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Showing Compound ajmaline (FDB030658)

Record Information
Version1.0
Creation date2015-05-07 19:43:46 UTC
Update date2019-11-26 03:21:51 UTC
Primary IDFDB030658
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameajmaline
DescriptionAjmaline, also known as (+)-ajmaline, 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. Ajmaline is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Ajmaline can be synthesized from ajmalan. Ajmaline is also a parent compound for other transformation products, including but not limited to, vinorine, norajmaline, and 17-O-acetylajmaline. Ajmaline can be found in a number of food items such as soursop, jew's ear, small-leaf linden, and soft-necked garlic, which makes ajmaline a potential biomarker for the consumption of these food products. Ajmaline can be found primarily in blood and urine. Ajmaline is a drug which is used for use as an antiarrhythmic agent. The compound was first isolated by Salimuzzaman Siddiqui in 1931 from the roots of Rauvolfia serpentina. He named it ajmaline, after Hakim Ajmal Khan, one of the most illustrious practitioners of Unani medicine in South Asia. Ajmaline can be found in most species of the Rauvolfia genus as well as Catharanthus roseus. In addition to Southeast Asia, Rauvolfia species have also been found in tropical regions of India, Africa, South America, and some oceanic islands. Other indole alkaloids found in Rauvolfia include reserpine, ajmalicine, serpentine, corynanthine, and yohimbine. While 86 alkaloids have been discovered throughout Rauvolfia vomitoria, ajmaline is mainly isolated from the stem bark and roots of the plant . The class I antiarrhythmic agents interfere with the sodium channel. A class IA agent lengthens the action potential (right shift) which brings about improvement in abnormal heart rhythms. This drug in particular has a high affinity for the Nav 1.5 sodium channel (DrugBank).
CAS Number4360-12-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility4.09 g/LALOGPS
logP1.72ALOGPS
logP1.85ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)13.28ChemAxon
pKa (Strongest Basic)7.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.94 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.57 m³·mol⁻¹ChemAxon
Polarizability36.75 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H26N2O2
IUPAC name(1R,9R,10S,12R,13S,14R,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-14,18-diol
InChI IdentifierInChI=1S/C20H26N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3/t10-,11-,14-,15-,16?,17-,18+,19+,20+/m0/s1
InChI KeyCJDRUOGAGYHKKD-HEFSZTOGSA-N
Isomeric SMILESCC[C@H]1[C@@H]2C[C@H]3[C@@H]4N(C)C5=CC=CC=C5[C@]44C[C@@H](C2[C@H]4O)N3[C@@H]1O
Average Molecular Weight326.4326
Monoisotopic Molecular Weight326.199428086
Classification
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
  • Dialkylarylamine
  • Quinuclidine
  • Tertiary aliphatic/aromatic amine
  • Azepane
  • Aralkylamine
  • Benzenoid
  • Piperidine
  • Cyclic alcohol
  • Secondary alcohol
  • Tertiary amine
  • Hemiaminal
  • Organoheterocyclic compound
  • Azacycle
  • Alkanolamine
  • Alcohol
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSajmaline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0bta-2498000000-49bdb2b520b940e4152bSpectrum
Predicted GC-MSajmaline, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a59-9006700000-c3e3a75dc9384667f4a8Spectrum
Predicted GC-MSajmaline, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSajmaline, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSajmaline, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSajmaline, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSajmaline, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSajmaline, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSajmaline, "Ajmaline,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0009000000-852cc00f822b12dde86f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0029000000-f1807eeec4b4f036d14f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-1492000000-fc9be42e8caaa18f3f1d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-622c9342ca8dd4c7306c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0029000000-b0778df2272e5a83567c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-055b-0092000000-b4a357ef59beb58eff9b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-dae1999fa32e1d569c502021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-26633a00421c4e37223e2021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-0289000000-81cc4c52227dacb339092021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-dac436f1ca51942427392021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0009000000-dac436f1ca51942427392021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0049000000-faf20d5a5170e947fc9b2021-10-11View Spectrum
NMRNot Available
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
Processing...
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