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CHEBI:3737 - cleistanthin A

ChEBI IDCHEBI:3737
ChEBI Namecleistanthin A
Stars
DefinitionA member of the class of cleistanthins that is the 4-O-3,4-di-O-methyl-β-D-xylopyranoside of 1,3-dihydronaphtho[2,3-c]furan-4-ol which is substituted by an oxo group at position 1, methoxy groups at positions 6 and 7, and a 1,3-benzodioxol-5-yl group at position 9. It is one of the toxic principles in Cleistanthus collinus.
Last Modified21 January 2015
DownloadsMolfile
FormulaC28H28O11
Net Charge0
Average Mass540.521
Monoisotopic Mass540.16316
SMILESCOc1cc2c(O[C@@H]3OC[C@@H](OC)[C@H](OC)[C@H]3O)c3c(c(-c4ccc5c(c4)OCO5)c2cc1OC)C(=O)OC3
InChIInChI=1S/C28H28O11/c1-31-18-8-14-15(9-19(18)32-2)25(39-28-24(29)26(34-4)21(33-3)11-36-28)16-10-35-27(30)23(16)22(14)13-5-6-17-20(7-13)38-12-37-17/h5-9,21,24,26,28-29H,10-12H2,1-4H3/t21-,24-,26+,28+/m1/s1
InChIKeyFCOQWUOWHWHTJP-DZXBDMBVSA-N
Species of MetaboliteComponentSourceComments
Cleistanthus collinus (ncbitaxon:1357584)
aerial part (BTO:0001658) Article (Chem. Pharm. Bull., 2003, 51(11), 1299-1300)
- Article (Tetrahedron, 1981, 37, 3641-3652)
Phyllanthus taxodiifolius (ncbitaxon:296045) aerial part (BTO:0001658) PubMed (16450297)
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.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
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.
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
diuretic  An agent that promotes the excretion of urine through its effects on kidney function.
ChEBI Ontology
Outgoing Relation(s)
cleistanthin A (CHEBI:3737) has role antihypertensive agent (CHEBI:35674)
cleistanthin A (CHEBI:3737) has role diuretic (CHEBI:35498)
cleistanthin A (CHEBI:3737) has role α-adrenergic antagonist (CHEBI:37890)
cleistanthin A (CHEBI:3737) is a cleistanthins (CHEBI:84406)
cleistanthin A (CHEBI:3737) is a xylose derivative (CHEBI:74865)
IUPAC Name 
9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-1,3-dihydronaphtho[2,3-c]furan-4-yl 3,4-di-O-methyl-β-D-xylopyranoside
Synonyms  Source
cleistanthinChEBI
Ciba Go. 4350ChemIDplus
Manual XrefsDatabases
C10548KEGG COMPOUND
C00002590KNApSAcK
US2012029179Patent
EP2393779Patent
Registry NumbersSources
Reaxys:5194207Reaxys
CAS:25047-48-7KEGG COMPOUND
CAS:25047-48-7ChemIDplus
Citations