25-Azacholesterol (CHEM035037)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:26:10 UTC
Update Date2016-11-09 01:21:14 UTC
Accession NumberCHEM035037
Identification
Common Name25-Azacholesterol
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta)-24-(dimethylamino)-Chol-5-en-3-olHMDB
24-(dimethylamino)Chol-5-en-3beta-olHMDB
24-(dimethylamino)Chol-5-en-3 beta-olMeSH, HMDB
Chemical FormulaC26H45NO
Average Molecular Mass387.642 g/mol
Monoisotopic Mass387.350 g/mol
CAS Registry Number1973-61-1
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-5-(dimethylamino)pentan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional Name25-azacholesterol
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCN(C)C
InChI IdentifierInChI=1S/C26H45NO/c1-18(7-6-16-27(4)5)22-10-11-23-21-9-8-19-17-20(28)12-14-25(19,2)24(21)13-15-26(22,23)3/h8,18,20-24,28H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26-/m1/s1
InChI KeyRZPPEFJMRVRCDD-XSLNCIIRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 25-azasteroids and derivatives. These are azasteroids where the carbon atom at position 25 is replaced by a nitrogen atom.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAzasteroids and derivatives
Direct Parent25-azasteroids and derivatives
Alternative Parents
Substituents
  • 25-azasteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen 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 Solubility0.00022 g/LALOGPS
logP5.74ALOGPS
logP5.21ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.52 m³·mol⁻¹ChemAxon
Polarizability50.04 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-1109000000-f5ff026e303e1f936133Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0537-5104900000-019f268d7a583a080fb4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0009000000-f51472900bc87c0a5f52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-009l-1029000000-ce2f5ffd6b9bbae51f14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-5289000000-31a238e0014232ddab59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-74f294bbd7bfc4e4a2acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-72958248b3206fa61b1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-2009000000-1a9f32b77ddd2fc5611bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-d3af83736c6337f4138cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4v-7279000000-1c3cb8189566196cb292Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9810000000-8eb0011e2f4a452bc336Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-37d8acdc244819d61e09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-5ff1c6d45a64ff5f57afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0009000000-eb7f6fb387795c01b9dbSpectrum
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 IDHMDB0001028
FooDB IDFDB022378
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5954
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID144573
ChEBI IDNot Available
PubChem Compound ID164906
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. COUNSELL RE, KLIMSTRA PD, NYSTED LN, RANNEY RE: HYPOCHOLESTEROLEMIC AGENTS. V. ISOMERIC AZACHOLESTEROLS. J Med Chem. 1965 Jan;8:45-8.
2. Counsell RE, Lu MC, el-Masry S, Weinhold PA: Inhibition of cholesterol side-chain cleavage by azacholesterols. Biochem Pharmacol. 1971 Oct;20(10):2912-5.
3. Kabara JJ, Holzschu DL, Catsoulacos DP: Structure-function activity of azasterols and nitrogen-containing steroids. Lipids. 1976 Oct;11(10):755-62.
4. Eberstein A, Goodgold J: Isotonic contraction of induced myotonic muscle of rat: after contraction and prolonged relaxation time. Exp Neurol. 1972 Jan;34(1):183-6.