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CHEBI:65766 - dicerandrol C

ChEBI IDCHEBI:65766
ChEBI Namedicerandrol C
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 and C-10a', hydroxy groups at C-1, C-1', C-8 and C-8', 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
FormulaC38H38O16
Net Charge0
Average Mass750.706
Monoisotopic Mass750.21599
SMILESCC(=O)OC[C@]12Oc3ccc(-c4ccc5c(c4O)C(=O)C4=C(O)C[C@@H](C)[C@@H](OC(C)=O)[C@@]4(COC(C)=O)O5)c(O)c3C(=O)C1=C(O)C[C@@H](C)[C@H]2OC(C)=O
InChIInChI=1S/C38H38O16/c1-15-11-23(43)29-33(47)27-25(53-37(29,13-49-17(3)39)35(15)51-19(5)41)9-7-21(31(27)45)22-8-10-26-28(32(22)46)34(48)30-24(44)12-16(2)36(52-20(6)42)38(30,54-26)14-50-18(4)40/h7-10,15-16,35-36,43-46H,11-14H2,1-6H3/t15-,16-,35-,36-,37+,38+/m1/s1
InChIKeyLYWOIRXBEDUAPM-ACMZUNAXSA-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 C (CHEBI:65766) has role antimicrobial agent (CHEBI:33281)
dicerandrol C (CHEBI:65766) has role antineoplastic agent (CHEBI:35610)
dicerandrol C (CHEBI:65766) has role metabolite (CHEBI:25212)
dicerandrol C (CHEBI:65766) is a acetate ester (CHEBI:47622)
dicerandrol C (CHEBI:65766) is a biaryl (CHEBI:64459)
dicerandrol C (CHEBI:65766) is a polyphenol (CHEBI:26195)
dicerandrol C (CHEBI:65766) is a xanthones (CHEBI:51149)
IUPAC Name 
(5R,5'R,6R,6'R,10aR,10a'R)-10a,10a'-bis[(acetyloxy)methyl]-1,1',8,8'-tetrahydroxy-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
Manual XrefsDatabases
10213918ChemSpider
Registry NumbersSources
Reaxys:8965881Reaxys
Citations