MiMeDB: Showing metabocard for trans-Aconitic acid (MMDBc0000176)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:38:39 UTC

Update Date

2024-04-30 19:31:20 UTC

Metabolite ID

MMDBc0000176

Metabolite Identification

Common Name

trans-Aconitic acid

Description

trans-Aconitic acid is normally present in normal human urine, and it has been suggested that is present in larger amounts with Reye's syndrome and organic aciduria. trans-Aconitic acid is a substrate of enzyme trans-aconitate 2-methyltransferase (EC 2.1.1.144) (PMID: 7096501 , 4019674 , 2950263 ). Trans-aconitate in the urine is a biomarker for the consumption of soy products.

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

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

Molecular Formula

C₆H₆O₆

Average Mass

174.1082

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-003s-3971000000-d4adfdbddf5dc3badb47	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-003s-3971000000-d4adfdbddf5dc3badb47	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1930000000-1043e640a069e4ed3c64	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06w9-4900000000-38239492ad0e66d6533b	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00di-9167000000-07ccdac5775cc3e75c95	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9300000000-1f04239a9a7133f89d08	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000f-9000000000-49f5c2a7959cfbbbe09f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000f-9100000000-d4857c30b96cf4786dbe	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00b9-1900000000-51343d1269f884535cca	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9100000000-b3ebe9a6fedcb9608872	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-2d6b96d6e5ed92f0fdee	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-000l-9000000000-d36114a1c7a0318b1f7a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-f4ae4a72d5f2beed9106	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9200000000-49eaf4d6558839930e52	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00b9-1900000000-51343d1269f884535cca	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9100000000-b3ebe9a6fedcb9608872	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-4f60fbd245c1d58cd7d5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000l-9000000000-d36114a1c7a0318b1f7a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-f4ae4a72d5f2beed9106	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-9200000000-49eaf4d6558839930e52	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9100000000-a70cb799a63ff364ca21	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9000000000-eabb8ab38f98bb81b1ee	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9200000000-2d22108854c0dad1b598	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9300000000-3cf209c9f766f6c0efe8	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-8e26562af9ae45eb3303	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02di-1900000000-7fec32a5e34c3b55d683	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01w0-9600000000-ee172c3013370ab0da31	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fr-1900000000-18635ce5a20ce1b78139	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-2900000000-58bb75a2a1b28dbffd73	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06rf-9300000000-19df730d01f07fcf6573	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000f-9100000000-814aded0eac117ddb550	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

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	Evidence Type	Host and Biospecimen	Data Source	Reference
Lung cancer	Association	Human Urine	HMDB	22157537
Eosinophilic esophagitis	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Eosinophilic esophagitis	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	76	Human ; Human feces; Sheep ; Pig	Microbial culture
Bacteria	Firmicutes	1		Microbial culture
Bacteria	Deinococcus-thermus	1
Bacteria	Actinobacteria	17	Human ; Cattle
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown
Eukaryota/Fungi	Basidiomycota	1	Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food			FooDB	31437929
Plant	Root	Glycine max	FooDB	31437929
Plant	Fruit	Solanum lycopersicum var. lycopersicum	FooDB	31437929

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			6.494	293.514	umol/mmol creatinine	Infant (0-1 year old)	Both	Amish lethal microcephaly	HMDB	12376931
Human Urine	Detected and Quantified	4.5	4.5			umol/mmol creatinine	Not Specified	Both	Lung cancer	HMDB	22157537
Human Urine	Detected and Quantified	6.6		1.8	25.1	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified			9.740	38.962	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	12376931
Human Urine	Detected and Quantified	5.507	4.865			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	8.81	8.486			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	11.506	16.612			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 and Quantified	23.287	25.2			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 and Quantified	<102.12				umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified	3.38				umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Shaykhutdinov RA, MacInnis GD, Dowlatabadi R, Weljie AM, Vogel HJ. Quantitative analysis of metabolite concentrations in human urine samples using 13C{1H} NMR spectroscopy. Metabolomics. 2009
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22932811
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Blood	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0000958

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

References

Synthesis Reference

Not Available

General References

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 ]
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. doi: 10.1016/s0378-4347(00)84004-9. [PubMed:4019674 ]
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. doi: 10.1016/s0021-9673(00)81990-1. [PubMed:7096501 ]

Showing metabocard for trans-Aconitic acid (MMDBc0000176)

MOL for #<Metabolite:0x00007fed1469cd10>

3D MOL for #<Metabolite:0x00007fed1469cd10>

3D SDF for #<Metabolite:0x00007fed1469cd10>

3D-SDF for #<Metabolite:0x00007fed1469cd10>

PDB for #<Metabolite:0x00007fed1469cd10>

3D PDB for #<Metabolite:0x00007fed1469cd10>

SMILES for #<Metabolite:0x00007fed1469cd10>

INCHI for #<Metabolite:0x00007fed1469cd10>

Structure for #<Metabolite:0x00007fed1469cd10>

3D Structure for #<Metabolite:0x00007fed1469cd10>