ECMDB: trans-Aconitic acid (ECMDB00958) (M2MDB000208)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (1)XML

Proteins (1)

Record Information

Version

2.0

Creation Date

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

Update Date

2015-09-13 15:15:20 -0600

Secondary Accession Numbers

ECMDB00958

Identification

Name:

trans-Aconitic acid

Description

Trans-aconitic acid is a member of the chemical class known as Tricarboxylic Acids and Derivatives. These are organic compounds containing three carboxylic acid groups (or salt/ester derivatives thereof). The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerization of citrate to isocitrate in the citric acid cycle. It is acted upon by the enzyme aconitase. Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid. (WikiPedia)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(1E)-1-Propene-1,2,3-tricarboxylate
(1E)-1-propene-1,2,3-tricarboxylic acid
(1E)-Prop-1-ene-1,2,3-tricarboxylic
(1E)1-Propene-1,2,3-tricarboxylate
(1E)1-Propene-1,2,3-tricarboxylic acid
(E)-prop-1-ene-1,2,3-tricarboxylate
(e)-1-Propene-1,2,3-tricarboxylate
(E)-1-propene-1,2,3-tricarboxylic acid
(e)-Aconitate
(E)-Aconitic acid
(E)-prop-1-ene-1,2,3-tricarboxylate
(E)-prop-1-ene-1,2,3-tricarboxylic acid
1-Propene-1-trans-2,3-tricarboxylate
1-Propene-1-trans-2,3-tricarboxylic acid
1-trans-Propene-1,2,3-tricarboxylate
1-trans-Propene-1,2,3-tricarboxylic acid
trans-aconitic acid
Acid
TRA
trans-1-Propene-1,2,3-tricarboxylate
Trans-1-Propene-1,2,3-tricarboxylic acid
Trans-Aconitate
Trans-Aconitic acid
trans-Propene-1,2,3-tricarboxylate
Trans-Propene-1,2,3-tricarboxylic acid

Chemical Formula:

C₆H₆O₆

Weight:

Average: 174.1082
Monoisotopic: 174.016437924

InChI Key:

GTZCVFVGUGFEME-HNQUOIGGSA-N

InChI:

InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1+

CAS number:

4023-65-8

IUPAC Name:

(1E)-prop-1-ene-1,2,3-tricarboxylic acid

Traditional IUPAC Name:

trans aconitic acid

SMILES:

OC(=O)C\C(=C/C(O)=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aconitic acid (CHEBI:32806 )

Physical Properties

State:

Solid

Charge:

-3

Melting point:

187 - 191 °C

Experimental Properties:

Property	Value	Source
LogP:	-0.728	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	6.72 g/L	ALOGPS
logP	-0.41	ALOGPS
logP	-0.52	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.23 m³·mol⁻¹	ChemAxon
Polarizability	13.96 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:

trans-Aconitic acid + S-Adenosylmethionine > E-3-Carboxy-2-pentenedioate 6-methyl ester + S-Adenosylhomocysteine
trans-Aconitic acid <> cis-Aconitic acid
trans-Aconitic acid cis-Aconitic acid
S-adenosyl-L-methionine + trans-Aconitic acid > S-Adenosylhomocysteine + (E)-3-(Methoxycarbonyl)pent-2-enedioate
S-Adenosylmethionine + trans-Aconitic acid <> S-Adenosylhomocysteine + E-3-Carboxy-2-pentenedioate 6-methyl ester

SMPDB Pathways:

Secondary Metabolites: Glyoxylate cycle

PW000967

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
96± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
72± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-003s-3971000000-d4adfdbddf5dc3badb47	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-003s-3971000000-d4adfdbddf5dc3badb47	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1930000000-1043e640a069e4ed3c64	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06w9-4900000000-38239492ad0e66d6533b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00di-9167000000-07ccdac5775cc3e75c95	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9300000000-1f04239a9a7133f89d08	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000f-9000000000-49f5c2a7959cfbbbe09f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000f-9100000000-d4857c30b96cf4786dbe	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00b9-1900000000-51343d1269f884535cca	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9100000000-b3ebe9a6fedcb9608872	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-2d6b96d6e5ed92f0fdee	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-000l-9000000000-d36114a1c7a0318b1f7a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-f4ae4a72d5f2beed9106	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9200000000-49eaf4d6558839930e52	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00b9-1900000000-51343d1269f884535cca	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9100000000-b3ebe9a6fedcb9608872	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-4f60fbd245c1d58cd7d5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000l-9000000000-d36114a1c7a0318b1f7a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-f4ae4a72d5f2beed9106	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-9200000000-49eaf4d6558839930e52	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9100000000-a70cb799a63ff364ca21	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9000000000-eabb8ab38f98bb81b1ee	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9200000000-2d22108854c0dad1b598	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9300000000-3cf209c9f766f6c0efe8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-8e26562af9ae45eb3303	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02di-1900000000-7fec32a5e34c3b55d683	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01w0-9600000000-ee172c3013370ab0da31	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fr-1900000000-18635ce5a20ce1b78139	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-2900000000-58bb75a2a1b28dbffd73	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06rf-9300000000-19df730d01f07fcf6573	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-000f-9100000000-814aded0eac117ddb550	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,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
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
Koide K, Toyama J, Inoue N, Koshikawa S, Akizawa T, Takahashi K, Hidaka S, Yamane Y, Shinoda K, Nakao M, et al.: [Uremic peak 2a in high performance liquid chromatography--acidic components and their membrane permeability]. Nihon Jinzo Gakkai Shi. 1986 Nov;28(11):1481-9. Pubmed: 2950263
Tanaka K, Hine DG: Compilation of gas chromatographic retention indices of 163 metabolically important organic acids, and their use in detection of patients with organic acidurias. J Chromatogr. 1982 Apr 30;239:301-22. Pubmed: 7096501
Tsai MY, Oliphant C, Josephson MW: Identification of metabolites diagnostic for organic acidurias by simultaneous dual-column capillary gas chromatography. J Chromatogr. 1985 May 31;341(1):1-10. Pubmed: 4019674
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:

Gutierrez, Eddie N.; Lamberti, Vincent. Preparation of aconitic acid. U.S. (1978), 5 pp. CODEN: USXXAM US 4123459 19781031 CAN 90:103423 AN 1979:103423

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	15708
HMDB ID	HMDB00958
Pubchem Compound ID	444212
Kegg ID	C02341
ChemSpider ID	392201
Wikipedia ID	Not Available
BioCyc ID	CPD-225
EcoCyc ID	CPD-225
Ligand Expo	TRA

Enzymes

Protein Details

1. Trans-aconitate 2-methyltransferase

General function:: Involved in trans-aconitate 2-methyltransferase activity
Specific function:: Catalyzes the S-adenosylmethionine monomethyl esterification of trans-aconitate at high affinity and of cis- aconitate, isocitrate, and citrate at lower velocities and affinities
Gene Name:: tam
Uniprot ID:: P76145
Molecular weight:: 29006

Reactions

S-adenosyl-L-methionine + trans-aconitate = S-adenosyl-L-homocysteine + (E)-3-(methoxycarbonyl)pent-2-enedioate.

trans-Aconitic acid (ECMDB00958) (M2MDB000208)

Structure for #<Compound:0xa56d2838>

Enzymes

Reactions