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CHEBI:2524 - ajmalicine

ChEBI IDCHEBI:2524
ChEBI Nameajmalicine
Stars
DefinitionA monoterpenoid indole alkaloid with formula C21H24N2O3, isolated from several Rauvolfia and Catharanthus species. It is a selective α1-adrenoceptor antagonist used for the treatment of high blood pressure.
Last Modified28 May 2021
DownloadsMolfile
FormulaC21H24N2O3
Net Charge0
Average Mass352.434
Monoisotopic Mass352.17869
SMILES[H][C@@]12C[C@]3([H])C(C(=O)OC)=CO[C@@H](C)[C@@]3([H])CN1CCc1c2nc2ccccc12
InChIInChI=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
InChIKeyGRTOGORTSDXSFK-XJTZBENFSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Melodinus khasianus (IPNI:80218-1) - PubMed (27584856)
Vinca major (ncbitaxon:185238) - Article (Cheng, G.G., Zhao, Y.L., Zhang, Y., Lunga, P.K., Hu, D.B., Li, Y., Gu, J., Song, C.W., Sun, W.B., Liu, Y.P. and Luo, X.D. (2014) Indole alkaloids from cultivated Vinca major. Tetrahedron, 70(45), 8723-8729.)
Catharanthus roseus (ncbitaxon:4058)
root (BTO:0001188) PubMed (22332772)
aerial part (BTO:0001658) PubMed (15930738)
Uncaria elliptica (IPNI:768231-1) bark (BTO:0001301) Article (Diyabalanage, T.K.K., Kumarihamy, B.M.M., Wannigama, G.P., Jayasinghe, L., Merlini, L. and Scaglioni, L. (1997) Alkaloids of Uncaria elliptica. Phytochemistry, 45(8), 1731-1732.)
Rauvolfia verticillata (ncbitaxon:329875) bark (BTO:0001301) Article (Kan, N.G. and Nikolaeva, L.A. (1991) Alkaloids of Rauwolfia species growing in Vietnam. Chem. Nat. Compd., 27(6), 718-720.) Isolated from root bark
Rauvolfia serpentina (ncbitaxon:4060) root (BTO:0001188) Article (Klohs, M.W., Draper, M.D., Keller, F., Malesh, W. and Petracek, F.J. (1954) Alkaloids of Rauwolfia serpentina benth. II. The isolation of naturally occurring py-tetrahydroserpentine (ajmalicine) and a contribution toward its structure. J. Am. Chem. Soc., 76(5), 1332-1334.)
Catharanthus lanceus (ncbitaxon:1750993) - PubMed (4387608)
Rauwolfia oreogiton (ncbitaxon:4059) bark (BTO:0001301) PubMed (4153471) Isolated from root bark
Roles Classification
Biological Roles:
alpha-adrenergic antagonist  An agent that binds to but does not activate α-adrenergic receptors thereby blocking the actions of endogenous or exogenous α-adrenergic agonists. α-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
vasodilator agent  A drug used to cause dilation of the blood vessels.
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
alpha-adrenergic antagonist  An agent that binds to but does not activate α-adrenergic receptors thereby blocking the actions of endogenous or exogenous α-adrenergic agonists. α-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
ChEBI Ontology
Outgoing Relation(s)
ajmalicine (CHEBI:2524) has role antihypertensive agent (CHEBI:35674)
ajmalicine (CHEBI:2524) has role vasodilator agent (CHEBI:35620)
ajmalicine (CHEBI:2524) has role α-adrenergic antagonist (CHEBI:37890)
ajmalicine (CHEBI:2524) is a methyl ester (CHEBI:25248)
ajmalicine (CHEBI:2524) is a monoterpenoid indole alkaloid (CHEBI:65323)
ajmalicine (CHEBI:2524) is a organic heteropentacyclic compound (CHEBI:38164)
ajmalicine (CHEBI:2524) is conjugate base of ajmalicine(1+) (CHEBI:142527)
Incoming Relation(s)
ajmalicine(1+) (CHEBI:142527) is conjugate acid of ajmalicine (CHEBI:2524)
IUPAC Name 
methyl (19α)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate
Synonyms  Source
ajmalicineKEGG COMPOUND
raubasineChemIDplus
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
(19α)-16,17-didehydro-19-methyl-oxayohimban-16-carboxylic acid methyl esterChEBI
δ-yohimbineChemIDplus
ajmalicinChemIDplus
Brand Names  Source
LamuranKEGG DRUG
DuxilChemIDplus
CircoleneChemIDplus
CristanylChEBI
SarpanChemIDplus
Manual XrefsDatabases
C09024KEGG COMPOUND
D08470KEGG DRUG
C00001678KNApSAcK
LSM-15373LINCS
AjmalicineWikipedia
AJNPDBeChem
Registry NumbersSources
Reaxys:97268Reaxys
CAS:483-04-5KEGG COMPOUND
CAS:483-04-5ChemIDplus
CAS:483-04-5NIST Chemistry WebBook
Citations