Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:58:39 UTC
Update Date2022-03-07 02:55:04 UTC
HMDB IDHMDB0036801
Secondary Accession Numbers
  • HMDB36801
Metabolite Identification
Common Nameent-16b,19-Kauranediol 19-acetate
Descriptionent-16b,19-Kauranediol 19-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-16b,19-Kauranediol 19-acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862929
Synonyms
ValueSource
ent-16b,19-Kauranediol 19-acetic acidGenerator
{14-hydroxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl}methyl acetic acidGenerator
Chemical FormulaC22H36O3
Average Molecular Weight348.5194
Monoisotopic Molecular Weight348.266445018
IUPAC Name{14-hydroxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl}methyl acetate
Traditional Name{14-hydroxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-5-yl}methyl acetate
CAS Registry Number30320-70-8
SMILES
CC(=O)OCC1(C)CCCC2(C)C3CCC4CC3(CC4(C)O)CCC12
InChI Identifier
InChI=1S/C22H36O3/c1-15(23)25-14-19(2)9-5-10-20(3)17(19)8-11-22-12-16(6-7-18(20)22)21(4,24)13-22/h16-18,24H,5-14H2,1-4H3
InChI KeyAELNFENJKQXLPW-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
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00081 g/LALOGPS
logP4.04ALOGPS
logP3.81ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)19.85ChemAxon
pKa (Strongest Basic)-0.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.48 m³·mol⁻¹ChemAxon
Polarizability41.15 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+183.39231661259
DarkChem[M-H]-178.32931661259
DeepCCS[M-2H]-214.32330932474
DeepCCS[M+Na]+189.5530932474
AllCCS[M+H]+188.432859911
AllCCS[M+H-H2O]+185.932859911
AllCCS[M+NH4]+190.732859911
AllCCS[M+Na]+191.332859911
AllCCS[M-H]-190.132859911
AllCCS[M+Na-2H]-190.832859911
AllCCS[M+HCOO]-191.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ent-16b,19-Kauranediol 19-acetateCC(=O)OCC1(C)CCCC2(C)C3CCC4CC3(CC4(C)O)CCC123339.1Standard polar33892256
ent-16b,19-Kauranediol 19-acetateCC(=O)OCC1(C)CCCC2(C)C3CCC4CC3(CC4(C)O)CCC122534.2Standard non polar33892256
ent-16b,19-Kauranediol 19-acetateCC(=O)OCC1(C)CCCC2(C)C3CCC4CC3(CC4(C)O)CCC122673.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
ent-16b,19-Kauranediol 19-acetate,1TMS,isomer #1CC(=O)OCC1(C)CCCC2(C)C1CCC13CC(CCC12)C(C)(O[Si](C)(C)C)C32618.8Semi standard non polar33892256
ent-16b,19-Kauranediol 19-acetate,1TBDMS,isomer #1CC(=O)OCC1(C)CCCC2(C)C1CCC13CC(CCC12)C(C)(O[Si](C)(C)C(C)(C)C)C32917.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - ent-16b,19-Kauranediol 19-acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lu-3198000000-a27e9df4e862117bd6f52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ent-16b,19-Kauranediol 19-acetate GC-MS (1 TMS) - 70eV, Positivesplash10-052f-6039300000-523f5bdde920bd9305372017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ent-16b,19-Kauranediol 19-acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ent-16b,19-Kauranediol 19-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-16b,19-Kauranediol 19-acetate 10V, Positive-QTOFsplash10-007t-0069000000-c2a44e3cca361d91d0dc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16b,19-Kauranediol 19-acetate 20V, Positive-QTOFsplash10-0079-1192000000-63122d631763ce12ac992016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16b,19-Kauranediol 19-acetate 40V, Positive-QTOFsplash10-00xu-2490000000-87de550e5e78e0c065aa2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16b,19-Kauranediol 19-acetate 10V, Negative-QTOFsplash10-0002-3019000000-90a28e6a813cd9fddf632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16b,19-Kauranediol 19-acetate 20V, Negative-QTOFsplash10-0a4j-9026000000-ec0dd0b37e63f70ccb912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16b,19-Kauranediol 19-acetate 40V, Negative-QTOFsplash10-0a4l-9041000000-0d42584b535a5c5a71832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16b,19-Kauranediol 19-acetate 10V, Positive-QTOFsplash10-054t-0095000000-10e97489717c4d6091ac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16b,19-Kauranediol 19-acetate 20V, Positive-QTOFsplash10-0abd-3395000000-969257aac845ad9f434a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16b,19-Kauranediol 19-acetate 40V, Positive-QTOFsplash10-052u-6930000000-ebb2e09a52bdb271fccf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16b,19-Kauranediol 19-acetate 10V, Negative-QTOFsplash10-0002-0039000000-f55fc19f06904bad8fc02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16b,19-Kauranediol 19-acetate 20V, Negative-QTOFsplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-16b,19-Kauranediol 19-acetate 40V, Negative-QTOFsplash10-0a4l-9000000000-97638d9306c7bf2438b32021-09-23Wishart 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 IDFDB015747
KNApSAcK IDNot Available
Chemspider ID547287
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound630219
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.