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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-02-23 12:38:32 UTC
Update Date2017-10-23 19:03:53 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
Thumb
Synonyms
ValueSource
(+)-threo-Isocitric acidChEBI
ISOCITRIC ACIDChEBI
(+)-threo-IsocitrateGenerator
D-threo-IsocitrateGenerator
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 saltMeSH
Isocitric acid, (11)C-labeledMeSH
Isocitric acid, disodium saltMeSH
Isocitric acid, calcium saltMeSH
Isocitric acid, potassium saltMeSH
Isocitric acid, sodium saltMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic 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

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0952000000-aeb4dfa5b7b1d6eba92fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1920000000-b56fdff61401e2340d50View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ba-7900000000-96194d87d52b155cf1b9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-02vi-7029500000-2bb65fc897e48cc21750View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0udi-0900000000-24949c0952ed64de7083View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0w29-1900000000-c9bdca817d12cb4b091bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-014l-9300000000-66e9d659711c1d339f76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0900000000-a75a4b486df1552d6d93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gla-4900000000-d04fec4218cafd6195dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-8900000000-4e5fbbb415df9fbc8f31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ke-1900000000-c364bae4640e201c366dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v4j-4900000000-d00f263a75673b7981c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pk9-9200000000-156693398229f972d717View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB012771
    KNApSAcK IDC00001188
    Chemspider ID4477081
    KEGG Compound IDC00451
    BioCyc IDCPD-1941
    BiGG ID34579
    Wikipedia LinkICI
    METLIN ID3328
    PubChem Compound5318532
    PDB IDICT
    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