(-)-Aspidospermine (CHEM024385)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:40:00 UTC
Update Date2016-11-09 01:17:53 UTC
Accession NumberCHEM024385
Identification
Common Name(-)-Aspidospermine
ClassSmall Molecule
DescriptionAn indole alkaloid having the structure of aspirospermidine methoxylated at C-17 and acetylated at N-1.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Acetyl-17-methoxyaspidospermidineChEBI
1-(17-Methoxyaspidospermidin-1-yl)-ethanoneHMDB
1-Acetyl-17-methoxyaspidospermidine, 9ciHMDB
(-)-AspidospermineChEBI
Chemical FormulaC22H30N2O2
Average Molecular Mass354.486 g/mol
Monoisotopic Mass354.231 g/mol
CAS Registry Number466-49-9
IUPAC Name1-[(1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2(7),3,5-trien-8-yl]ethan-1-one
Traditional Nameaspidospermine
SMILES[H][C@@]12CC[C@@]3(CC)CCCN4CC[C@]1(C1=C(N2C(C)=O)C(OC)=CC=C1)[C@@]34[H]
InChI IdentifierInChI=1S/C22H30N2O2/c1-4-21-10-6-13-23-14-12-22(20(21)23)16-7-5-8-17(26-3)19(16)24(15(2)25)18(22)9-11-21/h5,7-8,18,20H,4,6,9-14H2,1-3H3/t18-,20-,21-,22-/m1/s1
InChI KeyARQOGCYMPUOVHK-ZHHKINOHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAspidospermatan-type alkaloids
Sub ClassNot Available
Direct ParentAspidospermatan-type alkaloids
Alternative Parents
Substituents
  • Aspidosperma alkaloid
  • Plumeran-type alkaloid
  • Carbazole
  • Quinolidine
  • Indole or derivatives
  • Indolizidine
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • N-alkylpyrrolidine
  • Acetamide
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • 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 Solubility0.18 g/LALOGPS
logP3.34ALOGPS
logP2.78ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)9.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.78 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity102.27 m³·mol⁻¹ChemAxon
Polarizability40.16 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 (Non-derivatized) - 70eV, Positivesplash10-01tl-1029000000-96af6a463ae68aa05f3fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-65e65f5bd7e74a4d526eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w29-1029000000-89bdefe0c1c9697de5feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-2098000000-645f445fb2c7b32cccdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-240bf3ec656a869d732eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w29-0009000000-1b64cc789cf3df742940Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udj-0059000000-827fd6ef228d38dfaf6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-c0f2e042065aee132604Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-0029000000-4dde02d5047aec262fe9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053e-1092000000-a85ba17b2078c2965803Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-f7af0f531d28f8508f59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0009000000-f7af0f531d28f8508f59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-0229000000-306014f44651374af804Spectrum
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 IDHMDB0030361
FooDB IDFDB002207
Phenol Explorer IDNot Available
KNApSAcK IDC00024465
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID198027
ChEBI ID28463
PubChem Compound ID227613
Kegg Compound IDC09042
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1206502
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17623291
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18098818
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=5842754
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=7841224
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.