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Showing metabocard for Diethyl fumarate (HMDB0038601)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:55:35 UTC
Update Date2023-02-21 17:26:39 UTC
HMDB IDHMDB0038601
Secondary Accession Numbers
  • HMDB38601
Metabolite Identification
Common NameDiethyl fumarate
DescriptionDiethyl fumarate, also known as anti-psoriaticum or diethyl maleic acid, 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 Diethyl fumarate.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0038601 (Diethyl fumarate)

  Mrv0541 05061310332D          

 12 11  0  0  0  0            999 V2000
    3.3000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    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
   -0.4125   -2.1434    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
    0.8250   -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
    2.0625   -0.7145    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  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  1  0  0  0  0
M  END
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3D MOL for HMDB0038601 (Diethyl fumarate)

HMDB0038601
     RDKit          3D
Diethyl fumarate
 24 23  0  0  0  0  0  0  0  0999 V2000
    3.6524    1.2052   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6587   -0.1879   -0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978   -1.0553   -0.2182 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066   -0.7493   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0981    0.2886   -0.6600 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6017   -1.6826    0.6505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6568   -1.5628    0.8580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515   -0.4621    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1013    0.5150   -0.3049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -0.4519    0.6684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6614    0.6105    0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6111    0.6689   -1.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6728    1.6422   -0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792    1.0873    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9895    1.8850   -0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6764   -0.5798   -0.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4879   -0.1734   -2.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0794   -2.5942    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1555   -2.3701    1.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4412    1.5794    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7085    0.3516    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3270   -0.3489   -1.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8389    1.4250   -1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6018    0.9597   -1.7307 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
 10 11  1  0
 11 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  6 18  1  0
  7 19  1  0
 11 20  1  0
 11 21  1  0
 12 22  1  0
 12 23  1  0
 12 24  1  0
M  END
Download

3D SDF for HMDB0038601 (Diethyl fumarate)

  Mrv0541 05061310332D          

 12 11  0  0  0  0            999 V2000
    3.3000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    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
   -0.4125   -2.1434    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
    0.8250   -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
    2.0625   -0.7145    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  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038601

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-

> <INCHI_KEY>
IEPRKVQEAMIZSS-WAYWQWQTSA-N

> <FORMULA>
C8H12O4

> <MOLECULAR_WEIGHT>
172.1785

> <EXACT_MASS>
172.073558872

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.114787001214324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-diethyl (2Z)-but-2-enedioate

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.4311563566666663

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.533797904472049

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
43.64240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diethyl maleate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0038601 (Diethyl fumarate)

HMDB0038601
     RDKit          3D
Diethyl fumarate
 24 23  0  0  0  0  0  0  0  0999 V2000
    3.6524    1.2052   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6587   -0.1879   -0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978   -1.0553   -0.2182 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066   -0.7493   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0981    0.2886   -0.6600 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6017   -1.6826    0.6505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6568   -1.5628    0.8580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515   -0.4621    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1013    0.5150   -0.3049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -0.4519    0.6684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6614    0.6105    0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6111    0.6689   -1.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6728    1.6422   -0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792    1.0873    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9895    1.8850   -0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6764   -0.5798   -0.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4879   -0.1734   -2.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0794   -2.5942    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1555   -2.3701    1.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4412    1.5794    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7085    0.3516    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3270   -0.3489   -1.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8389    1.4250   -1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6018    0.9597   -1.7307 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
 10 11  1  0
 11 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  6 18  1  0
  7 19  1  0
 11 20  1  0
 11 21  1  0
 12 22  1  0
 12 23  1  0
 12 24  1  0
M  END
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PDB for HMDB0038601 (Diethyl 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       6.160  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.310  -4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.540  -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
HETATM   11  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1   11                                                       
CONECT    4    2   12                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9   11                                                  
CONECT    8    6   10   12                                                  
CONECT    9    7                                                            
CONECT   10    8                                                            
CONECT   11    3    7                                                       
CONECT   12    4    8                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for HMDB0038601 (Diethyl fumarate)

COMPND    HMDB0038601
HETATM    1  C1  UNL     1       3.652   1.205  -0.307  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.659  -0.188  -0.937  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.798  -1.055  -0.218  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.407  -0.749  -0.096  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.098   0.289  -0.660  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.602  -1.683   0.650  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.657  -1.563   0.858  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.451  -0.462   0.366  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.101   0.515  -0.305  1.00  0.00           O  
HETATM   10  O4  UNL     1      -2.846  -0.452   0.668  1.00  0.00           O  
HETATM   11  C7  UNL     1      -3.661   0.610   0.204  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.611   0.669  -1.327  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.673   1.642  -0.332  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.279   1.087   0.727  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.989   1.885  -0.877  1.00  0.00           H  
HETATM   16  H4  UNL     1       4.676  -0.580  -0.749  1.00  0.00           H  
HETATM   17  H5  UNL     1       3.488  -0.173  -2.011  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.079  -2.594   1.098  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.155  -2.370   1.460  1.00  0.00           H  
HETATM   20  H8  UNL     1      -3.441   1.579   0.669  1.00  0.00           H  
HETATM   21  H9  UNL     1      -4.709   0.352   0.441  1.00  0.00           H  
HETATM   22  H10 UNL     1      -3.327  -0.349  -1.656  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.839   1.425  -1.576  1.00  0.00           H  
HETATM   24  H12 UNL     1      -4.602   0.960  -1.731  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   18
CONECT    7    8   19
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   20   21
CONECT   12   22   23   24
END
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SMILES for HMDB0038601 (Diethyl fumarate)

CCOC(=O)\C=C/C(=O)OCC
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INCHI for HMDB0038601 (Diethyl fumarate)

InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H12O4
Average Molecular Weight172.1785
Monoisotopic Molecular Weight172.073558872
IUPAC Name1,4-diethyl (2Z)-but-2-enedioate
Traditional Namediethyl maleate
CAS Registry Number623-91-6
SMILES
CCOC(=O)\C=C/C(=O)OCC
InChI Identifier
InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-
InChI KeyIEPRKVQEAMIZSS-WAYWQWQTSA-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
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • 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
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point1 - 2 °CNot Available
Boiling Point218.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility14000 mg/L @ 30 °C (exp)The Good Scents Company Information System
LogP1.449 (est)The Good Scents Company Information System
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 IDFDB029781
KNApSAcK IDNot Available
Chemspider ID4436353
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5271566
PDB IDNot Available
ChEBI ID68508
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1018941
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Weirich EG: [History of the discovery of the antipsoriaticum chrysarobine]. Hautarzt. 1971 Mar;22(3):120-2. [PubMed:4928543 ]
  2. SYCH LI: [Changes of the functional condition of the neuroreceptor apparatus of the skin in psoriasis following application of antipsoriaticum and psoriacin]. Vestn Dermatol Venerol. 1957 Nov-Dec;31(6):11-7. [PubMed:13530531 ]
  3. SYCH LI: [Histomorphological changes in the skin and its neuro-receptor apparatus in patients with psoriasis treated with antipsoriaticum and psoriasin]. Vestn Rentgenol Radiol. 1961 Apr;35:29-33. [PubMed:13774345 ]
  4. LAPTEV VA: [Treatment of psoriasis by antipsoriaticum ointment]. Vestn Venerol Dermatol. 1956 Jul-Aug;30(4):11-2. [PubMed:13392389 ]
  5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  10. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.