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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:30:04 UTC
HMDB IDHMDB0000649
Secondary Accession Numbers
  • HMDB00649
Metabolite Identification
Common NameClionasterol
DescriptionClionasterol, also known as gamma-sitosterol or harzol, 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. Thus, clionasterol is considered to be a sterol. Based on a literature review a significant number of articles have been published on Clionasterol.
Structure
Data?1582752146
Synonyms
ValueSource
(3beta,24S)-Stigmast-5-en-3-olChEBI
22,23-DihydroporiferasterolChEBI
24-Ethylcholest-5-en-3 beta-olChEBI
24beta-Ethyl-5-cholesten-3beta-olChEBI
24beta-EthylcholesterolChEBI
24S-Ethylcholest-5-en-3beta-olChEBI
beta-DihydrofucosterolChEBI
gamma-SitosterolChEBI
Poriferast-5-en-3beta-olChEBI
(3b,24S)-Stigmast-5-en-3-olGenerator
(3Β,24S)-stigmast-5-en-3-olGenerator
24-Ethylcholest-5-en-3 b-olGenerator
24-Ethylcholest-5-en-3 β-olGenerator
24b-Ethyl-5-cholesten-3b-olGenerator
24Β-ethyl-5-cholesten-3β-olGenerator
24b-EthylcholesterolGenerator
24Β-ethylcholesterolGenerator
24S-Ethylcholest-5-en-3b-olGenerator
24S-Ethylcholest-5-en-3β-olGenerator
b-DihydrofucosterolGenerator
Β-dihydrofucosterolGenerator
g-SitosterolGenerator
Γ-sitosterolGenerator
Poriferast-5-en-3b-olGenerator
Poriferast-5-en-3β-olGenerator
24b-Ethylcholest-5-en-3b-olHMDB
24-EthylcholesterolHMDB
3beta-Stigmast-5-en-3-olHMDB
SitosterolHMDB
Sitosterol, (3beta,24xi)-isomerHMDB
Sitosterol, 26-(14)C-labeledHMDB
3beta-SitosterolHMDB
HarzolHMDB
beta-SitosterolHMDB
Sitosterol, (3beta)-isomerHMDB
Chemical FormulaC29H50O
Average Molecular Weight414.7067
Monoisotopic Molecular Weight414.386166222
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number83-47-6
SMILESNot Available
InChI Identifier
InChI=1S/C29H50O/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/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21+,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChI KeyKZJWDPNRJALLNS-FBZNIEFRSA-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
  • C24-propyl-sterol-skeleton
  • Stigmastane-skeleton
  • Triterpenoid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point147 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.6e-05 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular PropertiesNot Available
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+201.22631661259
DarkChem[M-H]-196.07131661259
AllCCS[M+H]+209.77632859911
AllCCS[M-H]-204.66432859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Clionasterol,1TMS,#1CC[C@@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3353.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Clionasterol,1TBDMS,#1CC[C@@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3581.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Clionasterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-052v-1109000000-ae76f369c8c1b1b4fe0a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clionasterol GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-4103900000-a09c1c265657e57bd0962017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clionasterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clionasterol 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 - Clionasterol 10V, Positive-QTOFsplash10-00kb-0019500000-b9eddfa8d56747167ada2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clionasterol 20V, Positive-QTOFsplash10-00kb-5139100000-42d184a108f9e994dc012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clionasterol 40V, Positive-QTOFsplash10-0002-9076000000-54ef98673160128cbacd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clionasterol 10V, Negative-QTOFsplash10-03di-0002900000-158617c2e43f1a46b58a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clionasterol 20V, Negative-QTOFsplash10-03di-0004900000-632250471791929b07e32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clionasterol 40V, Negative-QTOFsplash10-0002-2019000000-717c6229722cf73f3faa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clionasterol 10V, Positive-QTOFsplash10-014i-1118900000-620dc34d093f424c1d892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clionasterol 20V, Positive-QTOFsplash10-014l-9163100000-4a80c636d0cb9659262f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clionasterol 40V, Positive-QTOFsplash10-0a59-9521000000-76b9e6176a167e0b61b32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clionasterol 10V, Negative-QTOFsplash10-03di-0000900000-eda302082c5114b2ab3a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clionasterol 20V, Negative-QTOFsplash10-03di-0001900000-c37ac1577c1ddfa751342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clionasterol 40V, Negative-QTOFsplash10-06r2-4016900000-e870c8bbee027c7c3a5a2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
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 IDFDB112200
KNApSAcK IDC00023769
Chemspider ID402901
KEGG Compound IDC19654
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5621
PubChem Compound457801
PDB IDNot Available
ChEBI ID132823
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1839331
References
Synthesis ReferenceKind, C. Albert; Bergmann, Werner. Marine products. X. Clionasterol. Journal of Organic Chemistry (1942), 7 341-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Cerqueira F, Watanadilok R, Sonchaeng P, Kijjoa A, Pinto M, Quarles van Ufford H, Kroes B, Beukelman C, Nascimento MS: Clionasterol: a potent inhibitor of complement component C1. Planta Med. 2003 Feb;69(2):174-6. [PubMed:12624828 ]