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Showing Compound (R)-Pronuciferine (FDB002188)

Record Information
Version1.0
Creation date2010-04-08 22:05:16 UTC
Update date2020-02-24 19:10:27 UTC
Primary IDFDB002188
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(R)-Pronuciferine
Description(R)-Pronuciferine, also known as milthanthine or N-methylstepharine, belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol (R)-Pronuciferine is a very strong basic compound (based on its pKa) (R)-Pronuciferine has been detected, but not quantified in, several different foods, such as cherimoya, coffee and coffee products, poppies, and sacred lotus. This could make (R)-pronuciferine a potential biomarker for the consumption of these foods.
CAS Number2128-60-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(+)-PronuciferineHMDB
MilthanthineHMDB
N,O-DimethylcrotonosineHMDB
N-MethylstepharineHMDB
PronuciferinHMDB
PronuciferineHMDB
(+)-pronuciferinebiospider
N-methylstepharinebiospider
N,o-dimethylcrotonosinebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.51ALOGPS
logP2.46ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)7.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity92.27 m³·mol⁻¹ChemAxon
Polarizability33.46 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H21NO3
IUPAC name10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaen-4-one
InChI IdentifierInChI=1S/C19H21NO3/c1-20-9-6-12-10-15(22-2)18(23-3)17-16(12)14(20)11-19(17)7-4-13(21)5-8-19/h4-5,7-8,10,14H,6,9,11H2,1-3H3
InChI KeyWUYQEGNOQLRQAQ-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC)C2=C3C(CC22C=CC(=O)C=C2)N(C)CCC3=C1
Average Molecular Weight311.3749
Monoisotopic Molecular Weight311.152143543
Classification
Description Belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassProaporphines
Sub ClassNot Available
Direct ParentProaporphines
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.29%; H 6.80%; N 4.50%; O 15.41%DFC
Melting PointMp 127-129°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +106 (c, 0.41 in EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(R)-Pronuciferine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-0090000000-86334b4a99135535b468Spectrum
Predicted GC-MS(R)-Pronuciferine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0059000000-24ed1e33f6d78af242322016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0092000000-f4f2970614db51a81d972016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-2090000000-14cc8227698e8328a57e2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-35a9eef82c86df85fa6e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0079000000-79ce4bd105b65de6f1df2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03kc-0090000000-86e72526e0832cd9e0b82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-9f3b29c8dcdf015b99e92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0039000000-5009deaf9268e5c4f8a92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0909-1090000000-41fa0a4fc39efba03adc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-9bf675b2e28db05b0d3b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009000000-7c0bcc885755bb30ace82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1049000000-bd5ec9bb499964d23c7e2021-09-22View Spectrum
NMRNot Available
ChemSpider ID545754
ChEMBL IDNot Available
KEGG Compound IDC09611
Pubchem Compound ID628376
Pubchem Substance IDNot Available
ChEBI ID42
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30344
CRC / DFC (Dictionary of Food Compounds) IDCGQ83-M:CGQ84-N
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00001905
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.