Santamarin (CHEM025991)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:43:26 UTC
Update Date2016-11-09 01:18:11 UTC
Accession NumberCHEM025991
Identification
Common NameSantamarin
ClassSmall Molecule
DescriptionA sesquiterpene lactone of the eudesmanolide group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-SantamarineChEBI
(3AS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-decahydro-6alpha-hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-oneChEBI
(3AS,5ar,6R,9as,9BS)-6-hydroxy-5a,9-dimethyl-3-methylene-3a,4,5,5a,6,7,9a,9b-octahydro-3H-naphtho[1,2-b]furan-2-oneChEBI
(3AS,5ar,6R,9as,9BS)-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,9a,9b-hexahydro-3ah-benzo[g][1]benzofuran-2-oneChEBI
BalchaninChEBI
SantamarineChEBI
(3AS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-decahydro-6a-hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-oneGenerator
(3AS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-decahydro-6α-hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-oneGenerator
Chemical FormulaC15H20O3
Average Molecular Mass248.318 g/mol
Monoisotopic Mass248.141 g/mol
CAS Registry Number4290-13-5
IUPAC Name(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,9aH,9bH-naphtho[1,2-b]furan-2-one
Traditional Name(+)-santamarine
SMILESCC1=CC[C@@H](O)[C@]2(C)CC[C@@H]3[C@H](OC(=O)C3=C)[C@@H]12
InChI IdentifierInChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h4,10-13,16H,2,5-7H2,1,3H3/t10-,11+,12+,13-,15-/m0/s1
InChI KeyPLSSEPIRACGCBO-PFFFPCNUSA-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
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • 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
Water Solubility0.97 g/LALOGPS
logP2.44ALOGPS
logP2.15ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)14.63ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.71 m³·mol⁻¹ChemAxon
Polarizability27.41 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, Positivesplash10-001j-0290000000-789eefe074e1b12c084dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f8a-1940000000-dc7583a16431bb675821Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1003-9310000000-6677ba80414870d17185Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-d29ad4e4535fa5263291Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0190000000-997de3e007cc13186660Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3920000000-2246bdfb040620ee52ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-b55c1d7eb34f2d130acaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0390000000-aa9891c63c3267405779Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-1910000000-296693f45a2dbc58341aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-7b3a58b796a0e4263959Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-7e0e38a32353911a24e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016u-3390000000-b3cad309313dc9047892Spectrum
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 IDHMDB0302709
FooDB IDFDB005897
Phenol Explorer IDNot Available
KNApSAcK IDC00003363
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID163664
ChEBI ID9023
PubChem Compound ID188297
Kegg Compound IDC09544
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=6476889