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CHEBI:132868 - cyclomorusin A

ChEBI IDCHEBI:132868
ChEBI Namecyclomorusin A
Stars
DefinitionAn extended flavonoid that is cyclomulberrin in which the hydroxy group at position 10 has undergone oxidative cyclisation to position 3 of the 3-methylbut-2-en-1-yl substituent, with migration of the double bond into conjugation with the aromatic ring. It is a moderate inhibitor of acetylcholinesterase (IC50 = 16.2 - 36.6 μM), and a strong inhibitor of platelet-activating factor (PAF; 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine) induced platelet aggregation.
Last Modified25 August 2016
Submitterliuqingping
DownloadsMolfile
FormulaC25H22O6
Net Charge0
Average Mass418.445
Monoisotopic Mass418.14164
SMILESCC(C)=CC1Oc2cc(O)ccc2-c2oc3c4c(cc(O)c3c(=O)c21)OC(C)(C)C=C4
InChIInChI=1S/C25H22O6/c1-12(2)9-19-21-22(28)20-16(27)11-18-15(7-8-25(3,4)31-18)23(20)30-24(21)14-6-5-13(26)10-17(14)29-19/h5-11,19,26-27H,1-4H3
InChIKeyGDQXJMLXEYSICD-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Artocarpus altilis (ncbitaxon:194251) root (BTO:0001188) PubMed (12662107) Isolated from root cortex
Morus alba (ncbitaxon:3498) root (BTO:0001188) PubMed (25981820) Isolated from the root bark
Ficus hirta (ncbitaxon:309429) root (BTO:0001188) PubMed (24494557)
Morus nigra (ncbitaxon:85232) bark (BTO:0001301) PubMed (18330242)
Morus bombycis (ncbitaxon:66393) root (BTO:0001188) PubMed (17396934) Isolated from the root bark
Morus australis (ncbitaxon:66392) root (BTO:0001188) PubMed (17405024) Isolated from the root bark
Morus lhou (ncbitaxon:226896) bark (BTO:0001301) PubMed (18608767) Isolated from the stem bark
Morus alba var. atropurpurea (ncbitaxon:1453101) twig (BTO:0001411) PubMed (19149258)
Roles Classification
Biological Roles:
EC 1.14.18.1 (tyrosinase) inhibitor  Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 3.1.1.7 (acetylcholinesterase) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
Application:
platelet aggregation inhibitor  A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
ChEBI Ontology
Outgoing Relation(s)
cyclomorusin A (CHEBI:132868) has functional parent cyclomulberrin (CHEBI:132869)
cyclomorusin A (CHEBI:132868) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997)
cyclomorusin A (CHEBI:132868) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
cyclomorusin A (CHEBI:132868) has role plant metabolite (CHEBI:76924)
cyclomorusin A (CHEBI:132868) has role platelet aggregation inhibitor (CHEBI:50427)
cyclomorusin A (CHEBI:132868) is a cyclic ketone (CHEBI:3992)
cyclomorusin A (CHEBI:132868) is a extended flavonoid (CHEBI:71037)
cyclomorusin A (CHEBI:132868) is a organic heteropentacyclic compound (CHEBI:38164)
cyclomorusin A (CHEBI:132868) is a polyphenol (CHEBI:26195)
IUPAC Name 
6,11-dihydroxy-3,3-dimethyl-8-(2-methylprop-1-en-1-yl)-3H,7H,8H-chromeno[4,3-b]pyrano[2,3-h]chromen-7-one
Synonym  Source
cyclomorusinChemIDplus
Registry NumbersSources
Reaxys:1442991Reaxys
CAS:62596-34-3ChemIDplus
Citations