5beta-Cholestane-3alpha,7alpha,12alpha,23-tetrol (CHEM035290)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:38:15 UTC
Update Date2016-11-09 01:21:17 UTC
Accession NumberCHEM035290
Identification
Common Name5beta-Cholestane-3alpha,7alpha,12alpha,23-tetrol
ClassSmall Molecule
DescriptionA prostaglandin Falpha that is prostaglandin F1alpha bearing keto substituents at positions 6 and 15.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
6,15-Dioxo-9S,11R-dihydroxy-13E-prostenoic acidChEBI
6,15DK,13,14DH-PGF1aChEBI
6,15-Dioxo-9S,11R-dihydroxy-13E-prostenoateGenerator
6,15-Diketo,13,14-dihydro-PGF1alphaHMDB
6,15-Diketo-13,14-dihydro-PGF1aHMDB
6,15-Diketo,13,14-dihydroprostaglandin F1aHMDB
6,15-Diketo,13,14-dihydroprostaglandin F1αHMDB
(3a,5b,7a,12a)-Cholestane-3,7,12,23-tetrolHMDB
Chemical FormulaC27H48O4
Average Molecular Mass436.668 g/mol
Monoisotopic Mass436.355 g/mol
CAS Registry Number30673-09-7
IUPAC Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-4-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
Traditional Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-4-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CC(O)CC(C)C
InChI IdentifierInChI=1S/C27H48O4/c1-15(2)10-19(29)11-16(3)20-6-7-21-25-22(14-24(31)27(20,21)5)26(4)9-8-18(28)12-17(26)13-23(25)30/h15-25,28-31H,6-14H2,1-5H3/t16-,17+,18-,19?,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyVGCSSPQIZFVVCH-UVBCEDGCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Keto fatty acid
  • Cyclopentanol
  • Alpha,beta-unsaturated ketone
  • Cyclic alcohol
  • Enone
  • Acryloyl-group
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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 Solubility0.03 g/LALOGPS
logP3.47ALOGPS
logP3.59ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-0.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.54 m³·mol⁻¹ChemAxon
Polarizability53.14 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, Positivesplash10-00ko-2449800000-93820315c41fb7c76c17Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000i-2110159000-8b13bca0a8a63a5bcd32Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0000900000-7950bd2792cc6bad073fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-3005900000-a5d03f8ad5d28c8983aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-4009100000-817e6322f5b9047ab17dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0001900000-60349b29ea462565d721Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-1003900000-dead6b17fc57cf8148a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-7009600000-f2635f5c50245cf34447Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0004900000-aa0c91bf9f760064d700Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-8359700000-020c6e520227d67540cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-8930000000-bbaa5046aa9759972d67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-0c413525e4be8a74c95dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-42df38f6f19517fcfd4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0001900000-67dddf27bd385e67e912Spectrum
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 IDHMDB0001979
FooDB IDFDB022777
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4446160
ChEBI ID72595
PubChem Compound ID5283033
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Rosenkranz B, Fischer C, Weimer KE, Frolich JC: Metabolism of prostacyclin and 6-keto-prostaglandin F1 alpha in man. J Biol Chem. 1980 Nov 10;255(21):10194-8.
2. FitzGerald GA, Smith B, Pedersen AK, Brash AR: Increased prostacyclin biosynthesis in patients with severe atherosclerosis and platelet activation. N Engl J Med. 1984 Apr 26;310(17):1065-8.
3. Kothapalli D, Flores-Stewart SA, Assoian RK: Antimitogenic effects of prostacyclin on the G1 phase cyclin-dependent kinases. Prostaglandins Other Lipid Mediat. 2005 Dec;78(1-4):3-13. Epub 2005 May 31.
4. Ruan KH, Dogne JM: Implications of the molecular basis of prostacyclin biosynthesis and signaling in pharmaceutical designs. Curr Pharm Des. 2006;12(8):925-41.
5. Nakayama T: Prostacyclin analogues: prevention of cardiovascular diseases. Cardiovasc Hematol Agents Med Chem. 2006 Oct;4(4):351-9.
6. Fetalvero KM, Martin KA, Hwa J: Cardioprotective prostacyclin signaling in vascular smooth muscle. Prostaglandins Other Lipid Mediat. 2007 Jan;82(1-4):109-18. Epub 2006 Jul 7.