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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2013-04-09 21:19:03 UTC

Update Date

2023-02-21 17:29:40 UTC

HMDB ID

HMDB0060003

Secondary Accession Numbers

HMDB60003

Metabolite Identification

Common Name

Isovanillic acid

Description

Isovanillic acid, also known as acide isovanillique or 3-hydroxy-p-anisate, 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. Isovanillic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a selective inhibitor of aldehyde oxidase. Isovanillic acid is a metabolite of isovanillin. Isovanillin is a phenolic aldehyde, an organic compound and isomer of vanillin. It is not a substrate of that enzyme, and is metabolized by aldehyde dehydrogenase into isovanillic acid.

Structure

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

HEADER    PROTEIN                                 09-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-APR-13         0                                  
HETATM    1  C   UNK     0      11.660   7.150   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.326   6.380   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.326   4.840   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.660   4.070   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.994   4.840   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.994   6.380   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.327   7.150   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.993   4.070   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      11.660   2.530   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      14.327   8.690   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      15.661   6.380   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.993   2.530   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6   10   11                                                  
CONECT    8    3   12                                                       
CONECT    9    4                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
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
3-Hydroxy-p-anisic acid	ChEBI
3-Hydroxyanisic acid	ChEBI
Acide isovanillique	ChEBI
3-Hydroxy-p-anisate	Generator
3-Hydroxyanisate	Generator
Isovanillate	Generator
3-Hydroxy-4-methoxybenzoate	HMDB
Isovanillic acid	ChEBI
3-Hydroxy-4-methoxybenzoic acid	HMDB

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.1467

Monoisotopic Molecular Weight

168.042258744

IUPAC Name

3-hydroxy-4-methoxybenzoic acid

Traditional Name

isovanillic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

LBKFGYZQBSGRHY-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
Hydroxybenzoic acid
Methoxyphenol
Benzoic acid
Phenoxy compound
Benzoyl
Phenol ether
Methoxybenzene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:63798 )
methoxybenzoic acid (CHEBI:63798 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 19812218)

Source

Exogenous

Food

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0060003)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0060003)

Tea

Tea products (HMDB: HMDB0060003)

Fat and oil

Olive oil (HMDB: HMDB0060003)

Fruit

Fruits (HMDB: HMDB0060003)

Vegetable

Vegetables (HMDB: HMDB0060003)

Legumes (HMDB: HMDB0060003)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0060003)

Nut

Nuts (HMDB: HMDB0060003)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0060003)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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	4.42 g/L	ALOGPS
logP	1.81	ALOGPS
logP	1.17	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	4.15	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	15.89 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]+	137.176	31661259
DarkChem	[M-H]-	136.387	31661259
DeepCCS	[M+H]+	130.886	30932474
DeepCCS	[M-H]-	127.055	30932474
DeepCCS	[M-2H]-	164.355	30932474
DeepCCS	[M+Na]+	139.894	30932474
AllCCS	[M+H]+	135.9	32859911
AllCCS	[M+H-H2O]+	131.5	32859911
AllCCS	[M+NH4]+	140.0	32859911
AllCCS	[M+Na]+	141.2	32859911
AllCCS	[M-H]-	132.8	32859911
AllCCS	[M+Na-2H]-	133.8	32859911
AllCCS	[M+HCOO]-	135.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isovanillic acid	COC1=CC=C(C=C1O)C(O)=O	2742.5	Standard polar	33892256
Isovanillic acid	COC1=CC=C(C=C1O)C(O)=O	1547.6	Standard non polar	33892256
Isovanillic acid	COC1=CC=C(C=C1O)C(O)=O	1603.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isovanillic acid,1TMS,isomer #1	COC1=CC=C(C(=O)O)C=C1O[Si](C)(C)C	1740.2	Semi standard non polar	33892256
Isovanillic acid,1TMS,isomer #2	COC1=CC=C(C(=O)O[Si](C)(C)C)C=C1O	1706.0	Semi standard non polar	33892256
Isovanillic acid,2TMS,isomer #1	COC1=CC=C(C(=O)O[Si](C)(C)C)C=C1O[Si](C)(C)C	1763.5	Semi standard non polar	33892256
Isovanillic acid,1TBDMS,isomer #1	COC1=CC=C(C(=O)O)C=C1O[Si](C)(C)C(C)(C)C	1993.5	Semi standard non polar	33892256
Isovanillic acid,1TBDMS,isomer #2	COC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1O	1964.5	Semi standard non polar	33892256
Isovanillic acid,2TBDMS,isomer #1	COC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2226.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isovanillic acid EI-B (Non-derivatized)	splash10-0gb9-0900000000-660260d6741ecd0596f0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isovanillic acid EI-B (Non-derivatized)	splash10-0gb9-0900000000-660260d6741ecd0596f0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovanillic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0v4i-1900000000-c5f8b901bedc7425298b	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovanillic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00dj-7390000000-70ce0f538d85bc14166b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovanillic 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 - Isovanillic acid 10V, Positive-QTOF	splash10-014i-0900000000-74d5acf94885979a45bc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovanillic acid 20V, Positive-QTOF	splash10-014i-0900000000-1f440ab003326771b38c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovanillic acid 40V, Positive-QTOF	splash10-0pba-9700000000-61538cb4d5e11d9a644d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovanillic acid 10V, Negative-QTOF	splash10-014i-0900000000-f99b0820273ae5f60860	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovanillic acid 20V, Negative-QTOF	splash10-0600-0900000000-3aec4e7b83510da5f7dc	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovanillic acid 40V, Negative-QTOF	splash10-0a4i-5900000000-183253eef4e32ef30a77	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovanillic acid 10V, Positive-QTOF	splash10-01di-0900000000-3cc71901cc9d06891629	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovanillic acid 20V, Positive-QTOF	splash10-0uk9-2900000000-e68face2401bfccd751b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovanillic acid 40V, Positive-QTOF	splash10-0f79-9000000000-8336370be2810955110d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovanillic acid 10V, Negative-QTOF	splash10-00xr-0900000000-5caf52d47f9861640c51	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovanillic acid 20V, Negative-QTOF	splash10-0a4i-1900000000-b1375f695ecb3e248e98	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovanillic acid 40V, Negative-QTOF	splash10-0a4l-9300000000-efc8e562978bca30917e	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.328 +/- 0.093 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12575

PDB ID

Not Available

ChEBI ID

63798

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

Loke WM, Jenner AM, Proudfoot JM, McKinley AJ, Hodgson JM, Halliwell B, Croft KD: A metabolite profiling approach to identify biomarkers of flavonoid intake in humans. J Nutr. 2009 Dec;139(12):2309-14. doi: 10.3945/jn.109.113613. Epub 2009 Oct 7. [PubMed:19812218 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Isovanillic acid → 6-(5-carboxy-2-methoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Isovanillic acid → 3,4,5-trihydroxy-6-(3-hydroxy-4-methoxybenzoyloxy)oxane-2-carboxylic acid	details

Enzyme Details

2. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Reactions

Isovanillic acid → 2-{[hydroxy(3-hydroxy-4-methoxyphenyl)methylidene]amino}acetic acid	details

Enzyme Details

3. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

Isovanillic acid → 4-methoxy-3-(sulfooxy)benzoic acid	details

Showing metabocard for Isovanillic acid (HMDB0060003)

MOL for HMDB0060003 (Isovanillic acid)

3D MOL for HMDB0060003 (Isovanillic acid)

3D SDF for HMDB0060003 (Isovanillic acid)

3D-SDF for HMDB0060003 (Isovanillic acid)

PDB for HMDB0060003 (Isovanillic acid)

3D PDB for HMDB0060003 (Isovanillic acid)

SMILES for HMDB0060003 (Isovanillic acid)

INCHI for HMDB0060003 (Isovanillic acid)

Structure for HMDB0060003 (Isovanillic acid)

3D Structure for HMDB0060003 (Isovanillic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions