Oxyacanthine (CHEM024198)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:33:26 UTC
Update Date2016-11-09 01:17:50 UTC
Accession NumberCHEM024198
Identification
Common NameOxyacanthine
ClassSmall Molecule
DescriptionAlkaloid from Berberis vulgaris (barberry). Oxyacanthine is found in tea and fruits.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
6,6',7-Trimethoxy-2,2'-dimethyloxyacanthan-12'-olHMDB
6,6'7'-Trimethoxy-2,2'-dimethyl-oxyacanthan-12'-olHMDB
6,6'7-Trimethoxy-2,2'-dimethyl-oxyacanthan-12'-olHMDB
N-MethylocoteamineHMDB
N-MethylsepeerineHMDB
OxycanthineHMDB
Chemical FormulaC37H40N2O6
Average Molecular Mass608.723 g/mol
Monoisotopic Mass608.289 g/mol
CAS Registry Number548-40-3
IUPAC Name20,21,25-trimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3(36),4,6,9,11,18,20,22(33),24,26,31,34-dodecaen-6-ol
Traditional Name20,21,25-trimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3(36),4,6,9,11,18,20,22(33),24,26,31,34-dodecaen-6-ol
SMILESCOC1=C2OC3=C4C(CC5=CC=C(OC6=C(O)C=CC(CC7N(C)CCC(=C1)C7=C2)=C6)C=C5)N(C)CCC4=CC(OC)=C3OC
InChI IdentifierInChI=1S/C37H40N2O6/c1-38-14-12-24-19-32(41-3)33-21-27(24)28(38)17-23-8-11-30(40)31(18-23)44-26-9-6-22(7-10-26)16-29-35-25(13-15-39(29)2)20-34(42-4)36(43-5)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3
InChI KeyHGNHIFJNOKGSKI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassNot Available
Sub ClassNot Available
Direct ParentLignans, neolignans and related compounds
Alternative Parents
Substituents
  • Oxyneolignan skeleton
  • Diaryl ether
  • Tetrahydroisoquinoline
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.0074 g/LALOGPS
logP5.52ALOGPS
logP5.72ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)8.94ChemAxon
pKa (Strongest Basic)8.32ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.86 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity175.63 m³·mol⁻¹ChemAxon
Polarizability66.46 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-0000090000-c412b15bd9537b35a376Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-1000009000-1223820c9148dc5e06c5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Oxyacanthine,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0000009000-28831833ea904387d520Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0000009000-38aaab7723d1f732dda6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000039000-2bad9850c5dc0f081dd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7i-0000093000-2790909e7f0f30709acfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0j4j-0000090000-25372cf1899667ad464eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000009000-62bbbb52d6800c881d5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0000097000-49657eb97feeda86a735Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-0000190000-9c83502b2c4a0e62bf78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000009000-243a991931ec2986982aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-0000094000-c16ffa8f9e1a6a7a1b98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0000090000-baf9852cd591be14f779Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-5debb5ccf794890680efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000059000-9d376161adb6686be389Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pec-1000090000-60cd43712b70897111e5Spectrum
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 IDHMDB0030172
FooDB IDFDB001988
Phenol Explorer IDNot Available
KNApSAcK IDC00001897
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID329538
ChEBI ID7853
PubChem Compound ID371257
Kegg Compound IDC09598
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.