Record Information
Version 1.0
Update Date 1/22/2018 12:54:53 PM
Metabolite IDPAMDB000034
Identification
Name: Citric acid
Description:Citric acid is key intermediate in metabolism. It is a key component of the citric acid or TCA (Krebs) cycle. Citric acid is first consumed and then regenerated by this sequence of reactions to complete the cycle. Bacteria use the TCA cycle to generate energy, but since they lack mitochondria, the reaction sequence is performed in the cytosol with the proton gradient for ATP production being across the plasma membrane rather than the inner membrane of the mitochondria.
Structure
Thumb
Synonyms:
  • 2-Hydroxy-1,2,3-propanetricarboxylate
  • 2-Hydroxy-1,2,3-propanetricarboxylic acid
  • 3-Carboxy-3-hydroxypentane-1,5-dioate
  • 3-Carboxy-3-hydroxypentane-1,5-dioic acid
  • Aciletten
  • Anhydrous citrate
  • Anhydrous citric acid
  • b-Hydroxypyruvate
  • b-Hydroxypyruvic acid
  • b-Hydroxytricarballylate
  • b-Hydroxytricarballylic acid
  • Beta-Hydroxypyruvate
  • Beta-Hydroxypyruvic acid
  • Beta-Hydroxytricarballylate
  • Beta-Hydroxytricarballylic acid
  • Chemfill
  • Cit
  • Citr
  • Citraclean
  • Citrate
  • Citretten
  • Citric acid
  • Citro
  • E 330
  • Hydrocerol A
  • Kyselina citronova
  • Suby G
  • Uro-trainer
  • β-Hydroxypyruvate
  • β-Hydroxypyruvic acid
  • β-Hydroxytricarballylate
  • β-Hydroxytricarballylic acid
Chemical Formula: C6H8O7
Average Molecular Weight: 192.1235
Monoisotopic Molecular Weight: 192.02700261
InChI Key: KRKNYBCHXYNGOX-UHFFFAOYSA-N
InChI:InChI=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)
CAS number: 77-92-9
IUPAC Name:2-hydroxypropane-1,2,3-tricarboxylic acid
Traditional IUPAC Name: citric acid
SMILES:OC(=O)CC(O)(CC(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct Parent Tricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: 153 °C
Experimental Properties:
PropertyValueSource
Water Solubility:592.0 mg/ml [MERCK INDEX (1989)]PhysProp
LogP:-1.358PhysProp
Predicted Properties
PropertyValueSource
Water Solubility106.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.62 m3·mol-1ChemAxon
Polarizability15.54 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0002-0941000000-c310fda0e6a19bf6ae40View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0002-0941000000-f1dfda3e9abc7cfb6b2aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-006t-0952000000-ba3a1a80815f65afd05cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0951000000-48857e9baebe16d9fc8dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9531000000-b6fd7d038634694f0873View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-0593000000-b193bbba8c0cefdfe42aView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-2900000000-956001b034bbc0b7da96View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000l-9100000000-55e34e2c1616942fd4f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000f-9000000000-7b8be3e90a4daf85f04aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0911200000-af80d22f720facc4813aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-6f4fedbb19821898fb22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-8eff68ab89f7ce2262beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0fsi-0019300000-b370c4c3dd656c8eb729View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0912100000-05e8ceb6dd97f7b9af98View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-e4b67745443c48a63bd6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-92536abec982e0a653a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0190000000-35772df08490f451d828View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-35856cc258368d13e1ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-3900000000-7170fdcb9749e6d6c2fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-01p9-9500000000-9a502981b0a9e1ea35adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000i-9100000000-ed0c86b90e1f4966d025View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4r-9000000000-b8a975c2d639d8c91afbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-2900000000-30970a4250098e148658View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-002f-9400000000-fb757b614278bb898b54View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
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  • Tammen H, Schulte I, Hess R, Menzel C, Kellmann M, Mohring T, Schulz-Knappe P: Peptidomic analysis of human blood specimens: comparison between plasma specimens and serum by differential peptide display. Proteomics. 2005 Aug;5(13):3414-22. Pubmed: 16038021
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  • Wan KW, Malgesini B, Verpilio I, Ferruti P, Griffiths PC, Paul A, Hann AC, Duncan R: Poly(amidoamine) salt form: effect on pH-dependent membrane activity and polymer conformation in solution. Biomacromolecules. 2004 May-Jun;5(3):1102-9. Pubmed: 15132705
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Synthesis Reference: Evans, D. W. S. Hydrolysis of ethyl methylenecitrate [5,5-bis(ethoxycarbonylmethyl)-1,3-dioxolan-4-one] and an attempted synthesis of agaric acid. Journal of the Chemical Society (1959), 1313-14.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID16947
HMDB IDHMDB00094
Pubchem Compound ID19782904
Kegg IDC00158
ChemSpider ID305
WikipediaCitric acid
BioCyc IDCIT
EcoCyc IDCIT
Ligand ExpoFLC

Enzymes

General function:
Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:
Acetyl-CoA + H(2)O + oxaloacetate = citrate + CoA
Gene Name:
gltA
Locus Tag:
PA1580
Molecular weight:
47.7 kDa
Reactions
Acetyl-CoA + H(2)O + oxaloacetate = citrate + CoA.
General function:
Involved in metabolic process
Specific function:
May have an iron-responsive regulatory function
Gene Name:
acnA
Locus Tag:
PA1562
Molecular weight:
99.1 kDa
Reactions
Citrate = isocitrate.
General function:
Involved in metabolic process
Specific function:
Citrate = isocitrate
Gene Name:
acnB
Locus Tag:
PA1787
Molecular weight:
93.6 kDa
Reactions
Citrate = isocitrate.
(2S,3R)-3-hydroxybutane-1,2,3-tricarboxylate = (Z)-but-2-ene-1,2,3-tricarboxylate + H(2)O.

Transporters