Np mrd loader

Showing NP-Card for 2,4-hexadienedioic acid (NP0258420)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-07 23:51:59 UTC
Updated at2022-09-07 23:52:00 UTC
NP-MRD IDNP0258420
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,4-hexadienedioic acid
DescriptionMuconic acid, also known as muconate, 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. Muconic acid is a weakly acidic compound (based on its pKa). 2,4-hexadienedioic acid was first documented in 2013 (PMID: 23079953). A hexadienedioic acid with unsaturation at positions 2 and 4 (PMID: 23164574) (PMID: 24657371) (PMID: 24751381).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0258420 (2,4-hexadienedioic acid)


  Mrv1652305171805392D          

 10  9  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  2  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  4  1  0  0  0  0
 10  7  1  0  0  0  0
M  END
Download

3D MOL for NP0258420 (2,4-hexadienedioic acid)

     RDKit          3D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -3.3357   -1.4370   -1.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2466   -0.9602   -1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3474   -0.4444   -2.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204   -0.9825    0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9735   -0.5383    0.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965    0.0750    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2078    0.4899    0.9466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3961    1.1079    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    1.2600   -0.8340 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522    1.5453    1.1751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6338    0.3999   -2.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268   -1.4246    0.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9602   -0.6348    1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3276    0.2359   -0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1085    0.3437    2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855    0.9642    1.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8 10  1  0
  8  9  2  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 NP0258420 (2,4-hexadienedioic acid)


  Mrv1652305171805392D          

 10  9  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  2  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  4  1  0  0  0  0
 10  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0258420

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C=CC=CC(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)

> <INCHI_KEY>
TXXHDPDFNKHHGW-UHFFFAOYSA-N

> <FORMULA>
C6H6O4

> <MOLECULAR_WEIGHT>
142.11

> <EXACT_MASS>
142.026608673

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.796789385170584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
4.654855678562284

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8717705518676584

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
34.9256

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4-hexadienedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0258420 (2,4-hexadienedioic acid)

Download
PDB for NP0258420 (2,4-hexadienedioic acid)
HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.850   4.001   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.160   2.667   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7                                                            
CONECT    9    4                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

Download
3D PDB for NP0258420 (2,4-hexadienedioic acid)
Download
SMILES for NP0258420 (2,4-hexadienedioic acid)
OC(=O)C=CC=CC(O)=O
Download
INCHI for NP0258420 (2,4-hexadienedioic acid)
InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)
Download
View in JSmol
Synonyms
ValueSource
1,3-Butadiene-1,4-dicarboxylic acidChEBI
2,4-Hexadienedioic acidChEBI
Butadiene-1,4-dicarboxylic acidChEBI
1,3-Butadiene-1,4-dicarboxylateGenerator
2,4-HexadienedioateGenerator
Butadiene-1,4-dicarboxylateGenerator
MuconateGenerator
cis,trans-Muconic acidGenerator
Chemical FormulaC6H6O4
Average Mass142.1100 Da
Monoisotopic Mass142.02661 Da
IUPAC Namehexa-2,4-dienedioic acid
Traditional Name2,4-hexadienedioic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C=CC=CC(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)
InChI KeyTXXHDPDFNKHHGW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Polarizability12.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0062704  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMuconic acid  
METLIN IDNot Available
PubChem Compound310  
PDB IDNot Available
ChEBI ID38407  
Good Scents IDNot Available
References
General References
  1. Mudiam MK, Chauhan A, Singh KP, Gupta SK, Jain R, Ch R, Murthy RC: Determination of t,t-muconic acid in urine samples using a molecular imprinted polymer combined with simultaneous ethyl chloroformate derivatization and pre-concentration by dispersive liquid-liquid microextraction. Anal Bioanal Chem. 2013 Jan;405(1):341-9. doi: 10.1007/s00216-012-6474-9. Epub  2012 Oct 19. [PubMed:23079953  ] 
  2. Curran KA, Leavitt JM, Karim AS, Alper HS: Metabolic engineering of muconic acid production in Saccharomyces cerevisiae. Metab Eng. 2013 Jan;15:55-66. doi: 10.1016/j.ymben.2012.10.003. Epub 2012 Nov 17. [PubMed:23164574  ] 
  3. Choi YH, Kim JH, Lee BE, Hong YC: Urinary benzene metabolite and insulin resistance in elderly adults. Sci Total Environ. 2014 Jun 1;482-483:260-8. doi:  10.1016/j.scitotenv.2014.02.121. Epub 2014 Mar 20. [PubMed:24657371  ] 
  4. Xie NZ, Liang H, Huang RB, Xu P: Biotechnological production of muconic acid: current status and future prospects. Biotechnol Adv. 2014 May-Jun;32(3):615-22. doi: 10.1016/j.biotechadv.2014.04.001.  Epub 2014 Apr 18. [PubMed:24751381  ] 
  5. LOTUS database [Link]