Record Information
Version1.0
Creation date2015-05-07 19:57:49 UTC
Update date2019-11-26 03:21:52 UTC
Primary IDFDB030735
Secondary Accession Numbers
  • FDB012586
Chemical Information
FooDB Namecitrate
DescriptionCitrate, also known as anhydrous citric acid or 2-hydroxy-1,2,3-propanetricarboxylic acid, belongs to tricarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly three carboxyl groups. Citrate is soluble (in water) and a weakly acidic compound (based on its pKa). Citrate can be found in a number of food items such as ucuhuba, loquat, bayberry, and longan, which makes citrate a potential biomarker for the consumption of these food products. Citrate can be found primarily in most biofluids, including saliva, sweat, feces, and blood, as well as throughout all human tissues. Citrate exists in all living species, ranging from bacteria to humans. In humans, citrate is involved in several metabolic pathways, some of which include the oncogenic action of succinate, the oncogenic action of fumarate, the oncogenic action of 2-hydroxyglutarate, and congenital lactic acidosis. Citrate is also involved in several metabolic disorders, some of which include 2-ketoglutarate dehydrogenase complex deficiency, pyruvate dehydrogenase deficiency (E2), fumarase deficiency, and glutaminolysis and cancer. Moreover, citrate is found to be associated with lung Cancer, tyrosinemia I, maple syrup urine disease, and propionic acidemia. A citrate is a derivative of citric acid; that is, the salts, esters, and the polyatomic anion found in solution. An example of the former, a salt is trisodium citrate; an ester is triethyl citrate. When part of a salt, the formula of the citrate ion is written as C6H5O73− or C3H5O(COO)33− .
CAS Number77-92-9
Structure
Thumb
Synonyms
SynonymSource
2-Hydroxy-1,2,3-propanetricarboxylic acidChEBI
2-Hydroxytricarballylic acidChEBI
3-Carboxy-3-hydroxypentane-1,5-dioic acidChEBI
CitronensaeureChEBI
e330ChEBI
H3CitChEBI
Anhydrous citric acidKegg
Citric acid anhydrousKegg
2-Hydroxy-1,2,3-propanetricarboxylateGenerator
2-HydroxytricarballylateGenerator
3-Carboxy-3-hydroxypentane-1,5-dioateGenerator
Anhydrous citrateGenerator
Citrate anhydrousGenerator
CitrateGenerator
AcilettenHMDB
beta-HydroxytricarballylateHMDB
beta-Hydroxytricarballylic acidHMDB
ChemfillHMDB
CitracleanHMDB
CitrettenHMDB
CitroHMDB
e 330HMDB
Hydrocerol aHMDB
Kyselina citronovaHMDB
Suby gHMDB
uro-TrainerHMDB
Acid monohydrate, citricMeSH, HMDB
Monohydrate, citric acidMeSH, HMDB
Citric acid, anhydrousMeSH, HMDB
Citric acid monohydrateMeSH, HMDB
Uralyt uMeSH, HMDB
(2S,3R,4R,5S)-Hexane-1,2,3,4,5,6-hexolChEBI
L-IditChEBI
Cordycepic acidHMDB
D-DulcitolHMDB
D-GalactitolHMDB
DulciteHMDB
DulcitolHMDB
DulcoseHMDB
GalactitolHMDB
GlucitolHMDB
Hexahydric alcoholHMDB
HexahydroxyhexaneHMDB
HexitolHMDB
Iso-sorbideHMDB
IsotolHMDB
KarionHMDB
L-GulitolHMDB
Manna sugarHMDB
MannitHMDB
ManniteHMDB
MeglumineHMDB
MitobronitolHMDB
SionitHMDB
SiononHMDB
SiosanHMDB
SorboHMDB
SorbolHMDB
IditolHMDB
[2-CYTIDYLATE-o'-phosphonyloxyl]-ethyl-trimethyl-ammoniumChEBI
CDP-ColinaChEBI
CiticolinaChEBI
CiticolinumChEBI
Citidin difosfato de colinaChEBI
CyticholineChEBI
CytidindiphosphocholinChEBI
Cytidine 5'-(choline diphosphate)ChEBI
Cytidine 5'-(cholinyl pyrophosphate)ChEBI
Cytidine 5'-diphosphocholineChEBI
Cytidine 5'-diphosphoric cholineChEBI
NicholinKEGG
[2-CYTIDYLic acid-o'-phosphonyloxyl]-ethyl-trimethyl-ammoniumGenerator
Cytidine 5'-(choline diphosphoric acid)Generator
Cytidine 5'-(cholinyl pyrophosphoric acid)Generator
AudesHMDB
CDP-CholineHMDB
CerebHMDB
Choline 5'-cytidine diphosphateHMDB
Choline cytidine diphosphateHMDB
CiticholineHMDB
CitidolineHMDB
CitifarHMDB
ColiteHMDB
CorenalinHMDB
CyscholinHMDB
Cytidine 5'-diphosphate cholineHMDB
Cytidine 5-diphosphate-trihydrogenHMDB
Cytidine choline diphosphateHMDB
Cytidine diphosphate cholineHMDB
Cytidine diphosphate choline esterHMDB
Cytidine diphosphocholineHMDB
Cytidine diphosphorylcholineHMDB
Cytidine-5' diphosphocholineHMDB
Cytidine-5'-pyrophosphate-hydroxycholineHMDB
CytidolineHMDB
DifosfocinHMDB
Emicholine FHMDB
EnsignHMDB
HaocolinHMDB
HornbestHMDB
NeucolisHMDB
NicolinHMDB
NiticolinHMDB
p-Hydroxide[2-(trimethylammonio)ethyl] esterHMDB
ReaginHMDB
RecofnanHMDB
RecognanHMDB
RexortHMDB
SintoclarHMDB
SomazinaHMDB
SomazineHMDB
SuncholinHMDB
CidifosHMDB
Diphosphate choline, cytidineHMDB
Choline, CDPHMDB
CDP CholineHMDB
5'-Diphosphocholine, cytidineHMDB
Cytidine 5' diphosphocholineHMDB
Choline, cytidine diphosphateHMDB
[NH3]ChEBI
AmmoniacChEBI
AmmoniakChEBI
AmoniacoChEBI
NH3ChEBI
R-717ChEBI
Spirit OF hartshornChEBI
Ammonia anhydrousHMDB
Ammonia inhalantHMDB
Ammonia solution strongHMDB
Ammonia waterHMDB
Liquid ammoniaHMDB
Am-folHMDB
Ammonia (CONC 20% or greater)HMDB
Ammonia gasHMDB
Ammonia solutionHMDB
Ammonia solution strong (NF)HMDB
Ammonia water (JP15)HMDB
Ammoniacum gummiHMDB
Ammoniak kconzentrierterHMDB
AmmoniakgasHMDB
Ammonium ionHMDB
Anhydrous ammoniaHMDB
Aromatic ammonia vaporoleHMDB
AzaneHMDB
NH(3)HMDB
Nitro-silHMDB
Primaeres aminHMDB
Sekundaeres aminHMDB
Tertiaeres aminHMDB
1-beta-D-RibofuranosylcytosineChEBI
1beta-D-RibofuranosylcytosineChEBI
4-AMINO-1-BETA-D-ribofuranosyl-2(1H)-pyrimidinoneChEBI
4-Amino-1-beta-D-ribofuranosylpyrimidin-2(1H)-oneChEBI
4-Amino-1beta-D-ribofuranosyl-2(1H)-pyrimidinoneChEBI
CydChEBI
CytidinChEBI
Cytosine ribosideChEBI
Cytosine-1beta-D-ribofuranosideChEBI
ZytidinChEBI
PosilentKEGG
1-b-D-RibofuranosylcytosineGenerator
1-Β-D-ribofuranosylcytosineGenerator
1b-D-RibofuranosylcytosineGenerator
1Β-D-ribofuranosylcytosineGenerator
4-AMINO-1-b-D-ribofuranosyl-2(1H)-pyrimidinoneGenerator
4-AMINO-1-β-D-ribofuranosyl-2(1H)-pyrimidinoneGenerator
4-Amino-1-b-D-ribofuranosylpyrimidin-2(1H)-oneGenerator
4-Amino-1-β-D-ribofuranosylpyrimidin-2(1H)-oneGenerator
4-Amino-1b-D-ribofuranosyl-2(1H)-pyrimidinoneGenerator
4-Amino-1β-D-ribofuranosyl-2(1H)-pyrimidinoneGenerator
Cytosine-1b-D-ribofuranosideGenerator
Cytosine-1β-D-ribofuranosideGenerator
1-(b-D-Ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazineHMDB
1-(b-delta-Ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazineHMDB
1-b-D-Ribosyl-cytosineHMDB
1-beta-D-Ribofuranosyl-cytosineHMDB
1-beta-delta-Ribofuranosyl-cytosineHMDB
1-beta-delta-RibofuranosylcytosineHMDB
1-beta-delta-Ribosyl-cytosineHMDB
1beta-delta-RibofuranosylcytosineHMDB
1beta-RibofuranosylcytosineHMDB
4-Amino-1-beta-delta-ribofuranosyl-2(1H)-pyrimidinoneHMDB
Cytosine-1b-delta-ribofuranosideHMDB
Cytosine-1beta-delta-ribofuranosideHMDB
Cytosine ribonucleosideHMDB
Ribonucleoside, cytosineHMDB
Riboside, cytosineHMDB
1-(beta-D-Ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazineHMDB
1-(Β-D-ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazineHMDB
(3R,4S,5R)-Tetrahydro-2H-pyran-2,3,4,5-tetrolChEBI
D-(+)-XyloseChEBI
D-XylopentoseChEBI
Wood sugarChEBI
Xylo-pfanKEGG
D-Xylo-pentoseHMDB
XylomedHMDB
XyloseHMDB
XylosideHMDB
XylopyranoseHMDB
D XyloseHMDB
D-XylopyranoseHMDB
Aldehydo-D-xyloseHMDB
CMPChEBI
Cytidine-5'-monophosphateChEBI
CytidylateChEBI
Cytidylic acidChEBI
pCChEBI
Cytidine-5'-monophosphoric acidGenerator
Cytidine monophosphoric acidGenerator
Cytidine 5'-monophosphateHMDB
Cytidine 5'-monophosphoric acidHMDB
5'-CMPHMDB
5-CytidylateHMDB
5-Cytidylic acidHMDB
Cytidine 5'-monophosphorateHMDB
Cytidine 5'-phosphateHMDB
Cytidine 5'-phosphorateHMDB
Cytidine 5'-phosphoric acidHMDB
Cytidine mono(dihydrogen phosphate)HMDB
Acid, cytidylicHMDB
monoPhosphate, cytidineHMDB
2' CMPHMDB
2'-CMPHMDB
3' CMPHMDB
Acids, cytidylicHMDB
Cytidylic acidsHMDB
3'-CMPHMDB
Predicted Properties
PropertyValueSource
Water Solubility106 g/LALOGPS
logP-1.3ALOGPS
logP-1.3ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.62 m³·mol⁻¹ChemAxon
Polarizability15.54 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H8O7
IUPAC name2-hydroxypropane-1,2,3-tricarboxylic acid
InChI IdentifierInChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
InChI KeyKRKNYBCHXYNGOX-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC(O)(CC(O)=O)C(O)=O
Average Molecular Weight192.1235
Monoisotopic Molecular Weight192.02700261
Classification
Description belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0002-0941000000-c310fda0e6a19bf6ae40JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0002-0941000000-f1dfda3e9abc7cfb6b2aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-006t-0952000000-ba3a1a80815f65afd05cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0951000000-48857e9baebe16d9fc8dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9531000000-b6fd7d038634694f0873JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-0593000000-b193bbba8c0cefdfe42aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0941000000-c310fda0e6a19bf6ae40JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0941000000-f1dfda3e9abc7cfb6b2aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-0952000000-ba3a1a80815f65afd05cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0951000000-48857e9baebe16d9fc8dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9531000000-b6fd7d038634694f0873JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-0593000000-b193bbba8c0cefdfe42aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0941000000-573230e47a4efb1e36a5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002k-6900000000-d1a61a52f6efdec3101aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-02ib-6019300000-6d5ebea10441c6d4149aJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-2900000000-956001b034bbc0b7da96JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000l-9100000000-55e34e2c1616942fd4f2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000f-9000000000-7b8be3e90a4daf85f04aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0911200000-af80d22f720facc4813aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-6f4fedbb19821898fb22JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-8eff68ab89f7ce2262beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0fsi-0019300000-b370c4c3dd656c8eb729JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0912100000-05e8ceb6dd97f7b9af98JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-e4b67745443c48a63bd6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-92536abec982e0a653a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0190000000-35772df08490f451d828JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-35856cc258368d13e1ffJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-3900000000-7170fdcb9749e6d6c2fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-01p9-9500000000-9a502981b0a9e1ea35adJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000i-9100000000-ed0c86b90e1f4966d025JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4r-9000000000-b8a975c2d639d8c91afbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-2900000000-30970a4250098e148658JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-a587dddf188152c5d7b0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-3900000000-7170fdcb9749e6d6c2fbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0037-0900000000-06dccacb53e75edc8b8dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02cu-5900000000-bfea9d561968b2670b13JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-7900000000-b1d32e4661447b09a017JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0005-1900000000-d074598ec2180f8b600cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k92-3900000000-9917f196271a495d3d1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9600000000-513b016c7c951d1e0b12JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-002f-9400000000-fb757b614278bb898b54JSpectraViewer | 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 NMR1H 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
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference