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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:12:50 UTC
Update Date2022-03-07 02:53:43 UTC
HMDB IDHMDB0033481
Secondary Accession Numbers
  • HMDB33481
Metabolite Identification
Common NameBaptifoline
DescriptionBaptifoline, also known as alkaloid P3?, belongs to the class of organic compounds known as anagyrine-type alkaloids. These are lupin alkaloids with a structure based on the anagyrine skeleton. Anagyrine is a tetracyclic ketone containing a quinolizidine, and two pyridine rings fused together to form dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one. Baptifoline is a very strong basic compound (based on its pKa). Outside of the human body, baptifoline has been detected, but not quantified in, coffee and coffee products. This could make baptifoline a potential biomarker for the consumption of these foods.
Structure
Data?1563862412
Synonyms
ValueSource
(-)-BaptifolineHMDB
13-HydroxyanagyrineHMDB
Alkaloid P3?HMDB
BaptifolineMeSH
Chemical FormulaC15H20N2O2
Average Molecular Weight260.3315
Monoisotopic Molecular Weight260.152477894
IUPAC Name12-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4-dien-6-one
Traditional Name12-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4-dien-6-one
CAS Registry Number732-50-3
SMILES
OC1CCN2CC3CC(CN4C(=O)C=CC=C34)C2C1
InChI Identifier
InChI=1S/C15H20N2O2/c18-12-4-5-16-8-10-6-11(14(16)7-12)9-17-13(10)2-1-3-15(17)19/h1-3,10-12,14,18H,4-9H2
InChI KeyAOOCSKCGZYCEJX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anagyrine-type alkaloids. These are lupin alkaloids with a structure based on the anagyrine skeleton. Anagyrine is a tetracyclic ketone containing a quinolizidine, and two pyridine rings fused together to form dipyrido[1,2-a:1',2'-E][1,5]diazocin-4-one.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassLupin alkaloids
Sub ClassAnagyrine-type alkaloids
Direct ParentAnagyrine-type alkaloids
Alternative Parents
Substituents
  • Anagyrine-type alkaloid
  • Quinolizidine
  • Pyridinone
  • Aralkylamine
  • Piperidine
  • Pyridine
  • Heteroaromatic compound
  • Lactam
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • 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 Point210 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility22.4 g/LALOGPS
logP1.2ALOGPS
logP-0.52ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)15.17ChemAxon
pKa (Strongest Basic)8.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity75.62 m³·mol⁻¹ChemAxon
Polarizability27.89 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+159.91331661259
DarkChem[M-H]-159.25931661259
DeepCCS[M-2H]-194.18530932474
DeepCCS[M+Na]+169.73330932474
AllCCS[M+H]+163.232859911
AllCCS[M+H-H2O]+159.432859911
AllCCS[M+NH4]+166.832859911
AllCCS[M+Na]+167.832859911
AllCCS[M-H]-171.932859911
AllCCS[M+Na-2H]-171.732859911
AllCCS[M+HCOO]-171.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BaptifolineOC1CCN2CC3CC(CN4C(=O)C=CC=C34)C2C13245.3Standard polar33892256
BaptifolineOC1CCN2CC3CC(CN4C(=O)C=CC=C34)C2C12631.2Standard non polar33892256
BaptifolineOC1CCN2CC3CC(CN4C(=O)C=CC=C34)C2C12624.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Baptifoline,1TMS,isomer #1C[Si](C)(C)OC1CCN2CC3CC(CN4C3=CC=CC4=O)C2C12456.4Semi standard non polar33892256
Baptifoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCN2CC3CC(CN4C3=CC=CC4=O)C2C12712.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Baptifoline GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xr-2590000000-07f6ebf71fc39939f9f62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Baptifoline GC-MS (1 TMS) - 70eV, Positivesplash10-0300-6981000000-df090227ddc3c6127b1d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Baptifoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Baptifoline 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 - Baptifoline 10V, Positive-QTOFsplash10-01ox-0090000000-843960a8489ba4f1d0ec2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Baptifoline 20V, Positive-QTOFsplash10-01ox-0190000000-f0a5c4b7858f49c5f20f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Baptifoline 40V, Positive-QTOFsplash10-029i-3980000000-54bed17f205c1e0a2f932015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Baptifoline 10V, Negative-QTOFsplash10-0a4i-0090000000-bbddfb9941122293598c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Baptifoline 20V, Negative-QTOFsplash10-0a4l-0090000000-e65b7d3569bc1b821def2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Baptifoline 40V, Negative-QTOFsplash10-052r-1910000000-476f26b4ec1e0d9cf6472015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Baptifoline 10V, Positive-QTOFsplash10-03dl-0090000000-23a2d02f90f9c77c62eb2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Baptifoline 20V, Positive-QTOFsplash10-03di-0090000000-cceec67e03d09ea4c1c92021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Baptifoline 40V, Positive-QTOFsplash10-03dj-1920000000-0103307c92ac3f5847c22021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Baptifoline 10V, Negative-QTOFsplash10-0a4i-0090000000-a7fd50b20d0fcccddc5f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Baptifoline 20V, Negative-QTOFsplash10-0a4i-0090000000-07f5a21deeb00c44100c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Baptifoline 40V, Negative-QTOFsplash10-0udi-2890000000-0fdc09be8ab72096b5e82021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDFDB011525
KNApSAcK IDC00002212
Chemspider ID539881
KEGG Compound IDC10755
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound621307
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.. .