Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:59:37 UTC
Update Date2022-03-07 02:54:01 UTC
HMDB IDHMDB0034197
Secondary Accession Numbers
  • HMDB34197
Metabolite Identification
Common NameClerosterol
DescriptionClerosterol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Clerosterol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862526
Synonyms
ValueSource
(-)-(3beta,24S)-Stigmasta-5,25-dien-3-olHMDB
5,25-StigmastadienolHMDB
Delta5,23 StigmastadienolHMDB
Poriferasta-5,25-dien-3-olHMDB
Chemical FormulaC29H48O
Average Molecular Weight412.702
Monoisotopic Molecular Weight412.370516166
IUPAC Name14-(5-ethyl-6-methylhept-6-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional Name14-(5-ethyl-6-methylhept-6-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
CAS Registry Number2364-23-0
SMILES
CCC(CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)=C
InChI Identifier
InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,20-21,23-27,30H,2,7-9,11-18H2,1,3-6H3
InChI KeyGHGKPLPBPGYSOO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassStigmastanes and derivatives
Direct ParentStigmastanes and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Stigmastane-skeleton
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point147 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00014 g/LALOGPS
logP7.56ALOGPS
logP7.5ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.54 m³·mol⁻¹ChemAxon
Polarizability52.66 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.95131661259
DarkChem[M-H]-197.32631661259
DeepCCS[M-2H]-240.72330932474
DeepCCS[M+Na]+216.33330932474
AllCCS[M+H]+209.532859911
AllCCS[M+H-H2O]+207.532859911
AllCCS[M+NH4]+211.332859911
AllCCS[M+Na]+211.932859911
AllCCS[M-H]-206.132859911
AllCCS[M+Na-2H]-208.232859911
AllCCS[M+HCOO]-210.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ClerosterolCCC(CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)=C2539.3Standard polar33892256
ClerosterolCCC(CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)=C3148.7Standard non polar33892256
ClerosterolCCC(CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)=C3262.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Clerosterol,1TMS,isomer #1C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3360.9Semi standard non polar33892256
Clerosterol,1TBDMS,isomer #1C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3596.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-2109000000-0efa927eca729ac9be7a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol GC-MS (1 TMS) - 70eV, Positivesplash10-0avi-4103900000-516c28b4d7c46cc35d052017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 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 - Clerosterol 10V, Positive-QTOFsplash10-01ot-1019500000-d63f12206dc316570d1d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 20V, Positive-QTOFsplash10-0002-4139100000-3f42d18863fa1e8148382015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 40V, Positive-QTOFsplash10-0002-7097000000-c1eaf8d7ff7ae538983b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 10V, Negative-QTOFsplash10-03di-0002900000-f632741b248cfad566a12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 20V, Negative-QTOFsplash10-03di-0005900000-76947e1c0c9ba83a7e7d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 40V, Negative-QTOFsplash10-000t-2019000000-8e5c3833d27b6d04657c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 10V, Positive-QTOFsplash10-03di-3127900000-4c50b90f3f487da5918d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 20V, Positive-QTOFsplash10-0hhc-9124100000-a88a9e815eddbd2ccb1f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 40V, Positive-QTOFsplash10-0ced-9611000000-d6e01f5ae9d194d61e7b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 10V, Negative-QTOFsplash10-03di-0000900000-363450e12a0ea926276e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 20V, Negative-QTOFsplash10-03di-0000900000-06ea6d17f771f24b06382021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 40V, Negative-QTOFsplash10-08fu-0009600000-1e542d918e61d92836282021-09-24Wishart 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 IDFDB012494
KNApSAcK IDC00033727
Chemspider ID252580
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound286499
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. Sartorelli P, Andrade SP, Melhem MS, Prado FO, Tempone AG: Isolation of antileishmanial sterol from the fruits of Cassia fistula using bioguided fractionation. Phytother Res. 2007 Jul;21(7):644-7. [PubMed:17397117 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.