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Showing metabocard for Itaconic acid (HMDB0002092)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:36 UTC
Update Date2023-02-21 17:16:09 UTC
HMDB IDHMDB0002092
Secondary Accession Numbers
  • HMDB02092
Metabolite Identification
Common NameItaconic acid
DescriptionItaconic acid is a dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group. It has a role as a fungal metabolite and a human metabolite. It is a dicarboxylic acid and an olefinic compound. It derives from a succinic acid. It is a conjugate acid of an itaconate(2-). This dicarboxylic acid is a white solid that is soluble in water, ethanol, and acetone. Historically, itaconic acid was obtained by the distillation of citric acid, but currently it is produced by fermentation. The name itaconic acid was devised as an anagram of aconitic acid, another derivative of citric acid. Itaconic acid, also known as itaconate, belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain. Itaconic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Since the 1960s, it is produced industrially by the fermentation of carbohydrates such as glucose or molasses using fungi such as Aspergillus itaconicus or Aspergillus terreus. For A. terreus the itaconate pathway is mostly elucidated. The generally accepted route for itaconate is via glycolysis, tricarboxylic acid cycle, and a decarboxylation of cis-aconitate to itaconate via cis-aconitate-decarboxylase. The smut fungus Ustilago maydis uses an alternative route. Cis-aconitate is converted to the thermodynamically favoured trans-aconitate via aconitate-Δ-isomerase (Adi1). trans-Aconitate is further decarboxylated to itaconate by trans-aconitate-decarboxylase (Tad1). Itaconic acid is also produced in cells of macrophage lineage. It was shown that itaconate is a covalent inhibitor of the enzyme isocitrate lyase in vitro. As such, itaconate may possess antibacterial activities against bacteria expressing isocitrate lyase (such as Salmonella enterica and Mycobacterium tuberculosis). It is also sythesized in the laboratory, where dry distillation of citric acid affords itaconic anhydride, which undergoes hydrolysis to itaconic acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002092 (Itaconic acid)

  Mrv1652305201900032D          

  9  8  0  0  0  0            999 V2000
   18.0688  -11.8270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6413  -12.2396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7833  -13.0646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9267  -11.0020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4978  -11.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7833  -12.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9267  -11.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2123  -12.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2123  -13.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
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3D MOL for HMDB0002092 (Itaconic acid)

HMDB0002092
     RDKit          3D
Itaconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    0.4939    1.7886    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5291    0.4933   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5857   -0.4208   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289    0.0801   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2986    1.2535   -0.2507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9600   -0.8639   -0.5964 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8757   -0.1248   -0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596    0.6209    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9630   -1.4864   -0.2929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139    2.3336    0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150    2.3415    0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082   -1.2217    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041   -0.9627   -1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473   -1.8376   -0.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8126   -1.9936   -0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  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
  3 12  1  0
  3 13  1  0
  6 14  1  0
  9 15  1  0
M  END
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3D SDF for HMDB0002092 (Itaconic acid)

  Mrv1652305201900032D          

  9  8  0  0  0  0            999 V2000
   18.0688  -11.8270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6413  -12.2396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7833  -13.0646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9267  -11.0020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4978  -11.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7833  -12.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9267  -11.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2123  -12.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2123  -13.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002092

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)

> <INCHI_KEY>
LVHBHZANLOWSRM-UHFFFAOYSA-N

> <FORMULA>
C5H6O4

> <MOLECULAR_WEIGHT>
130.0987

> <EXACT_MASS>
130.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.058996822042474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylidenebutanedioic acid

> <ALOGPS_LOGP>
0.00

> <JCHEM_LOGP>
0.052824681999999894

> <ALOGPS_LOGS>
-0.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.492219330986345

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6521044530966424

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
27.9149

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.30e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
itaconic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0002092 (Itaconic acid)

HMDB0002092
     RDKit          3D
Itaconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    0.4939    1.7886    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5291    0.4933   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5857   -0.4208   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289    0.0801   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2986    1.2535   -0.2507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9600   -0.8639   -0.5964 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8757   -0.1248   -0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596    0.6209    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9630   -1.4864   -0.2929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139    2.3336    0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150    2.3415    0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082   -1.2217    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041   -0.9627   -1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473   -1.8376   -0.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8126   -1.9936   -0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  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
  3 12  1  0
  3 13  1  0
  6 14  1  0
  9 15  1  0
M  END
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PDB for HMDB0002092 (Itaconic acid)

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  O   UNK     0      33.728 -22.077   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      40.397 -22.847   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.062 -24.387   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      39.063 -20.537   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      36.396 -22.077   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.062 -22.847   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      39.063 -22.077   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      37.730 -22.847   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      37.730 -24.387   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    6                                                            
CONECT    4    7                                                            
CONECT    5    6    8                                                       
CONECT    6    1    3    5                                                  
CONECT    7    2    4    8                                                  
CONECT    8    5    7    9                                                  
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0002092 (Itaconic acid)

COMPND    HMDB0002092
HETATM    1  C1  UNL     1       0.494   1.789   0.045  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.529   0.493  -0.132  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.586  -0.421  -0.347  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.929   0.080  -0.384  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.299   1.254  -0.251  1.00  0.00           O  
HETATM    6  O2  UNL     1      -2.960  -0.864  -0.596  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.876  -0.125  -0.111  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.860   0.621   0.070  1.00  0.00           O  
HETATM    9  O4  UNL     1       1.963  -1.486  -0.293  1.00  0.00           O  
HETATM   10  H1  UNL     1       1.414   2.334   0.193  1.00  0.00           H  
HETATM   11  H2  UNL     1      -0.415   2.342   0.049  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.508  -1.222   0.461  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.404  -0.963  -1.334  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.847  -1.838  -0.339  1.00  0.00           H  
HETATM   15  H6  UNL     1       2.813  -1.994  -0.226  1.00  0.00           H  
CONECT    1    2    2   10   11
CONECT    2    3    7
CONECT    3    4   12   13
CONECT    4    5    5    6
CONECT    6   14
CONECT    7    8    8    9
CONECT    9   15
END
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SMILES for HMDB0002092 (Itaconic acid)

OC(=O)CC(=C)C(O)=O
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INCHI for HMDB0002092 (Itaconic acid)

InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-Methylenesuccinic acidChEBI
2-Propene-1,2-dicarboxylic acidChEBI
Methylenebutanedioic acidChEBI
Methylenesuccinic acidChEBI
Propylenedicarboxylic acidChEBI
2-MethylenesuccinateGenerator
2-Propene-1,2-dicarboxylateGenerator
MethylenebutanedioateGenerator
MethylenesuccinateGenerator
PropylenedicarboxylateGenerator
ItaconateGenerator
2-Hydroxy-3-naphthoyl-2-naphthylamineHMDB
Itaconic acid, copper saltHMDB
Itaconic acid, disodium saltHMDB
Itaconic acid, calcium saltHMDB
Itaconic acid, sodium saltHMDB
Chemical FormulaC5H6O4
Average Molecular Weight130.0987
Monoisotopic Molecular Weight130.02660868
IUPAC Name2-methylidenebutanedioic acid
Traditional Nameitaconic acid
CAS Registry Number97-65-4
SMILES
OC(=O)CC(=C)C(O)=O
InChI Identifier
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
InChI KeyLVHBHZANLOWSRM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentBranched fatty acids
Alternative Parents
Substituents
  • 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 locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point175 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility76.8 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available119.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00002147
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Blood
  • Sweat
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SweatDetected but not QuantifiedNot QuantifiedAdult BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012645
KNApSAcK IDC00033964
Chemspider ID789
KEGG Compound IDC00490
BioCyc IDITACONATE
BiGG ID35130
Wikipedia LinkItaconic_acid
METLIN ID6483
PubChem Compound811
PDB IDNot Available
ChEBI ID30838
Food Biomarker OntologyNot Available
VMH IDITACON
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Karadag E, Saraydin D, Cetinkaya S, Guven O: In vitro swelling studies and preliminary biocompatibility evaluation of acrylamide-based hydrogels. Biomaterials. 1996 Jan;17(1):67-70. [PubMed:8962950 ]
  2. Becker J, Lange A, Fabarius J, Wittmann C: Top value platform chemicals: bio-based production of organic acids. Curr Opin Biotechnol. 2015 Dec;36:168-75. doi: 10.1016/j.copbio.2015.08.022. Epub 2015 Sep 8. [PubMed:26360870 ]

Enzymes

Enzyme Details
1. Succinyl-CoA ligase [ADP/GDP-forming] subunit alpha, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Catalyzes the ATP- or GTP-dependent ligation of succinate and CoA to form succinyl-CoA. The nature of the beta subunit determines the nucleotide specificity (By similarity).
Gene Name:
SUCLG1
Uniprot ID:
P53597
Molecular weight:
36249.505
Enzyme Details
2. Succinyl-CoA ligase [GDP-forming] subunit beta, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Catalyzes the GTP-dependent ligation of succinate and CoA to form succinyl-CoA (By similarity).
Gene Name:
SUCLG2
Uniprot ID:
Q96I99
Molecular weight:
47731.605
Enzyme Details
3. Succinyl-CoA ligase [ADP-forming] subunit beta, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Catalyzes the ATP-dependent ligation of succinate and CoA to form succinyl-CoA (By similarity).
Gene Name:
SUCLA2
Uniprot ID:
Q9P2R7
Molecular weight:
50316.88