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Showing Compound Isocitric acid (FDB003281)

Record Information
Version1.0
Creation date2010-04-08 22:05:44 UTC
Update date2019-11-26 02:58:48 UTC
Primary IDFDB003281
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsocitric acid
DescriptionIsocitric acid, also known as isocitrate or i-cit, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Isocitric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Isocitric acid exists in all living species, ranging from bacteria to humans. Isocitric acid is found, on average, in the highest concentration within milk (cow). Isocitric acid has also been detected, but not quantified in, several different foods, such as apples, wild celeries, gooseberries, carrots, and soursops. This could make isocitric acid a potential biomarker for the consumption of these foods.
CAS Number320-77-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1-Hydroxypropane-1,2,3-tricarboxylic acidChEBI
1-Hydroxytricarballylic acidChEBI
1-Hydroxypropane-1,2,3-tricarboxylateGenerator
1-HydroxytricarballylateGenerator
IsocitrateGenerator
1-Hydroxy-1,2,3-propanetricarboxylateHMDB
1-Hydroxy-1,2,3-propanetricarboxylic acidHMDB
3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylateHMDB
3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acidHMDB
3-Carboxy-2,3-dideoxy-pentarateHMDB
3-Carboxy-2,3-dideoxy-pentaric acidHMDB
D-IsocitrateHMDB
I-citHMDB
Threo-D(S)-iso-citrateHMDB
Threo-DS-isocitrateHMDB
Isocitric acid, sodium saltHMDB
Isocitric acid, trisodium saltHMDB
Isocitric acid, disodium saltHMDB
Isocitric acid, (11)C-labeledHMDB
Isocitric acid, calcium saltHMDB
Isocitric acid, potassium saltHMDB
3-Carboxy-3,4-dideoxypentaric acid, 9CIdb_source
threo-D(S)-Iso-citrateHMDB
threo-Ds-isocitrateHMDB
Predicted Properties
PropertyValueSource
Water Solubility52.5 g/LALOGPS
logP-0.35ALOGPS
logP-1.4ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.72 m³·mol⁻¹ChemAxon
Polarizability15.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H8O7
IUPAC name1-hydroxypropane-1,2,3-tricarboxylic acid
InChI IdentifierInChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)
InChI KeyODBLHEXUDAPZAU-UHFFFAOYSA-N
Isomeric SMILESOC(C(CC(O)=O)C(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
  • Beta-hydroxy acid
  • Monosaccharide
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Secondary 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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 37.51%; H 4.20%; O 58.29%DFC
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSIsocitric acid, 4 TMS, GC-MS Spectrumsplash10-0002-1952000000-7c34751686a6bdb54cabSpectrum
GC-MSIsocitric acid, 4 TMS, GC-MS Spectrumsplash10-0002-0963000000-459b45ff9246b5f55914Spectrum
GC-MSIsocitric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0942000000-61204d02a28e43d21607Spectrum
GC-MSIsocitric acid, 4 TMS, GC-MS Spectrumsplash10-00di-9420000000-4e1a59fe735855d52ce2Spectrum
GC-MSIsocitric acid, 4 TMS, GC-MS Spectrumsplash10-00ea-3793000000-84858fa896697420275fSpectrum
GC-MSIsocitric acid, non-derivatized, GC-MS Spectrumsplash10-0002-1952000000-7c34751686a6bdb54cabSpectrum
GC-MSIsocitric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0963000000-459b45ff9246b5f55914Spectrum
GC-MSIsocitric acid, non-derivatized, GC-MS Spectrumsplash10-00di-9420000000-4e1a59fe735855d52ce2Spectrum
GC-MSIsocitric acid, non-derivatized, GC-MS Spectrumsplash10-00ea-3793000000-84858fa896697420275fSpectrum
Predicted GC-MSIsocitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ba-7900000000-96194d87d52b155cf1b9Spectrum
Predicted GC-MSIsocitric acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02vi-7029500000-2bb65fc897e48cc21750Spectrum
Predicted GC-MSIsocitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsocitric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsocitric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsocitric acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsocitric acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsocitric acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsocitric acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsocitric acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsocitric acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsocitric acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsocitric acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsocitric acid, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsocitric acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsocitric acid, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0901310000-883764bf7b686ca7fd172012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-66d03405eeb126c6ad9d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-cdad17a11f419421c7872012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0009000000-d3440c84a488b3e222122012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-3aa263561a7a49df7d3d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-1900000000-3636f87026e4206a16382012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-01w3-9600000000-ab1a2b9a29528a623d0b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0079-9000000000-3c33cefeb87f85efd5de2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-059m-9000000000-34775db8bbc0080186332012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-3aa263561a7a49df7d3d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-3636f87026e4206a16382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01w3-9600000000-ab1a2b9a29528a623d0b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0079-9000000000-3c33cefeb87f85efd5de2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-059m-9000000000-34775db8bbc0080186332017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-0900000000-66d03405eeb126c6ad9d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-cdad17a11f419421c7872017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-03k9-2900000000-e5336d859bf90bcd904c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03k9-2900000000-8ef1bf8afd67194ddf652021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-059f-9000000000-37227e36af9ba4db4a7e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-022i-9500000000-cb0234d7a355d54f17552021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03k9-3900000000-1b8cb16b24c65e87915b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03ki-9500000000-d264dd60719df8b72ef32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-bf62fc70edcee073c5172021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-02mi-9200000000-42ca838ca7f08cc3882e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-1900000000-8e1185b0504ea15477152012-07-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID1161
ChEMBL IDCHEMBL539669
KEGG Compound IDC00311
Pubchem Compound ID1198
Pubchem Substance IDNot Available
ChEBI ID30887
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00193
CRC / DFC (Dictionary of Food Compounds) IDCVK67-H:CVK67-H
EAFUS IDNot Available
Dr. Duke IDISOCITRIC-ACID
BIGG ID34579
KNApSAcK IDNot Available
HET ID1B0J
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDIsocitric_acid
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
Enzymes
NameGene NameUniProt ID
Aconitate hydratase, mitochondrialACO2Q99798
Pathways
NameSMPDB LinkKEGG Link
Citric Acid CycleSMP00057 map00020
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).