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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

Exogenous (HMDB: HMDB0033839)

Food

Food (HMDB: HMDB0033839)

Vegetable

Fruit vegetable

Olive (FooDB: FOOD00121)

Endogenous

Plant

Plant (HMDB: HMDB0033839)

Process

Not Available

Role

Biological role

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 Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.03 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6827 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.82 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1530.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	293.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	123.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	72.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	368.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	456.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	124.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	838.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	322.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1162.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	282.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	288.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	431.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	370.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	88.9 seconds	40023050

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

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 Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized