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CHEBI:65765 - dicerandrol B

ChEBI IDCHEBI:65765
ChEBI Namedicerandrol B
Stars
DefinitionA biaryl that is 5,5',7,7',9,9',10a,10a'-octahydro-6H,6'H-2,2'-bixanthene substituted by acetyloxy groups at C-5 and C-5', (acetyloxy)methyl group at C-10a, hydroxy groups at C-1, C-1', C-8 and C-8', hydroxymethyl group at 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 Modified7 January 2013
DownloadsMolfile
FormulaC36H36O15
Net Charge0
Average Mass708.669
Monoisotopic Mass708.20542
SMILESCC(=O)OC[C@]12Oc3ccc(-c4ccc5c(c4O)C(=O)C4=C(O)C[C@@H](C)[C@@H](OC(C)=O)[C@@]4(CO)O5)c(O)c3C(=O)C1=C(O)C[C@@H](C)[C@H]2OC(C)=O
InChIInChI=1S/C36H36O15/c1-14-10-21(41)27-31(45)25-23(50-35(27,12-37)33(14)48-17(4)39)8-6-19(29(25)43)20-7-9-24-26(30(20)44)32(46)28-22(42)11-15(2)34(49-18(5)40)36(28,51-24)13-47-16(3)38/h6-9,14-15,33-34,37,41-44H,10-13H2,1-5H3/t14-,15-,33-,34-,35+,36+/m1/s1
InChIKeyWRLHYRADHSNDLJ-NKSNWBLISA-N
Species of MetaboliteComponentSourceComments
Phomopsis longicolla (ncbitaxon:54899) - 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 B (CHEBI:65765) has role antimicrobial agent (CHEBI:33281)
dicerandrol B (CHEBI:65765) has role antineoplastic agent (CHEBI:35610)
dicerandrol B (CHEBI:65765) has role metabolite (CHEBI:25212)
dicerandrol B (CHEBI:65765) is a acetate ester (CHEBI:47622)
dicerandrol B (CHEBI:65765) is a biaryl (CHEBI:64459)
dicerandrol B (CHEBI:65765) is a polyphenol (CHEBI:26195)
dicerandrol B (CHEBI:65765) is a primary alcohol (CHEBI:15734)
dicerandrol B (CHEBI:65765) is a xanthones (CHEBI:51149)
IUPAC Name 
(5R,5'R,6R,6'R,10aR,10a'R)-10a-[(acetyloxy)methyl]-1,1',8,8'-tetrahydroxy-10a'-(hydroxymethyl)-6,6'-dimethyl-9,9'-dioxo-5,5',7,7',9,9',10a,10a'-octahydro-6H,6'H-2,2'-bixanthene-5,5'-diyl diacetate
Registry NumbersSources
Reaxys:8965660Reaxys
Citations