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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:00:12 UTC
Update Date2022-03-07 02:54:01 UTC
HMDB IDHMDB0034204
Secondary Accession Numbers
  • HMDB34204
Metabolite Identification
Common NameClerosterol 3-glucoside
DescriptionClerosterol 3-glucoside 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, clerosterol 3-glucoside is considered to be a sterol lipid molecule. Clerosterol 3-glucoside is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862527
Synonyms
ValueSource
10H-Phenothiastannin, 10,10-dimethyl-5,5-dioxideHMDB
10H-Phenothiastannin,10,10-dimethyl-5,5-dioxideHMDB
Chemical FormulaC35H58O6
Average Molecular Weight574.8314
Monoisotopic Molecular Weight574.423339588
IUPAC Name2-{[14-(5-ethyl-6-methylhept-6-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name2-{[14-(5-ethyl-6-methylhept-6-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
CAS Registry Number123621-00-1
SMILES
CCC(CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC1OC(CO)C(O)C(O)C1O)C(C)=C
InChI Identifier
InChI=1S/C35H58O6/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(14-16-34(23,5)28(25)15-17-35(26,27)6)40-33-32(39)31(38)30(37)29(19-36)41-33/h10,21-22,24-33,36-39H,2,7-9,11-19H2,1,3-6H3
InChI KeyFKZKAGYCKXYXKP-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
  • Stigmastane-skeleton
  • Triterpenoid
  • Steroidal glycoside
  • Delta-5-steroid
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Oxacycle
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point258 - 262 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.007 g/LALOGPS
logP5.43ALOGPS
logP5.73ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity161.96 m³·mol⁻¹ChemAxon
Polarizability69.27 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+231.89131661259
DarkChem[M-H]-227.12131661259
DeepCCS[M-2H]-265.68630932474
DeepCCS[M+Na]+241.11630932474
AllCCS[M+H]+240.332859911
AllCCS[M+H-H2O]+239.332859911
AllCCS[M+NH4]+241.232859911
AllCCS[M+Na]+241.432859911
AllCCS[M-H]-216.732859911
AllCCS[M+Na-2H]-220.832859911
AllCCS[M+HCOO]-225.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Clerosterol 3-glucosideCCC(CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC1OC(CO)C(O)C(O)C1O)C(C)=C2994.9Standard polar33892256
Clerosterol 3-glucosideCCC(CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC1OC(CO)C(O)C(O)C1O)C(C)=C3996.3Standard non polar33892256
Clerosterol 3-glucosideCCC(CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC1OC(CO)C(O)C(O)C1O)C(C)=C4462.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Clerosterol 3-glucoside,1TMS,isomer #1C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO[Si](C)(C)C)C(O)C(O)C5O)CCC4(C)C3CCC12C4606.8Semi standard non polar33892256
Clerosterol 3-glucoside,1TMS,isomer #2C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO)C(O[Si](C)(C)C)C(O)C5O)CCC4(C)C3CCC12C4603.2Semi standard non polar33892256
Clerosterol 3-glucoside,1TMS,isomer #3C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO)C(O)C(O[Si](C)(C)C)C5O)CCC4(C)C3CCC12C4585.5Semi standard non polar33892256
Clerosterol 3-glucoside,1TMS,isomer #4C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO)C(O)C(O)C5O[Si](C)(C)C)CCC4(C)C3CCC12C4586.5Semi standard non polar33892256
Clerosterol 3-glucoside,2TMS,isomer #1C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C5O)CCC4(C)C3CCC12C4526.2Semi standard non polar33892256
Clerosterol 3-glucoside,2TMS,isomer #2C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C5O)CCC4(C)C3CCC12C4499.2Semi standard non polar33892256
Clerosterol 3-glucoside,2TMS,isomer #3C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO[Si](C)(C)C)C(O)C(O)C5O[Si](C)(C)C)CCC4(C)C3CCC12C4517.3Semi standard non polar33892256
Clerosterol 3-glucoside,2TMS,isomer #4C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C5O)CCC4(C)C3CCC12C4504.1Semi standard non polar33892256
Clerosterol 3-glucoside,2TMS,isomer #5C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO)C(O[Si](C)(C)C)C(O)C5O[Si](C)(C)C)CCC4(C)C3CCC12C4506.4Semi standard non polar33892256
Clerosterol 3-glucoside,2TMS,isomer #6C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO)C(O)C(O[Si](C)(C)C)C5O[Si](C)(C)C)CCC4(C)C3CCC12C4505.2Semi standard non polar33892256
Clerosterol 3-glucoside,3TMS,isomer #1C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C5O)CCC4(C)C3CCC12C4435.9Semi standard non polar33892256
Clerosterol 3-glucoside,3TMS,isomer #2C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C5O[Si](C)(C)C)CCC4(C)C3CCC12C4417.1Semi standard non polar33892256
Clerosterol 3-glucoside,3TMS,isomer #3C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C5O[Si](C)(C)C)CCC4(C)C3CCC12C4420.4Semi standard non polar33892256
Clerosterol 3-glucoside,3TMS,isomer #4C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C5O[Si](C)(C)C)CCC4(C)C3CCC12C4459.6Semi standard non polar33892256
Clerosterol 3-glucoside,4TMS,isomer #1C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C5O[Si](C)(C)C)CCC4(C)C3CCC12C4412.0Semi standard non polar33892256
Clerosterol 3-glucoside,1TBDMS,isomer #1C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C5O)CCC4(C)C3CCC12C4823.6Semi standard non polar33892256
Clerosterol 3-glucoside,1TBDMS,isomer #2C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C5O)CCC4(C)C3CCC12C4837.5Semi standard non polar33892256
Clerosterol 3-glucoside,1TBDMS,isomer #3C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C5O)CCC4(C)C3CCC12C4818.3Semi standard non polar33892256
Clerosterol 3-glucoside,1TBDMS,isomer #4C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO)C(O)C(O)C5O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C4820.7Semi standard non polar33892256
Clerosterol 3-glucoside,2TBDMS,isomer #1C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C5O)CCC4(C)C3CCC12C4969.4Semi standard non polar33892256
Clerosterol 3-glucoside,2TBDMS,isomer #2C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C5O)CCC4(C)C3CCC12C4933.9Semi standard non polar33892256
Clerosterol 3-glucoside,2TBDMS,isomer #3C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C5O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C4960.0Semi standard non polar33892256
Clerosterol 3-glucoside,2TBDMS,isomer #4C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C5O)CCC4(C)C3CCC12C4941.2Semi standard non polar33892256
Clerosterol 3-glucoside,2TBDMS,isomer #5C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C5O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C4950.8Semi standard non polar33892256
Clerosterol 3-glucoside,2TBDMS,isomer #6C=C(C)C(CC)CCC(C)C1CCC2C3CC=C4CC(OC5OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C5O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C4942.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-7403190000-7cdecdaf6f39051e52942017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (1 TMS) - 70eV, Positivesplash10-001i-6414019000-ac8d3586a2dabe9f1ebc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS ("Clerosterol 3-glucoside,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TMS_4_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clerosterol 3-glucoside GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 3-glucoside 10V, Positive-QTOFsplash10-03fs-1107790000-1454da383499c8eba8fc2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 3-glucoside 20V, Positive-QTOFsplash10-03dj-2319500000-df55088f11a537885f8e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 3-glucoside 40V, Positive-QTOFsplash10-029b-6549200000-32bf5afb75b5df1c81aa2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 3-glucoside 10V, Negative-QTOFsplash10-0229-1202590000-29c697a31e94a423d6f12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 3-glucoside 20V, Negative-QTOFsplash10-03di-1203920000-1d11435c15f8622ec2a02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 3-glucoside 40V, Negative-QTOFsplash10-03dj-7009800000-1247f68c3746e7c620042015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 3-glucoside 10V, Positive-QTOFsplash10-004i-2000190000-83472440dd57dcc010072021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 3-glucoside 20V, Positive-QTOFsplash10-03dl-9124120000-3ec5e602eaf399e288fd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 3-glucoside 40V, Positive-QTOFsplash10-0gx1-9301410000-90c265094744299886862021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 3-glucoside 10V, Negative-QTOFsplash10-00di-0000090000-ca4e1f5b8a7c489805af2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 3-glucoside 20V, Negative-QTOFsplash10-00di-4100490000-8e1fbe2572cc073992392021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clerosterol 3-glucoside 40V, Negative-QTOFsplash10-0a4i-9002420000-91b74e417a13b4f621782021-09-25Wishart 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 IDFDB012502
KNApSAcK IDNot Available
Chemspider ID10474667
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14311739
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.