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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-01-09 12:11:21 UTC

Update Date

2023-02-21 17:29:14 UTC

HMDB ID

HMDB0059713

Secondary Accession Numbers

HMDB59713

Metabolite Identification

Common Name

3-Methoxysalicylic acid

Description

3-Methoxysalicylic acid, also known as O-vanillic acid or O-vanillate, belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. 3-Methoxysalicylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-Methoxysalicylic acid has been detected, but not quantified in, evening primroses. This could make 3-methoxysalicylic acid a potential biomarker for the consumption of these foods. 3-Methoxysalicylic acid (CAS Number 877-22-5) is a beige fine crystalline powder.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.078   3.468   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.309   2.697   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.309   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.697   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.697  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.309  -1.926   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.078  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.078   0.385   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.309   1.155   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.309  -3.468   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.309  -1.926   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.697  -1.155   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    3    7    9                                                  
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11    7   10   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
O-Vanillic acid	ChEBI
O-Vanillate	Generator
3-Methoxysalicylate	Generator
2-Hydroxy-3-methoxybenzoic acid	HMDB
2-Hydroxy-3-methoxybenzoate	Generator

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.1467

Monoisotopic Molecular Weight

168.042258744

IUPAC Name

2-hydroxy-3-methoxybenzoic acid

Traditional Name

3-methoxysalicyclic acid

CAS Registry Number

877-22-5

SMILES

COC1=CC=CC(C(O)=O)=C1O

InChI Identifier

InChI=1S/C8H8O4/c1-12-6-4-2-3-5(7(6)9)8(10)11/h2-4,9H,1H3,(H,10,11)

InChI Key

AUZQQIPZESHNMG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 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

M-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

M-methoxybenzoic acid or derivatives
Salicylic acid
Salicylic acid or derivatives
Hydroxybenzoic acid
Methoxyphenol
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Vinylogous acid
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:68496 )
methoxybenzoic acid (CHEBI:68496 )

Ontology

Not Available

Evening primrose (FooDB: FOOD00120)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	3.86 g/L	ALOGPS
logP	1.87	ALOGPS
logP	1.82	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.55	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.76 m³·mol⁻¹	ChemAxon
Polarizability	15.73 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]+	136.28	31661259
DarkChem	[M-H]-	135.449	31661259
DeepCCS	[M+H]+	135.626	30932474
DeepCCS	[M-H]-	132.58	30932474
DeepCCS	[M-2H]-	169.581	30932474
DeepCCS	[M+Na]+	144.734	30932474
AllCCS	[M+H]+	135.8	32859911
AllCCS	[M+H-H2O]+	131.4	32859911
AllCCS	[M+NH4]+	139.9	32859911
AllCCS	[M+Na]+	141.1	32859911
AllCCS	[M-H]-	131.6	32859911
AllCCS	[M+Na-2H]-	132.6	32859911
AllCCS	[M+HCOO]-	133.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methoxysalicylic acid	COC1=CC=CC(C(O)=O)=C1O	2659.0	Standard polar	33892256
3-Methoxysalicylic acid	COC1=CC=CC(C(O)=O)=C1O	1497.0	Standard non polar	33892256
3-Methoxysalicylic acid	COC1=CC=CC(C(O)=O)=C1O	1569.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methoxysalicylic acid,1TMS,isomer #1	COC1=CC=CC(C(=O)O[Si](C)(C)C)=C1O	1582.6	Semi standard non polar	33892256
3-Methoxysalicylic acid,1TMS,isomer #2	COC1=CC=CC(C(=O)O)=C1O[Si](C)(C)C	1668.1	Semi standard non polar	33892256
3-Methoxysalicylic acid,2TMS,isomer #1	COC1=CC=CC(C(=O)O[Si](C)(C)C)=C1O[Si](C)(C)C	1702.6	Semi standard non polar	33892256
3-Methoxysalicylic acid,1TBDMS,isomer #1	COC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1O	1842.2	Semi standard non polar	33892256
3-Methoxysalicylic acid,1TBDMS,isomer #2	COC1=CC=CC(C(=O)O)=C1O[Si](C)(C)C(C)(C)C	1922.3	Semi standard non polar	33892256
3-Methoxysalicylic acid,2TBDMS,isomer #1	COC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2173.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Methoxysalicylic acid EI-B (Non-derivatized)	splash10-0g4i-0900000000-6c062178ed4c1c680d3e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Methoxysalicylic acid EI-B (Non-derivatized)	splash10-0g4i-0900000000-6c062178ed4c1c680d3e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxysalicylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g4i-3900000000-5e54c3714d2e7a9befd8	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxysalicylic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-8390000000-6e3e2e42aa8eabde97c1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxysalicylic 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 - 3-Methoxysalicylic acid 10V, Positive-QTOF	splash10-014i-0900000000-85845ccd3d65e6ff7699	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxysalicylic acid 20V, Positive-QTOF	splash10-0g4i-0900000000-9fd06257f865a7e1a808	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxysalicylic acid 40V, Positive-QTOF	splash10-0udi-9400000000-1e3b713b8b16d20f91b8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxysalicylic acid 10V, Negative-QTOF	splash10-01b9-0900000000-d400f8e246374ba5e1e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxysalicylic acid 20V, Negative-QTOF	splash10-05fr-1900000000-2ce1148fc92ff320e638	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxysalicylic acid 40V, Negative-QTOF	splash10-0a4i-8900000000-50427ff925d936d3bd89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxysalicylic acid 10V, Negative-QTOF	splash10-014j-0900000000-9d84544044106bae91cc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxysalicylic acid 20V, Negative-QTOF	splash10-0a4i-0900000000-6bb365242e668fa976d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxysalicylic acid 40V, Negative-QTOF	splash10-0a4i-8900000000-6642ad5d547d72a11d9a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxysalicylic acid 10V, Positive-QTOF	splash10-0udi-0900000000-236d9b158189fb128c94	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxysalicylic acid 20V, Positive-QTOF	splash10-0uk9-3900000000-dee1b1121f73870ebb86	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxysalicylic acid 40V, Positive-QTOF	splash10-0udi-9200000000-fc84b481d6d8383938ce	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB012172

KNApSAcK ID

Not Available

Chemspider ID

63328

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70140

PDB ID

Not Available

ChEBI ID

68496

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

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]

Showing metabocard for 3-Methoxysalicylic acid (HMDB0059713)

MOL for HMDB0059713 (3-Methoxysalicylic acid)

3D MOL for HMDB0059713 (3-Methoxysalicylic acid)

3D SDF for HMDB0059713 (3-Methoxysalicylic acid)

3D-SDF for HMDB0059713 (3-Methoxysalicylic acid)

PDB for HMDB0059713 (3-Methoxysalicylic acid)

3D PDB for HMDB0059713 (3-Methoxysalicylic acid)

SMILES for HMDB0059713 (3-Methoxysalicylic acid)

INCHI for HMDB0059713 (3-Methoxysalicylic acid)

Structure for HMDB0059713 (3-Methoxysalicylic acid)

3D Structure for HMDB0059713 (3-Methoxysalicylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra