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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:55:35 UTC

Update Date

2023-02-21 17:26:39 UTC

HMDB ID

HMDB0038601

Secondary Accession Numbers

HMDB38601

Metabolite Identification

Common Name

Diethyl fumarate

Description

Diethyl 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Butenedioic acid (2Z)-, dimethyl ester	ChEBI
Maleic acid, diethyl ester	ChEBI
2-Butenedioate (2Z)-, dimethyl ester	Generator
Maleate, diethyl ester	Generator
Diethyl fumaric acid	Generator
2-Butenedioic acid (2E)-, 1,4-diethyl ester	HMDB
2-Butenedioic acid (2E)-, diethyl ester	HMDB
2-Butenedioic acid (e)-, diethyl ester	HMDB
2-Butenedioic acid (e)-, diethyl ester (9ci)	HMDB
2-Butenedioic acid(e)-,diethyl ester	HMDB
Anti-psoriaticum	HMDB
Diethyl (2E)-2-butenedioate	HMDB
Diethyl (2E)-but-2-enedioate	HMDB
Diethyl ester OF (e)-2-butenedioic acid	HMDB
Diethyl ester(2E)-2-butenedioic acid	HMDB
Diethyl ester(e)-2-butenedioic acid	HMDB
Diethylester kyseliny fumarove	HMDB
Ethyl fumarate	HMDB
Ethyl maleate	HMDB
Fumaric acid, diethyl ester	HMDB
Fumaric acid, diethyl ester (8ci)	HMDB
trans-2-Butenedioic acid diethyl ester	HMDB
Diethyl maleic acid	HMDB
Diethylmaleate	HMDB
Maleic acid, ethyl ester	HMDB
Diethyl maleic acid diester	HMDB
Maleic acid diethyl ester	HMDB
Ethyl hydrogen maleate	HMDB
Monoethyl maleate	HMDB

Chemical Formula

C₈H₁₂O₄

Average Molecular Weight

172.1785

Monoisotopic Molecular Weight

172.073558872

IUPAC Name

1,4-diethyl (2Z)-but-2-enedioate

Traditional Name

diethyl maleate

CAS Registry Number

623-91-6

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 Key

IEPRKVQEAMIZSS-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty 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 Framework

Aliphatic acyclic compounds

External Descriptors

ethyl ester (CHEBI:68508 )
maleate ester (CHEBI:68508 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	1 - 2 °C	Not Available
Boiling Point	218.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	14000 mg/L @ 30 °C (exp)	The Good Scents Company Information System
LogP	1.449 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.9 g/L	ALOGPS
logP	1.34	ALOGPS
logP	1.43	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	43.64 m³·mol⁻¹	ChemAxon
Polarizability	17.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.082	31661259
DarkChem	[M-H]-	135.334	31661259
DeepCCS	[M+H]+	136.698	30932474
DeepCCS	[M-H]-	134.035	30932474
DeepCCS	[M-2H]-	170.326	30932474
DeepCCS	[M+Na]+	145.577	30932474
AllCCS	[M+H]+	139.8	32859911
AllCCS	[M+H-H2O]+	136.0	32859911
AllCCS	[M+NH4]+	143.4	32859911
AllCCS	[M+Na]+	144.4	32859911
AllCCS	[M-H]-	139.1	32859911
AllCCS	[M+Na-2H]-	140.8	32859911
AllCCS	[M+HCOO]-	142.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diethyl fumarate	CCOC(=O)\C=C/C(=O)OCC	1815.5	Standard polar	33892256
Diethyl fumarate	CCOC(=O)\C=C/C(=O)OCC	1202.6	Standard non polar	33892256
Diethyl fumarate	CCOC(=O)\C=C/C(=O)OCC	1288.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Diethyl fumarate EI-B (Non-derivatized)	splash10-002b-9300000000-beca5d278a0d16ecf73b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl fumarate EI-B (Non-derivatized)	splash10-0f92-9600000000-7044fd2900eb33b94df7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl fumarate EI-B (Non-derivatized)	splash10-002b-9700000000-b8b2e754c193242cc346	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl fumarate EI-B (Non-derivatized)	splash10-002b-9400000000-1575d42a342b7e2bc810	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl fumarate EI-B (Non-derivatized)	splash10-004j-9300000000-83beca9d9c20ad1ddc25	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl fumarate EI-B (Non-derivatized)	splash10-002b-9400000000-d825de440937576c6f5c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl fumarate EI-B (Non-derivatized)	splash10-002b-9300000000-beca5d278a0d16ecf73b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl fumarate EI-B (Non-derivatized)	splash10-0f92-9600000000-7044fd2900eb33b94df7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl fumarate EI-B (Non-derivatized)	splash10-002b-9700000000-b8b2e754c193242cc346	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl fumarate EI-B (Non-derivatized)	splash10-002b-9400000000-1575d42a342b7e2bc810	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl fumarate EI-B (Non-derivatized)	splash10-004j-9300000000-83beca9d9c20ad1ddc25	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl fumarate EI-B (Non-derivatized)	splash10-002b-9400000000-d825de440937576c6f5c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethyl fumarate GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-9200000000-8e1f11a516bd083261fb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethyl fumarate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethyl fumarate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl fumarate 10V, Positive-QTOF	splash10-00di-2900000000-cf5c554e39e58beadb90	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl fumarate 20V, Positive-QTOF	splash10-009b-9700000000-1fb886bc65257e0241af	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl fumarate 40V, Positive-QTOF	splash10-009b-9100000000-06f7a2010bbcfdbe62ba	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl fumarate 10V, Negative-QTOF	splash10-00fr-2900000000-407d826921c885f93c39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl fumarate 20V, Negative-QTOF	splash10-00ba-9800000000-219e102f8184a4d01de6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl fumarate 40V, Negative-QTOF	splash10-0002-9100000000-868b95ec3f16141a4b06	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl fumarate 10V, Negative-QTOF	splash10-00di-7900000000-cd53f73918f682c929bb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl fumarate 20V, Negative-QTOF	splash10-000t-9100000000-efdb7d5f6138e08335e2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl fumarate 40V, Negative-QTOF	splash10-01ba-9000000000-b9952481740a6f8f40c0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl fumarate 10V, Positive-QTOF	splash10-004i-6900000000-ebc0c8b10e9b1626b07e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl fumarate 20V, Positive-QTOF	splash10-052b-9100000000-c4c7d5fcaeea78b6fb93	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl fumarate 40V, Positive-QTOF	splash10-05fr-9000000000-8f298320469ba3df32c7	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029781

KNApSAcK ID

Not Available

Chemspider ID

4436353

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5271566

PDB ID

Not Available

ChEBI ID

68508

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1018941

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Weirich EG: [History of the discovery of the antipsoriaticum chrysarobine]. Hautarzt. 1971 Mar;22(3):120-2. [PubMed:4928543 ]
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 ]
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 ]
LAPTEV VA: [Treatment of psoriasis by antipsoriaticum ointment]. Vestn Venerol Dermatol. 1956 Jul-Aug;30(4):11-2. [PubMed:13392389 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Diethyl fumarate (HMDB0038601)

MOL for HMDB0038601 (Diethyl fumarate)

3D MOL for HMDB0038601 (Diethyl fumarate)

3D SDF for HMDB0038601 (Diethyl fumarate)

3D-SDF for HMDB0038601 (Diethyl fumarate)

PDB for HMDB0038601 (Diethyl fumarate)

3D PDB for HMDB0038601 (Diethyl fumarate)

SMILES for HMDB0038601 (Diethyl fumarate)

INCHI for HMDB0038601 (Diethyl fumarate)

Structure for HMDB0038601 (Diethyl fumarate)

3D Structure for HMDB0038601 (Diethyl fumarate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra