ajamalicine (CHEM043529)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:01:00 UTC
Update Date2016-11-09 01:22:56 UTC
Accession NumberCHEM043529
Identification
Common Nameajamalicine
ClassSmall Molecule
DescriptionA monoterpenoid indole alkaloid with formula C21H24N2O3, isolated from several Rauvolfia and Catharanthus species. It is a selective alpha1-adrenoceptor antagonist used for the treatment of high blood pressure.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(19alpha)-16,17-Didehydro-19-methyl-oxayohimban-16-carboxylic acid methyl esterChEBI
AjmalicinChEBI
CircoleneChEBI
CristanylChEBI
delta-YohimbineChEBI
DuxilChEBI
LamuranChEBI
Methyl (4S,4ar,13BS,14as)-4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylateChEBI
RaubasineChEBI
SarpanChEBI
(19a)-16,17-Didehydro-19-methyl-oxayohimban-16-carboxylate methyl esterGenerator
(19a)-16,17-Didehydro-19-methyl-oxayohimban-16-carboxylic acid methyl esterGenerator
(19alpha)-16,17-Didehydro-19-methyl-oxayohimban-16-carboxylate methyl esterGenerator
(19Α)-16,17-didehydro-19-methyl-oxayohimban-16-carboxylate methyl esterGenerator
(19Α)-16,17-didehydro-19-methyl-oxayohimban-16-carboxylic acid methyl esterGenerator
Δ-yohimbineGenerator
Methyl (4S,4ar,13BS,14as)-4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylic acidGenerator
AjmalicineKEGG
AkuammigineMeSH
Ajmalicine, (19beta)-isomerMeSH
RauvasanMeSH
Ajmalicine, (hydrochloride(19beta,20alpha))-isomerMeSH
tetrahydro-AlstonineMeSH
Ajmalicine, (3beta,19alpha,20alpha)-isomerMeSH
19-EpiajmalicineMeSH
TetrahydroalstonineMeSH
Ajmalicine, (19alpha,20alpha)-isomerMeSH
Ajmalicine, (19beta,20alpha)-isomerMeSH
Ajmalicine, (3-beta,19beta)-isomerMeSH
Ajmalicine, (3beta,19alpha)-isomerMeSH
Ajmalicine, PO4(19alpha)-isomerMeSH
Ajmalicine, hydrochloride(19alpha)-isomerMeSH
Methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-19-carboxylic acidGenerator
Chemical FormulaC21H24N2O3
Average Molecular Mass352.434 g/mol
Monoisotopic Mass352.179 g/mol
CAS Registry Number483-04-5
IUPAC Namemethyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
Traditional Namemethyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
SMILES[H][C@@]1(C)OC=C(C(=O)OC)[C@@]2([H])C[C@]3([H])N(CCC4=C3NC3=CC=CC=C43)C[C@]12[H]
InChI IdentifierInChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16+,19-/m0/s1
InChI KeyGRTOGORTSDXSFK-XJTZBENFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassYohimbine alkaloids
Sub ClassNot Available
Direct ParentYohimbine alkaloids
Alternative Parents
Substituents
  • Ajmalicine-skeleton
  • 18-oxayohimban
  • Corynanthean skeleton
  • Yohimbine alkaloid
  • Beta-carboline
  • Pyridoindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aralkylamine
  • Benzenoid
  • Piperidine
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • 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
logP3.41ALOGPS
logP2.55ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)16.37ChemAxon
pKa (Strongest Basic)7.43ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.56 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity99.84 m³·mol⁻¹ChemAxon
Polarizability39.66 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-0udi-0029000000-d03a748d66c3c683b217Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0093000000-c60306ce258f8b45a901Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-4691000000-c9830f1a8a3eb57f5167Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-d00ca9fa39f91f00a1cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxu-0089000000-c1c9b8df63140dd4fbe7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-046r-3190000000-183e8742be4d35271413Spectrum
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 IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001678
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAjmalicine
Chemspider IDNot Available
ChEBI ID2524
PubChem Compound ID441975
Kegg Compound IDC09024
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15930738
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19151732
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22331368
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22332772
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24237015
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=26983347
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=27584856
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=4387608
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=6091834
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=6128043