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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:20:10 UTC
Update Date2022-03-07 02:54:07 UTC
HMDB IDHMDB0034489
Secondary Accession Numbers
  • HMDB34489
Metabolite Identification
Common Name(+)-Norushinsunine N-oxide
Description(+)-Norushinsunine N-oxide, also known as 1,2-dehydro-a-cyperone or 1,4,11-eudesmatrien-3-one, belongs to the class of organic compounds known as hydroxy-7-aporphines. These are aporphines containing a hydroxyl group at the 7-position. Based on a literature review very few articles have been published on (+)-Norushinsunine N-oxide.
Structure
Data?1563862570
Synonyms
ValueSource
1,2-Dehydro-a-cyperoneHMDB
1,2-Dehydro-α-cyperoneHMDB
(+)-Eudesma-1,4,11-trien-3-oneHMDB
(4AS-cis)-5,6,7,8-tetrahydro-1,4a-dimethyl-7-(1-methylethenyl)-2(4ah)-naphthalenoneHMDB
1,4,11-Eudesmatrien-3-oneHMDB
1,4,11-Selinatrien-3-oneHMDB
Chemical FormulaC18H17NO4
Average Molecular Weight311.3319
Monoisotopic Molecular Weight311.115758037
IUPAC Name13-hydroxy-11-methyl-3,5-dioxa-11λ⁵-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-one
Traditional Name13-hydroxy-11-methyl-3,5-dioxa-11λ⁵-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-one
CAS Registry NumberNot Available
SMILES
CN1(=O)CCC2=CC3=C(OCO3)C3=C2C1C(O)C1=CC=CC=C31
InChI Identifier
InChI=1S/C18H17NO4/c1-19(21)7-6-10-8-13-18(23-9-22-13)15-11-4-2-3-5-12(11)17(20)16(19)14(10)15/h2-5,8,16-17,20H,6-7,9H2,1H3
InChI KeyPQQSHMZUVWGXSV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy-7-aporphines. These are aporphines containing a hydroxyl group at the 7-position.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAporphines
Sub ClassHydroxy-7-aporphines
Direct ParentHydroxy-7-aporphines
Alternative Parents
Substituents
  • Hydroxy-7-aporphine
  • Benzoquinoline
  • Phenanthrene
  • Naphthalene
  • Quinoline
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Benzenoid
  • Trialkyl amine oxide
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Trisubstituted n-oxide
  • N-oxide
  • Acetal
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic zwitterion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point177 - 179 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.088 g/LALOGPS
logP0.4ALOGPS
logP1.28ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)13.23ChemAxon
pKa (Strongest Basic)0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area65.57 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.05 m³·mol⁻¹ChemAxon
Polarizability32.51 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+166.18831661259
DarkChem[M-H]-165.6131661259
DeepCCS[M-2H]-198.02130932474
DeepCCS[M+Na]+173.24830932474
AllCCS[M+H]+171.732859911
AllCCS[M+H-H2O]+168.332859911
AllCCS[M+NH4]+174.932859911
AllCCS[M+Na]+175.832859911
AllCCS[M-H]-178.632859911
AllCCS[M+Na-2H]-177.832859911
AllCCS[M+HCOO]-177.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+)-Norushinsunine N-oxideCN1(=O)CCC2=CC3=C(OCO3)C3=C2C1C(O)C1=CC=CC=C313588.9Standard polar33892256
(+)-Norushinsunine N-oxideCN1(=O)CCC2=CC3=C(OCO3)C3=C2C1C(O)C1=CC=CC=C312481.1Standard non polar33892256
(+)-Norushinsunine N-oxideCN1(=O)CCC2=CC3=C(OCO3)C3=C2C1C(O)C1=CC=CC=C312808.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(+)-Norushinsunine N-oxide,1TMS,isomer #1C[N+]1([O-])CCC2=CC3=C(OCO3)C3=C2C1C(O[Si](C)(C)C)C1=CC=CC=C132657.6Semi standard non polar33892256
(+)-Norushinsunine N-oxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1C2=CC=CC=C2C2=C3OCOC3=CC3=C2C1[N+](C)([O-])CC32904.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Norushinsunine N-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0017-0090000000-28ec1c65a82594597b1f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Norushinsunine N-oxide GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-4039000000-47d9a05065c9cb9a1b802017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Norushinsunine N-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Norushinsunine N-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 10V, Positive-QTOFsplash10-03di-0029000000-b20de51f96980777ea972017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 20V, Positive-QTOFsplash10-03dl-0095000000-9558c50cea58ed1eb01c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 40V, Positive-QTOFsplash10-0ik9-0390000000-17f980b55123a731b7922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 10V, Negative-QTOFsplash10-03di-0009000000-5f478af9fe23ca0c0a992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 20V, Negative-QTOFsplash10-03di-0009000000-0ca7b2da4155ee2ac2de2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 40V, Negative-QTOFsplash10-03di-8069000000-5a2749c549d162cffb6f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 10V, Positive-QTOFsplash10-03di-0009000000-4631b5d1b4d93faf70b72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 20V, Positive-QTOFsplash10-01ox-0095000000-3e2ccf94088105534dcc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 40V, Positive-QTOFsplash10-0309-0090000000-ee36a9fef69537f49ce32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 10V, Negative-QTOFsplash10-03di-0009000000-43e89ef889a2eb4f124e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 20V, Negative-QTOFsplash10-03di-0009000000-43e89ef889a2eb4f124e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 40V, Negative-QTOFsplash10-03di-0009000000-43e89ef889a2eb4f124e2021-09-22Wishart 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 IDFDB012978
KNApSAcK IDC00012761
Chemspider ID35013723
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13192441
PDB IDNot Available
ChEBI ID174973
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.. .