P. aeruginosa Metabolome Database: Fumaric acid (PAMDB000073)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000073

Identification

Name:

Fumaric acid

Description:

A precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. (wikipedia)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(2E)-But-2-enedioate
(2E)-But-2-enedioic acid
(E)-2-Butenedioate
(E)-2-Butenedioic acid
2-(E)-Butenedioate
2-(E)-Butenedioic acid
Allomaleate
Allomaleic acid
Boletate
Boletic acid
FC 33
Fum
Fumarate
Fumaric acid
Lichenate
Lichenic acid
Sodium fumarate
Sodium fumaric acid
Trans-1,2-Ethylenedicarboxylate
Trans-1,2-Ethylenedicarboxylic acid
Trans-2-Butenedioate
Trans-2-Butenedioic acid
Trans-Butenedioate
Trans-Butenedioic acid

Chemical Formula:

C₄H₄O₄

Average Molecular Weight:

116.0722

Monoisotopic Molecular Weight:

116.010958616

InChI Key:

VZCYOOQTPOCHFL-OWOJBTEDSA-N

InChI:

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

CAS number:

110-17-8

IUPAC Name:

(2E)-but-2-enedioic acid

Traditional IUPAC Name:

fumaric acid

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound 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
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

butenedioic acid (CHEBI:18012 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

549 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	7.0 mg/mL [US EPA (1981)]	PhysProp
LogP:	0.46 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	24.1 mg/mL	ALOGPS
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Ubiquinone-8 + Succinic acid > Fumaric acid + Ubiquinol-8
Fumaric acid + Water <> L-Malic acid
Fumaric acid + Menaquinol 8 > Menaquinone 8 + Succinic acid
2-Demethylmenaquinol 8 + Fumaric acid > 2-Demethylmenaquinone 8 + Succinic acid
Water + 2-Hydroxy-6-ketononatrienedioate > Fumaric acid + Hydrogen ion + 2-Hydroxy-2,4-pentadienoate
SAICAR <> Phosphoribosyl formamidocarboxamide + Fumaric acid
Adenylsuccinic acid <> Adenosine monophosphate + Fumaric acid
L-Aspartic acid + Fumaric acid > Hydrogen ion + Iminoaspartic acid + Succinic acid
3 Fumaric acid + Protoporphyrinogen IX > Protoporphyrin IX +3 Succinic acid
Argininosuccinic acid <> L-Arginine + Fumaric acid
L-Aspartic acid > Fumaric acid + Ammonium
Succinic acid + FAD <> FADH2 + Fumaric acid
Succinic acid + Acceptor <> Fumaric acid + Reduced acceptor
L-Aspartic acid <> Fumaric acid + Ammonia
4,5-Dihydroorotic acid + Fumaric acid <> Orotic acid + Succinic acid
SAICAR <> Fumaric acid + AICAR
2-Hydroxy-6-ketononatrienedioate + Water <> 2-Hydroxy-2,4-pentadienoate + Fumaric acid
adenylo-succinate > Fumaric acid + Adenosine monophosphate
L-arginino-succinate <> L-Arginine + Fumaric acid
L-Aspartic acid <> Hydrogen ion + Fumaric acid + Ammonia

More...

Pathways:

Alanine, aspartate and glutamate metabolism pae00250
Arginine and proline metabolism pae00330
Benzoate degradation via CoA ligation pae00632
Butanoate metabolism pae00650
Citrate cycle (TCA cycle) pae00020
Metabolic pathways pae01100
Microbial metabolism in diverse environments pae01120
Nicotinate and nicotinamide metabolism pae00760
Nitrogen metabolism pae00910
Oxidative phosphorylation pae00190
Phenylalanine metabolism pae00360
Purine metabolism pae00230
Pyruvate metabolism pae00620
Reductive carboxylate cycle (CO2 fixation) pae00720
Toluene degradation pae00623
Two-component system pae02020
Tyrosine metabolism pae00350

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-2940000000-e988056514d4ce4acc27	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-2960000000-a5ebaf2bbade922838ec	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-2950000000-32afa4d45e0e72b174b4	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-0002-0950000000-fe0f05c02c783d0b6f6b	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-006t-9530000000-0fc03f31f09dc8dbf4c6	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0002-3690000000-75089756992cdbe841e3	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-9100000000-57f13cd433a6fe4bf0b3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0229-9600000000-cd9e2979d0bb1e2a62f2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-03k9-8900000000-dc50dbf8a50872383d54	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0002-9100000000-b47e534bc82a6ed36e7c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
MS	Mass Spectrum (Electron Ionization)	splash10-0092-9000000000-003dd2d9303272b2ebea	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. Pubmed: 9693263
Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Dong, Changsheng; Ma, Xinming. Method for preparation of fumaric acid from the tail gas acid spray solution from oxidation of phthalic anhydride. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 5pp.

Material Safety Data Sheet (MSDS)

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Links

External Links:

Resource	Link
CHEBI ID	29806
HMDB ID	HMDB00134
Pubchem Compound ID	723
Kegg ID	C00122
ChemSpider ID	10197150
Wikipedia	Fumaric acid
BioCyc ID	FUM
EcoCyc ID	FUM
Ligand Expo	FUM

Enzymes

Protein Details

• Fumarate hydratase class II

General function:: Involved in fumarate hydratase activity
Specific function:: (S)-malate = fumarate + H(2)O
Gene Name:: fumC
Locus Tag:: PA0854
Molecular weight:: 49.1 kDa

Reactions

(S)-malate = fumarate + H(2)O.

Protein Details

• Succinate dehydrogenase iron-sulfur subunit

General function:: Involved in electron carrier activity
Specific function:: Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:: sdhB
Locus Tag:: PA1584
Molecular weight:: 26.2 kDa

Reactions

Succinate + acceptor = fumarate + reduced acceptor.

Protein Details

• Dihydroorotate dehydrogenase

General function:: Involved in catalytic activity
Specific function:: (S)-dihydroorotate + a quinone = orotate + a quinol
Gene Name:: pyrD
Locus Tag:: PA3050
Molecular weight:: 36.1 kDa

Reactions

(S)-dihydroorotate + a quinone = orotate + a quinol.

Protein Details

• Adenylosuccinate lyase

General function:: Involved in N6-(1,2-dicarboxyethyl)AMP AMP-lyase (fumarate-forming) activity
Specific function:: N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP
Gene Name:: purB
Locus Tag:: PA2629
Molecular weight:: 50.5 kDa

Reactions

N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP.
(S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate = fumarate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.

Protein Details

• Aspartate ammonia-lyase

General function:: Involved in aspartate ammonia-lyase activity
Specific function:: L-aspartate = fumarate + NH(3)
Gene Name:: aspA
Locus Tag:: PA5429
Molecular weight:: 51.1 kDa

Reactions

L-aspartate = fumarate + NH(3).

Protein Details

• Succinate dehydrogenase flavoprotein subunit

General function:: Involved in electron carrier activity
Specific function:: Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:: sdhA
Locus Tag:: PA1583
Molecular weight:: 63.5 kDa

Reactions

Succinate + acceptor = fumarate + reduced acceptor.

Protein Details

• Succinate dehydrogenase hydrophobic membrane anchor subunit

General function:: Involved in succinate dehydrogenase activity
Specific function:: Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:: sdhD
Locus Tag:: PA1582
Molecular weight:: 13.7 kDa

Protein Details

• L-aspartate oxidase

General function:: Involved in electron carrier activity
Specific function:: Catalyzes the oxidation of L-aspartate to iminoaspartate
Gene Name:: nadB
Locus Tag:: PA0761
Molecular weight:: 60 kDa

Reactions

L-aspartate + O(2) = iminosuccinate + H(2)O(2).

Protein Details

• Argininosuccinate lyase

General function:: Involved in argininosuccinate lyase activity
Specific function:: 2-(N(omega)-L-arginino)succinate = fumarate + L-arginine
Gene Name:: argH
Locus Tag:: PA5263
Molecular weight:: 51.6 kDa

Reactions

2-(N(omega)-L-arginino)succinate = fumarate + L-arginine.

Protein Details

• Succinate dehydrogenase cytochrome b556 subunit

General function:: Involved in succinate dehydrogenase activity
Specific function:: Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:: sdhC
Locus Tag:: PA1581
Molecular weight:: 13.7 kDa

Transporters

Protein Details

• Aerobic C4-dicarboxylate transport protein

General function:: Involved in symporter activity
Specific function:: Responsible for the aerobic transport of the dicarboxylates fumarate, L- and D-malate and to a lesser extent succinate, from the periplasm across the inner membrane
Gene Name:: dctA
Locus Tag:: PA1183
Molecular weight:: 46 kDa

Fumaric acid (PAMDB000073)

Structure for Fumaric acid (PAMDB000073)

Enzymes

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Transporters