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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:01:31 UTC
Update Date2022-03-07 02:54:43 UTC
HMDB IDHMDB0035969
Secondary Accession Numbers
  • HMDB35969
Metabolite Identification
Common NameCycloartanol
DescriptionCycloartanol belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. Thus, cycloartanol is considered to be a sterol lipid molecule. Cycloartanol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862800
Synonyms
ValueSource
9b,19-Cyclolanostan-3b-olHMDB
Cycloartan-3b-olHMDB
Chemical FormulaC30H52O
Average Molecular Weight428.7333
Monoisotopic Molecular Weight428.401816286
IUPAC Name(1S,3R,6S,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methylheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol
Traditional Name(1S,3R,6S,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methylheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol
CAS Registry Number4657-58-3
SMILES
[H][C@@]12CC[C@]3([H])[C@]4(C[C@@]14CC[C@]1(C)[C@H](CC[C@@]21C)[C@H](C)CCCC(C)C)CC[C@H](O)C3(C)C
InChI Identifier
InChI=1S/C30H52O/c1-20(2)9-8-10-21(3)22-13-15-28(7)24-12-11-23-26(4,5)25(31)14-16-29(23)19-30(24,29)18-17-27(22,28)6/h20-25,31H,8-19H2,1-7H3/t21-,22-,23+,24+,25+,27-,28+,29-,30+/m1/s1
InChI KeyYABASAWVVRQMEU-YBXTVTTCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCycloartanols and derivatives
Direct ParentCycloartanols and derivatives
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 Point101 - 102 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.9e-05 g/LALOGPS
logP6.85ALOGPS
logP7.95ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity131.18 m³·mol⁻¹ChemAxon
Polarizability55.85 ųChemAxon
Number of Rings5ChemAxon
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]+204.76231661259
DarkChem[M-H]-201.2331661259
DeepCCS[M-2H]-244.37930932474
DeepCCS[M+Na]+218.33930932474
AllCCS[M+H]+214.632859911
AllCCS[M+H-H2O]+212.932859911
AllCCS[M+NH4]+216.132859911
AllCCS[M+Na]+216.632859911
AllCCS[M-H]-207.832859911
AllCCS[M+Na-2H]-210.132859911
AllCCS[M+HCOO]-212.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cycloartanol[H][C@@]12CC[C@]3([H])[C@]4(C[C@@]14CC[C@]1(C)[C@H](CC[C@@]21C)[C@H](C)CCCC(C)C)CC[C@H](O)C3(C)C2740.6Standard polar33892256
Cycloartanol[H][C@@]12CC[C@]3([H])[C@]4(C[C@@]14CC[C@]1(C)[C@H](CC[C@@]21C)[C@H](C)CCCC(C)C)CC[C@H](O)C3(C)C3327.1Standard non polar33892256
Cycloartanol[H][C@@]12CC[C@]3([H])[C@]4(C[C@@]14CC[C@]1(C)[C@H](CC[C@@]21C)[C@H](C)CCCC(C)C)CC[C@H](O)C3(C)C3395.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cycloartanol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@@H](O[Si](C)(C)C)CC[C@@]45C[C@@]35CC[C@]12C3367.2Semi standard non polar33892256
Cycloartanol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]45C[C@@]35CC[C@]12C3570.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cycloartanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-3129700000-ddedf4806ebafcfe81662017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycloartanol GC-MS (1 TMS) - 70eV, Positivesplash10-0079-4011900000-d0e06492d699fc8219f82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycloartanol 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 - Cycloartanol 10V, Positive-QTOFsplash10-01t9-0002900000-3e115c22c77b8a3826cd2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartanol 20V, Positive-QTOFsplash10-0bvi-4029500000-9473ae56a28bd96c379c2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartanol 40V, Positive-QTOFsplash10-0a4i-4039000000-5b707b68e2c1d6e5c3af2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartanol 10V, Negative-QTOFsplash10-004i-0000900000-591f06012719671bc1232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartanol 20V, Negative-QTOFsplash10-004i-0000900000-b579c92dec74ed15da912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartanol 40V, Negative-QTOFsplash10-03dj-2009400000-c82abacfdc3e210db0aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartanol 10V, Negative-QTOFsplash10-004i-0000900000-ed006f256d0151ef06142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartanol 20V, Negative-QTOFsplash10-004i-0000900000-ed006f256d0151ef06142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartanol 40V, Negative-QTOFsplash10-004i-0001900000-bb9a4b0e3accb36451972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartanol 10V, Positive-QTOFsplash10-004i-6110900000-0f786e25332dd368e13b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartanol 20V, Positive-QTOFsplash10-0a4i-9122200000-62fbbb6a615ce4fb7a1b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartanol 40V, Positive-QTOFsplash10-0a4i-9252200000-8563099c49a9c1cc71ae2021-09-23Wishart 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 IDFDB014773
KNApSAcK IDNot Available
Chemspider ID10218455
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12760132
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.