CHEBI:3737 - cleistanthin A

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ChEBI Name cleistanthin A
ChEBI ID CHEBI:3737
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H28O11
Net Charge 0
Average Mass 540.51530
Monoisotopic Mass 540.16316
InChI InChI=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
InChIKey FCOQWUOWHWHTJP-DZXBDMBVSA-N
SMILES CO[C@@H]1CO[C@@H](Oc2c3COC(=O)c3c(-c3ccc4OCOc4c3)c3cc(OC)c(OC)cc23)[C@H](O)[C@H]1OC
Metabolite of Species Details
Cleistanthus collinus (NCBI:txid1357584) Found in aerial part (BTO:0001658). See: Chem. Pharm. Bull., 2003, 51(11), 1299-1300
Cleistanthus collinus (NCBI:txid1357584) See: Tetrahedron, 1981, 37, 3641-3652
Phyllanthus taxodiifolius (NCBI:txid296045) Found in aerial part (BTO:0001658). See: PubMed
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.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via cleistanthins )
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.
diuretic
An agent that promotes the excretion of urine through its effects on kidney function.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cleistanthin A (CHEBI:3737) has role α-adrenergic antagonist (CHEBI:37890)
cleistanthin A (CHEBI:3737) has role antihypertensive agent (CHEBI:35674)
cleistanthin A (CHEBI:3737) has role diuretic (CHEBI:35498)
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 Sources
Ciba Go. 4350 ChemIDplus
cleistanthin ChEBI
Manual Xrefs Databases
C00002590 KNApSAcK
C10548 KEGG COMPOUND
EP2393779 Patent
US2012029179 Patent
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Registry Numbers Types Sources
25047-48-7 CAS Registry Number ChemIDplus
5194207 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
21 January 2015