MiMeDB: Showing metabocard for Tartaric acid (MMDBc0000175)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:38:37 UTC

Update Date

2024-09-27 23:05:59 UTC

Metabolite ID

MMDBc0000175

Metabolite Identification

Common Name

Tartaric acid

Description

Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes and tamarinds, and is one of the main acids found in wine. It is added to other foods to give a sour taste, and is used as an antioxidant. Salts of tartaric acid are known as tartrates. It is a dihydroxy derivative of dicarboxylic acid. Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death. The minimum recorded fatal dose for a human is about 12 grams. In spite of that, it is included in many foods, especially sour-tasting sweets. As a food additive, tartaric acid is used as an antioxidant with E number E334, tartrates are other additives serving as antioxidants or emulsifiers. Naturally-occurring tartaric acid is chiral, meaning that it has molecules that are non-superimposable on their mirror-images. It is a useful raw material in organic chemistry for the synthesis of other chiral molecules. The naturally occurring form of the acid is L-(+)-tartaric acid or dextrotartaric acid. The mirror-image (enantiomeric) form, levotartaric acid or D-(-)-tartaric acid, and the achiral form, mesotartaric acid, can be made artificially. Tartarate is believed to play a role in inhibiting kidney stone formation. Most tartarate that is consumed by humans is metabolized by bacteria in the gastrointestinal tract -- primarily in the large instestine. Only about 15-20% of consumed tartaric acid is secreted in the urine unchanged. Tartaric acid is a biomarker for the consumption of wine and grapes (PMID: 24507823 ). Tartaric acid is also a fungal metabolite, elevated levels in the urine (especially in children) may be due to the presence of yeast (in the gut or bladder). It can be produced by Agrobacterium, Nocardia, Rhizobium, Saccharomyces as well (PMID: 7628083 ) (https://link.springer.com/article/10.1023/A:1005592104426). High levels of tartaric acid have been found in autistic children. In adults, tartaric acid may be due to the consumption of wine (https://www.greatplainslaboratory.com/articles-1/2015/11/13/candida-and-overgrowth-the-problem-bacteria-by-products) (PMID: 15738524 ; PMID: 24507823 ; PMID: 7628083 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₄H₆O₆

Average Mass

150.0868

Monoisotopic Mass

150.016437924

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

87-69-4

SMILES

Not Available

InChI Identifier

InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1

InChI Key

FEWJPZIEWOKRBE-JCYAYHJZSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Adipose Tissue
Blood
Feces
Platelet
Prostate
Urine

Tissue Locations

Adipose Tissue
Platelet
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191770	Tartrate-resistant acid phosphatase type 5	Unknown	P13686	Homo sapiens
MMDBp0191771	Prostatic acid phosphatase	Enzyme	P15309	Homo sapiens
MMDBp0194109	Lysophosphatidic acid phosphatase type 6	Enzyme	Q9NPH0	Homo sapiens
MMDBp0196039	Testicular acid phosphatase	Enzyme	Q9BZG2	Homo sapiens
MMDBp0196206	Putative uncharacterized protein ACP1	Enzyme	B5MCC7	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Lung cancer		Association	Human Urine	HMDB	22157537

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	11	Human ; Human feces	Microbial culture
Bacteria/Eubacteria	Actinobacteria	1		Microbial culture
Bacteria/Eubacteria	Firmicutes	1	Human feces
Bacteria	Proteobacteria	2	Human ; Human feces	Microbial culture
Archaea/Archaea	Euryarchaeota	1
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Not Available	U.S. Environmental Protection Agency	CompTox
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Source Type	Source Sub-type	Source Name	Data Source	Reference
Food	Not Available	Alcoholic beverage	FooDB	Maria Amargianitaki and Apostolos Spyros. NMR-based metabolomics in wine quality control and authentication. Amargianitaki and Spyros Chem. Biol. Technol. Agric. (2017) 4:9 DOI 10.1186/s40538-017-0092-x
Food	Not Available	Pale lager	FooDB	25745209
Food	Not Available	Palomino wine	FooDB	Pablo Est√©vez, M Luisa Gil and Elena Falqu√©. Effects of seven yeast strains on the volatile composition of Palomino wines. International Journal of Food Science & Technology, 2004, 39, Issue 1, p.61-69. https://doi.org/10.1046/j.0950-5423.2003.00755.x
Food	Not Available	Pinot noir red wine (six different countries)	FooDB	Alicia Robles, Magdalena Fabjanowicz, Tomasz Chmiel, Justyna P≈Çotka-Wasylka. Determination and identification of organic acids in wine samples. Problems and challenges. Trends in Analytical Chemistry 120 (2019) 115630. doi: 10.1016/j.trac.2019.115630
Food	Not Available	Spanish white wine	FooDB	Alicia Robles, Magdalena Fabjanowicz, Tomasz Chmiel, Justyna P≈Çotka-Wasylka. Determination and identification of organic acids in wine samples. Problems and challenges. Trends in Analytical Chemistry 120 (2019) 115630. doi: 10.1016/j.trac.2019.115630
Plant	Fruit	Avocado	FooDB	DUKE
Plant	Fruit	Common grape	FooDB	DUKE
Plant	Fruit	Star fruit	FooDB	DUKE
Plant	Fruit	Tamarind	FooDB	DUKE
Plant	Leaves	Tamarind	FooDB	DUKE
Plant	Seed	Sunflower	FooDB	DUKE

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	12		1.3	46	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	2702744
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	20573794
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Autosomal dominant polycystic kidney disease (ADPKD)	HMDB	21389975
Human Urine	Detected and Quantified	5		0	25	umol/mmol creatinine	Not Specified	Both	Lung cancer	HMDB	22157537
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Cardiosvacular risk	HMDB	22887155
Human Urine	Detected and Quantified	11.8		2.6	64.4	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal cancer	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25670064
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Bladder cancer	HMDB	28157703
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected and Quantified			0	60	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	31506554
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected and Quantified	13.217	13.438			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	38.183	53.107			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Diabetes mellitus	HMDB	Rosa Va ́zquez-Fresno et al. An NMR metabolomics approach reveals a combined-biomarkers model in a wine interventional trial with validation in free-living individuals of the PREDIMED study. Metabolomics (2015) 11:797- 806
Human Urine	Detected and Quantified	5		0	25	umol/mmol creatinine	Not Specified	Both	Lung cancer	HMDB	22157537
Human Urine	Detected and Quantified			0	60	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	31506554
Human Urine	Detected and Quantified	11.8		2.6	64.4	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	12		1.3	46	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	2702744
Human Urine	Detected and Quantified	38.183	53.107			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25670064
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	20573794
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Petrarulo M, Marangella M, Bianco O, Linari F: Ion-chromatographic determination of L-tartrate in urine samples. Clin Chem. 1991 Jan;37(1):90-3. [PubMed:1988215 ]
Shaw W, Kassen E, Chaves E: Increased urinary excretion of analogs of Krebs cycle metabolites and arabinose in two brothers with autistic features. Clin Chem. 1995 Aug;41(8 Pt 1):1094-104. [PubMed:7628083 ]
Lord RS, Burdette CK, Bralley JA: Significance of urinary tartaric acid. Clin Chem. 2005 Mar;51(3):672-3. doi: 10.1373/clinchem.2004.036368. [PubMed:15738524 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Regueiro J, Vallverdu-Queralt A, Simal-Gandara J, Estruch R, Lamuela-Raventos RM: Urinary tartaric acid as a potential biomarker for the dietary assessment of moderate wine consumption: a randomised controlled trial. Br J Nutr. 2014 May;111(9):1680-5. doi: 10.1017/S0007114513004108. Epub 2014 Feb 10. [PubMed:24507823 ]

Showing metabocard for Tartaric acid (MMDBc0000175)

MOL for #<Metabolite:0x00007f3ddde365d0>

3D MOL for #<Metabolite:0x00007f3ddde365d0>

3D SDF for #<Metabolite:0x00007f3ddde365d0>

3D-SDF for #<Metabolite:0x00007f3ddde365d0>

PDB for #<Metabolite:0x00007f3ddde365d0>

3D PDB for #<Metabolite:0x00007f3ddde365d0>

SMILES for #<Metabolite:0x00007f3ddde365d0>

INCHI for #<Metabolite:0x00007f3ddde365d0>

Structure for #<Metabolite:0x00007f3ddde365d0>

3D Structure for #<Metabolite:0x00007f3ddde365d0>