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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:03 UTC
Update Date2022-03-07 02:52:30 UTC
HMDB IDHMDB0030312
Secondary Accession Numbers
  • HMDB30312
Metabolite Identification
Common NameFloribundine
DescriptionFloribundine, also known as O-nornuciferine, belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Floribundine is a very strong basic compound (based on its pKa). Outside of the human body, floribundine has been detected, but not quantified in, a few different foods, such as cherimoya, coffee and coffee products, and tea. This could make floribundine a potential biomarker for the consumption of these foods.
Structure
Data?1563861967
Synonyms
ValueSource
(-)-N-MethylasimilobineHMDB
(-)-NornuciferineHMDB
1-Methoxy-6a-beta-aporphin-2-olHMDB
2-Hydroxy-1-methoxyaporphineHMDB
N-Methyl-asimilobineHMDB
N-MethylasimilobineHMDB
O-NornuciferineHMDB
Chemical FormulaC18H19NO2
Average Molecular Weight281.349
Monoisotopic Molecular Weight281.141578857
IUPAC Name16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-15-ol
Traditional Name16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-15-ol
CAS Registry Number3153-55-7
SMILES
COC1=C(O)C=C2CCN(C)C3CC4=CC=CC=C4C1=C23
InChI Identifier
InChI=1S/C18H19NO2/c1-19-8-7-12-10-15(20)18(21-2)17-13-6-4-3-5-11(13)9-14(19)16(12)17/h3-6,10,14,20H,7-9H2,1-2H3
InChI KeyAKXOIHNFHOEPHN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAporphines
Sub ClassNot Available
Direct ParentAporphines
Alternative Parents
Substituents
  • Aporphine
  • Benzoquinoline
  • Phenanthrene
  • 2-naphthol
  • Naphthalene
  • Quinoline
  • Tetrahydroisoquinoline
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • 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 Point195 - 196 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.87ALOGPS
logP3.24ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)7.08ChemAxon
pKa (Strongest Basic)10.35ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.7 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity84.47 m³·mol⁻¹ChemAxon
Polarizability31.32 ųChemAxon
Number of Rings4ChemAxon
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]+163.37431661259
DarkChem[M-H]-165.44431661259
DeepCCS[M-2H]-201.36630932474
DeepCCS[M+Na]+176.93130932474
AllCCS[M+H]+165.932859911
AllCCS[M+H-H2O]+162.232859911
AllCCS[M+NH4]+169.232859911
AllCCS[M+Na]+170.232859911
AllCCS[M-H]-174.232859911
AllCCS[M+Na-2H]-173.532859911
AllCCS[M+HCOO]-172.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FloribundineCOC1=C(O)C=C2CCN(C)C3CC4=CC=CC=C4C1=C233531.5Standard polar33892256
FloribundineCOC1=C(O)C=C2CCN(C)C3CC4=CC=CC=C4C1=C232333.9Standard non polar33892256
FloribundineCOC1=C(O)C=C2CCN(C)C3CC4=CC=CC=C4C1=C232547.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Floribundine,1TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C2CCN(C)C3CC4=CC=CC=C4C1=C232436.0Semi standard non polar33892256
Floribundine,1TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C2CCN(C)C3CC4=CC=CC=C4C1=C232664.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Floribundine GC-MS (Non-derivatized) - 70eV, Positivesplash10-014r-0190000000-20bed70e959559c390af2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Floribundine GC-MS (1 TMS) - 70eV, Positivesplash10-000i-2069000000-51e328f34b3c0e3ddc182017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Floribundine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Floribundine 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 - Floribundine 10V, Positive-QTOFsplash10-001i-0090000000-3a504e770e4ea492389a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floribundine 20V, Positive-QTOFsplash10-001i-0090000000-a57a24d36b80b8a0c4952016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floribundine 40V, Positive-QTOFsplash10-000i-2490000000-c98c65d932127cd8c5b32016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floribundine 10V, Negative-QTOFsplash10-001i-0090000000-f66a3af6dba71ee6c2f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floribundine 20V, Negative-QTOFsplash10-001i-0090000000-47e5b6f6b89143f4e7fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floribundine 40V, Negative-QTOFsplash10-08gl-1090000000-4f8f5185a4034c2be0472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floribundine 10V, Negative-QTOFsplash10-001i-0090000000-05f98fdd0e260ad540832021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floribundine 20V, Negative-QTOFsplash10-001i-0090000000-72c6c81920a1897516b02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floribundine 40V, Negative-QTOFsplash10-0a4i-0090000000-6cc04a7036ccf3d016392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floribundine 10V, Positive-QTOFsplash10-001i-0090000000-c1fc6cb60e21aea0e16a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floribundine 20V, Positive-QTOFsplash10-001i-0090000000-793d4982152e5aba68b82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floribundine 40V, Positive-QTOFsplash10-0hgc-0390000000-c5e4165f365da7c522d22021-09-24Wishart 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 IDFDB002150
KNApSAcK IDC00025991
Chemspider ID4477800
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5319512
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.. .