Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:04 UTC
Update Date2022-03-07 02:52:08 UTC
HMDB IDHMDB0029378
Secondary Accession Numbers
  • HMDB29378
Metabolite Identification
Common Name(-)-Thebaine
Description(-)-Thebaine belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic (-)-Thebaine is a very strong basic compound (based on its pKa). Minor constituent of opium.
Structure
Data?1582753410
SynonymsNot Available
Chemical FormulaC19H21NO3
Average Molecular Weight311.3749
Monoisotopic Molecular Weight311.152143543
IUPAC Name10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,14,16-pentaene
Traditional Name10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,14,16-pentaene
CAS Registry NumberNot Available
SMILES
COC1=CC=C2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C4
InChI Identifier
InChI=1S/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3
InChI KeyFQXXSQDCDRQNQE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • Phenanthrene
  • Tetralin
  • Coumaran
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point192.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.7 g/LALOGPS
logP2.68ALOGPS
logP1.53ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)8.38ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.93 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity90.66 m³·mol⁻¹ChemAxon
Polarizability33.85 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.14731661259
DarkChem[M-H]-168.56231661259
DeepCCS[M-2H]-205.1730932474
DeepCCS[M+Na]+180.39730932474
AllCCS[M+H]+175.432859911
AllCCS[M+H-H2O]+172.232859911
AllCCS[M+NH4]+178.432859911
AllCCS[M+Na]+179.332859911
AllCCS[M-H]-182.232859911
AllCCS[M+Na-2H]-181.732859911
AllCCS[M+HCOO]-181.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-ThebaineCOC1=CC=C2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C43961.1Standard polar33892256
(-)-ThebaineCOC1=CC=C2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C42534.0Standard non polar33892256
(-)-ThebaineCOC1=CC=C2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C42494.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Thebaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6t-0090000000-f2d758bd9f2c7d25eee82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Thebaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Thebaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Thebaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Thebaine LC-ESI-QQ , positive-QTOFsplash10-0bt9-8095000000-65e3965b2bd1c1efef992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Thebaine LC-ESI-QQ , positive-QTOFsplash10-0a4i-6091000000-ffa57ed65751978e70f62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Thebaine LC-ESI-QQ , positive-QTOFsplash10-0a4i-4190000000-cce3eceb7d285ca590502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Thebaine LC-ESI-QQ , positive-QTOFsplash10-0a4i-7290000000-2c44d64ff75d058c2ac82017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Thebaine 10V, Positive-QTOFsplash10-03di-0019000000-39a448b3d40ec9d12e712015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Thebaine 20V, Positive-QTOFsplash10-03di-1059000000-2e0d89d0f18a3a84253e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Thebaine 40V, Positive-QTOFsplash10-0ldl-3090000000-d1acc13f765f37b71b1c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Thebaine 10V, Negative-QTOFsplash10-03di-0009000000-c7e246f79453d627a81c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Thebaine 20V, Negative-QTOFsplash10-03di-1079000000-8b39f9d42c4e9db46d392015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Thebaine 40V, Negative-QTOFsplash10-0lyc-1090000000-aea1036f1a7cc5883fae2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Thebaine 10V, Positive-QTOFsplash10-03di-0009000000-9f3b29c8dcdf015b99e92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Thebaine 20V, Positive-QTOFsplash10-03di-0009000000-9f3b29c8dcdf015b99e92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Thebaine 40V, Positive-QTOFsplash10-03xr-2097000000-b498f59ba8b30aec4dad2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Thebaine 10V, Negative-QTOFsplash10-03di-0009000000-9bf675b2e28db05b0d3b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Thebaine 20V, Negative-QTOFsplash10-03di-0019000000-e6e38b238d4d20f4464f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Thebaine 40V, Negative-QTOFsplash10-03di-0092000000-2709608ec08b22155ac42021-09-24Wishart 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 IDFDB000454
KNApSAcK IDNot Available
Chemspider ID361110
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound408120
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .