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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
Data?1676999781
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
ValueSource
(2E,4E)-2,4-Hexadienedioic acidChEBI
(e,e)-2,4-Hexadienedioic acidChEBI
(e,e)-Muconic acidChEBI
trans,trans-1,3-Butadiene-1,4-dicarboxylic acidChEBI
trans,trans-2,4-Hexadienedioic acidChEBI
trans,trans-Buta-1,3-diene-1,4-dicarboxylic acidChEBI
(2E,4E)-2,4-HexadienedioateGenerator
(e,e)-2,4-HexadienedioateGenerator
(e,e)-MuconateGenerator
trans,trans-1,3-Butadiene-1,4-dicarboxylateGenerator
trans,trans-2,4-HexadienedioateGenerator
trans,trans-Buta-1,3-diene-1,4-dicarboxylateGenerator
trans-trans-MuconateGenerator
cis,cis-MuconateMeSH
Muconic acidMeSH
Muconic acid, (e,e)-isomerMeSH
trans-beta-Hydromuconic acidMeSH
1,3-Butadiene-1,4-dicarboxylateHMDB
1,3-Butadiene-1,4-dicarboxylic acidHMDB
Hexa-2,4-dienedioateHMDB
Hexa-2,4-dienedioic acidHMDB
trans,trans-Muconic acidHMDB
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
Not AvailableNot Available
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
PropertyValueSource
Water Solubility3.48 g/LALOGPS
logP0.67ALOGPS
logP0.49ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.93 m³·mol⁻¹ChemAxon
Polarizability12.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.17131661259
DarkChem[M-H]-129.32431661259
DeepCCS[M+H]+125.89430932474
DeepCCS[M-H]-122.06530932474
DeepCCS[M-2H]-159.1430932474
DeepCCS[M+Na]+134.52430932474
AllCCS[M+H]+130.932859911
AllCCS[M+H-H2O]+126.832859911
AllCCS[M+NH4]+134.832859911
AllCCS[M+Na]+135.932859911
AllCCS[M-H]-126.532859911
AllCCS[M+Na-2H]-128.632859911
AllCCS[M+HCOO]-130.932859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.42 minutes32390414
Predicted by Siyang on May 30, 202210.865 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.77 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1237.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid374.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid88.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid248.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid87.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid317.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid356.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)312.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid860.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid281.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1027.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid274.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid308.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate653.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA277.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water156.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
trans-trans-Muconic acidOC(=O)\C=C\C=C\C(O)=O2776.0Standard polar33892256
trans-trans-Muconic acidOC(=O)\C=C\C=C\C(O)=O1320.6Standard non polar33892256
trans-trans-Muconic acidOC(=O)\C=C\C=C\C(O)=O1539.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
trans-trans-Muconic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C=C/C(=O)O1583.1Semi standard non polar33892256
trans-trans-Muconic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C=C/C(=O)O[Si](C)(C)C1642.4Semi standard non polar33892256
trans-trans-Muconic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C=C/C(=O)O1841.7Semi standard non polar33892256
trans-trans-Muconic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C=C/C(=O)O[Si](C)(C)C(C)(C)C2116.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - trans-trans-Muconic acid GC-MS (2 TMS)splash10-00di-3950000000-4833ed03fecc5d1070872014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-trans-Muconic acid GC-MS (Non-derivatized)splash10-00di-3950000000-4833ed03fecc5d1070872017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-trans-Muconic acid GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-25984cbefee561769fe32017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-trans-Muconic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9400000000-1d771b996d6b60d972022017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-trans-Muconic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-8930000000-43cca1649a383c1789572017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-trans-Muconic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-trans-Muconic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 10V, Positive-QTOFsplash10-002f-1900000000-ba0597e9fe553580b7762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 20V, Positive-QTOFsplash10-004m-9700000000-bb11fdbd4cb83319bdcf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 40V, Positive-QTOFsplash10-0udi-9000000000-60049330475bcfa51fdd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 10V, Negative-QTOFsplash10-0006-1900000000-d089e6c88da6929f4c622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 20V, Negative-QTOFsplash10-0006-5900000000-d4f0aa2255b01aabc0bf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 40V, Negative-QTOFsplash10-0fdp-9300000000-bc5a2d5e39f202b87d9c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 10V, Positive-QTOFsplash10-004j-9600000000-3e5c79b293ac84a6a8312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 20V, Positive-QTOFsplash10-004i-9200000000-b7fce2b042b06e3cb2762021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 40V, Positive-QTOFsplash10-0udr-9000000000-5b8045afa89b9f96b99d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 10V, Negative-QTOFsplash10-0002-9200000000-5b62b2b14bc9b75cd8482021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 20V, Negative-QTOFsplash10-0fb9-9000000000-20df0bac53b1a654f39b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-trans-Muconic acid 40V, Negative-QTOFsplash10-0fb9-9000000000-e2a3f3d1e8945188e0222021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
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 Quantified0.16 +/- 0.02 umol/mmol creatinineAdult (>18 years old)Male
Benzene exposure		 details
UrineDetected and Quantified0.1 (0.05 - 0.3) umol/mmol creatinineAdult (>18 years old)BothSmoking 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)Download (PDF)
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 ]