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Showing metabocard for trans-trans-Muconic acid (HMDB0002349)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:49 UTC
Update Date2023-02-21 17:16:21 UTC
HMDB IDHMDB0002349
Secondary Accession Numbers
  • HMDB02349
Metabolite Identification
Common Nametrans-trans-Muconic acid
Descriptiontrans,trans-Muconic acid is a urinary metabolite of benzene and has been used as a biomarker of exposure to benzene in humans exposed to levels as low as 1 ppm. However, muconic acid may also be derived from sorbic acid and its salts. Dietary supplementation with 500 mg sorbic acid significantly increases the urinary trans,trans-muconic acid excretion. Under study conditions, 0.12% of the sorbic acid dose is excreted in urine as trans,trans-muconic acid thereby indicating that a typical dietary intake of 6-30 mg/day of sorbic acid accounts for 10-50% of the background of trans,trans-muconic acid excretion in nonsmokers, and for 5-25% in smokers (PMID: 8021961 , 1487326 , 9137998 , Int Arch Occup Environ Health. 1997;69(4):247-51.). trans,trans-Muconic acid has been found to be a metabolite in Escherichia coli and Pseudomonas putida (PMID: 26360870 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002349 (trans-trans-Muconic acid)

  Mrv1652303192023122D          

 10  9  0  0  0  0            999 V2000
 9992.3250 9992.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0390 9992.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7546 9992.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4701 9992.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1836 9992.8934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4701 9991.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6103 9992.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.8955 9992.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.1808 9992.4815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.8955 9993.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
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3D MOL for HMDB0002349 (trans-trans-Muconic acid)

HMDB0002349
     RDKit          3D
trans-trans-Muconic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -3.4697   -0.4643   -0.1612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9205    0.6360   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6913    1.7767    0.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4838    0.7428   -0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -0.2912   -0.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841   -0.1495   -0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5955   -1.1755   -0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0377   -1.0883   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7210   -2.1340   -0.2827 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328    0.1034   -0.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2030    1.9838    0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0119    1.7045    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0902   -1.2717   -0.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    0.8371    0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1309   -2.1437   -0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3448    0.9339    0.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
 10 16  1  0
M  END
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3D SDF for HMDB0002349 (trans-trans-Muconic acid)

  Mrv1652303192023122D          

 10  9  0  0  0  0            999 V2000
 9992.3250 9992.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0390 9992.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7546 9992.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4701 9992.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1836 9992.8934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4701 9991.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6103 9992.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.8955 9992.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.1808 9992.4815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.8955 9993.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002349

> <DATABASE_NAME>
hmdb

> <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-ZPUQHVIOSA-N

> <FORMULA>
C6H6O4

> <MOLECULAR_WEIGHT>
142.1094

> <EXACT_MASS>
142.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.650979668737211

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E)-hexa-2,4-dienedioic acid

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
0.486301342

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.654855678562283

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.87177055186766

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
34.925599999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trans, trans-muconic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0002349 (trans-trans-Muconic acid)

HMDB0002349
     RDKit          3D
trans-trans-Muconic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -3.4697   -0.4643   -0.1612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9205    0.6360   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6913    1.7767    0.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4838    0.7428   -0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -0.2912   -0.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841   -0.1495   -0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5955   -1.1755   -0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0377   -1.0883   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7210   -2.1340   -0.2827 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328    0.1034   -0.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2030    1.9838    0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0119    1.7045    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0902   -1.2717   -0.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    0.8371    0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1309   -2.1437   -0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3448    0.9339    0.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
 10 16  1  0
M  END
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PDB for HMDB0002349 (trans-trans-Muconic acid)

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0    8652.3408653.401   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8653.6738652.632   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8655.0098653.401   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8656.3448652.632   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8657.6768653.401   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8656.3448651.091   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8651.0068652.632   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8649.6728653.401   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8648.3378652.632   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8649.6728654.941   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0002349 (trans-trans-Muconic acid)

COMPND    HMDB0002349
HETATM    1  O1  UNL     1      -3.470  -0.464  -0.161  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.921   0.636  -0.029  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.691   1.777   0.094  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.484   0.743  -0.003  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.665  -0.291  -0.114  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.784  -0.150  -0.083  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.595  -1.175  -0.193  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.038  -1.088  -0.169  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.721  -2.134  -0.283  1.00  0.00           O  
HETATM   10  O4  UNL     1       3.733   0.103  -0.025  1.00  0.00           O  
HETATM   11  H1  UNL     1      -4.203   1.984   0.959  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.012   1.705   0.112  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.090  -1.272  -0.231  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.188   0.837   0.034  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.131  -2.144  -0.309  1.00  0.00           H  
HETATM   16  H6  UNL     1       3.345   0.934   0.401  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    5   12
CONECT    5    6   13
CONECT    6    7    7   14
CONECT    7    8   15
CONECT    8    9    9   10
CONECT   10   16
END
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SMILES for HMDB0002349 (trans-trans-Muconic acid)

OC(=O)\C=C\C=C\C(O)=O
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INCHI for HMDB0002349 (trans-trans-Muconic acid)

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+
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC6H6O4
Average Molecular Weight142.1094
Monoisotopic Molecular Weight142.02660868
IUPAC Name(2E,4E)-hexa-2,4-dienedioic acid
Traditional Nametrans, trans-muconic acid
CAS Registry Number3588-17-8
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 KeyTXXHDPDFNKHHGW-ZPUQHVIOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain 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 roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point301 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 mg/mL at 15 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.03 +/- 0.016 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.1 (0.05 - 0.3) umol/mmol creatinineAdult (>18 years old)BothSmoking details
UrineDetected and Quantified0.16 +/- 0.02 umol/mmol creatinineAdult (>18 years old)Male
Benzene exposure		 details
Associated Disorders and Diseases
Disease References
Benzene exposure
  1. Chanvaivit S, Navasumrit P, Hunsonti P, Autrup H, Ruchirawat M: Exposure assessment of benzene in Thai workers, DNA-repair capacity and influence of genetic polymorphisms. Mutat Res. 2007 Jan 10;626(1-2):79-87. Epub 2006 Nov 13. [PubMed:17095285 ]
Smoking
  1. Ruppert T, Scherer G, Tricker AR, Adlkofer F: trans,trans-muconic acid as a biomarker of non-occupational environmental exposure to benzene. Int Arch Occup Environ Health. 1997;69(4):247-51. [PubMed:9137998 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023893
KNApSAcK IDNot Available
Chemspider ID4512358
KEGG Compound IDNot Available
BioCyc ID25-DICHLORO-CISCIS-MUCONATE
BiGG IDNot Available
Wikipedia LinkMuconic_acid
METLIN ID6639
PubChem Compound5356793
PDB IDNot Available
ChEBI ID27036
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000390
Good Scents IDNot Available
References
Synthesis ReferenceErlenmeyer, H.; Schoenauer, W. A synthesis of trans-trans-muconic acid from fumaric acid. Helvetica Chimica Acta (1937), 20 1008-12.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Renner T, Baer-Koetzle M, Scherer G: Determination of sorbic acid in urine by gas chromatography-mass spectrometry. J Chromatogr A. 1999 Jun 25;847(1-2):127-33. [PubMed:10431356 ]
  2. Kim S, Vermeulen R, Waidyanatha S, Johnson BA, Lan Q, Rothman N, Smith MT, Zhang L, Li G, Shen M, Yin S, Rappaport SM: Using urinary biomarkers to elucidate dose-related patterns of human benzene metabolism. Carcinogenesis. 2006 Apr;27(4):772-81. Epub 2005 Dec 8. [PubMed:16339183 ]
  3. Wiwanitkit V, Suwansaksri J, Soogarun S: The urine trans, trans muconic acid biomarker and platelet count in a sample of subjects with benzene exposure. Clin Appl Thromb Hemost. 2004 Jan;10(1):73-6. [PubMed:14979410 ]
  4. Hecht SS: Human urinary carcinogen metabolites: biomarkers for investigating tobacco and cancer. Carcinogenesis. 2002 Jun;23(6):907-22. [PubMed:12082012 ]
  5. Ruppert T, Scherer G, Tricker AR, Adlkofer F: trans,trans-muconic acid as a biomarker of non-occupational environmental exposure to benzene. Int Arch Occup Environ Health. 1997;69(4):247-51. [PubMed:9137998 ]
  6. Bartczak A, Kline SA, Yu R, Weisel CP, Goldstein BD, Witz G, Bechtold WE: Evaluation of assays for the identification and quantitation of muconic acid, a benzene metabolite in human urine. J Toxicol Environ Health. 1994 Jul;42(3):245-58. [PubMed:8021961 ]
  7. Ducos P, Gaudin R, Bel J, Maire C, Francin JM, Robert A, Wild P: trans,trans-Muconic acid, a reliable biological indicator for the detection of individual benzene exposure down to the ppm level. Int Arch Occup Environ Health. 1992;64(5):309-13. [PubMed:1487326 ]
  8. 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 ]