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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:41 UTC
Update Date2022-03-07 02:52:29 UTC
HMDB IDHMDB0030247
Secondary Accession Numbers
  • HMDB30247
Metabolite Identification
Common NameOxynarcotine
DescriptionOxynarcotine, also known as nornarceine, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Based on a literature review very few articles have been published on Oxynarcotine.
Structure
Data?1563861959
Synonyms
ValueSource
NornarceineHMDB
2,3-Dimethoxy-6-(2-{4-methoxy-6-[2-(methylamino)ethyl]-2H-1,3-benzodioxol-5-yl}acetyl)benzoateHMDB
Chemical FormulaC22H25NO8
Average Molecular Weight431.4358
Monoisotopic Molecular Weight431.158016781
IUPAC Name2,3-dimethoxy-6-(2-{4-methoxy-6-[2-(methylamino)ethyl]-2H-1,3-benzodioxol-5-yl}acetyl)benzoic acid
Traditional Name2,3-dimethoxy-6-(2-{4-methoxy-6-[2-(methylamino)ethyl]-2H-1,3-benzodioxol-5-yl}acetyl)benzoic acid
CAS Registry Number483-89-6
SMILES
CNCCC1=CC2=C(OCO2)C(OC)=C1CC(=O)C1=C(C(O)=O)C(OC)=C(OC)C=C1
InChI Identifier
InChI=1S/C22H25NO8/c1-23-8-7-12-9-17-21(31-11-30-17)19(28-3)14(12)10-15(24)13-5-6-16(27-2)20(29-4)18(13)22(25)26/h5-6,9,23H,7-8,10-11H2,1-4H3,(H,25,26)
InChI KeyGLKPKUBRBLNOSC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Alkyl-phenylketone
  • M-methoxybenzoic acid or derivatives
  • O-methoxybenzoic acid or derivatives
  • Dimethoxybenzene
  • O-dimethoxybenzene
  • Benzodioxole
  • Benzoic acid or derivatives
  • Benzoic acid
  • Phenethylamine
  • Phenylketone
  • Anisole
  • Benzoyl
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Amino acid
  • Ketone
  • Amino acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Acetal
  • Ether
  • Secondary aliphatic amine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Secondary amine
  • Organic oxide
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • 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 Point229 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.035 g/LALOGPS
logP1.69ALOGPS
logP-0.45ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.5ChemAxon
pKa (Strongest Basic)9.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area112.55 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity111.6 m³·mol⁻¹ChemAxon
Polarizability44.04 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.84131661259
DarkChem[M-H]-199.14531661259
DeepCCS[M+H]+197.55130932474
DeepCCS[M-H]-195.19330932474
DeepCCS[M-2H]-228.71230932474
DeepCCS[M+Na]+203.86530932474
AllCCS[M+H]+201.132859911
AllCCS[M+H-H2O]+198.632859911
AllCCS[M+NH4]+203.432859911
AllCCS[M+Na]+204.132859911
AllCCS[M-H]-204.832859911
AllCCS[M+Na-2H]-205.432859911
AllCCS[M+HCOO]-206.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OxynarcotineCNCCC1=CC2=C(OCO2)C(OC)=C1CC(=O)C1=C(C(O)=O)C(OC)=C(OC)C=C14764.0Standard polar33892256
OxynarcotineCNCCC1=CC2=C(OCO2)C(OC)=C1CC(=O)C1=C(C(O)=O)C(OC)=C(OC)C=C13350.8Standard non polar33892256
OxynarcotineCNCCC1=CC2=C(OCO2)C(OC)=C1CC(=O)C1=C(C(O)=O)C(OC)=C(OC)C=C13414.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxynarcotine,1TMS,isomer #1CNCCC1=CC2=C(OCO2)C(OC)=C1CC(=O)C1=CC=C(OC)C(OC)=C1C(=O)O[Si](C)(C)C3300.4Semi standard non polar33892256
Oxynarcotine,1TMS,isomer #2COC1=CC=C(C(=O)CC2=C(CCN(C)[Si](C)(C)C)C=C3OCOC3=C2OC)C(C(=O)O)=C1OC3512.4Semi standard non polar33892256
Oxynarcotine,2TMS,isomer #1COC1=CC=C(C(=O)CC2=C(CCN(C)[Si](C)(C)C)C=C3OCOC3=C2OC)C(C(=O)O[Si](C)(C)C)=C1OC3452.6Semi standard non polar33892256
Oxynarcotine,2TMS,isomer #1COC1=CC=C(C(=O)CC2=C(CCN(C)[Si](C)(C)C)C=C3OCOC3=C2OC)C(C(=O)O[Si](C)(C)C)=C1OC3473.4Standard non polar33892256
Oxynarcotine,1TBDMS,isomer #1CNCCC1=CC2=C(OCO2)C(OC)=C1CC(=O)C1=CC=C(OC)C(OC)=C1C(=O)O[Si](C)(C)C(C)(C)C3508.5Semi standard non polar33892256
Oxynarcotine,1TBDMS,isomer #2COC1=CC=C(C(=O)CC2=C(CCN(C)[Si](C)(C)C(C)(C)C)C=C3OCOC3=C2OC)C(C(=O)O)=C1OC3708.9Semi standard non polar33892256
Oxynarcotine,2TBDMS,isomer #1COC1=CC=C(C(=O)CC2=C(CCN(C)[Si](C)(C)C(C)(C)C)C=C3OCOC3=C2OC)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1OC3828.6Semi standard non polar33892256
Oxynarcotine,2TBDMS,isomer #1COC1=CC=C(C(=O)CC2=C(CCN(C)[Si](C)(C)C(C)(C)C)C=C3OCOC3=C2OC)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1OC3852.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oxynarcotine GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-8391300000-3dd60d9c8ab01a125b942017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxynarcotine GC-MS (1 TMS) - 70eV, Positivesplash10-001l-9280600000-5c4afe3089cca2779de22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxynarcotine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxynarcotine GC-MS ("Oxynarcotine,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxynarcotine 10V, Positive-QTOFsplash10-01q9-0003900000-eda259411fafd8d644ee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxynarcotine 20V, Positive-QTOFsplash10-0lzc-1249500000-903692b900c9f88a06432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxynarcotine 40V, Positive-QTOFsplash10-0596-1839000000-59ecc73b5477689046d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxynarcotine 10V, Negative-QTOFsplash10-001r-0006900000-477992f445951ed2a7822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxynarcotine 20V, Negative-QTOFsplash10-00dr-0019200000-d89456dacba95072fd922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxynarcotine 40V, Negative-QTOFsplash10-00e9-0219000000-650d0dda086c657b5ce42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxynarcotine 10V, Negative-QTOFsplash10-001i-0002900000-ff8e720bb50d0c49ea9c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxynarcotine 20V, Negative-QTOFsplash10-0zni-0349600000-bdf75477862e52289cc22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxynarcotine 40V, Negative-QTOFsplash10-0kac-1938200000-0aaacdcc480d9b182f952021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxynarcotine 10V, Positive-QTOFsplash10-0f89-0001900000-9a444d281df4da2ad4b12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxynarcotine 20V, Positive-QTOFsplash10-0a4i-0219200000-a46e7ac253507e02e7582021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxynarcotine 40V, Positive-QTOFsplash10-0kbo-0639000000-f790c7ae70ff808feb3d2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB002070
KNApSAcK IDC00057403
Chemspider ID4478458
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5320347
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.. .