CHEBI:66486 - simalikalactone D

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name simalikalactone D
ChEBI ID CHEBI:66486
Definition A quassinoid isolated from Quassia amara and Quassia africana. It has been shown to exhibit antimalarial, cytotoxic and antiviral activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C25H34O9
Net Charge 0
Average Mass 478.53210
Monoisotopic Mass 478.22028
InChI InChI=1S/C25H34O9/c1-6-10(2)21(30)34-16-18-24(5)20(29)15(27)17-23(4)12(11(3)7-13(26)19(23)28)8-14(33-22(16)31)25(17,18)9-32-24/h7,10,12,14-20,27-29H,6,8-9H2,1-5H3/t10-,12+,14-,15-,16-,17-,18+,19-,20+,23+,24-,25-/m1/s1
InChIKey OKIKYYZNNZCZRX-ZPUVFWQWSA-N
SMILES [H][C@@]12C[C@@]3([H])C(C)=CC(=O)[C@@H](O)[C@]3(C)[C@@]3([H])[C@@H](O)[C@H](O)[C@]4(C)OC[C@@]13[C@@]4([H])[C@@H](OC(=O)[C@H](C)CC)C(=O)O2
Metabolite of Species Details
Simaba multiflora (IPNI:236532-2) See: PubMed
Quassia amara (NCBI:txid43725) Found in leaf (BTO:0000713). See: PubMed
Simaba guianensis (NCBI:txid459152) Found in bark (BTO:0001301). See: PubMed
Quassia africana (NCBI:txid459167) Found in root (BTO:0001188). Previous component: root bark; See: PubMed
Leitneria floridana (NCBI:txid83908) Found in aerial part (BTO:0001658). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antiviral agent
A substance that destroys or inhibits replication of viruses.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing simalikalactone D (CHEBI:66486) has role antimalarial (CHEBI:38068)
simalikalactone D (CHEBI:66486) has role antineoplastic agent (CHEBI:35610)
simalikalactone D (CHEBI:66486) has role antiviral agent (CHEBI:22587)
simalikalactone D (CHEBI:66486) has role metabolite (CHEBI:25212)
simalikalactone D (CHEBI:66486) is a δ-lactone (CHEBI:18946)
simalikalactone D (CHEBI:66486) is a cyclic ether (CHEBI:37407)
simalikalactone D (CHEBI:66486) is a enone (CHEBI:51689)
simalikalactone D (CHEBI:66486) is a organic heteropentacyclic compound (CHEBI:38164)
simalikalactone D (CHEBI:66486) is a quassinoid (CHEBI:72485)
simalikalactone D (CHEBI:66486) is a secondary α-hydroxy ketone (CHEBI:2468)
simalikalactone D (CHEBI:66486) is a secondary alcohol (CHEBI:35681)
simalikalactone D (CHEBI:66486) is a triol (CHEBI:27136)
IUPAC Name
(1β,11β,12α,15βb)-1,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-15-yl (2R)-2-methylbutanoate
Synonym Source
(+)-simalikalactone ChEBI
Manual Xrefs Databases
C00003731 KNApSAcK
C08783 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
35321-80-3 CAS Registry Number ChemIDplus
5386394 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11141127 PubMed citation Europe PMC
11842321 PubMed citation Europe PMC
16730421 PubMed citation Europe PMC
17340534 PubMed citation Europe PMC
8289064 PubMed citation Europe PMC
Last Modified
06 February 2018