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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:33 UTC

Update Date

2023-02-21 17:16:06 UTC

HMDB ID

HMDB0002050

Secondary Accession Numbers

HMDB02050

Metabolite Identification

Common Name

Dihydroxyfumaric acid

Description

Dihydroxyfumaric acid, also known as dihydroxyfumarate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. Dihydroxyfumaric acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make dihydroxyfumaric acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Dihydroxyfumaric acid.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dihydroxyfumarate	Generator
(2-)Dihydroxyfumarate	HMDB
(2E)-2,3-Dihydroxybut-2-enedioate	HMDB
(2E)-2,3-Dihydroxybut-2-enedioic acid	HMDB
3,4,4-Trihydroxy-2-oxobut-3-enoate	HMDB
3,4,4-Trihydroxy-2-oxobut-3-enoic acid	HMDB
DHF	HMDB
Dihydroxy-fumarate	Generator, HMDB

Chemical Formula

C₄H₄O₆

Average Molecular Weight

148.071

Monoisotopic Molecular Weight

148.00078786

IUPAC Name

3,4,4-trihydroxy-2-oxobut-3-enoic acid

Traditional Name

dihydroxy-fumaric acid

CAS Registry Number

133-38-0

SMILES

OC(O)=C(O)C(=O)C(O)=O

InChI Identifier

InChI=1S/C4H4O6/c5-1(3(7)8)2(6)4(9)10/h5,7-8H,(H,9,10)

InChI Key

KAPRQAPANAEVOD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Short-chain keto acid
Hydroxy fatty acid
Alpha-keto acid
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Unsaturated fatty acid
Acryloyl-group
Alpha-hydroxy ketone
Vinylogous acid
Alpha,beta-unsaturated ketone
Enone
Ketone
Carboxylic acid derivative
Carboxylic acid
Polyol
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Oxo fatty acids (LMFA01060194 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0002050)

Source

Endogenous

Endogenous (HMDB: HMDB0002050)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	387.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2.96 mg/mL at 12 °C	Not Available
LogP	-1.310 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	14.1 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-0.0088	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	2.01	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.86 m³·mol⁻¹	ChemAxon
Polarizability	10.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	123.825	30932474
DeepCCS	[M-H]-	120.097	30932474
DeepCCS	[M-2H]-	157.399	30932474
DeepCCS	[M+Na]+	132.571	30932474
AllCCS	[M+H]+	133.7	32859911
AllCCS	[M+H-H2O]+	129.6	32859911
AllCCS	[M+NH4]+	137.5	32859911
AllCCS	[M+Na]+	138.6	32859911
AllCCS	[M-H]-	122.3	32859911
AllCCS	[M+Na-2H]-	124.5	32859911
AllCCS	[M+HCOO]-	126.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydroxyfumaric acid	OC(O)=C(O)C(=O)C(O)=O	2044.7	Standard polar	33892256
Dihydroxyfumaric acid	OC(O)=C(O)C(=O)C(O)=O	1984.9	Standard non polar	33892256
Dihydroxyfumaric acid	OC(O)=C(O)C(=O)C(O)=O	1453.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydroxyfumaric acid,1TMS,isomer #1	C[Si](C)(C)OC(O)=C(O)C(=O)C(=O)O	1488.7	Semi standard non polar	33892256
Dihydroxyfumaric acid,1TMS,isomer #2	C[Si](C)(C)OC(C(=O)C(=O)O)=C(O)O	1408.0	Semi standard non polar	33892256
Dihydroxyfumaric acid,1TMS,isomer #3	C[Si](C)(C)OC(=O)C(=O)C(O)=C(O)O	1471.4	Semi standard non polar	33892256
Dihydroxyfumaric acid,2TMS,isomer #1	C[Si](C)(C)OC(O[Si](C)(C)C)=C(O)C(=O)C(=O)O	1491.1	Semi standard non polar	33892256
Dihydroxyfumaric acid,2TMS,isomer #2	C[Si](C)(C)OC(O)=C(O[Si](C)(C)C)C(=O)C(=O)O	1516.8	Semi standard non polar	33892256
Dihydroxyfumaric acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)C(=O)C(O)=C(O)O[Si](C)(C)C	1535.5	Semi standard non polar	33892256
Dihydroxyfumaric acid,2TMS,isomer #4	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O)O	1483.0	Semi standard non polar	33892256
Dihydroxyfumaric acid,3TMS,isomer #1	C[Si](C)(C)OC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)C(=O)O	1575.3	Semi standard non polar	33892256
Dihydroxyfumaric acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(=O)C(O)=C(O[Si](C)(C)C)O[Si](C)(C)C	1575.5	Semi standard non polar	33892256
Dihydroxyfumaric acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O)O[Si](C)(C)C	1598.4	Semi standard non polar	33892256
Dihydroxyfumaric acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)O[Si](C)(C)C	1687.0	Semi standard non polar	33892256
Dihydroxyfumaric acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(O)=C(O)C(=O)C(=O)O	1722.9	Semi standard non polar	33892256
Dihydroxyfumaric acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(C(=O)C(=O)O)=C(O)O	1696.2	Semi standard non polar	33892256
Dihydroxyfumaric acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(O)=C(O)O	1712.1	Semi standard non polar	33892256
Dihydroxyfumaric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(O[Si](C)(C)C(C)(C)C)=C(O)C(=O)C(=O)O	2008.6	Semi standard non polar	33892256
Dihydroxyfumaric acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(O)=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O	1979.6	Semi standard non polar	33892256
Dihydroxyfumaric acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(O)=C(O)O[Si](C)(C)C(C)(C)C	1985.7	Semi standard non polar	33892256
Dihydroxyfumaric acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C(C)(C)C)=C(O)O	1986.1	Semi standard non polar	33892256
Dihydroxyfumaric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O	2276.9	Semi standard non polar	33892256
Dihydroxyfumaric acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(O)=C(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2274.3	Semi standard non polar	33892256
Dihydroxyfumaric acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C(C)(C)C)=C(O)O[Si](C)(C)C(C)(C)C	2253.3	Semi standard non polar	33892256
Dihydroxyfumaric acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2538.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroxyfumaric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9300000000-56c3b4199e1a3f8a28d1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroxyfumaric acid GC-MS (4 TMS) - 70eV, Positive	splash10-00xr-9338200000-334075a41d8c5778e4bb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroxyfumaric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroxyfumaric acid 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 - Dihydroxyfumaric acid 10V, Positive-QTOF	splash10-001j-1900000000-12da6295b11ba9335f0a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroxyfumaric acid 20V, Positive-QTOF	splash10-0kmi-9600000000-388812a211dbdb3401d8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroxyfumaric acid 40V, Positive-QTOF	splash10-0ab9-9000000000-4881d65faf0696f1986b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroxyfumaric acid 10V, Negative-QTOF	splash10-0udi-3900000000-ea7ceae9f3953d2b9fea	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroxyfumaric acid 20V, Negative-QTOF	splash10-0udi-6900000000-af79222d5a15e48fa3f8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroxyfumaric acid 40V, Negative-QTOF	splash10-0a4i-9100000000-63cd9244350df0dee62f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroxyfumaric acid 10V, Negative-QTOF	splash10-0udi-3900000000-6a905821b40d13da66c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroxyfumaric acid 20V, Negative-QTOF	splash10-0pb9-9300000000-3df4e28780a888ec55cf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroxyfumaric acid 40V, Negative-QTOF	splash10-0006-9000000000-d6772050be074a7ab1d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroxyfumaric acid 10V, Positive-QTOF	splash10-0f89-4900000000-023a88c1e91b850b6bd5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroxyfumaric acid 20V, Positive-QTOF	splash10-0a4i-9000000000-559e64db799bd1ee1af6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroxyfumaric acid 40V, Positive-QTOF	splash10-0a4i-9000000000-ec0c495a1c047718ac5d	2021-09-22	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

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

FDB022816

KNApSAcK ID

Not Available

Chemspider ID

8299

KEGG Compound ID

C00975

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6460

PubChem Compound

8618

PDB ID

Not Available

ChEBI ID

4593

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1238531

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Dihydroxyfumaric acid (HMDB0002050)

MOL for HMDB0002050 (Dihydroxyfumaric acid)

3D MOL for HMDB0002050 (Dihydroxyfumaric acid)

3D SDF for HMDB0002050 (Dihydroxyfumaric acid)

3D-SDF for HMDB0002050 (Dihydroxyfumaric acid)

PDB for HMDB0002050 (Dihydroxyfumaric acid)

3D PDB for HMDB0002050 (Dihydroxyfumaric acid)

SMILES for HMDB0002050 (Dihydroxyfumaric acid)

INCHI for HMDB0002050 (Dihydroxyfumaric acid)

Structure for HMDB0002050 (Dihydroxyfumaric acid)

3D Structure for HMDB0002050 (Dihydroxyfumaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra