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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:52:09 UTC
Update Date2022-03-07 02:55:01 UTC
HMDB IDHMDB0036702
Secondary Accession Numbers
  • HMDB36702
Metabolite Identification
Common NameSideridiol
DescriptionSideridiol 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. Sideridiol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862912
SynonymsNot Available
Chemical FormulaC20H32O2
Average Molecular Weight304.4669
Monoisotopic Molecular Weight304.240230268
IUPAC Name5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-ol
Traditional Name5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-ol
CAS Registry Number19891-25-9
SMILES
CC1=CC23CC1CCC2C1(C)CCCC(C)(CO)C1CC3O
InChI Identifier
InChI=1S/C20H32O2/c1-13-10-20-11-14(13)5-6-15(20)19(3)8-4-7-18(2,12-21)16(19)9-17(20)22/h10,14-17,21-22H,4-9,11-12H2,1-3H3
InChI KeyBATFJLLEMUIAJD-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 Point196 - 197 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.043 g/LALOGPS
logP3.24ALOGPS
logP3.05ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)18.59ChemAxon
pKa (Strongest Basic)-0.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity90.01 m³·mol⁻¹ChemAxon
Polarizability36.27 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]+169.75231661259
DarkChem[M-H]-167.01731661259
DeepCCS[M-2H]-204.56330932474
DeepCCS[M+Na]+180.08730932474
AllCCS[M+H]+177.432859911
AllCCS[M+H-H2O]+174.432859911
AllCCS[M+NH4]+180.232859911
AllCCS[M+Na]+180.932859911
AllCCS[M-H]-182.432859911
AllCCS[M+Na-2H]-182.732859911
AllCCS[M+HCOO]-183.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SideridiolCC1=CC23CC1CCC2C1(C)CCCC(C)(CO)C1CC3O2784.0Standard polar33892256
SideridiolCC1=CC23CC1CCC2C1(C)CCCC(C)(CO)C1CC3O2499.6Standard non polar33892256
SideridiolCC1=CC23CC1CCC2C1(C)CCCC(C)(CO)C1CC3O2575.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sideridiol,1TMS,isomer #1CC1=CC23CC1CCC2C1(C)CCCC(C)(CO[Si](C)(C)C)C1CC3O2565.7Semi standard non polar33892256
Sideridiol,1TMS,isomer #2CC1=CC23CC1CCC2C1(C)CCCC(C)(CO)C1CC3O[Si](C)(C)C2567.5Semi standard non polar33892256
Sideridiol,2TMS,isomer #1CC1=CC23CC1CCC2C1(C)CCCC(C)(CO[Si](C)(C)C)C1CC3O[Si](C)(C)C2483.3Semi standard non polar33892256
Sideridiol,1TBDMS,isomer #1CC1=CC23CC1CCC2C1(C)CCCC(C)(CO[Si](C)(C)C(C)(C)C)C1CC3O2826.3Semi standard non polar33892256
Sideridiol,1TBDMS,isomer #2CC1=CC23CC1CCC2C1(C)CCCC(C)(CO)C1CC3O[Si](C)(C)C(C)(C)C2800.4Semi standard non polar33892256
Sideridiol,2TBDMS,isomer #1CC1=CC23CC1CCC2C1(C)CCCC(C)(CO[Si](C)(C)C(C)(C)C)C1CC3O[Si](C)(C)C(C)(C)C2987.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sideridiol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0590000000-91bb8ba8b72e91180d722017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sideridiol GC-MS (2 TMS) - 70eV, Positivesplash10-0089-4257900000-41beaf433288cdf22c6d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sideridiol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sideridiol 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 - Sideridiol 10V, Positive-QTOFsplash10-052r-0093000000-30ffd985077cc57568812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sideridiol 20V, Positive-QTOFsplash10-00kr-0190000000-58ca6562fd16642180d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sideridiol 40V, Positive-QTOFsplash10-06dl-5690000000-8b2b3a453f906d6c30412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sideridiol 10V, Negative-QTOFsplash10-0udi-0059000000-b2b1a05bef1a9ea2e3772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sideridiol 20V, Negative-QTOFsplash10-0uki-0094000000-c4a83de10f63f78a1fbb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sideridiol 40V, Negative-QTOFsplash10-0ab9-0090000000-acd2b0b4cb58b0ffbf4a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sideridiol 10V, Negative-QTOFsplash10-0udi-0009000000-f9d10b76ade80bd401ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sideridiol 20V, Negative-QTOFsplash10-0udi-0009000000-f9d10b76ade80bd401ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sideridiol 40V, Negative-QTOFsplash10-0udi-0029000000-a6d4533d8c8f1e2c9d582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sideridiol 10V, Positive-QTOFsplash10-0abi-0097000000-f0bd5296cd651471ba2f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sideridiol 20V, Positive-QTOFsplash10-0ab9-0897000000-4b4a0c4d66412c97a0dd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sideridiol 40V, Positive-QTOFsplash10-00dl-4943000000-84fceb022f7afbd8f0312021-09-23Wishart 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 IDFDB015638
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12315540
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.