Np mrd loader

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
Download

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

$$$$
Download

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
Download

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
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 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 NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
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 ]