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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:16:35 UTC
Update Date2022-03-07 02:57:05 UTC
HMDB IDHMDB0041583
Secondary Accession Numbers
  • HMDB41583
Metabolite Identification
Common NameSetariol
DescriptionSetariol belongs to the class of organic compounds known as 14-hydroxysteroids. These are steroids carrying a hydroxyl group at the 14-position of the steroid backbone. Setariol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863680
Synonyms
ValueSource
9,19-Cyclocholesta-7,20-diene-3,14,26-triolHMDB
Chemical FormulaC27H42O3
Average Molecular Weight414.6206
Monoisotopic Molecular Weight414.31339521
IUPAC Name15-(7-hydroxy-6-methylhept-1-en-2-yl)-16-methylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-ene-6,12-diol
Traditional Name15-(7-hydroxy-6-methylhept-1-en-2-yl)-16-methylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-10-ene-6,12-diol
CAS Registry Number142942-85-6
SMILES
CC(CO)CCCC(=C)C1CCC2(O)C3=CCC4CC(O)CCC44CC34CCC12C
InChI Identifier
InChI=1S/C27H42O3/c1-18(16-28)5-4-6-19(2)22-10-12-27(30)23-8-7-20-15-21(29)9-11-25(20)17-26(23,25)14-13-24(22,27)3/h8,18,20-22,28-30H,2,4-7,9-17H2,1,3H3
InChI KeyLHQZNTIWWWUEJH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 14-hydroxysteroids. These are steroids carrying a hydroxyl group at the 14-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent14-hydroxysteroids
Alternative Parents
Substituents
  • 14-hydroxysteroid
  • 3-hydroxysteroid
  • Fatty alcohol
  • Fatty acyl
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point270 - 271 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP4.78ALOGPS
logP3.79ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)17.42ChemAxon
pKa (Strongest Basic)0.007ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity121.69 m³·mol⁻¹ChemAxon
Polarizability50.27 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.72931661259
DarkChem[M-H]-193.07131661259
DeepCCS[M-2H]-242.12930932474
DeepCCS[M+Na]+217.46130932474
AllCCS[M+H]+207.232859911
AllCCS[M+H-H2O]+205.232859911
AllCCS[M+NH4]+209.032859911
AllCCS[M+Na]+209.532859911
AllCCS[M-H]-204.632859911
AllCCS[M+Na-2H]-206.232859911
AllCCS[M+HCOO]-208.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SetariolCC(CO)CCCC(=C)C1CCC2(O)C3=CCC4CC(O)CCC44CC34CCC12C3008.0Standard polar33892256
SetariolCC(CO)CCCC(=C)C1CCC2(O)C3=CCC4CC(O)CCC44CC34CCC12C3359.3Standard non polar33892256
SetariolCC(CO)CCCC(=C)C1CCC2(O)C3=CCC4CC(O)CCC44CC34CCC12C3593.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Setariol,1TMS,isomer #1C=C(CCCC(C)CO[Si](C)(C)C)C1CCC2(O)C3=CCC4CC(O)CCC45CC35CCC12C3605.0Semi standard non polar33892256
Setariol,1TMS,isomer #2C=C(CCCC(C)CO)C1CCC2(O[Si](C)(C)C)C3=CCC4CC(O)CCC45CC35CCC12C3612.6Semi standard non polar33892256
Setariol,1TMS,isomer #3C=C(CCCC(C)CO)C1CCC2(O)C3=CCC4CC(O[Si](C)(C)C)CCC45CC35CCC12C3631.0Semi standard non polar33892256
Setariol,2TMS,isomer #1C=C(CCCC(C)CO[Si](C)(C)C)C1CCC2(O[Si](C)(C)C)C3=CCC4CC(O)CCC45CC35CCC12C3587.4Semi standard non polar33892256
Setariol,2TMS,isomer #2C=C(CCCC(C)CO[Si](C)(C)C)C1CCC2(O)C3=CCC4CC(O[Si](C)(C)C)CCC45CC35CCC12C3671.5Semi standard non polar33892256
Setariol,2TMS,isomer #3C=C(CCCC(C)CO)C1CCC2(O[Si](C)(C)C)C3=CCC4CC(O[Si](C)(C)C)CCC45CC35CCC12C3597.1Semi standard non polar33892256
Setariol,3TMS,isomer #1C=C(CCCC(C)CO[Si](C)(C)C)C1CCC2(O[Si](C)(C)C)C3=CCC4CC(O[Si](C)(C)C)CCC45CC35CCC12C3537.0Semi standard non polar33892256
Setariol,1TBDMS,isomer #1C=C(CCCC(C)CO[Si](C)(C)C(C)(C)C)C1CCC2(O)C3=CCC4CC(O)CCC45CC35CCC12C3860.0Semi standard non polar33892256
Setariol,1TBDMS,isomer #2C=C(CCCC(C)CO)C1CCC2(O[Si](C)(C)C(C)(C)C)C3=CCC4CC(O)CCC45CC35CCC12C3842.9Semi standard non polar33892256
Setariol,1TBDMS,isomer #3C=C(CCCC(C)CO)C1CCC2(O)C3=CCC4CC(O[Si](C)(C)C(C)(C)C)CCC45CC35CCC12C3851.0Semi standard non polar33892256
Setariol,2TBDMS,isomer #1C=C(CCCC(C)CO[Si](C)(C)C(C)(C)C)C1CCC2(O[Si](C)(C)C(C)(C)C)C3=CCC4CC(O)CCC45CC35CCC12C4061.3Semi standard non polar33892256
Setariol,2TBDMS,isomer #2C=C(CCCC(C)CO[Si](C)(C)C(C)(C)C)C1CCC2(O)C3=CCC4CC(O[Si](C)(C)C(C)(C)C)CCC45CC35CCC12C4145.2Semi standard non polar33892256
Setariol,2TBDMS,isomer #3C=C(CCCC(C)CO)C1CCC2(O[Si](C)(C)C(C)(C)C)C3=CCC4CC(O[Si](C)(C)C(C)(C)C)CCC45CC35CCC12C4040.7Semi standard non polar33892256
Setariol,3TBDMS,isomer #1C=C(CCCC(C)CO[Si](C)(C)C(C)(C)C)C1CCC2(O[Si](C)(C)C(C)(C)C)C3=CCC4CC(O[Si](C)(C)C(C)(C)C)CCC45CC35CCC12C4251.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Setariol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000b-0139000000-ecae12880f2afae814d62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Setariol GC-MS (3 TMS) - 70eV, Positivesplash10-014i-3401229000-844705e96bea5a9eb8fa2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Setariol 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 - Setariol 10V, Positive-QTOFsplash10-002b-0009100000-16c586c2210d287824d82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Setariol 20V, Positive-QTOFsplash10-002b-1209000000-58d220b8ad87742a8f322017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Setariol 40V, Positive-QTOFsplash10-066r-4209000000-a4fdd578a9439dc93f382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Setariol 10V, Negative-QTOFsplash10-03di-0006900000-7c8c0b5147523e8c9f542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Setariol 20V, Negative-QTOFsplash10-01ot-0009400000-c91a367df67133f2296f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Setariol 40V, Negative-QTOFsplash10-014i-2009000000-804a3829ee499d28dbca2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Setariol 10V, Positive-QTOFsplash10-00mk-9506500000-7e2c1e3c2277862c11cd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Setariol 20V, Positive-QTOFsplash10-0cdi-9712100000-90722d765e1401d30ec52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Setariol 40V, Positive-QTOFsplash10-0670-9351200000-8d4ec82ffd8d52e1adce2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Setariol 10V, Negative-QTOFsplash10-03di-0000900000-382bbcadd43c6789b8322021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Setariol 20V, Negative-QTOFsplash10-03di-0005900000-3376f225c75019e73d0c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Setariol 40V, Negative-QTOFsplash10-03di-0004900000-6bf51e733c03ade024642021-09-24Wishart 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 IDFDB021575
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131753169
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.