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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:48:10 UTC
Update Date2019-07-23 06:26:45 UTC
HMDB IDHMDB0038483
Secondary Accession Numbers
  • HMDB38483
Metabolite Identification
Common NameAuxin a
DescriptionAuxin a, also known as auxin or auxentriolate, belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. Auxin a is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863205
Synonyms
ValueSource
5-(2,4-Di-sec-butyl-cyclopent-5-enyl)-2,3,5-trihydroxy-valeric acidChEBI
5-(3,5-Di-sec-butylcyclopent-1-enyl)-2,3,5-trihydroxyvaleric acidChEBI
5-C-(3,5-Bis(1-methylpropyl)-1-cyclopenten-1-yl)-4-deoxy-pentonic acidChEBI
Auxen triolic acidChEBI
Auxentriolic acidChEBI
Auxin-aChEBI
5-(2,4-Di-sec-butyl-cyclopent-5-enyl)-2,3,5-trihydroxy-valerateGenerator
5-(3,5-Di-sec-butylcyclopent-1-enyl)-2,3,5-trihydroxyvalerateGenerator
5-C-(3,5-Bis(1-methylpropyl)-1-cyclopenten-1-yl)-4-deoxy-pentonateGenerator
Auxen triolateGenerator
AuxentriolateGenerator
Acids, indolylaceticHMDB
AuxinHMDB
Indoleacetic acidsHMDB
AuxinsHMDB
Acids, indoleaceticHMDB
Indolylacetic acidsHMDB
5-[3,5-Bis(butan-2-yl)cyclopent-1-en-1-yl]-2,3,5-trihydroxypentanoateGenerator
Chemical FormulaC18H32O5
Average Molecular Weight328.4437
Monoisotopic Molecular Weight328.224974134
IUPAC Name5-[3,5-bis(butan-2-yl)cyclopent-1-en-1-yl]-2,3,5-trihydroxypentanoic acid
Traditional Name5-[3,5-bis(sec-butyl)cyclopent-1-en-1-yl]-2,3,5-trihydroxypentanoic acid
CAS Registry NumberNot Available
SMILES
CCC(C)C1CC(C(C)CC)C(=C1)C(O)CC(O)C(O)C(O)=O
InChI Identifier
InChI=1S/C18H32O5/c1-5-10(3)12-7-13(11(4)6-2)14(8-12)15(19)9-16(20)17(21)18(22)23/h8,10-13,15-17,19-21H,5-7,9H2,1-4H3,(H,22,23)
InChI KeyRKOUCPMGBBKLNK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMonocyclic monoterpenoids
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Fatty acyl
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point196 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.51 g/LALOGPS
logP3ALOGPS
logP2.24ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.79ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity89.4 m³·mol⁻¹ChemAxon
Polarizability36.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fs-8694000000-2d35c05df67e8b959530Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0zfr-5022197000-aea91607506891fc1dc2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fu-0198000000-96abea4dfa87529fb828Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-1291000000-fa556f72c2005293532fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9430000000-e6d21fcf98ed47739931Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-4297000000-986195f9ca9e0e895996Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ayi-4290000000-fae70c80e633627d3c1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i0-9150000000-503ad70891bf9201b4e0Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017851
KNApSAcK IDNot Available
Chemspider ID83749
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92772
PDB IDNot Available
ChEBI ID142254
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.