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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:53:34 UTC
Update Date2022-03-07 02:55:02 UTC
HMDB IDHMDB0036723
Secondary Accession Numbers
  • HMDB36723
Metabolite Identification
Common Name(ent-16alpha)-16-Kauranol
Description(ent-16alpha)-16-Kauranol belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D (ent-16alpha)-16-Kauranol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862915
Synonyms
ValueSource
(ent-16a)-16-KauranolGenerator
(ent-16Α)-16-kauranolGenerator
Chemical FormulaC20H34O
Average Molecular Weight290.4834
Monoisotopic Molecular Weight290.26096571
IUPAC Name5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-ol
Traditional Name5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-ol
CAS Registry Number5354-44-9
SMILES
CC1(O)CC23CC1CCC2C1(C)CCCC(C)(C)C1CC3
InChI Identifier
InChI=1S/C20H34O/c1-17(2)9-5-10-18(3)15(17)8-11-20-12-14(6-7-16(18)20)19(4,21)13-20/h14-16,21H,5-13H2,1-4H3
InChI KeyFZSRMADKTOBCNT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentKaurane diterpenoids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point210 - 211 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0002 g/LALOGPS
logP4.96ALOGPS
logP4.65ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)19.85ChemAxon
pKa (Strongest Basic)-0.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity87.55 m³·mol⁻¹ChemAxon
Polarizability35.83 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.27731661259
DarkChem[M-H]-164.08331661259
DeepCCS[M-2H]-208.36830932474
DeepCCS[M+Na]+183.67330932474
AllCCS[M+H]+175.232859911
AllCCS[M+H-H2O]+172.232859911
AllCCS[M+NH4]+178.032859911
AllCCS[M+Na]+178.832859911
AllCCS[M-H]-182.132859911
AllCCS[M+Na-2H]-182.532859911
AllCCS[M+HCOO]-183.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(ent-16alpha)-16-KauranolCC1(O)CC23CC1CCC2C1(C)CCCC(C)(C)C1CC32824.1Standard polar33892256
(ent-16alpha)-16-KauranolCC1(O)CC23CC1CCC2C1(C)CCCC(C)(C)C1CC32164.9Standard non polar33892256
(ent-16alpha)-16-KauranolCC1(O)CC23CC1CCC2C1(C)CCCC(C)(C)C1CC32208.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(ent-16alpha)-16-Kauranol,1TMS,isomer #1CC1(C)CCCC2(C)C1CCC13CC(CCC12)C(C)(O[Si](C)(C)C)C32265.6Semi standard non polar33892256
(ent-16alpha)-16-Kauranol,1TBDMS,isomer #1CC1(C)CCCC2(C)C1CCC13CC(CCC12)C(C)(O[Si](C)(C)C(C)(C)C)C32550.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (ent-16alpha)-16-Kauranol GC-MS (Non-derivatized) - 70eV, Positivesplash10-01u0-0190000000-d4a5336cb7c253ece2712017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (ent-16alpha)-16-Kauranol GC-MS (1 TMS) - 70eV, Positivesplash10-0002-4159000000-7455e7125fb7841de7e62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (ent-16alpha)-16-Kauranol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (ent-16alpha)-16-Kauranol 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 - (ent-16alpha)-16-Kauranol 10V, Positive-QTOFsplash10-00dl-0090000000-330e59126f493c30893c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 20V, Positive-QTOFsplash10-00dl-1190000000-d70a5a9f114476c77c3b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 40V, Positive-QTOFsplash10-052f-4590000000-c15a6303537c49bb2ba02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 10V, Positive-QTOFsplash10-00dl-0090000000-330e59126f493c30893c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 20V, Positive-QTOFsplash10-00dl-1190000000-d70a5a9f114476c77c3b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 40V, Positive-QTOFsplash10-052f-4590000000-c15a6303537c49bb2ba02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 10V, Negative-QTOFsplash10-000i-0090000000-bb467c3e256f4cf4f0d72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 20V, Negative-QTOFsplash10-000i-0090000000-1eea942e9bd1896a16912015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 40V, Negative-QTOFsplash10-05fr-0090000000-224bf71e6faab3d898f02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 10V, Negative-QTOFsplash10-000i-0090000000-bb467c3e256f4cf4f0d72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 20V, Negative-QTOFsplash10-000i-0090000000-1eea942e9bd1896a16912015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 40V, Negative-QTOFsplash10-05fr-0090000000-224bf71e6faab3d898f02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 10V, Positive-QTOFsplash10-006x-0090000000-3390d958b7243de4d75a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 20V, Positive-QTOFsplash10-00di-2980000000-235c5c659c172d54ad572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 40V, Positive-QTOFsplash10-0006-8960000000-dee56cbfc5515713763f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 10V, Negative-QTOFsplash10-000i-0090000000-e782630883d1b41306742021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 20V, Negative-QTOFsplash10-000i-0090000000-e782630883d1b41306742021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (ent-16alpha)-16-Kauranol 40V, Negative-QTOFsplash10-000i-0090000000-e782630883d1b41306742021-09-23Wishart 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 IDFDB015660
KNApSAcK IDNot Available
Chemspider ID541556
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound623309
PDB IDNot Available
ChEBI IDNot Available
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.