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(1R,2S)-Isocitric acid (FDB012771)

Record Information
Version1.0
Creation date2010-04-08 22:10:21 UTC
Update date2020-09-17 15:39:01 UTC
Primary IDFDB012771
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(1R,2S)-Isocitric acid
DescriptionD-threo-Isocitric acid, also known as isocitrate or isocitrIC ACID, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. D-threo-Isocitric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). D-threo-Isocitric acid exists in all living species, ranging from bacteria to humans. Outside of the human body, D-threo-Isocitric acid has been detected, but not quantified in, several different foods, such as rubus (blackberry, raspberry), fruits, citrus, green beans, and common beans. This could make D-threo-isocitric acid a potential biomarker for the consumption of these foods. The D-threo-diastereomer of isocitric acid.
CAS Number6061-97-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H8O7
IUPAC name(1R,2S)-1-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)/t2-,4+/m0/s1
InChI KeyODBLHEXUDAPZAU-ZAFYKAAXSA-N
Isomeric SMILESO[C@H]([C@H](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
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 37.51%; H 4.20%; O 58.29%DFC
Melting PointMp 105°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +30.6 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(1R,2S)-Isocitric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0952000000-aeb4dfa5b7b1d6eba92fSpectrum
GC-MS(1R,2S)-Isocitric acid, non-derivatized, GC-MS Spectrumsplash10-0002-1920000000-b56fdff61401e2340d50Spectrum
GC-MS(1R,2S)-Isocitric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0952000000-aeb4dfa5b7b1d6eba92fSpectrum
GC-MS(1R,2S)-Isocitric acid, non-derivatized, GC-MS Spectrumsplash10-0002-1920000000-b56fdff61401e2340d50Spectrum
Predicted GC-MS(1R,2S)-Isocitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ba-7900000000-96194d87d52b155cf1b9Spectrum
Predicted GC-MS(1R,2S)-Isocitric acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02vi-7029500000-2bb65fc897e48cc21750Spectrum
Predicted GC-MS(1R,2S)-Isocitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(1R,2S)-Isocitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0udi-0900000000-24949c0952ed64de70832012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0w29-1900000000-c9bdca817d12cb4b091b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-014l-9300000000-66e9d659711c1d339f762012-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0900000000-a75a4b486df1552d6d932016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gla-4900000000-d04fec4218cafd6195df2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-8900000000-4e5fbbb415df9fbc8f312016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ke-1900000000-c364bae4640e201c366d2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v4j-4900000000-d00f263a75673b7981c72016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pk9-9200000000-156693398229f972d7172016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0900000000-4e17b6a1e2aad4076c032021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-1900000000-15b65374b78661650dfa2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9100000000-f126784f2170bc8d341a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-1900000000-33d42ec37993dc6475132021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-4900000000-7b0e1ae548050695b9d62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufu-9600000000-3667240157dc2ec377ae2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, 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, 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
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID4477081
ChEMBL IDCHEMBL390356
KEGG Compound IDC00451
Pubchem Compound ID5318532
Pubchem Substance IDNot Available
ChEBI ID151
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01874
CRC / DFC (Dictionary of Food Compounds) IDCVK67-H:HKS03-D
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34579
KNApSAcK IDC00001188
HET IDICT
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.