alpha-Santonin (CHEM018240)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:05:12 UTC
Update Date2016-11-09 01:15:45 UTC
Accession NumberCHEM018240
Identification
Common Namealpha-Santonin
ClassSmall Molecule
DescriptionA santonin that is 3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione substituted by methyl groups at positions 3, 5a and 9.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-alpha-SantoninChEBI
(-)-SantoninChEBI
(11S)-6alpha-Hydroxy-3-oxoeudesma-1,4-dien-12-Oic acid gamma-lactoneChEBI
6alpha-Hydroxy-3-oxo-11-epiisoeusantona-1,4-dienic acid gamma-lactoneChEBI
Santoninic anhydrideChEBI
(-)-a-SantoninGenerator
(-)-Α-santoninGenerator
(11S)-6a-Hydroxy-3-oxoeudesma-1,4-dien-12-Oate g-lactoneGenerator
(11S)-6a-Hydroxy-3-oxoeudesma-1,4-dien-12-Oic acid g-lactoneGenerator
(11S)-6alpha-Hydroxy-3-oxoeudesma-1,4-dien-12-Oate gamma-lactoneGenerator
(11S)-6Α-hydroxy-3-oxoeudesma-1,4-dien-12-Oate γ-lactoneGenerator
(11S)-6Α-hydroxy-3-oxoeudesma-1,4-dien-12-Oic acid γ-lactoneGenerator
6a-Hydroxy-3-oxo-11-epiisoeusantona-1,4-dienate g-lactoneGenerator
6a-Hydroxy-3-oxo-11-epiisoeusantona-1,4-dienic acid g-lactoneGenerator
6alpha-Hydroxy-3-oxo-11-epiisoeusantona-1,4-dienate gamma-lactoneGenerator
6Α-hydroxy-3-oxo-11-epiisoeusantona-1,4-dienate γ-lactoneGenerator
6Α-hydroxy-3-oxo-11-epiisoeusantona-1,4-dienic acid γ-lactoneGenerator
a-SantoninGenerator
Α-santoninGenerator
SantoninMeSH
Chemical FormulaC15H18O3
Average Molecular Mass246.306 g/mol
Monoisotopic Mass246.126 g/mol
CAS Registry Number481-06-1
IUPAC Name(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione
Traditional Name(-)-santonin
SMILES[H][C@@]1(C)C(=O)O[C@]2([H])C3=C(C)C(=O)C=C[C@]3(C)CC[C@@]12[H]
InChI IdentifierInChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10-,13-,15-/m0/s1
InChI KeyXJHDMGJURBVLLE-BOCCBSBMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentEudesmanolides, secoeudesmanolides, and derivatives
Alternative Parents
Substituents
  • Eudesmanolide
  • Sesquiterpenoid
  • Naphthofuran
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Cyclic ketone
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP2.6ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.83 m³·mol⁻¹ChemAxon
Polarizability26.57 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0390000000-8de37b3b8a29d7b72190Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-3940000000-e981fed5f681ed396603Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9810000000-e5b6e3c5ca4d9d4f4b83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-9dd579e1dfab5c39d037Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0290000000-880f0c0b64e439abf18aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uka-2910000000-587274b8c13b87b9a417Spectrum
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 IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00003364
BiGG IDNot Available
BioCyc IDALPHA-SANTONIN
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSantonin
Chemspider IDNot Available
ChEBI ID16363
PubChem Compound ID221071
Kegg Compound IDC02206
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11098821
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15241928
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=2185125