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CHEBI:65765 - dicerandrol B

Default Structure
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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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