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CHEBI:65764 - dicerandrol A

Default Structure
ChEBI IDCHEBI:65764
ChEBI Namedicerandrol A
Stars
DefinitionA biaryl that is 5,5',7,7',9,9',10a,10a'-octahydro-6H,6'H-2,2'-bixanthene substituted by acetoxy groups at C-5 and C-5', hydroxy groups at C-1, C-1', C-8 and C-8', hydroxymethyl groups at C-10a and C-10a', methyl groups at C-6 and C-6' and oxo groups at C-9 and C-9' respectively. A dimeric tetrahydroxanthone derivative isolated from Phomopsis longicolla, it exhibits antibacterial and cytotoxic activities.
Last Modified4 January 2013
DownloadsMolfile
FormulaC34H34O14
Net Charge0
Average Mass666.632
Monoisotopic Mass666.19486
SMILESCC(=O)O[C@@H]1[C@H](C)CC(O)=C2C(=O)c3c(ccc(-c4ccc5c(c4O)C(=O)C4=C(O)C[C@@H](C)[C@@H](OC(C)=O)[C@@]4(CO)O5)c3O)O[C@@]21CO
InChIInChI=1S/C34H34O14/c1-13-9-19(39)25-29(43)23-21(47-33(25,11-35)31(13)45-15(3)37)7-5-17(27(23)41)18-6-8-22-24(28(18)42)30(44)26-20(40)10-14(2)32(46-16(4)38)34(26,12-36)48-22/h5-8,13-14,31-32,35-36,39-42H,9-12H2,1-4H3/t13-,14-,31-,32-,33+,34+/m1/s1
InChIKeyLMADRJRTQXNOEP-FNCICBJWSA-N
Species of MetaboliteComponentSourceComments
Phomopsis longicolla (ncbitaxon:54899) stem (BTO:0001300) PubMed (11520215) An endophytic fungus of the endangered mint plant Dicerandra frutescens
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
dicerandrol A (CHEBI:65764) has role antimicrobial agent (CHEBI:33281)
dicerandrol A (CHEBI:65764) has role antineoplastic agent (CHEBI:35610)
dicerandrol A (CHEBI:65764) has role metabolite (CHEBI:25212)
dicerandrol A (CHEBI:65764) is a acetate ester (CHEBI:47622)
dicerandrol A (CHEBI:65764) is a biaryl (CHEBI:64459)
dicerandrol A (CHEBI:65764) is a polyphenol (CHEBI:26195)
dicerandrol A (CHEBI:65764) is a primary alcohol (CHEBI:15734)
dicerandrol A (CHEBI:65764) is a xanthones (CHEBI:51149)
IUPAC Name 
(5R,5'R,6R,6'R,10aR,10a'R)-1,1',8,8'-tetrahydroxy-10a,10a'-bis(hydroxymethyl)-6,6'-dimethyl-9,9'-dioxo-5,5',7,7',9,9',10a,10a'-octahydro-6H,6'H-2,2'-bixanthene-5,5'-diyldiacetate
Registry NumbersSources
Reaxys:15827229Reaxys
Citations