980000000-52e34473df91d994216d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eudesmic acid 40V, Positive-QTOF	splash10-02cr-9300000000-d30765e812a3e28635f1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eudesmic acid 10V, Negative-QTOF	splash10-03xr-0690000000-64f9ab63acd4fc890db0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eudesmic acid 20V, Negative-QTOF	splash10-02t9-0950000000-ba3e78416d83199a2030	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eudesmic acid 40V, Negative-QTOF	splash10-00ri-0900000000-599b03ea5a852d30ff59	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

FDB012013

KNApSAcK ID

C00029476

Chemspider ID

8054

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Eudesmic_acid

METLIN ID

Not Available

PubChem Compound

8357

PDB ID

Not Available

ChEBI ID

454991

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1182631

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 Eudesmic acid (HMDB0033839)

MOL for HMDB0033839 (Eudesmic acid)

3D MOL for HMDB0033839 (Eudesmic acid)

3D SDF for HMDB0033839 (Eudesmic acid)

3D-SDF for HMDB0033839 (Eudesmic acid)

PDB for HMDB0033839 (Eudesmic acid)

3D PDB for HMDB0033839 (Eudesmic acid)

SMILES for HMDB0033839 (Eudesmic acid)

INCHI for HMDB0033839 (Eudesmic acid)

Structure for HMDB0033839 (Eudesmic acid)

3D Structure for HMDB0033839 (Eudesmic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra