Livestock Metabolome Database: Showing metabocard for Fumaric acid (LMDB00057)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:41:26 UTC

Update Date

2020-03-13 18:12:20 UTC

Lmdb

LMDB00057

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Fumaric acid

Description

Fumaric acid is a dicarboxylic acid. It is a precursor to L-malate in the Krebs tricarboxylic acid (TCA) cycle. It is formed by the oxidation of succinic acid by succinate dehydrogenase. Fumarate is converted by the enzyme fumarase to malate. Fumaric acid has recently been identified as an oncometabolite or an endogenous, cancer causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. Its oncogenic action appears to due to its ability to inhibit prolyl hydroxylase-containing enzymes. In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation. All three of the PHD enzymes are inhibited by fumarate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-2-Butenedioic acid	ChEBI
(e)-2-Butenedioic acid	ChEBI
e297	ChEBI
Fumarsaeure	ChEBI
trans-1,2-Ethylenedicarboxylic acid	ChEBI
trans-But-2-enedioic acid	ChEBI
trans-Butenedioic acid	ChEBI
(2E)-2-Butenedioate	Generator
(e)-2-Butenedioate	Generator
trans-1,2-Ethylenedicarboxylate	Generator
trans-But-2-enedioate	Generator
trans-Butenedioate	Generator
Fumarate	Generator
(2E)-But-2-enedioate	HMDB
(2E)-But-2-enedioic acid	HMDB
2-(e)-Butenedioate	HMDB
2-(e)-Butenedioic acid	HMDB
Allomaleate	HMDB
Allomaleic acid	HMDB
Boletate	HMDB
Boletic acid	HMDB
FC 33	HMDB
Lichenate	HMDB
Lichenic acid	HMDB
trans-2-Butenedioate	HMDB
trans-2-Butenedioic acid	HMDB
Furamag	HMDB
Mafusol	HMDB
Fumaric acid	HMDB

Chemical Formula

C₄H₄O₄

Average Molecular Weight

116.0722

Monoisotopic Molecular Weight

116.010958616

IUPAC Name

(2E)-but-2-enedioic acid

Traditional Name

fumaric acid

CAS Registry Number

110-17-8

SMILES

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

InChI Identifier

InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+

InChI Key

VZCYOOQTPOCHFL-OWOJBTEDSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Fatty acyl
Fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

butenedioic acid (CHEBI:18012 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.21	ALOGPS
logP	-0.041	ChemAxon
logS	-0.68	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	24.61 m³·mol⁻¹	ChemAxon
Polarizability	9.35 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-2940000000-e988056514d4ce4acc27	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-2960000000-a5ebaf2bbade922838ec	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-2950000000-32afa4d45e0e72b174b4	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0950000000-fe0f05c02c783d0b6f6b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-006t-9530000000-0fc03f31f09dc8dbf4c6	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0002-3690000000-75089756992cdbe841e3	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9100000000-2cf649749b42cc0c610c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-0890000000-b1c35cd55deb81254f66	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-2940000000-e988056514d4ce4acc27	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-2960000000-a5ebaf2bbade922838ec	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-2950000000-32afa4d45e0e72b174b4	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0950000000-fe0f05c02c783d0b6f6b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-9530000000-0fc03f31f09dc8dbf4c6	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0002-3690000000-75089756992cdbe841e3	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0940000000-177fdb9168659029ffaa	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ba-9200000000-52f88e04bac0ff8cdf17	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-8920000000-06da44f348d0fe0358b3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-9100000000-57f13cd433a6fe4bf0b3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0229-9600000000-cd9e2979d0bb1e2a62f2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-03k9-8900000000-dc50dbf8a50872383d54	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0002-9100000000-b47e534bc82a6ed36e7c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-04b277f233e1bd56c9af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-4900000000-99764eff7d7cb7bfaee3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-9000000000-453b921a0aaf64cfd558	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9000000000-cd7e7026d13bb5fe844b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00dj-9000000000-383c22a29e2769626c47	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ir3-9000000000-3013847e2e0f9bf18d29	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-00di-9000000000-9cc4f29b523ed34dc0b6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-00di-9000000000-d9885a6093f38dd8b9fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-00di-9000000000-46fdee94b5a787f1b81f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03k9-8900000000-3ff0fb725ec9dffc3688	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014m-9000000000-394fd8f1b59c7befec9d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9800000000-dbf34563376daeb2901f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xs-9200000000-113bf08cdc77707ed3ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fr-9000000000-f32d7ec65e8649bc2b0a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-408d53a9fff7acc8ca23	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-6900000000-f149e9e5a34e27dd4d4e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fxt-9000000000-cae5f71dc27daaf17d9e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-3d34cd791255c022876a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-55a5c43ec34fdd2cb0a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uk9-9000000000-7c9639a65d534cd8ff97	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-9000000000-c5eb63dc643f72e91ede	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0092-9000000000-003dd2d9303272b2ebea	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Brain
Colostrum
Feces
Jejunum
Kidney perfusate
Meat
Milk
Plasma
Ruminal Fluid
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Brain	Detected but not Quantified	Not Applicable	Not Available	Ovine	25959287	details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Jejunum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21584308	details
Kidney perfusate	Detected but not Quantified	Not Applicable	Not Available	Porcine	25502759	details
Meat	Detected and Quantified	107.37 +/- 14.42 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	123.02 +/- 19.31 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	160.89 +/- 17.1 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	84.76 +/- 11.89 uM	Not Available	Bovine	20831251	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Milk	Detected and Quantified	7-23 uM	Not Available	Bovine	22098372	details
Milk	Detected and Quantified	2-81 uM	Not Available	Bovine	20338431	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23394630	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23497994	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23182357	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	25108860	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	25087032	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	25502722	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details
Ruminal Fluid	Detected and Quantified	1.42 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	1.64 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	5.82 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	6.44 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	7.5 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	7.5 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	8.8 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	8.8 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	11.2 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	11.2 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	11.7 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	11.7 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	11 +/- 4 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	12 +/- 4 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	4 +/- 3.0 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	8 +/- 2 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	9 +/- 4 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	9 +/- 4 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	23.8 +/- 4.2 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	25.1 +/- 4.0 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	28.5 +/- 8.7 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	266 +/- 49 uM	Not Available	Caprine	22706048	details
Serum	Detected and Quantified	1.29 +/- 0.6 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21942754	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	18989615	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	26020888	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21584308	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21429726	details
Urine	Detected and Quantified	127 umol/mmol creatinine	Not Available	Porcine	23741447	details
Urine	Detected and Quantified	62 umol/mmol creatinine	Not Available	Porcine	23741447	details