CHEBI:131609 - pneumocandin B0

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ChEBI Name pneumocandin B0
ChEBI ID CHEBI:131609
ChEBI ASCII Name pneumocandin B0
Definition An echinocandin initially isolated as a very minor bioactive fermentation product of Glarea lozoyensis (originally known as Zalerion arboricola). Subsequent random mutagenesis work and optimisation of the fermentation medium permitted the industrial production of pneumocandin B0, which is used as the starting point for the synthesis of the antifungal drug caspofungin.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C50H80N8O17
Net Charge 0
Average Mass 1065.216
Monoisotopic Mass 1064.564
InChI InChI=1S/C50H80N8O17/c1-5-25(2)20-26(3)12-10-8-6-7-9-11-13-37(66)52-31-22-35(64)46(71)56-48(73)41-33(62)18-19-57(41)50(75)39(34(63)23-36(51)65)54-47(72)40(43(68)42(67)28-14-16-29(60)17-15-28)55-45(70)32-21-30(61)24-58(32)49(74)38(27(4)59)53-44(31)69/h14-17,25-27,30-35,38-43,46,59-64,67-68,71H,5-13,18-24H2,1-4H3,(H2,51,65)(H,52,66)(H,53,69)(H,54,72)(H,55,70)(H,56,73)/t25-,26+,27+,30+,31-,32-,33-,34+,35+,38-,39-,40-,41-,42-,43-,46+/m0/s1
InChIKey DQXPFAADCTZLNL-FXDJFZINSA-N
SMILES [C@@]12(N(C[C@@H](C1)O)C([C@H]([C@@H](C)O)NC(=O)[C@](C[C@H]([C@@H](O)NC([C@@H]3[C@H](CCN3C([C@H]([C@@H](CC(N)=O)O)NC(=O)[C@H]([C@@H]([C@H](C4=CC=C(C=C4)O)O)O)NC2=O)=O)O)=O)O)(NC(CCCCCCCC[C@H](C[C@H](CC)C)C)=O)[H])=O)[H]
Metabolite of Species Details
Glarea lozoyensis (NCBI:txid101852) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via antibiotic antifungal agent )
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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ChEBI Ontology
Outgoing pneumocandin B0 (CHEBI:131609) has role antifungal agent (CHEBI:35718)
pneumocandin B0 (CHEBI:131609) has role fungal metabolite (CHEBI:76946)
pneumocandin B0 (CHEBI:131609) is a echinocandin (CHEBI:57248)
pneumocandin B0 (CHEBI:131609) is a homodetic cyclic peptide (CHEBI:24613)
Incoming caspofungin (CHEBI:474180) has functional parent pneumocandin B0 (CHEBI:131609)
IUPAC Name
(10R,12S)-N-{(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6-[(1R)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl}-10,12-dimethyltetradecanamide
Synonyms Sources
L 688,786 ChemIDplus
L-688,786 ChemIDplus
L-688786 ChemIDplus
pneumocandin B(0) ChemIDplus
pneumocardin B(0) ChemIDplus
Database Link Database
Pneumocandin_Bo Wikipedia
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Registry Numbers Types Sources
135575-42-7 CAS Registry Number ChemIDplus
9316734 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
24086376 PubMed citation Europe PMC
24270605 PubMed citation Europe PMC
25527531 PubMed citation Europe PMC
Last Modified
24 March 2016