Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:49:35 UTC
Update Date2022-03-07 02:54:38 UTC
HMDB IDHMDB0035804
Secondary Accession Numbers
  • HMDB35804
Metabolite Identification
Common NameSchleicherastatin 5
DescriptionSchleicherastatin 5 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. Schleicherastatin 5 is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862774
Synonyms
ValueSource
3,22-Dihydroxystigmast-5-en-7-oneHMDB
Chemical FormulaC29H48O3
Average Molecular Weight444.6896
Monoisotopic Molecular Weight444.360345402
IUPAC Name14-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-one
Traditional Name14-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-one
CAS Registry Number256445-58-6
SMILES
CCC(CC(O)C(C)C1CCC2C3C(CCC12C)C1(C)CCC(O)CC1=CC3=O)C(C)C
InChI Identifier
InChI=1S/C29H48O3/c1-7-19(17(2)3)14-25(31)18(4)22-8-9-23-27-24(11-13-29(22,23)6)28(5)12-10-21(30)15-20(28)16-26(27)32/h16-19,21-25,27,30-31H,7-15H2,1-6H3
InChI KeyXWLHFTUCQDCSTJ-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 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 Point162 - 166 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0031 g/LALOGPS
logP5.01ALOGPS
logP5.97ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)17.39ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity132 m³·mol⁻¹ChemAxon
Polarizability54.42 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
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]+204.12731661259
DarkChem[M-H]-200.46831661259
DeepCCS[M-2H]-242.78730932474
DeepCCS[M+Na]+218.01430932474
AllCCS[M+H]+213.032859911
AllCCS[M+H-H2O]+211.132859911
AllCCS[M+NH4]+214.632859911
AllCCS[M+Na]+215.132859911
AllCCS[M-H]-208.632859911
AllCCS[M+Na-2H]-211.032859911
AllCCS[M+HCOO]-213.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Schleicherastatin 5CCC(CC(O)C(C)C1CCC2C3C(CCC12C)C1(C)CCC(O)CC1=CC3=O)C(C)C3908.8Standard polar33892256
Schleicherastatin 5CCC(CC(O)C(C)C1CCC2C3C(CCC12C)C1(C)CCC(O)CC1=CC3=O)C(C)C3426.2Standard non polar33892256
Schleicherastatin 5CCC(CC(O)C(C)C1CCC2C3C(CCC12C)C1(C)CCC(O)CC1=CC3=O)C(C)C3712.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Schleicherastatin 5,1TMS,isomer #1CCC(CC(O[Si](C)(C)C)C(C)C1CCC2C3C(=O)C=C4CC(O)CCC4(C)C3CCC12C)C(C)C3767.7Semi standard non polar33892256
Schleicherastatin 5,1TMS,isomer #2CCC(CC(O)C(C)C1CCC2C3C(=O)C=C4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C)C(C)C3805.0Semi standard non polar33892256
Schleicherastatin 5,1TMS,isomer #3CCC(CC(O)C(C)C1CCC2C3=C(O[Si](C)(C)C)C=C4CC(O)CCC4(C)C3CCC21C)C(C)C3716.6Semi standard non polar33892256
Schleicherastatin 5,2TMS,isomer #1CCC(CC(O[Si](C)(C)C)C(C)C1CCC2C3C(=O)C=C4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C)C(C)C3669.4Semi standard non polar33892256
Schleicherastatin 5,2TMS,isomer #2CCC(CC(O[Si](C)(C)C)C(C)C1CCC2C3=C(O[Si](C)(C)C)C=C4CC(O)CCC4(C)C3CCC21C)C(C)C3641.5Semi standard non polar33892256
Schleicherastatin 5,2TMS,isomer #3CCC(CC(O)C(C)C1CCC2C3=C(O[Si](C)(C)C)C=C4CC(O[Si](C)(C)C)CCC4(C)C3CCC21C)C(C)C3744.4Semi standard non polar33892256
Schleicherastatin 5,3TMS,isomer #1CCC(CC(O[Si](C)(C)C)C(C)C1CCC2C3=C(O[Si](C)(C)C)C=C4CC(O[Si](C)(C)C)CCC4(C)C3CCC21C)C(C)C3573.5Semi standard non polar33892256
Schleicherastatin 5,3TMS,isomer #1CCC(CC(O[Si](C)(C)C)C(C)C1CCC2C3=C(O[Si](C)(C)C)C=C4CC(O[Si](C)(C)C)CCC4(C)C3CCC21C)C(C)C3674.7Standard non polar33892256
Schleicherastatin 5,1TBDMS,isomer #1CCC(CC(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3C(=O)C=C4CC(O)CCC4(C)C3CCC12C)C(C)C3988.8Semi standard non polar33892256
Schleicherastatin 5,1TBDMS,isomer #2CCC(CC(O)C(C)C1CCC2C3C(=O)C=C4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C)C(C)C4010.8Semi standard non polar33892256
Schleicherastatin 5,1TBDMS,isomer #3CCC(CC(O)C(C)C1CCC2C3=C(O[Si](C)(C)C(C)(C)C)C=C4CC(O)CCC4(C)C3CCC21C)C(C)C3946.6Semi standard non polar33892256
Schleicherastatin 5,2TBDMS,isomer #1CCC(CC(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3C(=O)C=C4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C)C(C)C4101.4Semi standard non polar33892256
Schleicherastatin 5,2TBDMS,isomer #2CCC(CC(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3=C(O[Si](C)(C)C(C)(C)C)C=C4CC(O)CCC4(C)C3CCC21C)C(C)C4104.1Semi standard non polar33892256
Schleicherastatin 5,2TBDMS,isomer #3CCC(CC(O)C(C)C1CCC2C3=C(O[Si](C)(C)C(C)(C)C)C=C4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC21C)C(C)C4182.1Semi standard non polar33892256
Schleicherastatin 5,3TBDMS,isomer #1CCC(CC(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3=C(O[Si](C)(C)C(C)(C)C)C=C4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC21C)C(C)C4274.1Semi standard non polar33892256
Schleicherastatin 5,3TBDMS,isomer #1CCC(CC(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3=C(O[Si](C)(C)C(C)(C)C)C=C4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC21C)C(C)C4391.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Schleicherastatin 5 GC-MS (Non-derivatized) - 70eV, Positivesplash10-00p0-3023900000-eac41a0b402f4994d8462017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Schleicherastatin 5 GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4013390000-57e2333dec608acbf64a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Schleicherastatin 5 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Schleicherastatin 5 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 - Schleicherastatin 5 10V, Positive-QTOFsplash10-004j-0000900000-992f047838ca4f67e4402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Schleicherastatin 5 20V, Positive-QTOFsplash10-004j-4128900000-1cfd5bd134a6c8d74efa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Schleicherastatin 5 40V, Positive-QTOFsplash10-00p1-9426200000-b1bdcd06c88ee3eab8252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Schleicherastatin 5 10V, Negative-QTOFsplash10-0006-0000900000-617568e4f9d0b0460c2d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Schleicherastatin 5 20V, Negative-QTOFsplash10-002f-1001900000-61cbb92f20ec4930d5342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Schleicherastatin 5 40V, Negative-QTOFsplash10-00mt-9166700000-593e65bf681c021429522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Schleicherastatin 5 10V, Positive-QTOFsplash10-0002-1206900000-397d5f48b1ca783d50ac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Schleicherastatin 5 20V, Positive-QTOFsplash10-0006-5129100000-30c19477a9037923ad002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Schleicherastatin 5 40V, Positive-QTOFsplash10-000i-6192000000-a05b62477131769f22652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Schleicherastatin 5 10V, Negative-QTOFsplash10-0006-0000900000-bd91a2756ebb8372ba0c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Schleicherastatin 5 20V, Negative-QTOFsplash10-0006-1100900000-7de130acc724b1c88e5c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Schleicherastatin 5 40V, Negative-QTOFsplash10-0403-2203900000-1387d2679001276ab9c32021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
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 IDFDB014556
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73105735
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.