(S)-scoulerine (CHEM041781)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:41:51 UTC
Update Date2016-11-09 01:22:32 UTC
Accession NumberCHEM041781
Identification
Common Name(S)-scoulerine
ClassSmall Molecule
DescriptionA berberine alkaloid isolated from Corydalis saxicola.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-ScoulerineChEBI
(13AS)-5,8,13,13a-tetrahydro-3,10-dimethoxy-6H-dibenzo[a,g]quinolizine-2,9-diolChEBI
Aequaline, (S)-isomerMeSH
Discretamine, (S)-isomerMeSH
Discretamine, hydrochloride, (S)-isomerMeSH
ScoulerineMeSH
AequalineMeSH
DiscretamineMeSH
Discretamine, (+-)-isomerMeSH
Discretamine, (R)-isomerMeSH
Scoulerine, (S)-isomerMeSH
Chemical FormulaC19H21NO4
Average Molecular Mass327.374 g/mol
Monoisotopic Mass327.147 g/mol
CAS Registry NumberNot Available
IUPAC Name(12bS)-3,10-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene-4,11-diol
Traditional Namescoulerine
SMILES[H][C@@]12CC3=C(CN1CCC1=CC(OC)=C(O)C=C21)C(O)=C(OC)C=C3
InChI IdentifierInChI=1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1
InChI KeyKNWVMRVOBAFFMH-HNNXBMFYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassProtoberberine alkaloids and derivatives
Sub ClassNot Available
Direct ParentProtoberberine alkaloids and derivatives
Alternative Parents
Substituents
  • Protoberberine skeleton
  • Tetrahydroprotoberberine skeleton
  • Tetrahydroisoquinoline
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 Solubility0.25 g/LALOGPS
logP2.26ALOGPS
logP2.86ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.18ChemAxon
pKa (Strongest Basic)6.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.16 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity92.39 m³·mol⁻¹ChemAxon
Polarizability35.71 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-004i-0009000000-a6406c37c5a38fb14c40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0259000000-8934a4b70a5fffa52f5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02cg-0691000000-10a442a9de5a7ae08a3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-6e3aa03a41770554d21dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0029000000-3d97b2116f211dc8b71fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gx0-0290000000-b6ebcd9589894d29cac7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-354160c39518aa1987e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0129000000-bdd1a02d898924e60a15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0930000000-114dd08705b3da654af1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-82e8b7e0c70cdc0f9fe6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0039000000-2688aca3f291e16e783cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007o-0192000000-fd58d0eefaf205a92af4Spectrum
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 IDHMDB0304001
FooDB IDFDB030176
Phenol Explorer IDNot Available
KNApSAcK IDC00026092
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkScoulerine
Chemspider ID388725
ChEBI ID17129
PubChem Compound IDNot Available
Kegg Compound IDC02106
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18649321
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22029392