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Showing NP-Card for Itaconic acid (NP0000015)

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Record Information
Version2.0
Created at2006-05-22 14:17:36 UTC
Updated at2024-09-03 04:18:32 UTC
NP-MRD IDNP0000015
Natural Product DOIhttps://doi.org/10.57994/1426
Secondary Accession NumbersNone
Natural Product 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 NP0000015 (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
Download

3D MOL for NP0000015 (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
Download

3D SDF for NP0000015 (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>
NP0000015

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000015 (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
Download

PDB for NP0000015 (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
Download

3D PDB for NP0000015 (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 NP0000015 (Itaconic acid)

OC(=O)CC(=C)C(O)=O
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INCHI for NP0000015 (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 JSmol
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
MethylidenebutanedioateMeSH
Chemical FormulaC5H6O4
Average Mass130.0987 Da
Monoisotopic Mass130.02661 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-10-15View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-10-15View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-10-07View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
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
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lilium longiflorumLOTUS Database
Lotus corniculatusLOTUS Database
Medicago sativaLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pycnandra acuminataLOTUS Database
Sebertia acuminataKNApSAcK Database
Solanum tuberosumKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Triticum aestivumKNApSAcK Database
Ustilago cynodontisLOTUS Database
Ustilago maydisLOTUS Database
Vicia fabaKNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point175 °CNot Available
Boiling Point268.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility76.8 mg/mL at 20 °CNot Available
LogP-0.075 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility63 g/LALOGPS
logP0ALOGPS
logP0.053ChemAxon
logS-0.31ALOGPS
pKa (Strongest Acidic)3.65ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.91 m³·mol⁻¹ChemAxon
Polarizability11.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002092
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030947
KNApSAcK IDC00033964
Chemspider ID789
KEGG Compound IDC00490
BioCyc IDITACONATE
BiGG ID35130
Wikipedia LinkItaconic_acid
METLIN ID6483
PubChem Compound811
PDB IDNot Available
ChEBI ID30838
Good Scents IDrw1252991
References
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. Kanamasa S, Dwiarti L, Okabe M, Park EY: Cloning and functional characterization of the cis-aconitic acid decarboxylase (CAD) gene from Aspergillus terreus. Appl Microbiol Biotechnol. 2008 Aug;80(2):223-9. doi: 10.1007/s00253-008-1523-1. Epub 2008 Jun 27. [PubMed:18584171 ]