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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:15 UTC
Update Date2022-03-07 02:52:27 UTC
HMDB IDHMDB0030172
Secondary Accession Numbers
  • HMDB30172
Metabolite Identification
Common NameOxyacanthine
DescriptionOxyacanthine, also known as N-methylsepeerine, 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. Oxyacanthine is a very strong basic compound (based on its pKa). Oxyacanthine is a bitter tasting compound. Outside of the human body, oxyacanthine has been detected, but not quantified in, fruits and tea. This could make oxyacanthine a potential biomarker for the consumption of these foods.
Structure
Data?1563861948
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 Weight608.7233
Monoisotopic Molecular Weight608.288637022
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
CAS Registry Number548-40-3
SMILES
COC1=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 Identifier
InChI=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
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point212 - 214 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+230.99131661259
DarkChem[M-H]-229.29231661259
DeepCCS[M+H]+242.47630932474
DeepCCS[M-H]-240.60830932474
DeepCCS[M-2H]-273.84730932474
DeepCCS[M+Na]+248.27530932474
AllCCS[M+H]+245.032859911
AllCCS[M+H-H2O]+243.732859911
AllCCS[M+NH4]+246.132859911
AllCCS[M+Na]+246.532859911
AllCCS[M-H]-232.832859911
AllCCS[M+Na-2H]-234.232859911
AllCCS[M+HCOO]-235.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OxyacanthineCOC1=C2OC3=C4C(CC5=CC=C(OC6=C(O)C=CC(CC7N(C)CCC(=C1)C7=C2)=C6)C=C5)N(C)CCC4=CC(OC)=C3OC5651.4Standard polar33892256
OxyacanthineCOC1=C2OC3=C4C(CC5=CC=C(OC6=C(O)C=CC(CC7N(C)CCC(=C1)C7=C2)=C6)C=C5)N(C)CCC4=CC(OC)=C3OC4564.7Standard non polar33892256
OxyacanthineCOC1=C2OC3=C4C(CC5=CC=C(OC6=C(O)C=CC(CC7N(C)CCC(=C1)C7=C2)=C6)C=C5)N(C)CCC4=CC(OC)=C3OC4682.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxyacanthine,1TMS,isomer #1COC1=CC2=C3C=C1OC1=C(OC)C(OC)=CC4=C1C(CC1=CC=C(C=C1)OC1=CC(=CC=C1O[Si](C)(C)C)CC3N(C)CC2)N(C)CC44810.8Semi standard non polar33892256
Oxyacanthine,1TBDMS,isomer #1COC1=CC2=C3C=C1OC1=C(OC)C(OC)=CC4=C1C(CC1=CC=C(C=C1)OC1=CC(=CC=C1O[Si](C)(C)C(C)(C)C)CC3N(C)CC2)N(C)CC45018.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oxyacanthine GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-0000090000-c412b15bd9537b35a3762017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxyacanthine GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-1000009000-1223820c9148dc5e06c52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxyacanthine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxyacanthine GC-MS ("Oxyacanthine,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-20Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxyacanthine 6V, Positive-QTOFsplash10-0a4i-0000009000-28831833ea904387d5202021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxyacanthine 6V, Positive-QTOFsplash10-0a4i-0000009000-38aaab7723d1f732dda62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyacanthine 10V, Positive-QTOFsplash10-0a4i-0000039000-2bad9850c5dc0f081dd92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyacanthine 20V, Positive-QTOFsplash10-0a7i-0000093000-2790909e7f0f30709acf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyacanthine 40V, Positive-QTOFsplash10-0j4j-0000090000-25372cf1899667ad464e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyacanthine 10V, Negative-QTOFsplash10-0a4i-0000009000-62bbbb52d6800c881d5e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyacanthine 20V, Negative-QTOFsplash10-0a4l-0000097000-49657eb97feeda86a7352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyacanthine 40V, Negative-QTOFsplash10-0bt9-0000190000-9c83502b2c4a0e62bf782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyacanthine 10V, Negative-QTOFsplash10-0a4i-0000009000-243a991931ec2986982a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyacanthine 20V, Negative-QTOFsplash10-0a6r-0000094000-c16ffa8f9e1a6a7a1b982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyacanthine 40V, Negative-QTOFsplash10-03di-0000090000-baf9852cd591be14f7792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyacanthine 10V, Positive-QTOFsplash10-0a4i-0000009000-5debb5ccf794890680ef2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyacanthine 20V, Positive-QTOFsplash10-0a4i-0000059000-9d376161adb6686be3892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyacanthine 40V, Positive-QTOFsplash10-0pec-1000090000-60cd43712b70897111e52021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001988
KNApSAcK IDC00001897
Chemspider ID329538
KEGG Compound IDC09598
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound371257
PDB IDNot Available
ChEBI ID7853
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .