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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-02-23 12:38:32 UTC
Update Date2019-07-23 05:45:08 UTC
HMDB IDHMDB0001874
Secondary Accession Numbers
  • HMDB01874
Metabolite Identification
Common NameD-threo-Isocitric acid
DescriptionThreo-Isocitric acid is the substrate of isocitrate dehydrogenase (IDH), a NADP-dependent IDH that occurs in 2 structurally distinct forms: mitochondrial (OMIM 147650 ) and soluble (also called supernatant or cytoplasmic, OMIM 147700 ).
Structure
Data?1563860708
Synonyms
ValueSource
(+)-Threo-isocitric acidChEBI
ISOCITRIC ACIDChEBI
(+)-Threo-isocitrateGenerator
ISOCITRateGenerator
D-Threo-isocitrateGenerator
(1R,2S)-1-Hydroxypropane-1,2,3-tricarboxylateHMDB
(1R,2S)-1-Hydroxypropane-1,2,3-tricarboxylic acidHMDB
(2R,3S)-IsocitrateHMDB
3-Carboxy-2,3-dideoxy-L-threo-pentaric acidHMDB
D-(+)-Threo-isocitric acid(2R,3S)-isocitric acidHMDB
DS-Threo-isocitrateHMDB
DS-Threo-isocitric acidHMDB
ICIHMDB
ICTHMDB
Threo-D-(+)-isocitrateHMDB
Threo-D-(+)-isocitric acidHMDB
Threo-DS(+)-isocitrateHMDB
Threo-DS(+)-isocitric acidHMDB
Threo-isocitrateHMDB
Isocitric acid, trisodium saltHMDB
Isocitric acid, (11)C-labeledHMDB
Isocitric acid, disodium saltHMDB
Isocitric acid, calcium saltHMDB
Isocitric acid, potassium saltHMDB
Isocitric acid, sodium saltHMDB
Chemical FormulaC6H8O7
Average Molecular Weight192.1235
Monoisotopic Molecular Weight192.02700261
IUPAC Name(1R,2S)-1-hydroxypropane-1,2,3-tricarboxylic acid
Traditional Namethreo-DS(+)-isocitrate
CAS Registry Number6061-97-8
SMILES
O[C@H]([C@H](CC(O)=O)C(O)=O)C(O)=O
InChI Identifier
InChI=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)/t2-,4+/m0/s1
InChI KeyODBLHEXUDAPZAU-ZAFYKAAXSA-N
Chemical Taxonomy
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
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Polarizability15.54 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0952000000-aeb4dfa5b7b1d6eba92fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1920000000-b56fdff61401e2340d50JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0952000000-aeb4dfa5b7b1d6eba92fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1920000000-b56fdff61401e2340d50JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ba-7900000000-96194d87d52b155cf1b9JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-02vi-7029500000-2bb65fc897e48cc21750JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0udi-0900000000-24949c0952ed64de7083JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0w29-1900000000-c9bdca817d12cb4b091bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-014l-9300000000-66e9d659711c1d339f76JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0900000000-a75a4b486df1552d6d93JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gla-4900000000-d04fec4218cafd6195dfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-8900000000-4e5fbbb415df9fbc8f31JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ke-1900000000-c364bae4640e201c366dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v4j-4900000000-d00f263a75673b7981c7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pk9-9200000000-156693398229f972d717JSpectraViewer | MoNA
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
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB012771
    KNApSAcK IDC00001188
    Chemspider ID4477081
    KEGG Compound IDC00451
    BioCyc IDTHREO-DS-ISO-CITRATE
    BiGG ID34579
    Wikipedia LinkNot Available
    METLIN ID3328
    PubChem Compound5318532
    PDB IDNot Available
    ChEBI ID151
    References
    Synthesis ReferenceWong, Chi Huey; Whitesides, George M. Enzyme-catalyzed transhydrogenation between nicotinamide cofactors and its application in organic synthesis. Journal of the American Chemical Society (1982), 104(12), 3542-4.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General ReferencesNot Available