MiMeDB: Showing metabocard for Methylcitric acid (MMDBc0029507)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:25:08 UTC

Update Date

2022-08-31 13:37:19 UTC

MiMeDB 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

Chemical Formula

C₇H₁₀O₇

Average Molecular Weight

206.1501

Monoisotopic Molecular Weight

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

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

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Reference
Isovaleric acidemia		This associated disease is originally imported from HMDB metabolite HMDB0000379 concentration id 136245	Association	Human Urine	19343532	details
Propionic acidemia		This associated disease is originally imported from HMDB metabolite HMDB0000379 concentration id 136243	Association	Human Urine	28853722	details
Vitamin B12 deficiency	Increased	This associated disease is originally imported from HMDB metabolite HMDB0000379 concentration id 62104	Association	Human Cerebrospinal Fluid (CSF)	8345822	details
Biotinidase deficiency	Increased	This associated disease is originally imported from HMDB metabolite HMDB0000379 concentration id 58935	Association	Human Urine	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)	details
Biotinidase deficiency	Increased	This associated disease is originally imported from HMDB metabolite HMDB0000379 concentration id 58934	Association	Human Urine	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)	details

Microbial Sources

Phylum	Total species	Hosts and Body Sites	Microbial Links
Proteobacteria	117	Human ; Human Feces	Unknown; Metabolic reconstruction
Firmicutes	36	Human Feces; Human	Metabolic reconstruction
Actinobacteria	24	Human Feces; Human	Metabolic reconstruction
Euryarchaeota	1	Human Feces	Metabolic reconstruction
Bacteroidetes	1	Human	Metabolic reconstruction
Planctomycetes	1	Human Feces	Metabolic reconstruction
Crenarchaeota	1	Human Feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details
Animal	Milk	Bos taurus	FooDB	31437929	details

Host Biospecimen and Location

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

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

References

Synthesis Reference

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:0x000055b76e123100>

3D MOL for #<Metabolite:0x000055b76e123100>

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3D-SDF for #<Metabolite:0x000055b76e123100>

PDB for #<Metabolite:0x000055b76e123100>

3D PDB for #<Metabolite:0x000055b76e123100>

SMILES for #<Metabolite:0x000055b76e123100>

INCHI for #<Metabolite:0x000055b76e123100>

Structure for #<Metabolite:0x000055b76e123100>

3D Structure for #<Metabolite:0x000055b76e123100>