Citraconic acid

Identification

Name
Citraconic acid
Accession Number
DB04734
Type
Small Molecule
Groups
Experimental
Description

Citraconic acid is one of the isomeric dicarboxylic acids produced by the distillation of citric acid, or as metabolites by microorganisms, cis-CH3-C(CO2H)=CHCO2H; the trans-isomer is mesaconic acid.

Structure
Thumb
Synonyms
  • (Z)-2-Methyl-2-butenedioic acid
  • 2-Methyl-2-butenedioic acid
  • 2-methylmaleic acid
  • cis-2-methylbutenedioic acid
  • cis-Methylbutenedioic acid
  • citraconate
  • Citraconsäure
  • Methyl-maleinsäure
  • Methylmaleic acid
  • α-methylmaleic acid
External IDs
NSC-32949
Categories
UNII
0RQ6CXO9KD
CAS number
498-23-7
Weight
Average: 130.0987
Monoisotopic: 130.02660868
Chemical Formula
C5H6O4
InChI Key
HNEGQIOMVPPMNR-IHWYPQMZSA-N
InChI
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-
IUPAC Name
(2Z)-2-methylbut-2-enedioic acid
SMILES
C\C(=C\C(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UFumarate reductase flavoprotein subunitNot AvailableShewanella frigidimarina
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
C5-Branched Dibasic Acid MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Chiyuki Fujii, Yoshio Kosai, Iwao Kibayashi, "Method for preparation of citraconic acid and derivatives thereof." U.S. Patent US3931241, issued November, 1973.

US3931241
General References
Not Available
External Links
Human Metabolome Database
HMDB0000634
KEGG Compound
C02226
PubChem Compound
643798
PubChem Substance
46505839
ChemSpider
553689
ChEBI
17626
HET
CIZ
Wikipedia
Citraconic_acid
PDB Entries
5kts

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)93.5 °CPhysProp
water solubility7.83E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility15.9 mg/mLALOGPS
logP0.21ALOGPS
logP0.35ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)2.31ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.96 m3·mol-1ChemAxon
Polarizability11.17 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9004
Blood Brain Barrier+0.6692
Caco-2 permeable-0.6516
P-glycoprotein substrateNon-substrate0.6757
P-glycoprotein inhibitor INon-inhibitor0.9646
P-glycoprotein inhibitor IINon-inhibitor0.9843
Renal organic cation transporterNon-inhibitor0.9497
CYP450 2C9 substrateNon-substrate0.8227
CYP450 2D6 substrateNon-substrate0.9331
CYP450 3A4 substrateNon-substrate0.7247
CYP450 1A2 substrateNon-inhibitor0.9489
CYP450 2C9 inhibitorNon-inhibitor0.8722
CYP450 2D6 inhibitorNon-inhibitor0.9392
CYP450 2C19 inhibitorNon-inhibitor0.9528
CYP450 3A4 inhibitorNon-inhibitor0.9684
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9701
Ames testNon AMES toxic0.8707
CarcinogenicityNon-carcinogens0.5089
BiodegradationReady biodegradable0.869
Rat acute toxicity1.9626 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9697
hERG inhibition (predictor II)Non-inhibitor0.9826
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-053s-9830000000-9984d183d92e149a6ab4
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-000i-9300000000-e6df22429c37d2a7f548
GC-MS Spectrum - GC-MSGC-MSsplash10-053s-9830000000-9984d183d92e149a6ab4
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-1910000000-5eda2b2a1e8b0386b997
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-000i-9100000000-707e9072305131e101d9
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0006-9000000000-2a007e703ec5aa2df51a
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-000f-9200000000-5095d8b00331302fe65f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-2900000000-98ab39de610d4d7e428d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-000i-9000000000-1786e7db899e12344315
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-000i-9000000000-a1b543932fc265020973
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9000000000-d5dc2c9fdcd47f64c404
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-81b2f20752aef9eee2e9
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-000i-9200000000-ddad81eb9311ec64a8c7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-2900000000-98ab39de610d4d7e428d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-1786e7db899e12344315
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-a1b543932fc265020973
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-d5dc2c9fdcd47f64c404
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-81b2f20752aef9eee2e9
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-000i-9200000000-ddad81eb9311ec64a8c7
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Methyl-branched fatty acids
Alternative Parents
Unsaturated fatty acids / Dicarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
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
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
dicarboxylic acid (CHEBI:17626) / Dicarboxylic acids (LMFA01170099)

Targets

Kind
Protein
Organism
Shewanella frigidimarina
Pharmacological action
Unknown
General Function
Succinate dehydrogenase activity
Specific Function
Catalyzes fumarate reduction using artificial electron donors such as methyl viologen. The physiological reductant is unknown, but evidence indicates that flavocytochrome c participates in electron...
Gene Name
fccA
Uniprot ID
P0C278
Uniprot Name
Fumarate reductase flavoprotein subunit
Molecular Weight
60620.95 Da

Drug created on September 11, 2007 11:49 / Updated on November 02, 2018 06:04