17-O-acetylnorajmaline (CHEM041863)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:43:39 UTC
Update Date2016-11-09 01:22:33 UTC
Accession NumberCHEM041863
Identification
Common Name17-O-acetylnorajmaline
ClassSmall Molecule
Description17-o-acetylnorajmaline is a member of the class of compounds known as ajmaline-sarpagine alkaloids. Ajmaline-sarpagine alkaloids are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether. 17-o-acetylnorajmaline is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 17-o-acetylnorajmaline can be found in a number of food items such as black chokeberry, sapodilla, common pea, and cardamom, which makes 17-o-acetylnorajmaline a potential biomarker for the consumption of these food products.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC21H26N2O3
Average Molecular Mass354.450 g/mol
Monoisotopic Mass354.194 g/mol
CAS Registry NumberNot Available
IUPAC Name13-ethyl-14-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-yl acetate
Traditional Name13-ethyl-14-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-yl acetate
SMILESCCC1C(O)N2C3CC45C(NC6=CC=CC=C46)C2CC1C3C5OC(C)=O
InChI IdentifierInChI=1S/C21H26N2O3/c1-3-11-12-8-15-18-21(13-6-4-5-7-14(13)22-18)9-16(23(15)20(11)25)17(12)19(21)26-10(2)24/h4-7,11-12,15-20,22,25H,3,8-9H2,1-2H3
InChI KeyVAOXSMUPPRUEKF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAjmaline-sarpagine alkaloids
Sub ClassNot Available
Direct ParentAjmaline-sarpagine alkaloids
Alternative Parents
Substituents
  • Sarpagine-skeleton
  • Beta-carboline
  • Pyridoindole
  • Quinolizidine
  • Indole or derivatives
  • Dihydroindole
  • Quinuclidine
  • Azepane
  • Aralkylamine
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Piperidine
  • Hemiaminal
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Alkanolamine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • 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 Solubility0.27 g/LALOGPS
logP2.4ALOGPS
logP1.66ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)13.33ChemAxon
pKa (Strongest Basic)7.08ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.8 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.48 m³·mol⁻¹ChemAxon
Polarizability38.58 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0029000000-9745e12a1644ea32c8c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-1097000000-506f132cd47ed22fd04eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-3790000000-ba3dde278a378f2214d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w29-1009000000-45774a6b9c9fcdbcf19eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ik9-2029000000-3b18b0de4f3b597158d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06sl-3093000000-38fd1a1ec20cde7ffdf1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-47937e1bca34335c6cdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0029000000-8c6ef66116a76cdbbc3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-0019000000-b40526a6657c83e887fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2009000000-1e2571d577c6640e6c02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-5009000000-b5a1702fdea2aac4d9e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054p-9024000000-62c90d8025f77d6adfe9Spectrum
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 IDNot Available
FooDB IDFDB030276
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID4491170
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available