6-Deoxocastasterone (CHEM028094)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:13:00 UTC
Update Date2016-11-09 01:18:36 UTC
Accession NumberCHEM028094
Identification
Common Name6-Deoxocastasterone
ClassSmall Molecule
DescriptionA 3alpha-hydroxy steroid that is castasterone which is lacking the oxo substituent at position 6.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(22R,23R)-5alpha-Campestane-2alpha,3alpha,22,23-tetraolHMDB
(2alpha,3alpha,5alpha,22R,23R,24S)-Ergostane-2,3,22,23-tetrolHMDB
(2α,3α,5α,22R,23R,24S)-Ergostane-2,3,22,23-tetrolHMDB
6-DeoxocastasteroneHMDB
Chemical FormulaC28H50O4
Average Molecular Mass450.694 g/mol
Monoisotopic Mass450.371 g/mol
CAS Registry Number87833-54-3
IUPAC Name(1S,2S,4R,5S,7S,10R,11S,14R,15S)-14-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-4,5-diol
Traditional Name6-deoxocastasterone
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)[C@H](O)C[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C(C)C
InChI IdentifierInChI=1S/C28H50O4/c1-15(2)16(3)25(31)26(32)17(4)20-9-10-21-19-8-7-18-13-23(29)24(30)14-28(18,6)22(19)11-12-27(20,21)5/h15-26,29-32H,7-14H2,1-6H3/t16-,17-,18-,19-,20+,21-,22-,23-,24+,25+,26+,27+,28-/m0/s1
InChI KeyVXBLCLVRWCLEOX-BFYSZXNBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTetrahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • Ergostane-skeleton
  • Tetrahydroxy bile acid, alcohol, or derivatives
  • 23-hydroxysteroid
  • 22-hydroxysteroid
  • 3-hydroxysteroid
  • 2-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP3.7ALOGPS
logP4.42ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)13.46ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity128.55 m³·mol⁻¹ChemAxon
Polarizability54.88 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8l-2114900000-0ea2d7b1e7827d58b5e5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-3121059000-931d9c0b1c46e7e4e5d6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0102900000-1a2ab3e4929370c864a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fz9-6209400000-cfbc933808f2abf965feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9457200000-9e8ba0989a95d0b739d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0001900000-d94aed4a6c35dbe42f0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00rt-5308900000-f118dba5bdfc90592ab8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0601-9208100000-93a0ead28648bb8fc0c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-93af15f714f2bd1654b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1101900000-7fe2a2ac334e35fd4bacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3009800000-b55dc3c9c0f13f61b71cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0029300000-61388fca42706d1f64a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v4i-5139100000-2403cddd99985a35e011Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ll3-9811000000-a619fa6e0346cfeea41aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0033984
FooDB IDFDB012216
Phenol Explorer IDNot Available
KNApSAcK IDC00000199
BiGG IDNot Available
BioCyc IDCPD-723
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID21864867
ChEBI ID20712
PubChem Compound ID13870433
Kegg Compound IDC15802
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14502988
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=9927639
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. 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.
5. 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.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
8. The lipid handbook with CD-ROM