CHEBI:3454 - cassaine

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ChEBI Name cassaine
ChEBI ID CHEBI:3454
Definition A tricyclic diterpenoid isolated from several plant species of the genus Erythrophleum.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H39NO4
Net Charge 0
Average Mass 405.579
Monoisotopic Mass 405.28791
InChI InChI=1S/C24H39NO4/c1-15-16(13-21(28)29-12-11-25(5)6)7-8-17-22(15)18(26)14-19-23(2,3)20(27)9-10-24(17,19)4/h13,15,17,19-20,22,27H,7-12,14H2,1-6H3/b16-13+/t15-,17-,19-,20-,22-,24+/m0/s1
InChIKey GMHWATCMBXIANN-IOJUAHGHSA-N
SMILES [C@]12([C@](C([C@@H](O)CC1)(C)C)(CC(=O)[C@@]3([C@@]2(CC\C(\[C@@H]3C)=C/C(OCCN(C)C)=O)[H])[H])[H])C
Metabolite of Species Details
Erythrophleum guineense (NCBI:txid1206079) Found in bark (BTO:0001301). See: Book: Dictionary of Alkaloids with CD-ROM, John Buckingham et al, CRC press, 2010, pg 374, C-178.
Erythrophleum ivorense (NCBI:txid53877) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
poison
Any substance that causes disturbance to organisms by chemical reaction or other activity on the molecular scale, when a sufficient quantity is absorbed by the organism.
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of Na+/K+-transporting ATPase (EC 3.6.3.9).
Application(s): cardiotonic drug
A drug that has a strengthening effect on the heart or that can increase cardiac output.
local anaesthetic
Any member of a group of drugs that reversibly inhibit the propagation of signals along nerves. Wide variations in potency, stability, toxicity, water-solubility and duration of action determine the route used for administration, e.g. topical, intravenous, epidural or spinal block.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cassaine (CHEBI:3454) has parent hydride podocarpane (CHEBI:36548)
cassaine (CHEBI:3454) has role antihypertensive agent (CHEBI:35674)
cassaine (CHEBI:3454) has role cardiotonic drug (CHEBI:38147)
cassaine (CHEBI:3454) has role EC 3.6.3.9 (Na+/K+-transporting ATPase) inhibitor (CHEBI:63510)
cassaine (CHEBI:3454) has role local anaesthetic (CHEBI:36333)
cassaine (CHEBI:3454) has role plant metabolite (CHEBI:76924)
cassaine (CHEBI:3454) has role poison (CHEBI:64909)
cassaine (CHEBI:3454) is a enoate ester (CHEBI:51702)
cassaine (CHEBI:3454) is a organic hydroxy compound (CHEBI:33822)
cassaine (CHEBI:3454) is a tertiary amino compound (CHEBI:50996)
cassaine (CHEBI:3454) is a tricyclic diterpenoid (CHEBI:79084)
IUPAC Name
2-(dimethylamino)ethyl (2E)-[(13E)-3β-hydroxy-14α-methyl-7-oxopodocarpan-13-ylidene]acetate
Synonyms Sources
(+)-cassaine ChEBI
cassaine KEGG COMPOUND
nervocidine ChemIDplus
Manual Xrefs Databases
C00001626 KNApSAcK
C08670 KEGG COMPOUND
Cassaine Wikipedia
View more database links
Registry Number Type Source
468-76-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
125204 PubMed citation Europe PMC
130244 PubMed citation Europe PMC
18817389 PubMed citation Europe PMC
212685 PubMed citation Europe PMC
24295200 PubMed citation Europe PMC
25057897 PubMed citation Europe PMC
2735954 PubMed citation Europe PMC
2990948 PubMed citation Europe PMC
5135168 PubMed citation Europe PMC
5697074 PubMed citation Europe PMC
6046785 PubMed citation Europe PMC
Last Modified
12 June 2020