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Record Information
Version3.6
Creation Date2006-02-23 12:38:32 UTC
Update Date2016-02-11 01:05:03 UTC
HMDB IDHMDB01874
Secondary Accession NumbersNone
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-IsocitrateHMDB
(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
D-threo-IsocitrateHMDB
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
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 KeyInChIKey=ODBLHEXUDAPZAU-ZAFYKAAXSA-N
Chemical 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.
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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Mitochondria
  • Peroxisome
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.72 m3·mol-1ChemAxon
Polarizability15.54 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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, 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
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
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
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
NuGOwiki LinkHMDB01874
Metagene LinkHMDB01874
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