CHEBI:78661 - borrelidin

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ChEBI Name borrelidin
ChEBI ID CHEBI:78661
Definition A macrolide that is isolated from several Streptomyces species and displays antibiotic, antineoplastic and antimalarial properties.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB2354291, eMolecules:976195
Download Molfile XML SDF
Formula C28H43NO6
Net Charge 0
Average Mass 489.64410
Monoisotopic Mass 489.30904
InChI InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25+,27+/m0/s1
InChIKey OJCKRNPLOZHAOU-JTHVHBRGSA-N
SMILES C[C@H]1C[C@@H](C)C[C@H](C)[C@@H](O)\C(=C/C=C/C[C@@H](OC(=O)C[C@H](O)[C@@H](C)C1)[C@@H]1CCC[C@H]1C(O)=O)C#N
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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.
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 borrelidin (CHEBI:78661) has role antifungal agent (CHEBI:35718)
borrelidin (CHEBI:78661) has role antimalarial (CHEBI:38068)
borrelidin (CHEBI:78661) has role antimicrobial agent (CHEBI:33281)
borrelidin (CHEBI:78661) has role antineoplastic agent (CHEBI:35610)
borrelidin (CHEBI:78661) has role apoptosis inducer (CHEBI:68495)
borrelidin (CHEBI:78661) has role bacterial metabolite (CHEBI:76969)
borrelidin (CHEBI:78661) is a aliphatic nitrile (CHEBI:80291)
borrelidin (CHEBI:78661) is a diol (CHEBI:23824)
borrelidin (CHEBI:78661) is a macrolide (CHEBI:25106)
borrelidin (CHEBI:78661) is a monocarboxylic acid (CHEBI:25384)
borrelidin (CHEBI:78661) is a secondary alcohol (CHEBI:35681)
IUPAC Name
(1R,2R)-2-[(2R,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentanecarboxylic acid
Synonym Source
Treponemycin ChemIDplus
Manual Xrefs Databases
C15687 KEGG COMPOUND
CPD0-1348 MetaCyc
View more database links
Registry Numbers Types Sources
5782155 Reaxys Registry Number Reaxys
7184-60-3 CAS Registry Number KEGG COMPOUND
7184-60-3 CAS Registry Number ChemIDplus
Citations Types Sources
21343942 PubMed citation Europe PMC
21472957 PubMed citation Europe PMC
21678129 PubMed citation Europe PMC
22242825 PubMed citation Europe PMC
22313786 PubMed citation Europe PMC
22707527 PubMed citation Europe PMC
22822423 PubMed citation Europe PMC
22967236 PubMed citation Europe PMC
23488671 PubMed citation Europe PMC
24131731 PubMed citation Europe PMC
24155182 PubMed citation Europe PMC
24562907 PubMed citation Europe PMC
24778714 PubMed citation Europe PMC
24794971 PubMed citation Europe PMC
3680012 PubMed citation Europe PMC
Last Modified
01 May 2015