MiMeDB: Showing metabocard for Methylcitric acid (MMDBc0029507)

Animal

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:25:08 UTC

Update Date

2024-04-30 19:36:30 UTC

Metabolite ID

MMDBc0029507

Metabolite Identification

Common Name

Methylcitric acid

Description

Methylcitric acid (MCA) is formed by condensation of accumulated propionyl- CoA and oxalacetate by the enzyme si-citrate synthase (EC 4.1.3.7). MCA molecule has two stereogenic centers so that it can occur in the form of four stereoisomers.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₇H₁₀O₇

Average Mass

206.1501

Monoisotopic Mass

206.042652674

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

6061-96-7

SMILES

Not Available

InChI Identifier

InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)

InChI Key

YNOXCRMFGMSKIJ-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	527.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	331.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	55.5
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	263.6
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	276.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	322.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	628.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	625.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	994.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	167.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	269.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	177.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	40.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	524.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	701.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	67.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	242.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	827.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	618.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Methylcitric acid_TMS_1	CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O)C(=O)O	standard non polar	2025-10-23	2216.96
Gas Chromatography	Methylcitric acid_TMS_2	CC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	2022.47
Gas Chromatography	Methylcitric acid_TMS_3	CC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	1485.34
Gas Chromatography	Methylcitric acid_TMS_4	CC(C(=O)O)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2144.77
Gas Chromatography	Methylcitric acid_TMS_5	CC(C(=O)O[Si](C)(C)C)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	1444.78
Gas Chromatography	Methylcitric acid_TMS_6	CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	1722.05
Gas Chromatography	Methylcitric acid_TMS_7	CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1909.23
Gas Chromatography	Methylcitric acid_TMS_8	CC(C(=O)O)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	1754.41
Gas Chromatography	Methylcitric acid_TMS_9	CC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1923.93
Gas Chromatography	Methylcitric acid_TMS_10	CC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2026.59
Gas Chromatography	Methylcitric acid_TMS_11	CC(C(=O)O[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	2589.4
Gas Chromatography	Methylcitric acid_TMS_12	CC(C(=O)O[Si](C)(C)C)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2226.56
Gas Chromatography	Methylcitric acid_TMS_13	CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1927.39
Gas Chromatography	Methylcitric acid_TMS_14	CC(C(=O)O)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1959.3
Gas Chromatography	Methylcitric acid_TMS_15	CC(C(=O)O[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2664.04
Gas Chromatography	Methylcitric acid_TMS_1	CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O)C(=O)O	standard polar	2025-10-23	1482.1
Gas Chromatography	Methylcitric acid_TMS_2	CC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2097.64
Gas Chromatography	Methylcitric acid_TMS_3	CC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2172.8
Gas Chromatography	Methylcitric acid_TMS_4	CC(C(=O)O)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2151.98
Gas Chromatography	Methylcitric acid_TMS_5	CC(C(=O)O[Si](C)(C)C)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2381.4
Gas Chromatography	Methylcitric acid_TMS_6	CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2162.99
Gas Chromatography	Methylcitric acid_TMS_7	CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2359.69
Gas Chromatography	Methylcitric acid_TMS_8	CC(C(=O)O)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	1477.87
Gas Chromatography	Methylcitric acid_TMS_9	CC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2173.85
Gas Chromatography	Methylcitric acid_TMS_10	CC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2259.24
Gas Chromatography	Methylcitric acid_TMS_11	CC(C(=O)O[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	1594.46
Gas Chromatography	Methylcitric acid_TMS_12	CC(C(=O)O[Si](C)(C)C)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1526.83
Gas Chromatography	Methylcitric acid_TMS_13	CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1759.58
Gas Chromatography	Methylcitric acid_TMS_14	CC(C(=O)O)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1771.78
Gas Chromatography	Methylcitric acid_TMS_15	CC(C(=O)O[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1567.0

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta
Urine

Tissue Locations

Placenta

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Isovaleric acidemia		Association	Human Urine	HMDB	19343532
Propionic acidemia		Association	Human Urine	HMDB	28853722
Vitamin b12 deficiency	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	8345822
Biotinidase deficiency	Increased	Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Biotinidase deficiency	Increased	Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	117	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human sputum; Human unknown; Human pleural fluid plaque	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	36	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	24	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified		0.780	3.600	umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	isovaleric acidemia	HMDB	19343532
Human Urine	Detected and Quantified		1.470	1.560	umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	isovaleric acidemia	HMDB	19343532
Human Urine	Detected and Quantified	31			umol/mmol creatinine	Adult (>18 years old)	Not Specified	Propionic acidemia	HMDB	28853722
Human Cerebrospinal fluid (csf)	Detected and Quantified		1.37	16.3	uM	Not Specified	Not Specified	cobalamin deficiency	HMDB	8345822
Human Urine	Detected and Quantified	<15			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	28853722
Human Blood	Detected and Quantified	0.059	0.021	0.097	uM	Adult (>18 years old)	Both	Normal	HMDB	8345822
Human Blood	Detected and Quantified	0.1	0.08	0.26	uM	Adult (>18 years old)	Both	Normal	HMDB	12113988
Human Cerebrospinal fluid (csf)	Detected and Quantified		0.323	1.07	uM	Not Specified	Not Specified	Normal	HMDB	8345822
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.50	0.24	0.80	uM	Adult (>18 years old)	Both	Normal	HMDB	8345822
Human Urine	Detected and Quantified	0.59	0.05	1.15	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	8345822
Human Urine	Detected and Quantified		1.2	1.8	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified		1.4	2.9	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified	2.6	1.6	6.2	umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	3.2	2.0	8.1	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	3.4	1.4	8.5	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	6.7	0.7	19.6	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	7.7	3.3	28.6	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	30.0	10.0	50.0	umol/mmol creatinine	Children (1-13 years old)	Both	Biotinidase deficiency	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Urine	Detected and Quantified	7.0	2.0	12.0	umol/mmol creatinine	Adult (>18 years old)	Both	Biotinidase deficiency	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Urine	Detected and Quantified	<6.09			umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Placenta	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Thompson GN, Chalmers RA: Increased urinary metabolite excretion during fasting in disorders of propionate metabolism. Pediatr Res. 1990 Apr;27(4 Pt 1):413-6. doi: 10.1203/00006450-199004000-00021. [PubMed:2342832 ]
Bergstrom T, Greter J, Levin AH, Steen G, Tryding N, Wass U: Propionyl-CoA carboxylase deficiency: case report, effect of low-protein diet and identification of 3-oxo-2-methylvaleric acid 3-hydroxy-2-methylvaleric acid, and maleic acid in urine. Scand J Clin Lab Invest. 1981 Apr;41(2):117-26. doi: 10.3109/00365518109092023. [PubMed:7313494 ]
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 ]
Allen RH, Stabler SP, Savage DG, Lindenbaum J: Elevation of 2-methylcitric acid I and II levels in serum, urine, and cerebrospinal fluid of patients with cobalamin deficiency. Metabolism. 1993 Aug;42(8):978-88. doi: 10.1016/0026-0495(93)90010-l. [PubMed:8345822 ]
Busch M, Stein G, Poppitz W, Hein G, Muller A: Validated capillary gas chromatographic-mass spectrometric assay to determine 2-methylcitric acid I and II levels in human serum by using a pulsed splitless injection procedure. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Aug 5;775(2):215-23. doi: 10.1016/s1570-0232(02)00293-3. [PubMed:12113988 ]
Krawczyk H, Gradowska W: 1H NMR spectra of methylcitric acid in urine. J Inherit Metab Dis. 2007 Apr;30(2):263. doi: 10.1007/s10545-007-0420-6. Epub 2007 Feb 14. [PubMed:17295121 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Methylcitric acid (MMDBc0029507)

MOL for #<Metabolite:0x00007f9ab6705d48>

3D MOL for #<Metabolite:0x00007f9ab6705d48>

3D SDF for #<Metabolite:0x00007f9ab6705d48>

3D-SDF for #<Metabolite:0x00007f9ab6705d48>

PDB for #<Metabolite:0x00007f9ab6705d48>

3D PDB for #<Metabolite:0x00007f9ab6705d48>

SMILES for #<Metabolite:0x00007f9ab6705d48>

INCHI for #<Metabolite:0x00007f9ab6705d48>

Structure for #<Metabolite:0x00007f9ab6705d48>

3D Structure for #<Metabolite:0x00007f9ab6705d48>