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Showing metabocard for cis,cis-Muconic acid (HMDB06331)

Record Information
Version 3.5
Creation Date 2007-05-22 18:53:22 -0600
Update Date 2013-02-08 17:14:46 -0700
HMDB ID HMDB06331
Secondary Accession Numbers None
Metabolite Identification
Common Name cis,cis-Muconic acid
Description Cis-cis-muconic acid is a presumptive metabolite of benzene. Muconic acid was first isolated from the urine of rabbits and dogs in 1909 ( M. Jaffe, Z Physiol Chem 62:58-67). It was originally thought that if muconic acid were formed by opening of the benzene ring in vivo then the cis-cis isomer should be the initial (and primary) product. However subsequent studies conducted in the 1950's proved that trans-trans-muconic acid is a true metabolite of benzene in mammals (Parke DV, Williams RT. Biochem J 51:339-348 (1952)). Furthermore, dosing rabbits with phenol or catechol also resulted in the urinary excretion of trans-trans-muconic acid. The oxidative ring opening of benzene first gives rise to cis-cis-muconaldehyde, which then isomerizes to cis-trans- and trans-trans-muconaldehyde; the latter is oxidized in vivo to trans-trans-muconic acid. Isomerization of the trans-trans form may take place in vivo to yield small amounts if the cis-cis and cis-trans form of muconic acid. Cis-cis muconic acid may also be generated from microbial fermentation of benzoic acid. Certain strains of arthobacter are particularly efficient at this process.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (Z,Z)-2,4-hexadienedioate
  2. (Z,Z)-2,4-hexadienedioic acid
  3. 2,4-Hexadienedioate
  4. 2,4-Hexadienedioic acid
  5. cis,cis-2,4-Hexadienedioate
  6. cis,cis-2,4-Hexadienedioic acid
  7. Cis,cis-hexadienedioate
  8. Cis,cis-hexadienedioic acid
  9. Cis,cis-muconate
  10. Muconic acid
Chemical Formula C6H6O4
Average Molecular Weight 142.1094
Monoisotopic Molecular Weight 142.02660868
IUPAC Name (2Z,4Z)-hexa-2,4-dienedioic acid
Traditional IUPAC Name muconic acid
CAS Registry Number 1119-72-8
SMILES OC(=O)\C=C/C=C\C(O)=O
InChI Identifier InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1-,4-2-
InChI Key TXXHDPDFNKHHGW-CCAGOZQPSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Unsaturated Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Dicarboxylic Acids and Derivatives
  • Organic Compounds
  • hexadienedioic acid(ChEBI)
Substituents
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid
  • Enone
Direct Parent Unsaturated Fatty Acids
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
  • Microbial
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.48 g/L ALOGPS
LogP 0.67 ALOGPS
LogP 0.49 ChemAxon
LogS -1.61 ALOGPS
pKa (strongest acidic) 3.87 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 74.6 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 34.93 ChemAxon
Polarizability 12.58 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023893
KNApSAcK ID Not Available
Chemspider ID 4444151 Link_out
KEGG Compound ID C02480 Link_out
BioCyc ID Not Available
BiGG ID 36677 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06331 Link_out
Metagene Link HMDB06331 Link_out
METLIN ID Not Available
PubChem Compound 5280518 Link_out
PDB ID CCU Link_out
ChEBI ID 16508 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Jaffé M. Cleavage of the benzene ring in the organism. 1. The excretion of muconic acid in the urine after ingestion of benzene. Z Physiol Chem 62:58-67 (1909)
  2. Parke DV, Williams RT. Studies in detoxication 44. The metabolism of benzene. The muconic acid excreted by rabbits receiving benzene. Determination of the isomeric muconic acids. Biochem J 51:339-348 (1952).