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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:04:21 UTC
Update Date2022-03-07 02:54:22 UTC
HMDB IDHMDB0035128
Secondary Accession Numbers
  • HMDB35128
Metabolite Identification
Common NameParkeol
DescriptionParkeol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review a significant number of articles have been published on Parkeol.
Structure
Data?1563862670
Synonyms
ValueSource
4,4,14alpha-Trimethyl-5alpha-cholesta-9(11),24-dien-3beta-olChEBI
5alpha-Lanosta-9(11),24-dien-3beta-olChEBI
Delta(9(11),24)-Lanostadien-3beta-olChEBI
Lanost-9(11)-en-3beta-olKegg
4,4,14a-Trimethyl-5a-cholesta-9(11),24-dien-3b-olGenerator
4,4,14Α-trimethyl-5α-cholesta-9(11),24-dien-3β-olGenerator
5a-Lanosta-9(11),24-dien-3b-olGenerator
5Α-lanosta-9(11),24-dien-3β-olGenerator
delta(9(11),24)-Lanostadien-3b-olGenerator
Δ(9(11),24)-lanostadien-3β-olGenerator
Lanost-9(11)-en-3b-olGenerator
Lanost-9(11)-en-3β-olGenerator
Lanost-9(11)-en-3 beta-olMeSH
Lanost-9(11)-en-3-olMeSH
Chemical FormulaC30H50O
Average Molecular Weight426.7174
Monoisotopic Molecular Weight426.386166222
IUPAC Name(2S,7R,10S,11S,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(17)-en-5-ol
Traditional Name(2S,7R,10S,11S,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(17)-en-5-ol
CAS Registry Number514-45-4
SMILES
[H][C@@]12CC[C@@]3([H])C(C)(C)C(O)CC[C@]3(C)C1=CC[C@]1(C)[C@H](CC[C@@]21C)[C@H](C)CCC=C(C)C
InChI Identifier
InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,15,21-22,24-26,31H,9,11-14,16-19H2,1-8H3/t21-,22-,24-,25+,26?,28-,29-,30+/m1/s1
InChI KeyMLVSYGCURCOSKP-LFXYTPDNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • 14-alpha-methylsteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point162 - 165 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00011 g/LALOGPS
logP7.96ALOGPS
logP7.75ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity134.81 m³·mol⁻¹ChemAxon
Polarizability55.16 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+205.60631661259
DarkChem[M-H]-198.17531661259
DeepCCS[M-2H]-245.09530932474
DeepCCS[M+Na]+219.76330932474
AllCCS[M+H]+215.232859911
AllCCS[M+H-H2O]+213.432859911
AllCCS[M+NH4]+216.932859911
AllCCS[M+Na]+217.432859911
AllCCS[M-H]-216.132859911
AllCCS[M+Na-2H]-218.132859911
AllCCS[M+HCOO]-220.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Parkeol[H][C@@]12CC[C@@]3([H])C(C)(C)C(O)CC[C@]3(C)C1=CC[C@]1(C)[C@H](CC[C@@]21C)[C@H](C)CCC=C(C)C2950.5Standard polar33892256
Parkeol[H][C@@]12CC[C@@]3([H])C(C)(C)C(O)CC[C@]3(C)C1=CC[C@]1(C)[C@H](CC[C@@]21C)[C@H](C)CCC=C(C)C3312.3Standard non polar33892256
Parkeol[H][C@@]12CC[C@@]3([H])C(C)(C)C(O)CC[C@]3(C)C1=CC[C@]1(C)[C@H](CC[C@@]21C)[C@H](C)CCC=C(C)C3367.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Parkeol,1TMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)C(O[Si](C)(C)C)CC[C@]4(C)C3=CC[C@]12C3399.9Semi standard non polar33892256
Parkeol,1TBDMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3=CC[C@]12C3628.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Parkeol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-1019400000-4684ce900e2bdc7460722017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Parkeol GC-MS (1 TMS) - 70eV, Positivesplash10-00lr-3001900000-8451a437af3bdb2462bf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Parkeol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parkeol 10V, Positive-QTOFsplash10-0a6r-0002900000-2cfcf7ce4b5b21140eae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parkeol 20V, Positive-QTOFsplash10-0pdi-3149500000-61a41ba954dca61360932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parkeol 40V, Positive-QTOFsplash10-0uxr-4249100000-2bb374a801f5e66d3c9e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parkeol 10V, Negative-QTOFsplash10-004i-0000900000-120a00ee008954da444d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parkeol 20V, Negative-QTOFsplash10-004i-0000900000-017947c10e39f58df6952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parkeol 40V, Negative-QTOFsplash10-0a4l-1009400000-afc7034885289079e0af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parkeol 10V, Negative-QTOFsplash10-004i-0000900000-590c9e4adfdd12b64d932021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parkeol 20V, Negative-QTOFsplash10-004i-0000900000-e46a7ceb14ec0697db5a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parkeol 40V, Negative-QTOFsplash10-004i-1001900000-67a4126d96742d377bfc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parkeol 10V, Positive-QTOFsplash10-0a6u-9101200000-a16a2818c311409821762021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parkeol 20V, Positive-QTOFsplash10-0aou-9102000000-1dfa95bffb6fb59ced742021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parkeol 40V, Positive-QTOFsplash10-0aou-9501000000-2cb83003c3cd64db470c2021-09-24Wishart LabView Spectrum
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
FooDB IDNot Available
KNApSAcK IDC00023785
Chemspider ID23255009
KEGG Compound IDC19918
BioCyc IDCPD-13879
BiGG IDNot Available
Wikipedia LinkParkeol
METLIN IDNot Available
PubChem Compound12313974
PDB IDNot Available
ChEBI ID63460
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.