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CHEBI:65525 - bromophycolide A

ChEBI IDCHEBI:65525
ChEBI Namebromophycolide A
Stars
DefinitionA diterpenoid that is a macrolide isolated from the Fijian red alga Callophycus serratus. It has been found to exhibit moderate cytotoxicity against several human tumour cell lines via specific apotopic cell death. It also displays anti-HIV, antibacterial, antifungal and antimalarial activity.
Last Modified28 November 2012
DownloadsMolfile
FormulaC27H37Br3O4
Net Charge0
Average Mass665.301
Monoisotopic Mass662.02420
SMILESCC1=C2Cc3cc(ccc3O)C(=O)O[C@H](C(C)(C)Br)CC[C@](C)(O)[C@H](Br)CC[C@]2(C)[C@@H](Br)CC1
InChIInChI=1S/C27H37Br3O4/c1-16-6-9-21(28)26(4)12-10-22(29)27(5,33)13-11-23(25(2,3)30)34-24(32)17-7-8-20(31)18(14-17)15-19(16)26/h7-8,14,21-23,31,33H,6,9-13,15H2,1-5H3/t21-,22+,23-,26-,27-/m0/s1
InChIKeySKIHYPQTROYIIT-VHXXJFIISA-N
Species of MetaboliteComponentSourceComments
Callophycus serratus (ncbitaxon:632897) - PubMed (16268553)
Roles Classification
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
ChEBI Ontology
Outgoing Relation(s)
bromophycolide A (CHEBI:65525) has role anti-HIV agent (CHEBI:64946)
bromophycolide A (CHEBI:65525) has role antibacterial agent (CHEBI:33282)
bromophycolide A (CHEBI:65525) has role antifungal agent (CHEBI:35718)
bromophycolide A (CHEBI:65525) has role antimalarial (CHEBI:38068)
bromophycolide A (CHEBI:65525) has role antineoplastic agent (CHEBI:35610)
bromophycolide A (CHEBI:65525) has role metabolite (CHEBI:25212)
bromophycolide A (CHEBI:65525) is a diterpenoid (CHEBI:23849)
bromophycolide A (CHEBI:65525) is a macrolide (CHEBI:25106)
bromophycolide A (CHEBI:65525) is a organobromine compound (CHEBI:37141)
bromophycolide A (CHEBI:65525) is a phenols (CHEBI:33853)
bromophycolide A (CHEBI:65525) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
(9S,12S,13R,15aS,16S)-13,16-dibromo-9-(2-bromopropan-2-yl)-3,12-dihydroxy-12,15a,19-trimethyl-1,9,10,11,12,13,14,15,15a,16,17,18-dodecahydro-7H-6,2-(metheno)-8-benzoxacycloheptadecin-7-one
Manual XrefsDatabases
10480986ChemSpider
Registry NumbersSources
Reaxys:10220528Reaxys
Citations