Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:57:48 UTC
Update Date2022-03-07 02:54:19 UTC
HMDB IDHMDB0035024
Secondary Accession Numbers
  • HMDB35024
Metabolite Identification
Common Nameent-16-Kauren-19-ol acetate
Descriptionent-16-Kauren-19-ol acetate 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-16-Kauren-19-ol acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862652
Synonyms
ValueSource
ent-16-Kauren-19-ol acetic acidGenerator
{5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl}methyl acetic acidGenerator
Chemical FormulaC22H34O2
Average Molecular Weight330.5042
Monoisotopic Molecular Weight330.255880332
IUPAC Name{5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl}methyl acetate
Traditional Name{5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl}methyl acetate
CAS Registry Number41756-45-0
SMILES
CC(=O)OCC1(C)CCCC2(C)C3CCC4CC3(CC4=C)CCC12
InChI Identifier
InChI=1S/C22H34O2/c1-15-12-22-11-8-18-20(3,14-24-16(2)23)9-5-10-21(18,4)19(22)7-6-17(15)13-22/h17-19H,1,5-14H2,2-4H3
InChI KeyFNLMCLYZRZJKQZ-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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point117 - 118 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00023 g/LALOGPS
logP4.43ALOGPS
logP4.78ChemAxon
logS-6.2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity96.57 m³·mol⁻¹ChemAxon
Polarizability39.61 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]+180.10731661259
DarkChem[M-H]-172.66831661259
DeepCCS[M-2H]-212.11230932474
DeepCCS[M+Na]+187.57430932474
AllCCS[M+H]+185.432859911
AllCCS[M+H-H2O]+182.732859911
AllCCS[M+NH4]+187.932859911
AllCCS[M+Na]+188.632859911
AllCCS[M-H]-188.332859911
AllCCS[M+Na-2H]-188.832859911
AllCCS[M+HCOO]-189.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ent-16-Kauren-19-ol acetateCC(=O)OCC1(C)CCCC2(C)C3CCC4CC3(CC4=C)CCC123051.0Standard polar33892256
ent-16-Kauren-19-ol acetateCC(=O)OCC1(C)CCCC2(C)C3CCC4CC3(CC4=C)CCC122399.8Standard non polar33892256
ent-16-Kauren-19-ol acetateCC(=O)OCC1(C)CCCC2(C)C3CCC4CC3(CC4=C)CCC122518.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - ent-16-Kauren-19-ol acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxu-4598000000-a390f491e6a0749166732017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ent-16-Kauren-19-ol acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ent-16-Kauren-19-ol acetate 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-16-Kauren-19-ol acetate 10V, Positive-QTOFsplash10-0089-0198000000-44e5cffa5de6d59393cc2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16-Kauren-19-ol acetate 20V, Positive-QTOFsplash10-00di-1291000000-9c5f6013f8216415ef4a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16-Kauren-19-ol acetate 40V, Positive-QTOFsplash10-00r6-2891000000-2a3aa1a32d1df30cc4b72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16-Kauren-19-ol acetate 10V, Negative-QTOFsplash10-004i-4029000000-5fbb594e7875665f86282015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16-Kauren-19-ol acetate 20V, Negative-QTOFsplash10-0a6r-9034000000-9b9d0e5cadbce0c41ee52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16-Kauren-19-ol acetate 40V, Negative-QTOFsplash10-0a4l-9040000000-79f717167e0cdb3f05242015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16-Kauren-19-ol acetate 10V, Negative-QTOFsplash10-004r-0097000000-0c67486846c1c33a9dd62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16-Kauren-19-ol acetate 20V, Negative-QTOFsplash10-0a4i-9010000000-84de56527127e8338bc62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16-Kauren-19-ol acetate 40V, Negative-QTOFsplash10-0a4l-9000000000-ba302970fb3f2298b81a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16-Kauren-19-ol acetate 10V, Positive-QTOFsplash10-0a59-0093000000-fe74ef33d517d6a470e02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16-Kauren-19-ol acetate 20V, Positive-QTOFsplash10-0ab9-3392000000-00a5e92241c89070bfd62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16-Kauren-19-ol acetate 40V, Positive-QTOFsplash10-05a9-2920000000-0229795c42f817b98f3c2021-09-22Wishart 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 IDFDB013629
KNApSAcK IDNot Available
Chemspider ID468201
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound537596
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.