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Record Information
Version3.6
Creation Date2009-02-24 15:43:08 UTC
Update Date2013-05-29 19:46:54 UTC
HMDB IDHMDB11717
Secondary Accession NumbersNone
Metabolite Identification
Common NameNonate
DescriptionNonic acid or the anion, nonate, is a derivative of succinic acid, which is a dicarboxylic acid. The anion, succinate, is a component of the citric acid cycle capable of donating electrons to the electron transfer chain. Succinate dehydrogenase (SDH) plays an important role in the mitochondria, being both part of the respiratory chain and the Krebs cycle. SDH with a covalently attached FAD prosthetic group, binds enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the whole Krebs cycle. The succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e. g. malate. (PMID 16143825 ) Mutations in the four genes encoding the subunits of the mitochondrial respiratory chain succinate dehydrogenase are associated with a wide spectrum of clinical presentations (i.e.: Huntington's disease. (PMID 11803021 ).
Structure
Thumb
Synonyms
  1. (2R) - 2- pentylbutanedioate
  2. (2R) - 2- pentylbutanedioic acid
  3. (2R) - 2- pentylsuccinic acid
  4. 2- Pentylsuccinic acid
  5. Nonic acid
  6. Nonic acid ethanedisulfonate
Chemical FormulaC9H16O4
Average Molecular Weight188.2209
Monoisotopic Molecular Weight188.104859
IUPAC Name(2S)-2-pentylbutanedioic acid
Traditional Name(2S)-2-pentylbutanedioic acid
CAS Registry NumberNot Available
SMILES
CCCCC[C@@H](CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C9H16O4/c1-2-3-4-5-7(9(12)13)6-8(10)11/h7H,2-6H2,1H3,(H,10,11)(H,12,13)/t7-/m0/s1
InChI KeyFNZSVEHJZREFPF-ZETCQYMHSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
Sub ClassDicarboxylic Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Branched Fatty Acids
Substituents
  • Carboxylic Acid
Direct ParentDicarboxylic Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility3.86 g/LALOGPS
logP1.27ALOGPS
logP1.92ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.47ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity46.52ChemAxon
Polarizability19.97ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate Cancer
details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028402
KNApSAcK IDNot Available
Chemspider ID13183696
KEGG Compound IDNot Available
BioCyc ID2-DH-3-DO-D-ARABINONATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11717
Metagene LinkHMDB11717
METLIN IDNot Available
PubChem Compound16058309
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Briere JJ, Favier J, El Ghouzzi V, Djouadi F, Benit P, Gimenez AP, Rustin P: Succinate dehydrogenase deficiency in human. Cell Mol Life Sci. 2005 Oct;62(19-20):2317-24. Pubmed: 16143825
  2. Rustin P, Rotig A: Inborn errors of complex II--unusual human mitochondrial diseases. Biochim Biophys Acta. 2002 Jan 17;1553(1-2):117-22. Pubmed: 11803021