Showing NP-Card for Citraconic acid (NP0001482)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-09 22:33:18 UTC
NP-MRD IDNP0001482
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001482 (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 NP0001482 (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
Download

3D SDF for NP0001482 (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>
NP0001482

> <DATABASE_NAME>
NP-MRD

> <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 NP0001482 (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 NP0001482 (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 NP0001482 (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 NP0001482 (Citraconic acid)

C\C(=C\C(O)=O)C(O)=O
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INCHI for NP0001482 (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 JSmol
Synonyms
Chemical FormulaC5H6O4
Average Mass130.0987 Da
Monoisotopic Mass130.02661 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point88 - 94 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility783 mg/mLNot Available
LogPNot AvailableNot Available
Predicted 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
HMDB IDHMDB0000634
DrugBank IDDB04734
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. Stoltz JF, Nicolas A: Study of amino groups of the human platelet membrane. Acta Haematol. 1978;60(5):304-9. [PubMed:101016 ]
  3. 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 ]
  4. Hunziker N, Olmos L: [Basophils in the infiltrate of guinea pig experimental contact dermatitis. Dinitrochlorobenzene and citraconic anhydride (author's transl)]. Dermatologica. 1976;152(5):270-80. [PubMed:955226 ]
  5. 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. doi: 10.1007/BF01805683. [PubMed:116077 ]
  6. 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 ]