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CHEBI:131609 - pneumocandin B0

ChEBI IDCHEBI:131609
ChEBI Namepneumocandin B0
Stars
ASCII Namepneumocandin B0
DefinitionAn 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.
Last Modified24 March 2016
SubmitterGareth Owen
DownloadsMolfile
FormulaC50H80N8O17
Net Charge0
Average Mass1065.229
Monoisotopic Mass1064.56414
SMILES[H][C@@]12C[C@@H](O)CN1C(=O)[C@H]([C@@H](C)O)NC(=O)[C@@]([H])(NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)C[C@@H](O)[C@@H](O)NC(=O)[C@@H]1[C@@H](O)CCN1C(=O)[C@H]([C@H](O)CC(N)=O)NC(=O)[C@H]([C@H](O)[C@@H](O)c1ccc(O)cc1)NC2=O
InChIInChI=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
InChIKeyDQXPFAADCTZLNL-FXDJFZINSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Glarea lozoyensis (ncbitaxon:101852) - PubMed (24270605)
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
EC 2.4.1.34 (1,3-beta-glucan synthase) inhibitor  A EC 2.4.1.* (hexosyltransferase) inhibitor that inhibits the action of 1,3-β-glucan synthase (EC 2.4.1.34).
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
L-688,786ChemIDplus
pneumocardin B(0)ChemIDplus
L-688786ChemIDplus
L 688,786ChemIDplus
pneumocandin B(0)ChemIDplus
Manual XrefsDatabases
Pneumocandin_BoWikipedia
Registry NumbersSources
Reaxys:9316734Reaxys
CAS:135575-42-7ChemIDplus
Citations