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Showing metabocard for cis,cis-Muconic acid (HMDB0006331)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-23 00:53:22 UTC
Update Date2022-03-07 02:49:31 UTC
HMDB IDHMDB0006331
Secondary Accession Numbers
  • HMDB06331
Metabolite Identification
Common Namecis,cis-Muconic acid
Descriptioncis-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 was formed by the 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 1950s 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. cis-cis-Muconic acid can also be found in Pseudomonas and Escherichia coli (https://link.springer.com/article/10.1007/BF00250491) (PMID:26360870 ).
Structure
Data?1582752381
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006331 (cis,cis-Muconic acid)


  Mrv1652305271900062D          

 10  9  0  0  0  0            999 V2000
 9993.2135 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9277 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7546 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4682 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1837 9993.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4682 9992.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3880 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6733 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9586 9993.3504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6733 9994.5873    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 HMDB0006331 (cis,cis-Muconic acid)

HMDB0006331
     RDKit          3D
cis,cis-Muconic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.0259   -2.0091   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437   -0.8240   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7536   -0.5880   -0.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    0.3671   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2518    0.4136    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -0.7871    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8343   -0.7499    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072    0.4245    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.2333    0.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795    1.7439    0.3501 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1866    0.0990    0.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0728    1.3710   -0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.4201    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -1.7840    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3584   -1.7469    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4442    2.4164   -0.3844 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 HMDB0006331 (cis,cis-Muconic acid)


  Mrv1652305271900062D          

 10  9  0  0  0  0            999 V2000
 9993.2135 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9277 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7546 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4682 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1837 9993.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4682 9992.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3880 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6733 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9586 9993.3504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6733 9994.5873    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>
HMDB0006331

> <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-CCAGOZQPSA-N

> <FORMULA>
C6H6O4

> <MOLECULAR_WEIGHT>
142.1094

> <EXACT_MASS>
142.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.537125034306658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,4Z)-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>
muconic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0006331 (cis,cis-Muconic acid)

HMDB0006331
     RDKit          3D
cis,cis-Muconic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.0259   -2.0091   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437   -0.8240   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7536   -0.5880   -0.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    0.3671   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2518    0.4136    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -0.7871    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8343   -0.7499    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072    0.4245    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.2333    0.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795    1.7439    0.3501 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1866    0.0990    0.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0728    1.3710   -0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.4201    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -1.7840    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3584   -1.7469    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4442    2.4164   -0.3844 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 HMDB0006331 (cis,cis-Muconic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8653.9998654.254   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8655.3328655.023   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8656.8758655.023   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8658.2078654.254   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8659.5438655.023   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8658.2078652.713   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8652.4588654.254   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8651.1238655.023   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8649.7898654.254   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8651.1238656.563   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 HMDB0006331 (cis,cis-Muconic acid)

COMPND    HMDB0006331
HETATM    1  O1  UNL     1       2.026  -2.009  -0.139  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.344  -0.824  -0.117  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.754  -0.588  -0.218  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.567   0.367  -0.008  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.252   0.414   0.098  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.523  -0.787   0.111  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.834  -0.750   0.215  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.607   0.425   0.323  1.00  0.00           C  
HETATM    9  O3  UNL     1      -3.897   0.233   0.417  1.00  0.00           O  
HETATM   10  O4  UNL     1      -2.280   1.744   0.350  1.00  0.00           O  
HETATM   11  H1  UNL     1       4.187   0.099   0.366  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.073   1.371  -0.008  1.00  0.00           H  
HETATM   13  H3  UNL     1      -0.219   1.420   0.175  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.040  -1.784   0.033  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.358  -1.747   0.217  1.00  0.00           H  
HETATM   16  H6  UNL     1      -2.444   2.416  -0.384  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 HMDB0006331 (cis,cis-Muconic acid)

OC(=O)\C=C/C=C\C(O)=O
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INCHI for HMDB0006331 (cis,cis-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
(2Z,4Z)-HEXA-2,4-dienedioIC ACIDChEBI
(Z,Z)-2,4-Hexadienedioic acidChEBI
cis,cis-2,4-Hexadienedioic acidChEBI
cis,cis-HexadienedioateKegg
(2Z,4Z)-HEXA-2,4-dienedioateGenerator
(Z,Z)-2,4-HexadienedioateGenerator
cis,cis-2,4-HexadienedioateGenerator
cis,cis-Hexadienedioic acidGenerator
cis,cis-MuconateGenerator
trans-trans-MuconateHMDB
2,4-HexadienedioateHMDB
2,4-Hexadienedioic acidHMDB
Muconic acidHMDB
Muconic acid, (e,e)-isomerHMDB
trans-beta-Hydromuconic acidHMDB
trans,trans-Muconic acidHMDB
Chemical FormulaC6H6O4
Average Molecular Weight142.1094
Monoisotopic Molecular Weight142.02660868
IUPAC Name(2Z,4Z)-hexa-2,4-dienedioic acid
Traditional Namemuconic acid
CAS Registry Number1119-72-8
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 KeyTXXHDPDFNKHHGW-CCAGOZQPSA-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 locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot 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
Polarizability12.54 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]+130.88631661259
DarkChem[M-H]-127.20531661259
DeepCCS[M+H]+127.99830932474
DeepCCS[M-H]-124.1730932474
DeepCCS[M-2H]-161.11730932474
DeepCCS[M+Na]+136.59230932474
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. 2.42 minutes32390414
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. -1.7 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
cis,cis-Muconic acidOC(=O)\C=C/C=C\C(O)=O2776.0Standard polar33892256
cis,cis-Muconic acidOC(=O)\C=C/C=C\C(O)=O1320.6Standard non polar33892256
cis,cis-Muconic acidOC(=O)\C=C/C=C\C(O)=O1539.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
cis,cis-Muconic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C\C=C/C(=O)O1583.1Semi standard non polar33892256
cis,cis-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
cis,cis-Muconic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C\C=C/C(=O)O1841.7Semi standard non polar33892256
cis,cis-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 - cis,cis-Muconic acid GC-MS (2 TMS)splash10-00di-3950000000-4833ed03fecc5d1070872018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis,cis-Muconic acid GC-MS (Non-derivatized)splash10-00di-3950000000-4833ed03fecc5d1070872018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis,cis-Muconic acid GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-25984cbefee561769fe32018-05-25HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis,cis-Muconic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9400000000-1d771b996d6b60d972022017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis,cis-Muconic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-8930000000-43cca1649a383c1789572017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis,cis-Muconic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis,cis-Muconic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - cis,cis-Muconic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-0a4i-9500000000-9bfca1b46934aca914172012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis,cis-Muconic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0a4i-9100000000-f73acaf474e29ae6ad022012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis,cis-Muconic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-0a4i-9100000000-f2b4bdcda5ec550eb7922012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis,cis-Muconic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0006-2900000000-1ba3b45cf195a5a99f0c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis,cis-Muconic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0a4i-9000000000-dfbcd30eacb1562a4b6e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis,cis-Muconic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0a4i-9000000000-55d282ca59f262ec65712012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis,cis-Muconic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0a4i-9000000000-6d6fa71ac1d98156ceb52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis,cis-Muconic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0a4i-9000000000-b0b000b29f1354ee4c062012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis,cis-Muconic acid LC-ESI-QQ , negative-QTOFsplash10-0006-2900000000-1ba3b45cf195a5a99f0c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis,cis-Muconic acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-9000000000-dfbcd30eacb1562a4b6e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis,cis-Muconic acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-9000000000-55d282ca59f262ec65712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis,cis-Muconic acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-9000000000-6d6fa71ac1d98156ceb52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis,cis-Muconic acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-9000000000-b0b000b29f1354ee4c062017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis,cis-Muconic acid 10V, Positive-QTOFsplash10-004i-1900000000-af70de4037dff7de94512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis,cis-Muconic acid 20V, Positive-QTOFsplash10-004j-9700000000-9bf9b99450c76793d87b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis,cis-Muconic acid 40V, Positive-QTOFsplash10-0ug0-9000000000-227dbb1efce65ff24c432017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis,cis-Muconic acid 10V, Negative-QTOFsplash10-0006-1900000000-70540641b312f5201a472017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis,cis-Muconic acid 20V, Negative-QTOFsplash10-006x-3900000000-2f635f40772c5e68fd4d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis,cis-Muconic acid 40V, Negative-QTOFsplash10-0fi4-9400000000-803dce4e7fbd2d6c9ac72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis,cis-Muconic acid 10V, Negative-QTOFsplash10-0002-9200000000-5b62b2b14bc9b75cd8482021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis,cis-Muconic acid 20V, Negative-QTOFsplash10-0fb9-9000000000-20df0bac53b1a654f39b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis,cis-Muconic acid 40V, Negative-QTOFsplash10-0fb9-9000000000-e2a3f3d1e8945188e0222021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis,cis-Muconic acid 10V, Positive-QTOFsplash10-004j-9600000000-3e5c79b293ac84a6a8312021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis,cis-Muconic acid 20V, Positive-QTOFsplash10-004i-9200000000-b7fce2b042b06e3cb2762021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis,cis-Muconic acid 40V, Positive-QTOFsplash10-0udr-9000000000-5b8045afa89b9f96b99d2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleMissing teeth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
Associated Disorders and Diseases
Disease References
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023893
KNApSAcK IDC00007490
Chemspider ID4444151
KEGG Compound IDC02480
BioCyc IDNot Available
BiGG ID36677
Wikipedia LinkMuconic acid
METLIN IDNot Available
PubChem Compound5280518
PDB IDNot Available
ChEBI ID16508
Food Biomarker OntologyNot Available
VMH IDCCMUAC
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. (). 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). .
  3. (). 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).. .