MiMeDB: Showing metabocard for Methyl vanillate (MMDBc0033683)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:58:51 UTC

Update Date

2022-08-31 22:37:43 UTC

MiMeDB ID

MMDBc0033683

Metabolite Identification

Common Name

Methyl vanillate

Description

Methyl vanillate is a member of the class of compounds known as m-methoxybenzoic acids and derivatives. These compounds are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. Methyl vanillate is considered to be a slightly soluble in water acidic compound. Methyl vanillate can be synthesized from vanillic acid. Vanillic acid is a phenolic acid or chlorogenic acid that is an oxidized form of vanillin. Vanillic acid is also an intermediate in the production of vanillin from ferulic acid. It is found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. Vanillic acid is also found in wine and vinegar. Vanillic acid is a metabolic by-product of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea, and vanilla-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5'-nucleotidase activity (PMID:16899266 ). Vanillic acid is also a microbial metabolite found in several bacterial genera including Amycolatopsis, Delftia, and Pseudomonas (PMID:11152072 , 10543794 , 11728709 , 9579070 ). Methyl vanillate has been identified in foods such as cow's milk (PMID:4682334 ) and beer (PMID:20800742 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₉H₁₀O₄

Average Molecular Weight

182.1733

Monoisotopic Molecular Weight

182.057908808

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

3943-74-6

SMILES

Not Available

InChI Identifier

InChI=1S/C9H10O4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10H,1-2H3

InChI Key

BVWTXUYLKBHMOX-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Fungi	Ascomycota	1	Human Feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

Not Available

References

Synthesis Reference

Not Available

General References

Brewington CR, Parks OW, Schwartz DP: Conjugated compounds in cow's milk. J Agric Food Chem. 1973 Jan-Feb;21(1):38-9. doi: 10.1021/jf60185a015. [PubMed:4682334 ]
Venturi V, Zennaro F, Degrassi G, Okeke BC, Bruschi CV: Genetics of ferulic acid bioconversion to protocatechuic acid in plant-growth-promoting Pseudomonas putida WCS358. Microbiology (Reading). 1998 Apr;144 ( Pt 4):965-973. doi: 10.1099/00221287-144-4-965. [PubMed:9579070 ]
Overhage J, Priefert H, Steinbuchel A: Biochemical and genetic analyses of ferulic acid catabolism in Pseudomonas sp. Strain HR199. Appl Environ Microbiol. 1999 Nov;65(11):4837-47. doi: 10.1128/AEM.65.11.4837-4847.1999. [PubMed:10543794 ]
Achterholt S, Priefert H, Steinbuchel A: Identification of Amycolatopsis sp. strain HR167 genes, involved in the bioconversion of ferulic acid to vanillin. Appl Microbiol Biotechnol. 2000 Dec;54(6):799-807. doi: 10.1007/s002530000431. [PubMed:11152072 ]
Plaggenborg R, Steinbuchel A, Priefert H: The coenzyme A-dependent, non-beta-oxidation pathway and not direct deacetylation is the major route for ferulic acid degradation in Delftia acidovorans. FEMS Microbiol Lett. 2001 Nov 27;205(1):9-16. doi: 10.1111/j.1574-6968.2001.tb10918.x. [PubMed:11728709 ]
Dhananjaya BL, Nataraju A, Rajesh R, Raghavendra Gowda CD, Sharath BK, Vishwanath BS, D'Souza CJ: Anticoagulant effect of Naja naja venom 5'nucleotidase: demonstration through the use of novel specific inhibitor, vanillic acid. Toxicon. 2006 Sep 15;48(4):411-21. doi: 10.1016/j.toxicon.2006.06.017. Epub 2006 Jul 7. [PubMed:16899266 ]
Sterckx FL, Saison D, Delvaux FR: Determination of volatile monophenols in beer using acetylation and headspace solid-phase microextraction in combination with gas chromatography and mass spectrometry. Anal Chim Acta. 2010 Aug 31;676(1-2):53-9. doi: 10.1016/j.aca.2010.07.043. Epub 2010 Aug 5. [PubMed:20800742 ]

Showing metabocard for Methyl vanillate (MMDBc0033683)

MOL for #<Metabolite:0x00007f08e8507dd0>

3D MOL for #<Metabolite:0x00007f08e8507dd0>

3D SDF for #<Metabolite:0x00007f08e8507dd0>

3D-SDF for #<Metabolite:0x00007f08e8507dd0>

PDB for #<Metabolite:0x00007f08e8507dd0>

3D PDB for #<Metabolite:0x00007f08e8507dd0>

SMILES for #<Metabolite:0x00007f08e8507dd0>

INCHI for #<Metabolite:0x00007f08e8507dd0>

Structure for #<Metabolite:0x00007f08e8507dd0>

3D Structure for #<Metabolite:0x00007f08e8507dd0>