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Showing metabocard for Citraconic acid (HMDB0000634)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:01 UTC
HMDB IDHMDB0000634
Secondary Accession Numbers
  • HMDB00634
Metabolite Identification
Common NameCitraconic acid
DescriptionCitraconic acid, also known as 2-methylmaleate or methylmaleic acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Citraconic acid is a dicarboxylic acid consisting of maleic acid having a methyl substituent at the 2-position. Citraconic acid exists as a white solid. It is the cis-isomer of mesaconic acid and is one of the pyrocitric acids formed upon the heating of citric acid. Citraconic acid has been detected in the urine of both normal and fasting individuals (PMID: 6778884 ). Citraconic acid is also elevated in the urine of individuals with methylmalonic acidaemia who have suffered ketotic attacks (PMID: 116077 ). Altered serum levels of citraconic acid have been detected in patients with primary biliary cholangitis (PMID: 28400566 ).
Structure
Data?1676999701
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000634 (Citraconic acid)


  Mrv1652309042000042D          

  9  8  0  0  0  0            999 V2000
   -2.0087    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -0.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087    1.1035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5798    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5798    1.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942    1.5160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346    1.5160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for HMDB0000634 (Citraconic acid)

HMDB0000634
     RDKit          3D
Citraconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.6418   -1.2910    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5457   -0.2449    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5657   -0.4613   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    0.2920   -0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614    1.3498    0.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8088   -0.1972   -1.2591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    0.8988    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865    0.9739    1.5794 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0837    1.9177    1.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -1.2208   -0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1290   -2.2655    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -1.1705    0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5664   -1.4050   -1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8389   -0.0846   -2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346    2.9087    1.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  6 14  1  0
  9 15  1  0
M  END
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3D SDF for HMDB0000634 (Citraconic acid)


  Mrv1652309042000042D          

  9  8  0  0  0  0            999 V2000
   -2.0087    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -0.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087    1.1035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5798    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5798    1.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942    1.5160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346    1.5160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000634

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-

> <INCHI_KEY>
HNEGQIOMVPPMNR-IHWYPQMZSA-N

> <FORMULA>
C5H6O4

> <MOLECULAR_WEIGHT>
130.0987

> <EXACT_MASS>
130.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.166206395628047

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-2-methylbut-2-enedioic acid

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
0.35463615800000003

> <ALOGPS_LOGS>
-0.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.792150443903295

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4984426139122826

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
28.964100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
citraconic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000634 (Citraconic acid)

HMDB0000634
     RDKit          3D
Citraconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.6418   -1.2910    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5457   -0.2449    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5657   -0.4613   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    0.2920   -0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614    1.3498    0.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8088   -0.1972   -1.2591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    0.8988    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865    0.9739    1.5794 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0837    1.9177    1.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -1.2208   -0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1290   -2.2655    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -1.1705    0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5664   -1.4050   -1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8389   -0.0846   -2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346    2.9087    1.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  6 14  1  0
  9 15  1  0
M  END
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PDB for HMDB0000634 (Citraconic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -3.750   0.520   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.083  -0.250   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -3.750   2.060   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.416  -0.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.416  -1.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.082   0.520   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.082   2.060   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.416   2.830   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.251   2.830   0.000  0.00  0.00           O+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0000634 (Citraconic acid)

COMPND    HMDB0000634
HETATM    1  C1  UNL     1      -1.642  -1.291   0.028  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.546  -0.245   0.206  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.566  -0.461  -0.427  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.764   0.292  -0.482  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.961   1.350   0.104  1.00  0.00           O  
HETATM    6  O2  UNL     1       2.809  -0.197  -1.259  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.751   0.899   1.025  1.00  0.00           C  
HETATM    8  O3  UNL     1      -1.887   0.974   1.579  1.00  0.00           O  
HETATM    9  O4  UNL     1       0.084   1.918   1.302  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.082  -1.221  -0.977  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.129  -2.265   0.174  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.419  -1.170   0.794  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.566  -1.405  -1.029  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.839  -0.085  -2.266  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.135   2.909   1.228  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    7
CONECT    3    4   13
CONECT    4    5    5    6
CONECT    6   14
CONECT    7    8    8    9
CONECT    9   15
END
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SMILES for HMDB0000634 (Citraconic acid)

C\C(=C\C(O)=O)C(O)=O
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INCHI for HMDB0000634 (Citraconic acid)

InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(Z)-2-Methyl-2-butenedioic acidChEBI
2-Methyl-2-butenedioic acidChEBI
2-Methylmaleic acidChEBI
alpha-Methylmaleic acidChEBI
cis-2-Methylbutenedioic acidChEBI
cis-Methylbutenedioic acidChEBI
CitraconsaeureChEBI
Methyl-maleinsaeureChEBI
Methylmaleic acidChEBI
CitraconateKegg
(Z)-2-Methyl-2-butenedioateGenerator
2-Methyl-2-butenedioateGenerator
2-MethylmaleateGenerator
a-MethylmaleateGenerator
a-Methylmaleic acidGenerator
alpha-MethylmaleateGenerator
Α-methylmaleateGenerator
Α-methylmaleic acidGenerator
cis-2-MethylbutenedioateGenerator
cis-MethylbutenedioateGenerator
MethylmaleateGenerator
Citraconic acid, ammonium saltHMDB
Citraconic acid, calcium saltHMDB
Citraconic acid, sodium saltHMDB
Methylfumaric acidHMDB
(e)-2-Methyl-2-butenedioic acidHMDB
Citraconic acid, (e)-isomerHMDB
Mesaconic acidHMDB
MonomethylfumarateHMDB
Chemical FormulaC5H6O4
Average Molecular Weight130.0987
Monoisotopic Molecular Weight130.02660868
IUPAC Name(2Z)-2-methylbut-2-enedioic acid
Traditional Namecitraconic acid
CAS Registry Number498-23-7
SMILES
C\C(=C\C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-
InChI KeyHNEGQIOMVPPMNR-IHWYPQMZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point88 - 94 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility783 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available119.0http://allccs.zhulab.cn/database/detail?ID=AllCCS00002139
Predicted Molecular Properties
PropertyValueSource
Water Solubility15.9 g/LALOGPS
logP0.21ALOGPS
logP0.35ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)2.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.96 m³·mol⁻¹ChemAxon
Polarizability11.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.73531661259
DarkChem[M-H]-121.10231661259
AllCCS[M+H]+130.26332859911
AllCCS[M-H]-123.73632859911
DeepCCS[M+H]+127.33130932474
DeepCCS[M-H]-123.66130932474
DeepCCS[M-2H]-161.07630932474
DeepCCS[M+Na]+136.14830932474
AllCCS[M+H]+130.332859911
AllCCS[M+H-H2O]+126.132859911
AllCCS[M+NH4]+134.232859911
AllCCS[M+Na]+135.332859911
AllCCS[M-H]-123.732859911
AllCCS[M+Na-2H]-126.432859911
AllCCS[M+HCOO]-129.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.2.27 minutes32390414
Predicted by Siyang on May 30, 202210.5042 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.3 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid117.7 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1036.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid384.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid69.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid246.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid79.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid285.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid319.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)356.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid690.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid193.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid984.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid232.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid317.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate814.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA283.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water431.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Citraconic acidC\C(=C\C(O)=O)C(O)=O2186.6Standard polar33892256
Citraconic acidC\C(=C\C(O)=O)C(O)=O1163.3Standard non polar33892256
Citraconic acidC\C(=C\C(O)=O)C(O)=O1289.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citraconic acid,1TMS,isomer #1C/C(=C/C(=O)O[Si](C)(C)C)C(=O)O1324.8Semi standard non polar33892256
Citraconic acid,1TMS,isomer #2C/C(=C/C(=O)O)C(=O)O[Si](C)(C)C1326.7Semi standard non polar33892256
Citraconic acid,2TMS,isomer #1C/C(=C/C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1388.2Semi standard non polar33892256
Citraconic acid,1TBDMS,isomer #1C/C(=C/C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1567.9Semi standard non polar33892256
Citraconic acid,1TBDMS,isomer #2C/C(=C/C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C1567.1Semi standard non polar33892256
Citraconic acid,2TBDMS,isomer #1C/C(=C/C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1802.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Citraconic acid GC-MS (2 TMS)splash10-053s-9830000000-9984d183d92e149a6ab42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Citraconic acid EI-B (Non-derivatized)splash10-000i-9300000000-e6df22429c37d2a7f5482017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Citraconic acid GC-MS (Non-derivatized)splash10-053s-9830000000-9984d183d92e149a6ab42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Citraconic acid GC-EI-TOF (Non-derivatized)splash10-0002-1910000000-5eda2b2a1e8b0386b9972017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citraconic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01q3-9200000000-640fe5e61db043d72d252017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citraconic acid GC-MS (2 TMS) - 70eV, Positivesplash10-05g3-9540000000-ba938fe63ed9356955c62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citraconic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citraconic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citraconic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citraconic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citraconic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citraconic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-000i-9100000000-707e9072305131e101d92012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0006-9000000000-2a007e703ec5aa2df51a2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-000f-9200000000-5095d8b00331302fe65f2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-004i-2900000000-98ab39de610d4d7e428d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-000i-9000000000-1786e7db899e123443152012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-000i-9000000000-a1b543932fc2650209732012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0006-9000000000-d5dc2c9fdcd47f64c4042012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0006-9000000000-81b2f20752aef9eee2e92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-000i-9200000000-ddad81eb9311ec64a8c72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid LC-ESI-QQ , negative-QTOFsplash10-004i-2900000000-98ab39de610d4d7e428d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid LC-ESI-QQ , negative-QTOFsplash10-000i-9000000000-1786e7db899e123443152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid LC-ESI-QQ , negative-QTOFsplash10-000i-9000000000-a1b543932fc2650209732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-d5dc2c9fdcd47f64c4042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-81b2f20752aef9eee2e92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid LC-ESI-QTOF , negative-QTOFsplash10-000i-9200000000-ddad81eb9311ec64a8c72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid n/a 9V, positive-QTOFsplash10-001i-9000000000-243e35b5f07a2e9728512020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid QTOF 4V, positive-QTOFsplash10-03di-1900000000-e8a9dc6bff676e7ead5a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid QTOF 5V, positive-QTOFsplash10-03di-1900000000-d2e84a4209df386737702020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citraconic acid QTOF 7V, positive-QTOFsplash10-03di-2900000000-214b108bacb2c899d8002020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citraconic acid 10V, Positive-QTOFsplash10-01q9-4900000000-86e2b44f3c8ee5a18c482017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citraconic acid 20V, Positive-QTOFsplash10-02g9-9200000000-6d6e041c039e8649caf32017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citraconic acid 40V, Positive-QTOFsplash10-00kf-9000000000-7eeaf466a984bad3e0c82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citraconic acid 10V, Negative-QTOFsplash10-004r-6900000000-69d0c4409d2eb535ceeb2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citraconic acid 20V, Negative-QTOFsplash10-002r-9400000000-a67e18d9101e6c4863ec2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citraconic acid 40V, Negative-QTOFsplash10-00ko-9100000000-6c212f68da0a408b4ea12017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified2.2 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.6 (0.9-2.1) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified2.0 (1.2-2.6) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.35-0.84 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.33-0.51 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB04734
Phenol Explorer Compound IDNot Available
FooDB IDFDB022155
KNApSAcK IDC00052049
Chemspider ID553689
KEGG Compound IDC02226
BioCyc ID2-METHYLMALEATE
BiGG IDNot Available
Wikipedia LinkCitraconic_acid
METLIN ID5607
PubChem Compound643798
PDB IDNot Available
ChEBI ID17626
Food Biomarker OntologyNot Available
VMH ID2MMALE
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBerg, Rudolph G. Catalytic preparation of citraconic and itaconic acids. U.S. (1972), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Duran M, Bruinvis L, Ketting D, Wadman SK: Deranged isoleucine metabolism during ketotic attacks in patients with methylmalonic acidaemia. J Inherit Metab Dis. 1978;1(3):105-7. [PubMed:116077 ]
  2. Liebich HM, Pickert A, Stierle U, Woll J: Gas chromatography-mass spectrometry of saturated and unsaturated dicarboxylic acids in urine. J Chromatogr. 1980 Oct 31;199:181-9. [PubMed:6778884 ]
  3. Stoltz JF, Nicolas A: Study of amino groups of the human platelet membrane. Acta Haematol. 1978;60(5):304-9. [PubMed:101016 ]
  4. Alelu-Paz R, Iturrieta-Zuazo I, Byne W, Haroutunian V, Garcia-Villanueva M, Rabano A, Garcia-Amado M, Prensa L, Gimenez-Amaya JM: A new antigen retrieval technique for human brain tissue. PLoS One. 2008;3(10):e3378. doi: 10.1371/journal.pone.0003378. Epub 2008 Oct 13. [PubMed:18852880 ]
  5. Hao J, Yang T, Zhou Y, Gao GY, Xing F, Peng Y, Tao YY, Liu CH: Serum Metabolomics Analysis Reveals a Distinct Metabolic Profile of Patients with Primary Biliary Cholangitis. Sci Rep. 2017 Apr 11;7(1):784. doi: 10.1038/s41598-017-00944-9. [PubMed:28400566 ]