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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-10-13 04:19:07 UTC

HMDB ID

HMDB0000072

Secondary Accession Numbers

HMDB0000461
HMDB00072
HMDB00461

Metabolite Identification

Common Name

cis-Aconitic acid

Description

cis-Aconitic acid, also known as cis-aconitate or acid, acontic, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. cis-Aconitic acid exists in all living species, ranging from bacteria to plants to humans. In humans, cis-aconitic acid is involved in the metabolic disorder called the glutaminolysis and cancer pathway. cis-Aconitic acid is a bland tasting compound. cis-Aconitic acid is found, on average, in the highest concentration within milk (cow). cis-Aconitic acid has also been detected, but not quantified in, several different foods, such as french plantains (Musa X paradisiaca), yams (Dioscorea), horseradishes (Armoracia rusticana), sweet potatos (Ipomoea batatas), and persimmons (Diospyros). This could make cis-aconitic acid a potential biomarker for the consumption of these foods. cis-Aconitic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on cis-Aconitic acid.

Structure

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

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: cis-Aconitic acid.mol                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   0.770   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.001  -1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334   1.540   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.667   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.001  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2    7    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3    9   10                                                  
CONECT    5    3    6                                                       
CONECT    6    5   11   12                                                  
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9    4                                                            
CONECT   10    4                                                            
CONECT   11    6                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z)-1-Propene-1,2,3-tricarboxylic acid	ChEBI
cis-1-Propene-1,2,3-tricarboxylic acid	ChEBI
(Z)-1-Propene-1,2,3-tricarboxylate	Generator
cis-1-Propene-1,2,3-tricarboxylate	Generator
cis-Aconitate	Generator
(1Z)-1-Propene-1,2,3-tricarboxylate	HMDB
(1Z)-1-Propene-1,2,3-tricarboxylic acid	HMDB
(Z)-Aconitate	HMDB
(Z)-Aconitic acid	HMDB
1-cis-2,3-Propenetricarboxylate	HMDB
1-cis-2,3-Propenetricarboxylic acid	HMDB
1-Propene-1,2,3-tricarboxylate	HMDB
1-Propene-1,2,3-tricarboxylic acid	HMDB
cis-Aconate	HMDB
cis-Aconic acid	HMDB
cis-Oxaloacetate	HMDB
cis-Oxaloacetic acid	HMDB
Acid, citridic	HMDB
Acid, citridinic	HMDB
Aconitic acid	HMDB
Acontic acid	HMDB
Adonic acid	HMDB
Achilleic acid	HMDB
Acid, acontic	HMDB
Acid, equisetic	HMDB
Citridinic acid	HMDB
Acid, achilleic	HMDB
Aconitate	HMDB
Citridic acid	HMDB
Pyrocitric acid	HMDB
Acid, aconitic	HMDB
Acid, adonic	HMDB
Acid, carboxyglutaconic	HMDB
Acid, pyrocitric	HMDB
Carboxyglutaconic acid	HMDB
Equisetic acid	HMDB

Chemical Formula

C₆H₆O₆

Average Molecular Weight

174.1082

Monoisotopic Molecular Weight

174.016437924

IUPAC Name

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

Traditional Name

cis-aconitic acid

CAS Registry Number

585-84-2

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-IWQZZHSRSA-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:32805 )

Ontology

Physiological effect

Adverse health effect

Digestive system disorder

Gastrointestinal disorder

Upper GI Disorder

Eosinophilic esophagitis

Genetic disorder

Inborn errors of metabolism

Organic acidemia

Fumarase deficiency

2-ketoglutarate dehydrogenase complex deficiency

Disposition

Biological location

Excreta

Cellular substructure

Macromolecular complex

Cytoplasm

Organ

Prostate

Ingestion

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Citric acid cycle

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	125 °C	Not Available
Boiling Point	542.00 to 543.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	400 mg/mL	Not Available
LogP	-0.140	The Good Scents Company Information System

Experimental Spectral Properties

Experimental Collision Cross Sections

Predictor	Adduct Type	Data Source	CCS Value (Å²)	Reference
DeepCCS	[M-H]-	Astarita_neg	124.7	30932474
DeepCCS	[M-H]-	Baker	132.378	30932474
DeepCCS	[M+H]+	Baker	152.214	30932474
AllCCS	[M-H]-	Not Available	132.378	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001769
AllCCS	[M+H]+	Not Available	152.214	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001769

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.72 g/L	ALOGPS
logP	10^(-0.41) g/L	ALOGPS
logP	10^(-0.52) g/L	ChemAxon
logS	10^(-1.4) g/L	ALOGPS
pKa (Strongest Acidic)	2.11	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	14.16 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 Spectral Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.934	31661259
DarkChem	[M-H]-	134.332	31661259
AllCCS	[M+H]+	137.87	32859911
AllCCS	[M-H]-	129.608	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-Aconitic acid,1TMS,#1	C[Si](C)(C)OC(=O)C/C(=C/C(=O)O)C(=O)O	1718.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
cis-Aconitic acid,1TMS,#2	C[Si](C)(C)OC(=O)/C=C(/CC(=O)O)C(=O)O	1699.9	Semi standard non polar	https://arxiv.org/abs/1905.12712
cis-Aconitic acid,1TMS,#3	C[Si](C)(C)OC(=O)/C(=C\C(=O)O)CC(=O)O	1670.3	Semi standard non polar	https://arxiv.org/abs/1905.12712
cis-Aconitic acid,2TMS,#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	https://arxiv.org/abs/1905.12712
cis-Aconitic acid,2TMS,#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	https://arxiv.org/abs/1905.12712
cis-Aconitic acid,2TMS,#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	https://arxiv.org/abs/1905.12712
cis-Aconitic acid,3TMS,#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	https://arxiv.org/abs/1905.12712
cis-Aconitic acid,1TBDMS,#1	CC(C)(C)[Si](C)(C)OC(=O)C/C(=C/C(=O)O)C(=O)O	1965.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
cis-Aconitic acid,1TBDMS,#2	CC(C)(C)[Si](C)(C)OC(=O)/C=C(/CC(=O)O)C(=O)O	1950.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
cis-Aconitic acid,1TBDMS,#3	CC(C)(C)[Si](C)(C)OC(=O)/C(=C\C(=O)O)CC(=O)O	1943.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
cis-Aconitic acid,2TBDMS,#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	https://arxiv.org/abs/1905.12712
cis-Aconitic acid,2TBDMS,#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	https://arxiv.org/abs/1905.12712
cis-Aconitic acid,2TBDMS,#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	https://arxiv.org/abs/1905.12712
cis-Aconitic acid,3TBDMS,#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	https://arxiv.org/abs/1905.12712

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - cis-Aconitic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0002-1940000000-24c70788b42e3006de46	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - cis-Aconitic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0940000000-3ab0a8161f2ec8f04452	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - cis-Aconitic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00dj-9630000000-1dc322333cb48ef39588	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - cis-Aconitic acid GC-MS (3 TMS)	splash10-004i-3591000000-a58ec1ba633b098e0867	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - cis-Aconitic acid GC-EI-TOF (Non-derivatized)	splash10-0002-1940000000-24c70788b42e3006de46	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - cis-Aconitic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0940000000-3ab0a8161f2ec8f04452	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - cis-Aconitic acid GC-EI-TOF (Non-derivatized)	splash10-00dj-9630000000-1dc322333cb48ef39588	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - cis-Aconitic acid GC-MS (Non-derivatized)	splash10-004i-3591000000-a58ec1ba633b098e0867	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-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 - cis-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 - cis-Aconitic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Breast Milk
Cerebrospinal Fluid (CSF)
Saliva
Sweat
Urine

Tissue Locations

Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Citric Acid Cycle
Congenital lactic acidosis		Not Available
Fumarase deficiency		Not Available
Mitochondrial complex II deficiency		Not Available
2-ketoglutarate dehydrogenase complex deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Breast Milk	Detected and Quantified	10.1 +/- 3.1 uM	Adult (>18 years old)	Female	Normal	24027187	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2 uM	Children (1-13 years old)	Both	Normal	8412012	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	20.0 (13.0-27.0) uM	Adult (>18 years old)	Both	Normal	9693263	details
Saliva	Detected and Quantified	3.17 +/- 1.17 uM	Adult (>18 years old)	Female	Normal	23857558	details
Saliva	Detected and Quantified	0.172 +/- 0.179 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.176 +/- 0.107 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.358 +/- 0.198 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.363 +/- 0.169 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Sweat	Detected and Quantified	< 10 uM	Adult (60 years old)	Male	Normal	22194922	details
Sweat	Detected and Quantified	< 10 uM	Adult (40 years old)	Male	Normal	22194922	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22932811	details
Urine	Detected and Quantified	67.9 (14.3-100.7) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	73.8 (64.0-130.3) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	37.9 (17.3-63.3) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	29.8 (14.7-93.1) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	2.0-23.6 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	7-30.6 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	8-26.0 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	8-40.7 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	54.5 (32.4-76.6) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	14708889	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)	Both	Normal	28157703	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	48-103 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	20.9 (3.8-95.3) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	13 (2.7-44) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	9.740-38.962 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	12376931	details
Urine	Detected and Quantified	35.95 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Shaykhutdinov RA,...	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	58-85 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	33.685 +/- 14.03 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22024767	details
Urine	Detected and Quantified	10.3(5.2-16.3) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected and Quantified	2.80 +/- 2.11 uM	Adult (>18 years old)	Male	Alzheimer's disease	23857558	details
Saliva	Detected and Quantified	2.17 +/- 0.53 uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	23857558	details
Saliva	Detected and Quantified	2.72 +/- 0.53 uM	Adult (>18 years old)	Both	Lewy body disease	23857558	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	6.494-293.514 umol/mmol creatinine	Infant (0-1 year old)	Both	Amish lethal microcephaly	12376931	details
Urine	Detected and Quantified	38.74 +/- 40.952 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	32.0 (0.0-70.0) umol/mmol creatinine	Adult (>18 years old)	Both	Lung cancer	18953024	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22024767	details

Associated Disorders and Diseases

Disease References

Alzheimer's disease
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lung Cancer
Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
Eosinophilic esophagitis
(). Mordechai, Hien, and David S. Wishart. .
Schizophrenia
Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
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

104300 (Alzheimer's disease)
600274 (Frontotemporal dementia)
211980 (Lung Cancer)
610247 (Eosinophilic esophagitis)
181500 (Schizophrenia)
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

Citric acid cycle

METLIN ID

5130

PubChem Compound

643757

PDB ID

Not Available

ChEBI ID

32805

Food Biomarker Ontology

Not Available

VMH ID

HC00342

MarkerDB ID

MDB00000038

Good Scents ID

rw1057191

References

Synthesis Reference

Gutierrez, Eddie N.; Lamberti, Vincent. cis and trans Aconitic acids and their salts. U.S. (1978), 16 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Swart PJ, Kuipers EM, Smit C, Van Der Strate BW, Harmsen MC, Meijer DK: Lactoferrin. Antiviral activity of lactoferrin. Adv Exp Med Biol. 1998;443:205-13. [PubMed:9781360 ]
Stromme JH, Borud O, Moe PJ: Fatal lactic acidosis in a newborn attributable to a congenital defect of pyruvate dehydrogenase. Pediatr Res. 1976 Jan;10(1):62-6. [PubMed:813176 ]
Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. [PubMed:9693263 ]
Swart PJ, Kuipers ME, Smit C, Pauwels R, deBethune MP, de Clercq E, Meijer DK, Huisman JG: Antiviral effects of milk proteins: acylation results in polyanionic compounds with potent activity against human immunodeficiency virus types 1 and 2 in vitro. AIDS Res Hum Retroviruses. 1996 Jun 10;12(9):769-75. [PubMed:8738428 ]
Matsuishi T, Urabe F, Percy AK, Komori H, Yamashita Y, Schultz RS, Ohtani Y, Kuriya N, Kato H: Abnormal carbohydrate metabolism in cerebrospinal fluid in Rett syndrome. J Child Neurol. 1994 Jan;9(1):26-30. [PubMed:8151077 ]

Enzymes

Enzyme Details

1. Aconitate hydratase, mitochondrial

General function:: Involved in metabolic process
Specific function:: Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
Gene Name:: ACO2
Uniprot ID:: Q99798
Molecular weight:: 85424.745

Reactions

Citric acid → cis-Aconitic acid + Water	details
Isocitric acid → cis-Aconitic acid + Water	details

Enzyme Details

2. Cytoplasmic aconitate hydratase

General function:: Involved in metabolic process
Specific function:: Iron sensor. Binds a 4Fe-4S cluster and functions as aconitase when cellular iron levels are high. Functions as mRNA binding protein that regulates uptake, sequestration and utilization of iron when cellular iron levels are low. Binds to iron-responsive elements (IRES) in target mRNA species when iron levels are low. Binding of a 4Fe-4S cluster precludes RNA binding. Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
Gene Name:: ACO1
Uniprot ID:: P21399
Molecular weight:: 98398.14

Reactions

Citric acid → cis-Aconitic acid + Water	details
Isocitric acid → cis-Aconitic acid + Water	details

Showing metabocard for cis-Aconitic acid (HMDB0000072)

MOL for HMDB0000072 (cis-Aconitic acid)

3D MOL for HMDB0000072 (cis-Aconitic acid)

3D SDF for HMDB0000072 (cis-Aconitic acid)

3D-SDF for HMDB0000072 (cis-Aconitic acid)

PDB for HMDB0000072 (cis-Aconitic acid)

3D PDB for HMDB0000072 (cis-Aconitic acid)

SMILES for HMDB0000072 (cis-Aconitic acid)

INCHI for HMDB0000072 (cis-Aconitic acid)

Structure for HMDB0000072 (cis-Aconitic acid)

3D Structure for HMDB0000072 (cis-Aconitic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions