CHEBI:2524 - ajmalicine

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ChEBI Name ajmalicine
ChEBI ID CHEBI:2524
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H24N2O3
Net Charge 0
Average Mass 352.428
Monoisotopic Mass 352.179
InChI InChI=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
InChIKey GRTOGORTSDXSFK-XJTZBENFSA-N
SMILES C=1C=CC=2NC=3[C@]4(N(CCC3C2C1)C[C@]5([C@@](C(=CO[C@H]5C)C(OC)=O)(C4)[H])[H])[H]
Metabolite of Species Details
Uncaria elliptica (IPNI:768231-1) Found in bark (BTO:0001301). See: 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.
Melodinus khasianus (IPNI:80218-1) See: PubMed
Catharanthus lanceus (NCBI:txid1750993) See: PubMed
Vinca major (NCBI:txid185238) See: 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.
Rauvolfia verticillata (NCBI:txid329875) Found in bark (BTO:0001301). Isolated from root bark See: Kan, N.G. and Nikolaeva, L.A. (1991) Alkaloids of Rauwolfia species growing in Vietnam. Chem. Nat. Compd., 27(6), 718-720.
Catharanthus roseus (NCBI:txid4058) Found in root (BTO:0001188). See: PubMed
Catharanthus roseus (NCBI:txid4058) Found in aerial part (BTO:0001658). See: PubMed
Rauwolfia oreogiton (NCBI:txid4059) Found in bark (BTO:0001301). Isolated from root bark See: PubMed
Rauvolfia serpentina (NCBI:txid4060) Found in root (BTO:0001188). See: 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.
Roles Classification
Biological Role(s): alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-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.
(via alkaloid )
Application(s): 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 alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
vasodilator agent
A drug used to cause dilation of the blood vessels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ajmalicine (CHEBI:2524) has role α-adrenergic antagonist (CHEBI:37890)
ajmalicine (CHEBI:2524) has role antihypertensive agent (CHEBI:35674)
ajmalicine (CHEBI:2524) has role vasodilator agent (CHEBI:35620)
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 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 Sources
(19α)-16,17-didehydro-19-methyl-oxayohimban-16-carboxylic acid methyl ester ChEBI
ajmalicin ChemIDplus
ajmalicine KEGG COMPOUND
δ-yohimbine ChemIDplus
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-carboxylate ChEBI
raubasine ChemIDplus
Brand Names Sources
Circolene ChemIDplus
Cristanyl ChEBI
Duxil ChemIDplus
Lamuran KEGG DRUG
Sarpan ChemIDplus
Manual Xrefs Databases
Ajmalicine Wikipedia
C00001678 KNApSAcK
C09024 KEGG COMPOUND
D08470 KEGG DRUG
LSM-15373 LINCS
View more database links
Registry Numbers Types Sources
483-04-5 CAS Registry Number NIST Chemistry WebBook
483-04-5 CAS Registry Number ChemIDplus
97268 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15930738 PubMed citation Europe PMC
19151732 PubMed citation Europe PMC
22331368 PubMed citation Europe PMC
22332772 PubMed citation Europe PMC
24237015 PubMed citation Europe PMC
26983347 PubMed citation Europe PMC
27584856 PubMed citation Europe PMC
4387608 PubMed citation Europe PMC
6091834 PubMed citation Europe PMC
6128043 PubMed citation Europe PMC
Last Modified
12 November 2018
General Comment
2018-11-09 Relevant Articles: Brown, R.T., Chapple, C.L., Duckworth, D.M. and Platt, R. (1976) Conversion of secologanin into elenolic acid and 18-oxayohimban alkaloids. J. Chem. Soc., Perkin Trans. 1, 2, 160-162.