ECMDB: Tartaric acid (ECMDB00956) (M2MDB000206)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)Transporters (5)XML

Proteins (183)

Record Information

Version

2.0

Creation Date

2012-05-31 13:02:24 -0600

Update Date

2015-09-13 12:56:09 -0600

Secondary Accession Numbers

ECMDB00956

Identification

Name:

Tartaric acid

Description

Tartaric acid is a white crystalline organic acid. Salts of tartaric acid are known as tartrates. It is a dihydroxy derivative of dicarboxylic acid. 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. (Wikipedia) In E. coli K-12, tartaric acid is involved in glyoxylate and dicarboxylate metabolism. (KEGG)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(+)-(2R,3R)-Tartarate
(+)-(2R,3R)-Tartaric acid
(+)-tartarate
(+)-tartaric acid
(+)-tartrate
(+)-tartric acid
(1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylate
(1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acid
(2R,3R)-2,3-dihydroxybutanedioate
(2R,3R)-2,3-dihydroxybutanedioic acid
(2R,3R)-2,3-dihydroxysuccinate
(2R,3R)-2,3-dihydroxysuccinic acid
(2R,3R)-2,3-tartarate
(2R,3R)-2,3-tartaric acid
(2R,3R)-Tartarate
(2R,3R)-Tartaric acid
(2R,3R)-tartrate
(2R,3R)-tartric acid
(R,R)-(+)-tartarate
(R,R)-(+)-tartaric acid
(R,R)-tartarate
(R,R)-tartaric acid
(R,R)-tartrate
(R,R)-tartric acid
1,2-Dihydroxyethane-1,2-dicarboxylate
1,2-Dihydroxyethane-1,2-dicarboxylic acid
2,3-Dihydroxy-succinate
2,3-Dihydroxy-succinic acid
2,3-Dihydroxybutanedioate
2,3-Dihydroxybutanedioic acid
2,3-Dihydroxysuccinate
2,3-Dihydroxysuccinic acid
D-a,b-Dihydroxysuccinate
D-a,b-Dihydroxysuccinic acid
D-Tartarate
D-Tartaric acid
Dextrotartarate
Dextrotartaric acid
L(+)-Tartarate
L(+)-Tartaric acid
L-(+)-Tartarate
L-(+)-Tartaric acid
L-Tartarate
L-Tartaric acid
L-Threarate
L-Threaric acid
Natural tartarate
Natural tartaric acid
Rechtsweinsaeure
TAR
Tartarate
Tartaric acid
Tartrate
Tartric acid
Threarate
Threaric acid
TLA
Weinsaeure

Chemical Formula:

C₄H₆O₆

Weight:

Average: 150.0868
Monoisotopic: 150.016437924

InChI Key:

FEWJPZIEWOKRBE-JCYAYHJZSA-N

InChI:

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

CAS number:

87-69-4

IUPAC Name:

(2R,3R)-2,3-dihydroxybutanedioic acid

Traditional IUPAC Name:

L(+)-tartaric acid

SMILES:

O[C@H]([C@@H](O)C(O)=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

Sugar acid
Short-chain hydroxy acid
Beta-hydroxy acid
Fatty acid
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Secondary alcohol
1,2-diol
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tartaric acid (CHEBI:15671 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

169 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	582 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	161 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-1.8	ChemAxon
logS	0.03	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.21 m³·mol⁻¹	ChemAxon
Polarizability	11.33 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Tartaric acid <> Water + Oxalacetic acid
Tartaric acid <> Glyceric acid + Carbon dioxide
Tartaric acid + NAD <> 2-Hydroxy-3-oxosuccinate + NADH + Hydrogen ion
Tartaric acid > Oxalacetic acid + Water

SMPDB Pathways:

glycolate and glyoxylate degradation II	PW002021
inner membrane transport	PW000786

KEGG Pathways:

Butanoate metabolism ec00650
Glyoxylate and dicarboxylate metabolism ec00630

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0930000000-19235937e21066a9c484	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-000f-0961000000-559c31b016f4fb3700d2	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-0961000000-1b17d674621eb9d88c3c	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0930000000-19235937e21066a9c484	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000f-0961000000-559c31b016f4fb3700d2	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-9200000000-df0ce9fba754b55674b1	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000b-7900000000-d247ec12b77f427e9a76	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-05fu-9000000000-4bf01ad116d24a453817	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9000000000-4da65da10f3a34f77688	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-ecb902731b9f6eb3764d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0072-9700000000-1e8e6f410c1d71af856e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-f13ad2560d3e6818db9c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-05fu-9000000000-f46a01eb933ba6fbceac	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-08dec35ca6a80add253a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-ecb902731b9f6eb3764d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0072-9700000000-1e8e6f410c1d71af856e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-f13ad2560d3e6818db9c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-05fu-9000000000-f46a01eb933ba6fbceac	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-08dec35ca6a80add253a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-05fu-9000000000-2bc9b64b80733677dbe6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-e65d82322cd0037aa733	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0072-9600000000-0276f4093011ce886f64	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-007a-9300000000-5ad0de9efcf7b25ff3dc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-1900000000-6a73140cfa5a0c0234e3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-9600000000-ca8758d1e65f5dbe35d9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a70-9100000000-1630b812321816f95d11	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05bb-7900000000-146a1c7b189a7bbacda0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9500000000-f7af07684007cf14bdce	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-a8f5502da9e4d13e4144	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4s-4900000000-4b81a8a41abed679d134	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9200000000-b73e0df104053da76268	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-056r-9000000000-16517a02beb9427ceaff	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Lord RS, Burdette CK, Bralley JA: Significance of urinary tartaric acid. Clin Chem. 2005 Mar;51(3):672-3. Pubmed: 15738524
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
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. Pubmed: 19212411
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Milas, N. A.; Terry, Ethel M. Oxidation of fumaric and of maleic acids to tartaric acid. Journal of the American Chemical Society (1925), 47 1412-8.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	15671
HMDB ID	HMDB00956
Pubchem Compound ID	444305
Kegg ID	C00898
ChemSpider ID	392277
Wikipedia	Tartaric acid
BioCyc ID	TARTRATE
EcoCyc ID	TARTRATE
Ligand Expo	TLA

Enzymes

Protein Details

1. L(+)-tartrate dehydratase subunit alpha

General function:: Involved in lyase activity
Specific function:: (R,R)-tartrate = oxaloacetate + H(2)O
Gene Name:: ttdA
Uniprot ID:: P05847
Molecular weight:: 32733

Reactions

(R,R)-tartrate = oxaloacetate + H(2)O.

Protein Details

2. L(+)-tartrate dehydratase subunit beta

General function:: Involved in hydro-lyase activity
Specific function:: (R,R)-tartrate = oxaloacetate + H(2)O
Gene Name:: ttdB
Uniprot ID:: P0AC35
Molecular weight:: 22679

Reactions

(R,R)-tartrate = oxaloacetate + H(2)O.

Protein Details

3. D-malate dehydrogenase [decarboxylating]

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the NAD(+)-dependent oxidative decarboxylation of D-malate into pyruvate. Is essential for aerobic growth on D- malate as the sole carbon source. But is not required for anaerobic D-malate utilization, although DmlA is expressed and active in those conditions. Appears to be not able to use L- tartrate as a substrate for dehydrogenation instead of D-malate
Gene Name:: dmlA
Uniprot ID:: P76251
Molecular weight:: 40315

Reactions

(R)-malate + NAD(+) = pyruvate + CO(2) + NADH.

Transporters

Protein Details

1. L-tartrate/succinate antiporter

General function:: Involved in transporter activity
Specific function:: Catalyzes the uptake of tartrate in exchange for intracellular succinate. Essential for anaerobic L-tartrate fermentation
Gene Name:: ttdT
Uniprot ID:: P39414
Molecular weight:: 52906

Protein Details

2. Outer membrane protein N

General function:: Involved in transporter activity
Specific function:: Non-specific porin
Gene Name:: ompN
Uniprot ID:: P77747
Molecular weight:: 41220

Protein Details

3. Outer membrane pore protein E

General function:: Involved in transporter activity
Specific function:: Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:: phoE
Uniprot ID:: P02932
Molecular weight:: 38922

Protein Details

4. Outer membrane protein F

General function:: Involved in transporter activity
Specific function:: OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:: ompF
Uniprot ID:: P02931
Molecular weight:: 39333

Protein Details

5. Outer membrane protein C

General function:: Involved in transporter activity
Specific function:: Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:: ompC
Uniprot ID:: P06996
Molecular weight:: 40368

Tartaric acid (ECMDB00956) (M2MDB000206)

Structure for #<Compound:0xa60f85b0>

Enzymes

Reactions

Reactions

Reactions

Transporters