Record Information
Version1.0
Creation date2015-05-07 18:55:55 UTC
Update date2019-11-26 03:21:40 UTC
Primary IDFDB030270
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name16-epivellosimine
Description16-epivellosimine is a member of the class of compounds known as macroline alkaloids. Macroline alkaloids are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. 16-epivellosimine is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 16-epivellosimine can be found in a number of food items such as bitter gourd, red raspberry, orange bell pepper, and star anise, which makes 16-epivellosimine a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
16-Epi-vellosimineMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.51ALOGPS
logP2.46ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)15.29ChemAxon
pKa (Strongest Basic)5.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area36.1 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.18 m³·mol⁻¹ChemAxon
Polarizability33.14 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H20N2O
IUPAC name(1S,12S,13S,14R,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4(9),5,7-tetraene-13-carbaldehyde
InChI IdentifierInChI=1S/C19H20N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,10,13,15,17-18,20H,7-9H2,1H3/b11-2-/t13-,15-,17-,18-/m0/s1
InChI KeyMHASSCPGKAMILD-MIOJWWSHSA-N
Isomeric SMILES[H]C(=O)[C@]1([H])[C@@H]2CC3=C(NC4=C3C=CC=C4)[C@]3([H])C[C@H]1\C(CN23)=C/C
Average Molecular Weight292.3749
Monoisotopic Molecular Weight292.157563272
Classification
Description Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMacroline alkaloids
Sub ClassNot Available
Direct ParentMacroline alkaloids
Alternative Parents
Substituents
  • Macroline skeleton
  • Sarpagine-skeleton
  • Vobasan skeleton
  • Beta-carboline
  • Pyridoindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Quinuclidine
  • Aralkylamine
  • Benzenoid
  • Piperidine
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aldehyde
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)Not AvailableSpectrum
Predicted GC-MS16-epivellosimine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-502966b71b3fa4b51088Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0090000000-4071f18f2e91b42c21efSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0059-2980000000-df284da1af082841e13dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-eb9636b759144711f704Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-0090000000-566d1bb0322a9b8a7e90Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0090000000-6466f92d5f8fff4b027fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-30850ca9637e3e228dfdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0090000000-d3385634a3967ef0b42cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-072a-0190000000-27d6f13478b5896b1cf5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-74a3146908205cd6ebecSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0090000000-972804a8372b111e10d0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-0090000000-59d95f3c81fe9761c0ccSpectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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