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Fumaric acid (YMDB00101)

Identification
YMDB IDYMDB00101
NameFumaric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-Serine, also known as (S)-serine or L-ser, belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Serine is a very strong basic compound (based on its pKa). L-Serine exists in all living species, ranging from bacteria to humans. L-Serine is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (2E)-2-Butenedioic acid
  • (2E)-But-2-enedioate
  • (2E)-But-2-enedioic acid
  • (E)-2-Butenedioate
  • (E)-2-Butenedioic acid
  • (E)-2-butenedioic acid, ion(2-)
  • (E)-HO2CCH=CHCO2H
  • 1, 2-Ethenedicarboxylic acid, trans-
  • 1,2-Ethenedicarboxylic acid, trans-
  • 1,2-Ethylenedicarboxylic acid, (E)
  • 2-(E)-Butenedioate
  • 2-(E)-Butenedioic acid
  • 2-butenedioic acid
  • 2-Butenedioic acid (E)-
  • 2-Butenedioic acid, (E)-
  • Allomaleate
  • Allomaleic acid
  • Boletate
  • Boletic acid
  • Butenedioic acid, (E)-
  • Fumarate
  • Fumaric acid
  • Kyselina fumarova
  • Lichenate
  • Lichenic acid
  • sodium fumarate
  • trans-1,2-Ethylenedicarboxylate
  • trans-1,2-Ethylenedicarboxylic acid
  • trans-2-Butenedioate
  • trans-2-Butenedioic acid
  • trans-Butenedioate
  • trans-Butenedioic acid
  • Tumaric acid
  • (2S)-2-Amino-3-hydroxypropanoic acid
  • (S)-(-)-Serine
  • (S)-2-Amino-3-hydroxypropanoic acid
  • (S)-alpha-Amino-beta-hydroxypropionic acid
  • (S)-Serine
  • beta-Hydroxy-L-alanine
  • beta-Hydroxyalanine
  • L-(-)-Serine
  • L-2-Amino-3-hydroxypropionic acid
  • L-3-Hydroxy-2-aminopropionic acid
  • L-3-Hydroxy-alanine
  • L-Ser
  • L-Serin
  • S
  • Ser
  • SERINE
  • (2S)-2-Amino-3-hydroxypropanoate
  • (S)-2-Amino-3-hydroxypropanoate
  • (S)-a-Amino-b-hydroxypropionate
  • (S)-a-Amino-b-hydroxypropionic acid
  • (S)-alpha-Amino-beta-hydroxypropionate
  • (S)-Α-amino-β-hydroxypropionate
  • (S)-Α-amino-β-hydroxypropionic acid
  • b-Hydroxy-L-alanine
  • Β-hydroxy-L-alanine
  • b-Hydroxyalanine
  • Β-hydroxyalanine
  • L-2-Amino-3-hydroxypropionate
  • L-3-Hydroxy-2-aminopropionate
  • (-)-Serine
  • (S)-2-Amino-3-hydroxy-propanoate
  • (S)-2-Amino-3-hydroxy-propanoic acid
  • (S)-b-Amino-3-hydroxypropionate
  • (S)-b-Amino-3-hydroxypropionic acid
  • (S)-beta-Amino-3-hydroxypropionate
  • (S)-beta-Amino-3-hydroxypropionic acid
  • 2-Amino-3-hydroxypropanoate
  • 2-Amino-3-hydroxypropanoic acid
  • 3-Hydroxy-L-alanine
  • L Serine
  • e297
  • Fumarsaeure
  • trans-But-2-enedioic acid
  • (2E)-2-Butenedioate
  • trans-But-2-enedioate
  • FC 33
  • Furamag
  • Ammonium fumarate
  • Magnesium fumarate
  • Mafusol
  • 1-Hydroxyethane
  • [CH2Me(OH)]
  • [OEtH]
  • Alcohol
  • Alcohol etilico
  • Alcool ethylique
  • Alkohol
  • Aethanol
  • Aethylalkohol
  • C2H5OH
  • Dehydrated ethanol
  • Etanol
  • Ethyl alcohol
  • EtOH
  • Hydroxyethane
  • Methylcarbinol
  • Spiritus vini
  • Anhydrous ethanol
  • Absolute alcohol
  • Absolute ethanol
  • Absolute ethyl alcohol
  • Alcare hand degermer
  • Alcohols
  • Alcool etilico
  • Algrain
  • Alkoholu etylowego
  • Anhydrol
  • Anhydrous alcohol
  • Cologne spirit
  • Cologne spirits
  • Dehydrated alcohol
  • Denatured alcohol
  • Denatured ethanol
  • Desinfektol el
  • Diluted alcohol
  • Distilled spirits
  • Ethanol 200 proof
  • Ethanol solution
  • Ethicap
  • Ethyl alc
  • Ethyl alcohol anhydrous
  • Ethyl alcohol in alcoholic beverages
  • Ethyl alcohol usp
  • Ethyl hydrate
  • Ethyl hydroxide
  • Fermentation alcohol
  • Grain alcohol
  • Hinetoless
  • Infinity pure
  • Jaysol
  • Jaysol S
  • Lux
  • Molasses alcohol
  • Potato alcohol
  • Punctilious ethyl alcohol
  • Pyro
  • Silent spirit
  • Spirit
  • Spirits OF wine
  • Spirt
  • Synasol
  • Tecsol
  • Tecsol C
  • Thanol
  • Undenatured ethanol
  • Alcohol, absolute
  • Alcohol, ethyl
  • Alcohol, grain
  • Bilineurine
  • CHOLINE ion
  • N,N,N-Trimethylethanol-ammonium
  • N-Trimethylethanolamine
  • Trimethylethanolamine
  • Choline cation
  • (2-Hydroxyethyl)trimethyl ammonium
  • (2-Hydroxyethyl)trimethylammonium
  • (beta-Hydroxyethyl)trimethylammonium
  • 2-Hydroxy-N,N,N-trimethyl-ethanaminium
  • 2-Hydroxy-N,N,N-trimethylethanaminium
  • Biocolina
  • Biocoline
  • Cholinum
  • Hepacholine
  • Hormocline
  • Lipotril
  • N,N,N-Trimethylethanolammonium
  • Neocolina
  • Paresan
  • Choline O-sulfate
  • Citrate, choline
  • Fagine
  • Hydroxide, choline
  • Vidine
  • Bursine
  • Chloride, choline
  • Choline chloride
  • Choline citrate
  • Bitartrate, choline
  • Choline bitartrate
  • Choline hydroxide
  • Choline O sulfate
  • O-Sulfate, choline
  • D-GLC
  • D-GLCP
  • Dextrose
  • GLC-OH
  • Glucose
  • Grape sugar
  • D-Glucopyranose
  • Purified glucose
  • Roferose ST
  • (+)-Glucose
  • Anhydrous dextrose
  • Cerelose
  • Cerelose 2001
  • Clearsweet 95
  • Clintose L
  • Corn sugar
  • CPC Hydrate
  • D(+)-Glucose
  • Dextropur
  • Dextrosol
  • Glucodin
  • Glucolin
  • Goldsugar
  • Meritose
  • Staleydex 111
  • Staleydex 95m
  • Tabfine 097(HS)
  • Vadex
  • D Glucose
  • Glucose, (DL)-isomer
  • Glucose, (L)-isomer
  • Glucose, (beta-D)-isomer
  • Glucose monohydrate
  • Glucose, (alpha-D)-isomer
  • L Glucose
  • L-Glucose
  • Dextrose, anhydrous
  • Monohydrate, glucose
  • 3-Hydroxy-1,3,5(10)-estratrien-17-one
  • Follicular hormone
  • Folliculin
  • Oestrone
  • (+)-Estrone
  • 1,3,5(10)-Estratrien-3-ol-17-one
  • 3-Hydroxy-17-keto-estra-1,3,5-triene
  • 3-Hydroxyestra-1,3,5(10)-trien-17-one
  • 3-Hydroxyestra-1,3,5(10)-triene-17-one
  • 3-Hydroxyoestra-1,3,5(10)-trien-17-one
  • D1,3,5(10)-Estratrien-3-ol-17-one
  • Estrone, (+-)-isomer
  • Hyrex brand OF estrone
  • Estrone, (9 beta)-isomer
  • Estrovarin
  • Kestrone
  • Wehgen
  • Estrone, (8 alpha)-isomer
  • Hauck brand OF estrone
  • Unigen
  • Vortech brand OF estrone
  • alpha,beta-Hydroxypropionic acid
  • D-GroA
  • R-Glyceric acid
  • Glycerate
  • (R)-Glycerate
  • a,b-Hydroxypropionate
  • a,b-Hydroxypropionic acid
  • alpha,beta-Hydroxypropionate
  • Α,β-hydroxypropionate
  • Α,β-hydroxypropionic acid
  • R-Glycerate
  • (R)-Glyceric acid
  • D-Glycerate
  • D-Glyceric acid
  • (2R)-2,3-Dihydroxypropanoic acid
  • (R)-2,3-Dihydroxypropanoic acid
  • D-2,3-Dihydroxypropanoic acid
  • (S)-2-Aminopentanedioic acid
  • (S)-Glutamic acid
  • Acide glutamique
  • Acido glutamico
  • Acidum glutamicum
  • E
  • Glu
  • Glutamate
  • GLUTAMIC ACID
  • L-Glu
  • L-Glutaminic acid
  • L-Glutaminsaeure
  • (S)-2-Aminopentanedioate
  • (S)-Glutamate
  • L-Glutaminate
  • L-Glutamate
  • (2S)-2-Aminopentanedioate
  • (2S)-2-Aminopentanedioic acid
  • (S)-(+)-Glutamate
  • (S)-(+)-Glutamic acid
  • 1-Amino-propane-1,3-dicarboxylate
  • 1-Amino-propane-1,3-dicarboxylic acid
  • 1-Aminopropane-1,3-dicarboxylate
  • 1-Aminopropane-1,3-dicarboxylic acid
  • 2-Aminoglutarate
  • 2-Aminoglutaric acid
  • 2-Aminopentanedioate
  • 2-Aminopentanedioic acid
  • a-Aminoglutarate
  • a-Aminoglutaric acid
  • a-Glutamate
  • a-Glutamic acid
  • Aciglut
  • alpha-Aminoglutarate
  • alpha-Aminoglutaric acid
  • alpha-Glutamate
  • alpha-Glutamic acid
  • Aminoglutarate
  • Aminoglutaric acid
  • Glt
  • Glusate
  • Glut
  • Glutacid
  • Glutamicol
  • Glutamidex
  • Glutaminate
  • Glutaminic acid
  • Glutaminol
  • Glutaton
  • L-(+)-Glutamate
  • L-(+)-Glutamic acid
  • L-a-Aminoglutarate
  • L-a-Aminoglutaric acid
  • L-alpha-Aminoglutarate
  • L-alpha-Aminoglutaric acid
  • D Glutamate
  • Glutamate, potassium
  • Glutamic acid, (D)-isomer
  • L Glutamic acid
  • D-Glutamate
  • L Glutamate
  • Aluminum L glutamate
  • Aluminum L-glutamate
  • L-Glutamate, aluminum
  • Potassium glutamate
  • 1-beta-D-Galactopyranosyl-4-alpha-D-glucopyranose
  • 4-O-beta-D-Galactopyranosyl-alpha-D-glucopyranose
  • Anhydrous lactose
  • beta-D-Galp-(1->4)-alpha-D-GLCP
  • Lactose
  • Milk sugar
  • 1-b-D-Galactopyranosyl-4-a-D-glucopyranose
  • 1-Β-D-galactopyranosyl-4-α-D-glucopyranose
  • 4-O-b-D-Galactopyranosyl-a-D-glucopyranose
  • 4-O-Β-D-galactopyranosyl-α-D-glucopyranose
  • b-D-Galp-(1->4)-a-D-GLCP
  • Β-D-galp-(1->4)-α-D-GLCP
  • a-Lactose
  • Α-lactose
  • (+)-Lactose
  • 1-beta-delta-Galactopyranosyl-4-alpha-delta-glucopyranose
  • 4-O-Hexopyranosylhexose
  • Aletobiose
  • Dilactose
  • Fast-flo lactose
  • Flowlac 100
  • Galactinum
  • GLC-(4-1)Gal
  • Granulac 140m
  • Lactin
  • Lactin (carbohydrate)
  • Lactobiose
  • Lactohale 300
  • Lactose anhydride
  • Lactose fast-flo
  • Osmolactan
  • Pharmatosa DCL 21
  • Pharmatose 21
  • Pharmatose 325m
  • Pharmatose DCL 15
  • Prismalac
  • Respitose ML 003
  • Respitose SV 003
  • Saccharum lactin
  • Sachelac
  • Sorbalac 400
  • Sorbolac 400
  • Spherolac
  • Super-tab
  • Tablettose
  • Tablettose 70
  • Tablettose 80
  • Zeparox ep
  • Lactose, anhydrous
  • (-)-3-(3,4-Dihydroxyphenyl)-L-alanine
  • (-)-Dopa
  • 3,4-Dihydroxy-L-phenylalanine
  • 3,4-DIHYDROXYPHENYLALANINE
  • 3-Hydroxy-L-tyrosine
  • beta-(3,4-Dihydroxyphenyl)-L-alanine
  • beta-(3,4-Dihydroxyphenyl)alanine
  • Dihydroxy-L-phenylalanine
  • Dopar
  • L-beta-(3,4-Dihydroxyphenyl)alanine
  • Levodopa
  • Levodopum
  • b-(3,4-Dihydroxyphenyl)-L-alanine
  • Β-(3,4-dihydroxyphenyl)-L-alanine
  • b-(3,4-Dihydroxyphenyl)alanine
  • Β-(3,4-dihydroxyphenyl)alanine
  • L-b-(3,4-Dihydroxyphenyl)alanine
  • L-Β-(3,4-dihydroxyphenyl)alanine
  • (2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoate
  • (2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid
  • 3,4-Dihydroxyphenyl-L-alanine
  • 3-(3,4-Dihydroxyphenyl)-L-alanine
  • b-(3,4-Dihydroxyphenyl)-a-L-alanine
  • Bendopa
  • beta-(3,4-Dihydroxyphenyl)-alpha-L-alanine
  • Cidandopa
  • Dihydroxyphenylalanine
  • Dopaflex
  • Dopaidan
  • Dopal
  • Dopalina
  • Doparkine
  • Doparl
  • Dopasol
  • Dopaston
  • Dopastone
  • Dopastral
  • Dopicar
  • Doprin
  • Eldopal
  • Eldopar
  • Eldopatec
  • Eurodopa
  • Helfo-dopa
  • Insulamina
  • L-(-)-Dopa
  • L-3-(3,4-Dihydroxyphenyl)-alanine
  • L-4-5-Dihydroxyphenylalanine
  • L-b-(3,4-Dihydroxyphenyl)-a-alanine
  • L-beta-(3,4-Dihydroxyphenyl)-alpha-alanine
  • L-Dihydroxyphenylalanine
  • Laradopa
  • Larodopa
  • Ledopa
  • Levedopa
  • Levopa
  • Maipedopa
  • Parda
  • Pardopa
  • Prodopa
  • Syndopa
  • Veldopa
  • Weldopa
  • 3 Hydroxy L tyrosine
  • Roche brand OF levodopa
  • L 3,4 Dihydroxyphenylalanine
  • L-3,4-Dihydroxyphenylalanine
  • Medphano brand OF levodopa
  • L Dopa
  • Roberts brand OF levodopa
  • (S)-4-(2-Amino-2-carboxyethyl)imidazole
  • (S)-alpha-Amino-1H-imidazole-4-propanoic acid
  • (S)-alpha-Amino-1H-imidazole-4-propionic acid
  • H
  • His
  • HISTIDINE
  • L-(-)-Histidine
  • L-Histidin
  • (S)-a-Amino-1H-imidazole-4-propanoate
  • (S)-a-Amino-1H-imidazole-4-propanoic acid
  • (S)-alpha-Amino-1H-imidazole-4-propanoate
  • (S)-Α-amino-1H-imidazole-4-propanoate
  • (S)-Α-amino-1H-imidazole-4-propanoic acid
  • (S)-a-Amino-1H-imidazole-4-propionate
  • (S)-a-Amino-1H-imidazole-4-propionic acid
  • (S)-alpha-Amino-1H-imidazole-4-propionate
  • (S)-Α-amino-1H-imidazole-4-propionate
  • (S)-Α-amino-1H-imidazole-4-propionic acid
  • (S)-1H-Imidazole-4-alanine
  • (S)-2-Amino-3-(4-imidazolyl)propionsaeure
  • (S)-Histidine
  • (S)1H-Imidazole-4-alanine
  • 3-(1H-Imidazol-4-yl)-L-alanine
  • Amino-1H-imidazole-4-propanoate
  • Amino-1H-imidazole-4-propanoic acid
  • Amino-4-imidazoleproprionate
  • Amino-4-imidazoleproprionic acid
  • Glyoxaline-5-alanine
  • Histidine, L isomer
  • Histidine, L-isomer
  • L-Isomer histidine
CAS number110-17-8
WeightAverage: 116.0722
Monoisotopic: 116.010958616
InChI KeyVZCYOOQTPOCHFL-OWOJBTEDSA-N
InChIInChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
IUPAC Name(2E)-but-2-enedioic acid
Traditional IUPAC Namefumaric acid
Chemical FormulaC4H4O4
SMILESOC(=O)\C=C\C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentSerine and derivatives
Alternative Parents
Substituents
  • Serine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point549 °C
Experimental Properties
PropertyValueReference
Water Solubility7 mg/mL at 25 oC [US EPA (1981)]PhysProp
LogP0.46 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
logP-0.041ChemAxon
pKa (Strongest Acidic)3.55ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.61 m³·mol⁻¹ChemAxon
Polarizability9.35 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondrion
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB012739
SourFDB012739
SMPDB Pathways
Citric Acid CyclePW000952 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid Cycle 1434561204PW000970 ThumbThumb?image type=greyscaleThumb?image type=simple
Oxidative phosphorylationPW002461 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylalanine metabolismPW002437 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA CyclePW002377 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Oxidative phosphorylationec00190 Map00190
Phenylalanine metabolismec00360 Map00360
Tyrosine metabolismec00350 Map00350
SMPDB Reactions
(S)-Malic acid ↔ Fumaric acid + water
Succinic acid + Coenzyme Q10 + FAD ↔ Fumaric acid + QH2 + FADH2
L-Aspartic acid → Fumaric acid + Ammonia
Adenylsuccinic acid → Fumaric acid + Adenosine monophosphate
Argininosuccinic acid → Fumaric acid + L-Arginine
KEGG Reactions
SAICAR ↔ 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + Fumaric acid
Adenylsuccinic acid ↔ Adenosine monophosphate + Fumaric acid
Argininosuccinic acid ↔ L-Arginine + Fumaric acid
Fumaric acid + water ↔ (S)-malate(2-)
Fumaric acid + L-Dihydroorotic acid → Orotic acid + Succinic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-2940000000-e988056514d4ce4acc27JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-2960000000-a5ebaf2bbade922838ecJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-2950000000-32afa4d45e0e72b174b4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0950000000-fe0f05c02c783d0b6f6bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-006t-9530000000-0fc03f31f09dc8dbf4c6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0002-3690000000-75089756992cdbe841e3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9100000000-2cf649749b42cc0c610cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-0890000000-b1c35cd55deb81254f66JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2940000000-e988056514d4ce4acc27JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2960000000-a5ebaf2bbade922838ecJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2950000000-32afa4d45e0e72b174b4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0950000000-fe0f05c02c783d0b6f6bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-9530000000-0fc03f31f09dc8dbf4c6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0002-3690000000-75089756992cdbe841e3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0940000000-177fdb9168659029ffaaJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ba-9200000000-52f88e04bac0ff8cdf17JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-8920000000-06da44f348d0fe0358b3JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9100000000-57f13cd433a6fe4bf0b3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0229-9600000000-cd9e2979d0bb1e2a62f2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-03k9-8900000000-dc50dbf8a50872383d54JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0002-9100000000-b47e534bc82a6ed36e7cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9800000000-dbf34563376daeb2901fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-9200000000-113bf08cdc77707ed3adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9000000000-f32d7ec65e8649bc2b0aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-408d53a9fff7acc8ca23JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-6900000000-f149e9e5a34e27dd4d4eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fxt-9000000000-cae5f71dc27daaf17d9eJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0092-9000000000-003dd2d9303272b2ebeaJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Peleg, Y., Rokem, J. S., Goldberg, I., Pines, O. (1990). "Inducible overexpression of the FUM1 gene in Saccharomyces cerevisiae: localization of fumarase and efficient fumaric acid bioconversion to L-malic acid." Appl Environ Microbiol 56:2777-2783.2275532
  • Palmieri, L., Lasorsa, F. M., De Palma, A., Palmieri, F., Runswick, M. J., Walker, J. E. (1997). "Identification of the yeast ACR1 gene product as a succinate-fumarate transporter essential for growth on ethanol or acetate." FEBS Lett 417:114-118.9395087
  • Przybyla-Zawislak, B., Gadde, D. M., Ducharme, K., McCammon, M. T. (1999). "Genetic and biochemical interactions involving tricarboxylic acid cycle (TCA) function using a collection of mutants defective in all TCA cycle genes." Genetics 152:153-166.10224250
  • Nagy, M., Lacroute, F., Thomas, D. (1992). "Divergent evolution of pyrimidine biosynthesis between anaerobic and aerobic yeasts." Proc Natl Acad Sci U S A 89:8966-8970.1409592
  • Muratsubaki, H., Enomoto, K. (1998). "One of the fumarate reductase isoenzymes from Saccharomyces cerevisiae is encoded by the OSM1 gene." Arch Biochem Biophys 352:175-181.9587404
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
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.
External Links:
ResourceLink
CHEBI ID18012
HMDB IDHMDB00134
Pubchem Compound ID723
Kegg IDC00122
ChemSpider ID24532688
FOODB IDFDB012739
WikipediaFumaric_acid
BioCyc IDFUM

Enzymes

Protein Details
1. Adenylosuccinate lyase
General function:
Involved in catalytic activity
Specific function:
N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP
Gene Name:
ADE13
Uniprot ID:
Q05911
Molecular weight:
54509.89844
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
2. Argininosuccinate lyase
General function:
Involved in argininosuccinate lyase activity
Specific function:
2-(N(omega)-L-arginino)succinate = fumarate + L-arginine
Gene Name:
ARG4
Uniprot ID:
P04076
Molecular weight:
51988.69922
Reactions
2-(N(omega)-L-arginino)succinate → fumarate + L-arginine.
Protein Details
3. Fumarate reductase
General function:
Involved in electron carrier activity
Specific function:
Could be a fumarate reductase
Gene Name:
Not Available
Uniprot ID:
P32614
Molecular weight:
50843.69922
Reactions
Succinate + NAD(+) → fumarate + NADH.
Protein Details
4. Osmotic growth protein 1
General function:
Involved in electron carrier activity
Specific function:
Could be a fumarate reductase
Gene Name:
OSM1
Uniprot ID:
P21375
Molecular weight:
55064.80078
Reactions
Protein Details
5. Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial
General function:
Involved in electron carrier activity
Specific function:
Catalytic subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). SDH1 and SDH2 form the catalytic dimer. Electrons flow from succinate to the FAD bound to SDH1, and sequentially through the iron-sulfur clusters bound to SDH2 and enter the membrane dimer formed by SDH3 and SDH4
Gene Name:
SDH1
Uniprot ID:
Q00711
Molecular weight:
70228.79688
Reactions
Succinate + ubiquinone → fumarate + ubiquinol.
Protein Details
6. Succinate dehydrogenase [ubiquinone] flavoprotein subunit 2, mitochondrial
General function:
Involved in electron carrier activity
Specific function:
Probable minor catalytic subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Probably forms a catalytic dimer with SDH2. Electrons flow from succinate to the FAD bound to the catalytic subunit, and sequentially through the iron-sulfur clusters bound to SDH2 and enter the membrane dimer formed by SDH3 and SDH4
Gene Name:
Not Available
Uniprot ID:
P47052
Molecular weight:
69382.0
Reactions
Succinate + ubiquinone → fumarate + ubiquinol.
Protein Details
7. Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial
General function:
Involved in 2 iron, 2 sulfur cluster binding
Specific function:
Subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). SDH1 and SDH2 form the catalytic dimer. Electrons flow from succinate to the FAD bound to SDH1, and sequentially through the iron-sulfur clusters bound to SDH2 and enter the membrane dimer formed by SDH3 and SDH4
Gene Name:
SDH2
Uniprot ID:
P21801
Molecular weight:
30230.90039
Reactions
Succinate + ubiquinone → fumarate + ubiquinol.
Protein Details
8. Fumarate hydratase, mitochondrial
General function:
Involved in fumarate hydratase activity
Specific function:
(S)-malate = fumarate + H(2)O
Gene Name:
FUM1
Uniprot ID:
P08417
Molecular weight:
53151.5
Reactions
(S)-malate → fumarate + H(2)O.
Protein Details
9. Dihydroorotate dehydrogenase
General function:
Involved in catalytic activity
Specific function:
In the de novo pyrimidine biosynthesic pathway, catalyzes the stereospecific oxidation of (S)-dihydroorotate to orotate and the reduction of fumarate to succinate. Does not use oxaloacetate and NAD or NADP as electron acceptors
Gene Name:
URA1
Uniprot ID:
P28272
Molecular weight:
34800.60156
Reactions
(S)-dihydroorotate + O(2) → orotate + H(2)O(2).
(S)-dihydroorotate + a quinone → orotate + a quinol

Transporters

Protein Details
1. Succinate/fumarate mitochondrial transporter
General function:
Involved in binding
Specific function:
Transports cytoplasmic succinate, derived from isocitrate by the action of isocitrate lyase in the cytosol, into the mitochondrial matrix in exchange for fumarate
Gene Name:
SFC1
Uniprot ID:
P33303
Molecular weight:
35340.10156