CHEBI:65525 - bromophycolide A

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ChEBI Name bromophycolide A
ChEBI ID CHEBI:65525
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H37Br3O4
Net Charge 0
Average Mass 665.29200
Monoisotopic Mass 662.02420
InChI InChI=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
InChIKey SKIHYPQTROYIIT-VHXXJFIISA-N
SMILES CC1=C2Cc3cc(ccc3O)C(=O)O[C@@H](CC[C@](C)(O)[C@H](Br)CC[C@]2(C)[C@@H](Br)CC1)C(C)(C)Br
Metabolite of Species Details
Callophycus serratus (NCBI:txid632897) See: PubMed
Roles Classification
Biological Role(s): antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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.
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.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Xref Database
10480986 ChemSpider
View more database links
Registry Number Type Source
10220528 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16268553 PubMed citation Europe PMC
21309525 PubMed citation Europe PMC
22214291 PubMed citation Europe PMC
Last Modified
28 November 2012