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Showing NP-Card for trans-trans-Muconic acid (NP0002748)

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Record Information
Version2.0
Created at2020-11-23 19:39:26 UTC
Updated at2021-08-12 19:52:02 UTC
NP-MRD IDNP0002748
Secondary Accession NumbersNone
Natural Product Identification
Common Nametrans-trans-Muconic acid
Provided ByBMRBBMRB logo
DescriptionTrans-trans-Muconic acid, also known as (2E,4E)-2,4-hexadienedioate or (e,e)-muconic acid, 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. Trans-trans-Muconic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. trans-trans-Muconic acid was first documented in 1999 (PMID: 10431356). Based on a literature review a small amount of articles have been published on trans-trans-Muconic acid (PMID: 16339183) (PMID: 14979410) (PMID: 12082012).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002748 (trans-trans-Muconic acid)


     RDKit          2D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -3.3646   -1.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2653   -0.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5118    0.6751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9195    0.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6729   -0.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729    0.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2653    0.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3646    1.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5118   -0.6751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8577    0.0127    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8202    1.9998    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722   -1.8279    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722    1.8279    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202   -1.9998    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8577   -0.0127    0.0000 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
Download

3D MOL for NP0002748 (trans-trans-Muconic acid)

NP0002748
     RDKit          3D

 16 15  0  0  0  0  0  0  0  0999 V2000
    3.7697   -1.2432   -1.5609 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8692   -1.0733   -0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0783   -1.5119    0.5794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6076   -0.4316   -1.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6652   -0.2597   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6097    0.3847   -0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5285    0.5391    0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8125    1.1687    0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1426    1.6140   -0.8420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030    1.2809    1.3232 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7608   -1.1319    1.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4540   -0.0911   -2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -0.6171    0.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423    0.7518   -1.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640    0.1583    1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1700    0.4624    1.7136 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
Download

3D SDF for NP0002748 (trans-trans-Muconic acid)


     RDKit          2D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -3.3646   -1.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2653   -0.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5118    0.6751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9195    0.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6729   -0.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729    0.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2653    0.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3646    1.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5118   -0.6751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8577    0.0127    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8202    1.9998    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722   -1.8279    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722    1.8279    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202   -1.9998    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8577   -0.0127    0.0000 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
> <DATABASE_ID>
NP0002748

> <DATABASE_NAME>
NP-MRD

> <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 NP0002748 (trans-trans-Muconic acid)

NP0002748
     RDKit          3D

 16 15  0  0  0  0  0  0  0  0999 V2000
    3.7697   -1.2432   -1.5609 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8692   -1.0733   -0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0783   -1.5119    0.5794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6076   -0.4316   -1.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6652   -0.2597   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6097    0.3847   -0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5285    0.5391    0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8125    1.1687    0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1426    1.6140   -0.8420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030    1.2809    1.3232 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7608   -1.1319    1.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4540   -0.0911   -2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -0.6171    0.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423    0.7518   -1.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640    0.1583    1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1700    0.4624    1.7136 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
Download

PDB for NP0002748 (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 NP0002748 (trans-trans-Muconic acid)

COMPND    NP0002748
HETATM    1  O1  UNL     1       3.770  -1.243  -1.561  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.869  -1.073  -0.713  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.078  -1.512   0.579  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.608  -0.432  -1.030  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.665  -0.260  -0.120  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.610   0.385  -0.425  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.529   0.539   0.511  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.813   1.169   0.276  1.00  0.00           C  
HETATM    9  O3  UNL     1      -3.143   1.614  -0.842  1.00  0.00           O  
HETATM   10  O4  UNL     1      -3.703   1.281   1.323  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.761  -1.132   1.212  1.00  0.00           H  
HETATM   12  H2  UNL     1       1.454  -0.091  -2.047  1.00  0.00           H  
HETATM   13  H3  UNL     1       0.868  -0.617   0.880  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.842   0.752  -1.412  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.264   0.158   1.496  1.00  0.00           H  
HETATM   16  H6  UNL     1      -4.170   0.462   1.714  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 NP0002748 (trans-trans-Muconic acid)

OC(=O)\C=C\C=C\C(O)=O
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INCHI for NP0002748 (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 JSmol
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
1,3-Butadiene-1,4-dicarboxylateHMDB
1,3-Butadiene-1,4-dicarboxylic acidHMDB
Hexa-2,4-dienedioateHMDB
Hexa-2,4-dienedioic acidHMDB
Muconic acidHMDB, MeSH
trans,trans-Muconic acidHMDB
trans-beta-Hydromuconic acidMeSH, HMDB
cis,cis-MuconateMeSH, HMDB
Muconic acid, (e,e)-isomerMeSH, HMDB
Chemical FormulaC6H6O4
Average Mass142.1094 Da
Monoisotopic Mass142.02661 Da
IUPAC Name(2E,4E)-hexa-2,4-dienedioic acid
Traditional Nametrans, trans-muconic acid
CAS Registry NumberNot Available
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0002349
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022974
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
Good Scents IDNot Available
References
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. doi: 10.1016/s0021-9673(98)01035-8. [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. doi: 10.1093/carcin/bgi297. Epub 2005 Dec 8. [PubMed:16339183 ]
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