16-epivellosimine (CHEM041858)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:43:33 UTC
Update Date2016-11-09 01:22:33 UTC
Accession NumberCHEM041858
Identification
Common Name16-epivellosimine
ClassSmall Molecule
DescriptionAn indole alkaloid that is vellosimine in which the carbon bearing the aldehyde function has been epimerised.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
16-Epi-vellosimineMeSH
Chemical FormulaC19H20N2O
Average Molecular Mass292.375 g/mol
Monoisotopic Mass292.158 g/mol
CAS Registry NumberNot Available
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
Traditional 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
SMILES[H]\C(C)=C1/CN2[C@@]3([H])C[C@]1([H])[C@]([H])(C=O)[C@]2([H])CC1=C3NC2=CC=CC=C12
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.51ALOGPS
logP2.46ChemAxon
logS-3.4ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-502966b71b3fa4b51088Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0090000000-4071f18f2e91b42c21efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0059-2980000000-df284da1af082841e13dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-eb9636b759144711f704Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-0090000000-566d1bb0322a9b8a7e90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0090000000-6466f92d5f8fff4b027fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-30850ca9637e3e228dfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0090000000-d3385634a3967ef0b42cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-072a-0190000000-27d6f13478b5896b1cf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-74a3146908205cd6ebecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0090000000-972804a8372b111e10d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-0090000000-59d95f3c81fe9761c0ccSpectrum
MSMass Spectrum (Electron Ionization)Not AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0304026
FooDB IDFDB030270
Phenol Explorer IDNot Available
KNApSAcK IDC00051789
BiGG IDNot Available
BioCyc ID16-EPIVELLOSIMINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID9510274
ChEBI ID16425
PubChem Compound IDNot Available
Kegg Compound IDC11633
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17404987
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20392128