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Showing metabocard for Mesaconic acid (HMDB0000749)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-09-22 18:34:14 UTC
HMDB IDHMDB0000749
Secondary Accession Numbers
  • HMDB00749
Metabolite Identification
Common NameMesaconic acid
DescriptionMesaconic acid, also known as 2-methylfumarate or citronic 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. Mesaconic acid is a dicarboxylic butenoic acid, with a methyl group in position 2 and the double bound between carbons 2 and 3. Mesaconic acid was first studied for its physical properties in 1874 by Jacobus van ‘t Hoff (https://web.archive.org/web/20051117102410/http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van%27t-Hoff-1874.html). It is now known to be involved in the biosynthesis of vitamin B12 and it is also a competitor inhibitor of the reduction of fumarate.
Structure
Data?1582752154
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000749 (Mesaconic acid)


  Mrv1652305271900202D          

  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
    0.1346   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.9589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491    0.2785    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
  6  7  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  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 HMDB0000749 (Mesaconic acid)

HMDB0000749
     RDKit          3D
Mesaconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.0546    1.1373    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5199    0.0960   -0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -0.6398   -0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.4114   -0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457   -1.1216   -1.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3062    0.5342    0.3501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -0.1657   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659    0.5381    0.3320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4157   -1.1344   -1.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834    1.9793    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9778    1.6453    1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4733    0.7713    1.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616   -1.4257   -1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8003    0.3349    1.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2692   -2.1377   -1.0094 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 HMDB0000749 (Mesaconic acid)


  Mrv1652305271900202D          

  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
    0.1346   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.9589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491    0.2785    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
  6  7  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000749

> <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-NSCUHMNNSA-N

> <FORMULA>
C5H6O4

> <MOLECULAR_WEIGHT>
130.0987

> <EXACT_MASS>
130.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.241128315164042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-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>
4.568292663140774

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.722300394674801

> <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>
mesaconic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000749 (Mesaconic acid)

HMDB0000749
     RDKit          3D
Mesaconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.0546    1.1373    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5199    0.0960   -0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -0.6398   -0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.4114   -0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457   -1.1216   -1.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3062    0.5342    0.3501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -0.1657   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659    0.5381    0.3320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4157   -1.1344   -1.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834    1.9793    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9778    1.6453    1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4733    0.7713    1.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616   -1.4257   -1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8003    0.3349    1.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2692   -2.1377   -1.0094 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 HMDB0000749 (Mesaconic acid)

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  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       0.251  -0.250   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.251  -1.790   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.585   0.520   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 HMDB0000749 (Mesaconic acid)

COMPND    HMDB0000749
HETATM    1  C1  UNL     1      -0.055   1.137   0.875  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.520   0.096  -0.050  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.379  -0.640  -0.699  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.790  -0.411  -0.490  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.646  -1.122  -1.116  1.00  0.00           O  
HETATM    6  O2  UNL     1       2.306   0.534   0.350  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.936  -0.166  -0.288  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.766   0.538   0.332  1.00  0.00           O  
HETATM    9  O4  UNL     1      -2.416  -1.134  -1.149  1.00  0.00           O  
HETATM   10  H1  UNL     1       0.483   1.979   0.368  1.00  0.00           H  
HETATM   11  H2  UNL     1      -0.978   1.645   1.289  1.00  0.00           H  
HETATM   12  H3  UNL     1       0.473   0.771   1.762  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.062  -1.426  -1.397  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.800   0.335   1.222  1.00  0.00           H  
HETATM   15  H6  UNL     1      -2.269  -2.138  -1.009  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 HMDB0000749 (Mesaconic acid)

C\C(=C/C(O)=O)C(O)=O
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INCHI for HMDB0000749 (Mesaconic 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 Stereo Labels
Synonyms
ValueSource
(e)-2-Methyl-2-butenedioic acidChEBI
(e)-Citraconic acidChEBI
2-Methylfumaric acidChEBI
Citronic acidChEBI
Methylfumaric acidChEBI
trans-1-Propene-1,2-dicarboxylic acidChEBI
trans-2-Methyl-2-butenedioic acidChEBI
2-MethylfumarateKegg
(e)-2-Methyl-2-butenedioateGenerator
(e)-CitraconateGenerator
CitronateGenerator
MethylfumarateGenerator
trans-1-Propene-1,2-dicarboxylateGenerator
trans-2-Methyl-2-butenedioateGenerator
MesaconateGenerator
(Z)-2-Methyl-2-butenedioic acidHMDB
Citraconic acidHMDB
Citraconic acid, (e)-isomerHMDB
Citraconic acid, ammonium saltHMDB
Citraconic acid, calcium saltHMDB
Citraconic acid, sodium saltHMDB
Methylmaleic acidHMDB
MonomethylfumarateHMDB
(2E)-2-Methyl-2-butenedioateHMDB
(2E)-2-Methyl-2-butenedioic acidHMDB
Chemical FormulaC5H6O4
Average Molecular Weight130.0987
Monoisotopic Molecular Weight130.02660868
IUPAC Name(2E)-2-methylbut-2-enedioic acid
Traditional Namemesaconic acid
CAS Registry Number498-24-8
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-NSCUHMNNSA-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
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point200 - 202 °CNot Available
Boiling Point336.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility26.3 mg/mL at 18 °CNot Available
LogP0.540 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility15.9 g/LALOGPS
logP0.21ALOGPS
logP0.35ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)3.72ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.96 m³·mol⁻¹ChemAxon
Polarizability11.24 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]+129.08731661259
DarkChem[M-H]-122.35631661259
AllCCS[M+H]+130.26332859911
AllCCS[M-H]-123.73632859911
DeepCCS[M+H]+126.98830932474
DeepCCS[M-H]-123.30730932474
DeepCCS[M-2H]-160.68530932474
DeepCCS[M+Na]+135.78130932474
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
Mesaconic acidC\C(=C/C(O)=O)C(O)=O2186.6Standard polar33892256
Mesaconic acidC\C(=C/C(O)=O)C(O)=O1163.3Standard non polar33892256
Mesaconic acidC\C(=C/C(O)=O)C(O)=O1289.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mesaconic acid,1TMS,isomer #1C/C(=C\C(=O)O[Si](C)(C)C)C(=O)O1324.8Semi standard non polar33892256
Mesaconic acid,1TMS,isomer #2C/C(=C\C(=O)O)C(=O)O[Si](C)(C)C1326.7Semi standard non polar33892256
Mesaconic acid,2TMS,isomer #1C/C(=C\C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1388.2Semi standard non polar33892256
Mesaconic acid,1TBDMS,isomer #1C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1567.9Semi standard non polar33892256
Mesaconic acid,1TBDMS,isomer #2C/C(=C\C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C1567.1Semi standard non polar33892256
Mesaconic 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 - Mesaconic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-1910000000-7b5cb889d8459c0edd012014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mesaconic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9500000000-b21cd4d2b489173d29332014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mesaconic acid GC-MS (2 TMS)splash10-053r-2940000000-4329a46b213ac4abcca92014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mesaconic acid GC-EI-TOF (Non-derivatized)splash10-0002-1910000000-7b5cb889d8459c0edd012017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mesaconic acid GC-EI-TOF (Non-derivatized)splash10-00di-9500000000-b21cd4d2b489173d29332017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mesaconic acid GC-MS (Non-derivatized)splash10-053r-2940000000-4329a46b213ac4abcca92017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesaconic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01q3-9200000000-99f5b89fc0026d764b2b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesaconic acid GC-MS (2 TMS) - 70eV, Positivesplash10-05g3-9540000000-ba938fe63ed9356955c62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesaconic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesaconic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesaconic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesaconic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesaconic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesaconic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesaconic 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 - Mesaconic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000j-9400000000-e10edb30d7748a7adb052012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesaconic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00m0-9000000000-6ef60fd2abfbb5741bca2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesaconic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0159-9000000000-e14ffb74e5a8298232a32012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesaconic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-000i-9100000000-8749d95b95760456aeed2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesaconic acid LC-ESI-QTOF , negative-QTOFsplash10-000i-9100000000-8749d95b95760456aeed2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesaconic acid 10V, Positive-QTOFsplash10-03di-5900000000-48835a534a81752d30852017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesaconic acid 20V, Positive-QTOFsplash10-00kr-9100000000-dcbf0f65cbb6f9b6b5782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesaconic acid 40V, Positive-QTOFsplash10-000i-9000000000-632723c704c4db90a4b62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesaconic acid 10V, Negative-QTOFsplash10-004r-5900000000-4b2260c72d18030ec9122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesaconic acid 20V, Negative-QTOFsplash10-002r-9500000000-1fd59395c864782b12b92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesaconic acid 40V, Negative-QTOFsplash10-014u-9000000000-b6d65140f365dabf3b3a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesaconic acid 10V, Positive-QTOFsplash10-01p9-9400000000-ebf4634a042628bb8a442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesaconic acid 20V, Positive-QTOFsplash10-00ko-9000000000-e04449c635203c9d3da02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesaconic acid 40V, Positive-QTOFsplash10-0006-9000000000-1b2c407328e3780e996e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesaconic acid 10V, Negative-QTOFsplash10-000i-9000000000-ec20127c74818b1f634d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesaconic acid 20V, Negative-QTOFsplash10-000i-9000000000-8867d7b163c801abd1852021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesaconic acid 40V, Negative-QTOFsplash10-014l-9000000000-55fcd5974652df6210542021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022221
KNApSAcK IDC00051539
Chemspider ID10289044
KEGG Compound IDC01732
BioCyc IDNot Available
BiGG ID38272
Wikipedia LinkMesaconic_acid
METLIN ID4130
PubChem Compound638129
PDB IDMEZ
ChEBI ID16600
Food Biomarker OntologyNot Available
VMH IDMESCON
MarkerDB IDNot Available
Good Scents IDrw1257141
References
Synthesis ReferenceShriner, R. L.; Ford, S. G.; Roll, L. J. Mesaconic acid. Organic Syntheses (1931), XI 74-5.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Truscott RJ, Malegan D, McCairns E, Burke D, Hick L, Sims P, Halpern B, Tanaka K, Sweetman L, Nyhan WL, Hammond J, Bumack C, Haan EA, Danks DM: New metabolites in isovaleric acidemia. Clin Chim Acta. 1981 Mar 5;110(2-3):187-203. [PubMed:6452974 ]