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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:19:34 UTC

HMDB ID

HMDB0000379

Secondary Accession Numbers

HMDB0003610
HMDB00379
HMDB03610

Metabolite Identification

Common Name

2-Methylcitric acid

Description

2-Methylcitric acid, also known as 2-methylcitrate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 2-Methylcitric acid exists in all living organisms, ranging from bacteria to humans. 2-Methylcitric acid has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make 2-methylcitric acid a potential biomarker for the consumption of these foods. 2-Methylcitric acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 2-Methylcitric acid, with regard to humans, has been found to be associated with the diseases such as crohn's disease; 2-methylcitric acid has also been linked to several inborn metabolic disorders including propionic acidemia, isovaleric acidemia, vitamin B12 deficiency, and biotinidase deficiency. Based on a literature review a significant number of articles have been published on 2-Methylcitric acid.

Structure

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


  Mrv0541 02231218292D          

 14 13  0  0  0  0            999 V2000
    8.8380   -4.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9005   -5.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2505   -5.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3130   -6.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8380   -6.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0755   -4.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0755   -5.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9005   -7.0549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1379   -6.3404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0130   -6.3404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2505   -7.0549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7900   -4.3885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3610   -4.3885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0755   -6.4509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  7  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  2  0  0  0  0
  7 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000379

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(O)=O)C(O)(CC(O)=O)C(O)=O

> <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

> <FORMULA>
C7H10O7

> <MOLECULAR_WEIGHT>
206.1501

> <EXACT_MASS>
206.042652674

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
17.21399595260961

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid

> <ALOGPS_LOGP>
-0.89

> <JCHEM_LOGP>
-0.7797011736666666

> <ALOGPS_LOGS>
-0.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.7852796669207125

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.18324322639043

> <JCHEM_PKA_STRONGEST_BASIC>
-4.260390633991254

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
40.19840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylcitric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      16.498  -9.168   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.348 -10.502   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.268 -10.502   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.118 -11.835   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.498 -11.835   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.808  -8.962   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.808 -10.502   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      20.348 -13.169   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      22.657 -11.835   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      14.958 -11.835   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      17.268 -13.169   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      20.141  -8.192   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      17.474  -8.192   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      18.808 -12.042   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    7    4                                                       
CONECT    3    1    5    7                                                  
CONECT    4    2    8    9                                                  
CONECT    5    3   10   11                                                  
CONECT    6    7   12   13                                                  
CONECT    7    2    3    6   14                                             
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    5                                                            
CONECT   12    6                                                            
CONECT   13    6                                                            
CONECT   14    7                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-1,2,3-butanetricarboxylic acid	ChEBI
2-Hydroxy-1,2,3-butanetricarboxylate	Generator
2-Methylcitrate	Generator
(2S,3S)-2-Methylcitrate	HMDB
2-Hydroxybutane-1,2,3-tricarboxylate	HMDB
2-Hydroxybutane-1,2,3-tricarboxylic acid	HMDB
2-Methylcitric acid, 3H-labeled	HMDB
3-Carboxy-3-hydroxy-2-methylpentanedioic acid	HMDB
Methylcitric acid	HMDB

Chemical Formula

C₇H₁₀O₇

Average Molecular Weight

206.1501

Monoisotopic Molecular Weight

206.042652674

IUPAC Name

2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid

Traditional Name

methylcitric acid

CAS Registry Number

6061-96-7

SMILES

CC(C(O)=O)C(O)(CC(O)=O)C(O)=O

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

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
Hydroxy acid
Alpha-hydroxy acid
Tertiary alcohol
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tricarboxylic acid (CHEBI:30835 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	175 g/L	ALOGPS
logP	-0.89	ALOGPS
logP	-0.78	ChemAxon
logS	-0.07	ALOGPS
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.2 m³·mol⁻¹	ChemAxon
Polarizability	17.21 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]+	145.407	31661259
DarkChem	[M-H]-	139.725	31661259
AllCCS	[M+H]+	144.37	32859911
AllCCS	[M-H]-	137.906	32859911
DeepCCS	[M+H]+	133.634	30932474
DeepCCS	[M-H]-	130.629	30932474
DeepCCS	[M-2H]-	167.149	30932474
DeepCCS	[M+Na]+	142.687	30932474
AllCCS	[M+H]+	144.4	32859911
AllCCS	[M+H-H2O]+	140.7	32859911
AllCCS	[M+NH4]+	147.7	32859911
AllCCS	[M+Na]+	148.7	32859911
AllCCS	[M-H]-	137.9	32859911
AllCCS	[M+Na-2H]-	138.9	32859911
AllCCS	[M+HCOO]-	140.1	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.	1.76 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2852 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.68 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	331.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	628.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	322.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	40.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	67.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	276.1 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	263.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	625.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	618.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	56.8 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	827.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	242.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	701.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	269.0 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	524.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methylcitric acid	CC(C(O)=O)C(O)(CC(O)=O)C(O)=O	2881.4	Standard polar	33892256
2-Methylcitric acid	CC(C(O)=O)C(O)(CC(O)=O)C(O)=O	1239.5	Standard non polar	33892256
2-Methylcitric acid	CC(C(O)=O)C(O)(CC(O)=O)C(O)=O	1733.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methylcitric acid,1TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O)C(=O)O	1738.0	Semi standard non polar	33892256
2-Methylcitric acid,1TMS,isomer #2	CC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O	1768.2	Semi standard non polar	33892256
2-Methylcitric acid,1TMS,isomer #3	CC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O	1741.3	Semi standard non polar	33892256
2-Methylcitric acid,1TMS,isomer #4	CC(C(=O)O)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C	1707.6	Semi standard non polar	33892256
2-Methylcitric acid,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O	1787.3	Semi standard non polar	33892256
2-Methylcitric acid,2TMS,isomer #2	CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O	1773.3	Semi standard non polar	33892256
2-Methylcitric acid,2TMS,isomer #3	CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C	1749.9	Semi standard non polar	33892256
2-Methylcitric acid,2TMS,isomer #4	CC(C(=O)O)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O	1789.1	Semi standard non polar	33892256
2-Methylcitric acid,2TMS,isomer #5	CC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1776.1	Semi standard non polar	33892256
2-Methylcitric acid,2TMS,isomer #6	CC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1743.7	Semi standard non polar	33892256
2-Methylcitric acid,3TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O	1797.7	Semi standard non polar	33892256
2-Methylcitric acid,3TMS,isomer #2	CC(C(=O)O[Si](C)(C)C)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1815.1	Semi standard non polar	33892256
2-Methylcitric acid,3TMS,isomer #3	CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1796.4	Semi standard non polar	33892256
2-Methylcitric acid,3TMS,isomer #4	CC(C(=O)O)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1809.1	Semi standard non polar	33892256
2-Methylcitric acid,4TMS,isomer #1	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	1884.7	Semi standard non polar	33892256
2-Methylcitric acid,1TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O)C(=O)O	1979.3	Semi standard non polar	33892256
2-Methylcitric acid,1TBDMS,isomer #2	CC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O	1987.8	Semi standard non polar	33892256
2-Methylcitric acid,1TBDMS,isomer #3	CC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1994.3	Semi standard non polar	33892256
2-Methylcitric acid,1TBDMS,isomer #4	CC(C(=O)O)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1977.2	Semi standard non polar	33892256
2-Methylcitric acid,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O	2210.2	Semi standard non polar	33892256
2-Methylcitric acid,2TBDMS,isomer #2	CC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2227.3	Semi standard non polar	33892256
2-Methylcitric acid,2TBDMS,isomer #3	CC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2227.9	Semi standard non polar	33892256
2-Methylcitric acid,2TBDMS,isomer #4	CC(C(=O)O)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O	2214.4	Semi standard non polar	33892256
2-Methylcitric acid,2TBDMS,isomer #5	CC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2211.9	Semi standard non polar	33892256
2-Methylcitric acid,2TBDMS,isomer #6	CC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2236.0	Semi standard non polar	33892256
2-Methylcitric acid,3TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O	2464.1	Semi standard non polar	33892256
2-Methylcitric acid,3TBDMS,isomer #2	CC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2454.5	Semi standard non polar	33892256
2-Methylcitric acid,3TBDMS,isomer #3	CC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2437.2	Semi standard non polar	33892256
2-Methylcitric acid,3TBDMS,isomer #4	CC(C(=O)O)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2455.0	Semi standard non polar	33892256
2-Methylcitric acid,4TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2665.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0hhi-3900000000-c705fb286a4c575f9852	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (4 TMS) - 70eV, Positive	splash10-00b9-8029800000-dc9ef9d5a5a220f1ae9f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcitric acid 10V, Positive-QTOF	splash10-000i-0900000000-be0da5c29220e9e50325	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcitric acid 20V, Positive-QTOF	splash10-05i0-9600000000-2bead66ba2514df6497f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcitric acid 40V, Positive-QTOF	splash10-1093-7900000000-e7a5530b8562d859e032	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcitric acid 10V, Negative-QTOF	splash10-0900-1910000000-0a84eb8e0df2e6eb450d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcitric acid 20V, Negative-QTOF	splash10-07vi-4900000000-e89ea7de4d7e433cae1e	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcitric acid 40V, Negative-QTOF	splash10-0a4i-9300000000-c68ffdf8bf6f5380005e	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcitric acid 10V, Positive-QTOF	splash10-0ab9-9720000000-dfe31f5432e1eccb8ed3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcitric acid 20V, Positive-QTOF	splash10-0a4i-9100000000-1cfd78c68dd469eef744	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcitric acid 40V, Positive-QTOF	splash10-0a4i-9000000000-21ac8232326ad1ff9cb4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcitric acid 10V, Negative-QTOF	splash10-0cdu-0920000000-84f91e237b14a40e1dd3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcitric acid 20V, Negative-QTOF	splash10-014i-1900000000-6f38bc0fc7fc8a824600	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcitric acid 40V, Negative-QTOF	splash10-00ku-9400000000-2c55ccaee8c29d5510a8	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.1 (0.08-0.26) uM	Adult (>18 years old)	Both	Normal	12113988	details
Blood	Detected and Quantified	0.059 (0.021-0.097) uM	Adult (>18 years old)	Both	Normal	8345822	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.50 (0.24-0.80) uM	Adult (>18 years old)	Both	Normal	8345822	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.323-1.07 uM	Not Specified	Not Specified	Normal	8345822	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	6.7 (0.7-19.6) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	7.7 (3.3-28.6) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	3.4 (1.4-8.5) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	3.2 (2.0-8.1) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	2.6 (1.6-6.2) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	0.59 (0.05-1.15) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	8345822	details
Urine	Detected and Quantified	<6.09 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	1.4-2.9 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	1.2-1.8 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	<15 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	28853722	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.37-16.3 uM	Not Specified	Not Specified	cobalamin deficiency	8345822	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohns disease	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Iron deficiency	26848182	details
Urine	Detected and Quantified	7.0 (2.0-12.0) umol/mmol creatinine	Adult (>18 years old)	Both	Biotinidase deficiency	MetaGene: Metabol...	details
Urine	Detected and Quantified	30.0 (10.0-50.0) umol/mmol creatinine	Children (1-13 years old)	Both	Biotinidase deficiency	MetaGene: Metabol...	details
Urine	Detected and Quantified	31 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Propionic acidemia	28853722	details
Urine	Detected and Quantified	0.780-3.600 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	isovaleric acidemia	19343532	details
Urine	Detected and Quantified	1.470-1.560 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	isovaleric acidemia	19343532	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Vitamin B12 deficiency
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. [PubMed:8345822 ]
Crohn's disease
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Iron deficiency
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Biotinidase deficiency
G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Propionic acidemia
Riemersma M, Hazebroek MR, Helderman-van den Enden ATJM, Salomons GS, Ferdinandusse S, Brouwers MCGJ, van der Ploeg L, Heymans S, Glatz JFC, van den Wijngaard A, Krapels IPC, Bierau J, Brunner HG: Propionic acidemia as a cause of adult-onset dilated cardiomyopathy. Eur J Hum Genet. 2017 Nov;25(11):1195-1201. doi: 10.1038/ejhg.2017.127. Epub 2017 Aug 30. [PubMed:28853722 ]
Isovaleric acidemia
Loots DT: Abnormal tricarboxylic acid cycle metabolites in isovaleric acidaemia. J Inherit Metab Dis. 2009 Jun;32(3):403-11. doi: 10.1007/s10545-009-1071-6. Epub 2009 Apr 5. [PubMed:19343532 ]

Associated OMIM IDs

266600 (Crohn's disease)
253260 (Biotinidase deficiency)
606054 (Propionic acidemia)
243500 (Isovaleric acidemia)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021997

KNApSAcK ID

Not Available

Chemspider ID

500

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

39369

Wikipedia Link

Not Available

METLIN ID

5368

PubChem Compound

515

PDB ID

Not Available

ChEBI ID

30835

Food Biomarker Ontology

Not Available

VMH ID

2MCIT

MarkerDB ID

MDB00000155

Good Scents ID

Not Available

References

Synthesis Reference

Ewering, Christian; Braemer, Christian Oliver; Steinbuechel, Alexander. Production of 2-methylcitric acid by a recombinant Ralstonia eutropha strain. PCT Int. Appl. (2007), 30pp. CODEN: PIXXD2 WO 2007101866 A2 20070913 CAN 147:363646 AN 2007:1033111

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [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. [PubMed:12113988 ]
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. [PubMed:7313494 ]
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. [PubMed:2342832 ]
Krawczyk H, Gradowska W: 1H NMR spectra of methylcitric acid in urine. J Inherit Metab Dis. 2007 Apr;30(2):263. 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 2-Methylcitric acid (HMDB0000379)

MOL for HMDB0000379 (2-Methylcitric acid)

3D MOL for HMDB0000379 (2-Methylcitric acid)

3D SDF for HMDB0000379 (2-Methylcitric acid)

3D-SDF for HMDB0000379 (2-Methylcitric acid)

PDB for HMDB0000379 (2-Methylcitric acid)

3D PDB for HMDB0000379 (2-Methylcitric acid)

SMILES for HMDB0000379 (2-Methylcitric acid)

INCHI for HMDB0000379 (2-Methylcitric acid)

Structure for HMDB0000379 (2-Methylcitric acid)

3D Structure for HMDB0000379 (2-Methylcitric acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra