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Showing metabocard for Ethyl hydrogen fumarate (HMDB0040207)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:44:43 UTC
Update Date2023-02-21 17:27:53 UTC
HMDB IDHMDB0040207
Secondary Accession Numbers
  • HMDB40207
Metabolite Identification
Common NameEthyl hydrogen fumarate
DescriptionEthyl hydrogen fumarate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a significant number of articles have been published on Ethyl hydrogen fumarate.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0040207 (Ethyl hydrogen fumarate)

  Mrv0541 05061311412D          

 10  9  0  0  0  0            999 V2000
   -2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    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
    1.2375   -0.7145    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
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    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
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  2  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
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3D MOL for HMDB0040207 (Ethyl hydrogen fumarate)

HMDB0040207
     RDKit          3D
Ethyl hydrogen fumarate
 18 17  0  0  0  0  0  0  0  0999 V2000
   -2.7972    0.4673    0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3803   -0.7176   -0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1576   -1.2692   -0.1069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0131   -0.4388   -0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2179    0.7008   -0.5027 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2039   -1.0512    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3577   -0.4529    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003    0.9105    0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8199    1.7441   -0.3668 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284    1.3614    0.2225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8887    0.3849    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737    1.3806   -0.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2323    0.5462    1.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2800   -0.4688   -1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1341   -1.5100   -0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1976   -2.1048    0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1817   -1.0957    0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4853    1.6133   -0.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  6 16  1  0
  7 17  1  0
 10 18  1  0
M  END
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3D SDF for HMDB0040207 (Ethyl hydrogen fumarate)

  Mrv0541 05061311412D          

 10  9  0  0  0  0            999 V2000
   -2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    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
    1.2375   -0.7145    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
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    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
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  2  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040207

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)\C=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3-

> <INCHI_KEY>
XLYMOEINVGRTEX-ARJAWSKDSA-N

> <FORMULA>
C6H8O4

> <MOLECULAR_WEIGHT>
144.1253

> <EXACT_MASS>
144.042258744

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
13.422244569061608

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-4-ethoxy-4-oxobut-2-enoic acid

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
0.6951210126666666

> <ALOGPS_LOGS>
-0.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0787403645946103

> <JCHEM_PKA_STRONGEST_BASIC>
-6.834751266595363

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
34.1247

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-4-ethoxy-4-oxobut-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0040207 (Ethyl hydrogen fumarate)

HMDB0040207
     RDKit          3D
Ethyl hydrogen fumarate
 18 17  0  0  0  0  0  0  0  0999 V2000
   -2.7972    0.4673    0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3803   -0.7176   -0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1576   -1.2692   -0.1069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0131   -0.4388   -0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2179    0.7008   -0.5027 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2039   -1.0512    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3577   -0.4529    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003    0.9105    0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8199    1.7441   -0.3668 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284    1.3614    0.2225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8887    0.3849    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737    1.3806   -0.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2323    0.5462    1.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2800   -0.4688   -1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1341   -1.5100   -0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1976   -2.1048    0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1817   -1.0957    0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4853    1.6133   -0.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  6 16  1  0
  7 17  1  0
 10 18  1  0
M  END
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PDB for HMDB0040207 (Ethyl hydrogen fumarate)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.540  -2.667   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      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   10                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7    8                                                  
CONECT    6    4    9   10                                                  
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    6                                                            
CONECT   10    2    6                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0040207 (Ethyl hydrogen fumarate)

COMPND    HMDB0040207
HETATM    1  C1  UNL     1      -2.797   0.467   0.296  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.380  -0.718  -0.550  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.158  -1.269  -0.107  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.013  -0.439  -0.107  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.218   0.701  -0.503  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.204  -1.051   0.354  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.358  -0.453   0.428  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.600   0.910   0.064  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.820   1.744  -0.367  1.00  0.00           O  
HETATM   10  O4  UNL     1       3.928   1.361   0.222  1.00  0.00           O  
HETATM   11  H1  UNL     1      -3.889   0.385   0.533  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.674   1.381  -0.343  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.232   0.546   1.225  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.280  -0.469  -1.622  1.00  0.00           H  
HETATM   15  H5  UNL     1      -3.134  -1.510  -0.426  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.198  -2.105   0.676  1.00  0.00           H  
HETATM   17  H7  UNL     1       3.182  -1.096   0.810  1.00  0.00           H  
HETATM   18  H8  UNL     1       4.485   1.613  -0.583  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   16
CONECT    7    8   17
CONECT    8    9    9   10
CONECT   10   18
END
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SMILES for HMDB0040207 (Ethyl hydrogen fumarate)

CCOC(=O)\C=C/C(O)=O
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INCHI for HMDB0040207 (Ethyl hydrogen fumarate)

InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3-
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Ethyl hydrogen fumaric acidGenerator
(2E)-4-Ethoxy-4-oxo-2-butenoic acidHMDB
2-Butenedioic acid (e)-, monoethyl esterHMDB
Fumaric acid monoethyl esterHMDB
Monoethyl fumarateHMDB
Potassium ethyl fumarateHMDB
Ethyl hydrogen maleateMeSH
Diethyl maleateMeSH
Diethyl maleic acid diesterMeSH
Ethyl maleateMeSH
Maleic acid diethyl esterMeSH
Maleic acid, ethyl esterMeSH
DiethylmaleateMeSH
Monoethyl maleateMeSH
Chemical FormulaC6H8O4
Average Molecular Weight144.1253
Monoisotopic Molecular Weight144.042258744
IUPAC Name(2Z)-4-ethoxy-4-oxobut-2-enoic acid
Traditional Name(2Z)-4-ethoxy-4-oxobut-2-enoic acid
CAS Registry Number2459-05-4
SMILES
CCOC(=O)\C=C/C(O)=O
InChI Identifier
InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3-
InChI KeyXLYMOEINVGRTEX-ARJAWSKDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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 Point66 - 68 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019919
KNApSAcK IDNot Available
Chemspider ID4510650
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5354457
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.