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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:20 UTC

HMDB ID

HMDB0000958

Secondary Accession Numbers

HMDB00958

Metabolite Identification

Common Name

trans-Aconitic acid

Description

trans-Aconitic acid, also known as trans-aconitate or (e)-aconitic acid, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. trans-Aconitic acid exists in all living species, ranging from bacteria to humans. trans-Aconitic acid is a dry, musty, and nut tasting compound. Outside of the human body, trans-aconitic acid has been detected, but not quantified in several different foods, such as garden tomato fruits, root vegetables, soy beans, and rices. trans-Aconitic acid is normally present in human urine, and it has been suggested that is present in larger amounts with Reye's syndrome and organic aciduria. trans-Aconitic acid in the urine is a biomarker for the consumption of soy products. trans-Aconitic acid is a substrate of enzyme trans-Aconitic acid 2-methyltransferase (EC2.1.1.144).

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      24.982 -11.695   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      23.649  -7.845   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      23.649  -9.385   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      24.982  -5.535   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      30.317  -7.075   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      28.983  -9.385   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      26.316  -9.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.316  -7.845   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.650  -7.075   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.982 -10.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.982  -7.075   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.983  -7.845   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6   12                                                            
CONECT    7    8   10                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   12                                                       
CONECT   10    1    3    7                                                  
CONECT   11    2    4    8                                                  
CONECT   12    5    6    9                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(1E)-1-Propene-1,2,3-tricarboxylic acid	ChEBI
(e)-1-Propene-1,2,3-tricarboxylic acid	ChEBI
(1E)-1-Propene-1,2,3-tricarboxylate	Generator
(e)-1-Propene-1,2,3-tricarboxylate	Generator
trans-Aconitate	Generator
(1E)-Prop-1-ene-1,2,3-tricarboxylic	HMDB
(1E)1-Propene-1,2,3-tricarboxylate	HMDB
(1E)1-Propene-1,2,3-tricarboxylic acid	HMDB
(e)-Aconitic acid	HMDB
1-Propene-1-trans-2,3-tricarboxylic acid	HMDB
1-trans-Propene-1,2,3-tricarboxylic acid	HMDB
Acid	HMDB
TRA	HMDB
trans-1-Propene-1,2,3-tricarboxylic acid	HMDB
trans-Propene-1,2,3-tricarboxylic acid	HMDB
Acid, aconitic	HMDB
Acid, adonic	HMDB
Acid, carboxyglutaconic	HMDB
Acid, citridic	HMDB
Adonic acid	HMDB
Achilleic acid	HMDB
Acid, acontic	HMDB
Acid, pyrocitric	HMDB
Carboxyglutaconic acid	HMDB
Equisetic acid	HMDB
Pyrocitric acid	HMDB
Acid, achilleic	HMDB
Acid, equisetic	HMDB
Aconitate	HMDB
Citridic acid	HMDB
Citridinic acid	HMDB
Acid, citridinic	HMDB
Aconitic acid	HMDB
Acontic acid	HMDB

Chemical Formula

C₆H₆O₆

Average Molecular Weight

174.1082

Monoisotopic Molecular Weight

174.016437924

IUPAC Name

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

Traditional Name

trans aconitic acid

CAS Registry Number

4023-65-8

SMILES

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

InChI Identifier

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+

InChI Key

GTZCVFVGUGFEME-HNQUOIGGSA-N

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 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	187 - 191 °C	Not Available
Boiling Point	542.00 to 543.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	472.5 mg/mL	Not Available
LogP	-0.140	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	131.875	30932474
[M+H]+	Baker	153.018	30932474
[M-H]-	Not Available	131.875	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001770
[M+H]+	Not Available	153.018	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001770

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	139.679	31661259
DarkChem	[M-H]-	133.066	31661259
AllCCS	[M+H]+	137.87	32859911
AllCCS	[M-H]-	129.608	32859911
DeepCCS	[M+H]+	132.555	30932474
DeepCCS	[M-H]-	128.795	30932474
DeepCCS	[M-2H]-	166.404	30932474
DeepCCS	[M+Na]+	141.943	30932474
AllCCS	[M+H]+	137.9	32859911
AllCCS	[M+H-H2O]+	134.0	32859911
AllCCS	[M+NH4]+	141.5	32859911
AllCCS	[M+Na]+	142.5	32859911
AllCCS	[M-H]-	129.6	32859911
AllCCS	[M+Na-2H]-	131.0	32859911
AllCCS	[M+HCOO]-	132.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.35 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6917 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.12 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	167.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	949.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	366.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	57.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	213.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	87.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	282.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	310.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	492.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	669.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	131.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1018.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	237.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	284.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	935.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	250.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	554.0 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trans-Aconitic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C/C(=C\C(=O)O)C(=O)O	1718.6	Semi standard non polar	33892256
trans-Aconitic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C/C(=C\C(=O)O)C(=O)O	1643.9	Standard non polar	33892256
trans-Aconitic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C/C(=C\C(=O)O)C(=O)O	2955.1	Standard polar	33892256
trans-Aconitic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)/C=C(\CC(=O)O)C(=O)O	1699.9	Semi standard non polar	33892256
trans-Aconitic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)/C=C(\CC(=O)O)C(=O)O	1644.1	Standard non polar	33892256
trans-Aconitic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)/C=C(\CC(=O)O)C(=O)O	2727.0	Standard polar	33892256
trans-Aconitic acid,1TMS,isomer #3	C[Si](C)(C)OC(=O)/C(=C/C(=O)O)CC(=O)O	1670.3	Semi standard non polar	33892256
trans-Aconitic acid,1TMS,isomer #3	C[Si](C)(C)OC(=O)/C(=C/C(=O)O)CC(=O)O	1586.1	Standard non polar	33892256
trans-Aconitic acid,1TMS,isomer #3	C[Si](C)(C)OC(=O)/C(=C/C(=O)O)CC(=O)O	2852.7	Standard polar	33892256
trans-Aconitic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C(\CC(=O)O[Si](C)(C)C)C(=O)O	1780.3	Semi standard non polar	33892256
trans-Aconitic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C(\CC(=O)O[Si](C)(C)C)C(=O)O	1753.0	Standard non polar	33892256
trans-Aconitic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C(\CC(=O)O[Si](C)(C)C)C(=O)O	2173.8	Standard polar	33892256
trans-Aconitic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C/C(=C\C(=O)O)C(=O)O[Si](C)(C)C	1742.9	Semi standard non polar	33892256
trans-Aconitic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C/C(=C\C(=O)O)C(=O)O[Si](C)(C)C	1666.4	Standard non polar	33892256
trans-Aconitic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C/C(=C\C(=O)O)C(=O)O[Si](C)(C)C	2236.4	Standard polar	33892256
trans-Aconitic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)/C=C(\CC(=O)O)C(=O)O[Si](C)(C)C	1722.5	Semi standard non polar	33892256
trans-Aconitic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)/C=C(\CC(=O)O)C(=O)O[Si](C)(C)C	1691.1	Standard non polar	33892256
trans-Aconitic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)/C=C(\CC(=O)O)C(=O)O[Si](C)(C)C	2094.2	Standard polar	33892256
trans-Aconitic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C(\CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1745.8	Semi standard non polar	33892256
trans-Aconitic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C(\CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1740.7	Standard non polar	33892256
trans-Aconitic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C(\CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1845.8	Standard polar	33892256
trans-Aconitic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C/C(=C\C(=O)O)C(=O)O	1965.7	Semi standard non polar	33892256
trans-Aconitic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C/C(=C\C(=O)O)C(=O)O	1857.0	Standard non polar	33892256
trans-Aconitic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C/C(=C\C(=O)O)C(=O)O	2813.3	Standard polar	33892256
trans-Aconitic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C=C(\CC(=O)O)C(=O)O	1950.7	Semi standard non polar	33892256
trans-Aconitic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C=C(\CC(=O)O)C(=O)O	1882.4	Standard non polar	33892256
trans-Aconitic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C=C(\CC(=O)O)C(=O)O	2687.7	Standard polar	33892256
trans-Aconitic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)/C(=C/C(=O)O)CC(=O)O	1943.6	Semi standard non polar	33892256
trans-Aconitic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)/C(=C/C(=O)O)CC(=O)O	1793.3	Standard non polar	33892256
trans-Aconitic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)/C(=C/C(=O)O)CC(=O)O	2752.9	Standard polar	33892256
trans-Aconitic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C(\CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2263.6	Semi standard non polar	33892256
trans-Aconitic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C(\CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2175.6	Standard non polar	33892256
trans-Aconitic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C(\CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2354.2	Standard polar	33892256
trans-Aconitic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C/C(=C\C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2205.9	Semi standard non polar	33892256
trans-Aconitic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C/C(=C\C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2085.9	Standard non polar	33892256
trans-Aconitic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C/C(=C\C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2370.9	Standard polar	33892256
trans-Aconitic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)/C=C(\CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2172.6	Semi standard non polar	33892256
trans-Aconitic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)/C=C(\CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2087.7	Standard non polar	33892256
trans-Aconitic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)/C=C(\CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2302.2	Standard polar	33892256
trans-Aconitic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C(\CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2399.3	Semi standard non polar	33892256
trans-Aconitic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C(\CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2330.6	Standard non polar	33892256
trans-Aconitic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C(\CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2277.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - trans-Aconitic acid GC-MS (3 TMS)	splash10-003s-3971000000-d4adfdbddf5dc3badb47	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - trans-Aconitic acid GC-MS (Non-derivatized)	splash10-003s-3971000000-d4adfdbddf5dc3badb47	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - trans-Aconitic acid GC-EI-TOF (Non-derivatized)	splash10-0002-1930000000-1043e640a069e4ed3c64	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-Aconitic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-06w9-4900000000-38239492ad0e66d6533b	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-Aconitic acid GC-MS (3 TMS) - 70eV, Positive	splash10-00di-9167000000-07ccdac5775cc3e75c95	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-Aconitic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000f-9100000000-814aded0eac117ddb550	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-9300000000-1f04239a9a7133f89d08	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000f-9000000000-49f5c2a7959cfbbbe09f	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-000f-9100000000-d4857c30b96cf4786dbe	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-00b9-1900000000-51343d1269f884535cca	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-000i-9100000000-b3ebe9a6fedcb9608872	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-000i-9000000000-2d6b96d6e5ed92f0fdee	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-000l-9000000000-d36114a1c7a0318b1f7a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0006-9000000000-f4ae4a72d5f2beed9106	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-000i-9200000000-49eaf4d6558839930e52	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ , negative-QTOF	splash10-00b9-1900000000-51343d1269f884535cca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ , negative-QTOF	splash10-000i-9100000000-b3ebe9a6fedcb9608872	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ , negative-QTOF	splash10-000i-9000000000-4f60fbd245c1d58cd7d5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ , negative-QTOF	splash10-000l-9000000000-d36114a1c7a0318b1f7a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ , negative-QTOF	splash10-0006-9000000000-f4ae4a72d5f2beed9106	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QTOF , negative-QTOF	splash10-000i-9200000000-49eaf4d6558839930e52	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid 40V, Negative-QTOF	splash10-00di-9100000000-a70cb799a63ff364ca21	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid 20V, Negative-QTOF	splash10-000f-9000000000-eabb8ab38f98bb81b1ee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid 35V, Negative-QTOF	splash10-000i-9200000000-2d22108854c0dad1b598	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - trans-Aconitic acid 35V, Negative-QTOF	splash10-000i-9300000000-3cf209c9f766f6c0efe8	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Aconitic acid 10V, Positive-QTOF	splash10-004i-0900000000-8e26562af9ae45eb3303	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Aconitic acid 20V, Positive-QTOF	splash10-02di-1900000000-7fec32a5e34c3b55d683	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Aconitic acid 40V, Positive-QTOF	splash10-01w0-9600000000-ee172c3013370ab0da31	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Aconitic acid 10V, Negative-QTOF	splash10-00fr-1900000000-18635ce5a20ce1b78139	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Aconitic acid 20V, Negative-QTOF	splash10-00b9-2900000000-58bb75a2a1b28dbffd73	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Aconitic acid 40V, Negative-QTOF	splash10-06rf-9300000000-19df730d01f07fcf6573	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	3.38 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Shaykhutdinov RA,...	details
Urine	Detected and Quantified	6.6 (1.8-25.1) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22932811	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	11.506 +/- 16.612 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	23.287 +/- 25.2 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	<102.12 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	9.740-38.962 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	12376931	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	4.5 +/- 4.5 umol/mmol creatinine	Not Specified	Both	Lung cancer	22157537	details
Urine	Detected and Quantified	5.507 +/- 4.865 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	8.81 +/- 8.486 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	14.559 +/- 8.807 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected and Quantified	6.494-293.514 umol/mmol creatinine	Infant (0-1 year old)	Both	Amish lethal microcephaly	12376931	details

Associated Disorders and Diseases

Disease References

Lung Cancer
Stretch C, Eastman T, Mandal R, Eisner R, Wishart DS, Mourtzakis M, Prado CM, Damaraju S, Ball RO, Greiner R, Baracos VE: Prediction of skeletal muscle and fat mass in patients with advanced cancer using a metabolomic approach. J Nutr. 2012 Jan;142(1):14-21. doi: 10.3945/jn.111.147751. Epub 2011 Dec 7. [PubMed:22157537 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Amish lethal microcephaly
Kelley RI, Robinson D, Puffenberger EG, Strauss KA, Morton DH: Amish lethal microcephaly: a new metabolic disorder with severe congenital microcephaly and 2-ketoglutaric aciduria. Am J Med Genet. 2002 Nov 1;112(4):318-26. doi: 10.1002/ajmg.10529. [PubMed:12376931 ]

Associated OMIM IDs

211980 (Lung Cancer)
610247 (Eosinophilic esophagitis)
607196 (Amish lethal microcephaly)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

444212

PDB ID

Not Available

ChEBI ID

32806

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000291

Good Scents ID

rw1001681

References

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)

General References

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 ]
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 ]

Showing metabocard for trans-Aconitic acid (HMDB0000958)

MOL for HMDB0000958 (trans-Aconitic acid)

3D MOL for HMDB0000958 (trans-Aconitic acid)

3D SDF for HMDB0000958 (trans-Aconitic acid)

3D-SDF for HMDB0000958 (trans-Aconitic acid)

PDB for HMDB0000958 (trans-Aconitic acid)

3D PDB for HMDB0000958 (trans-Aconitic acid)

SMILES for HMDB0000958 (trans-Aconitic acid)

INCHI for HMDB0000958 (trans-Aconitic acid)

Structure for HMDB0000958 (trans-Aconitic acid)

3D Structure for HMDB0000958 (trans-Aconitic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra