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CHEBI:167054 - acrophiarin

ChEBI IDCHEBI:167054
ChEBI Nameacrophiarin
Stars
DefinitionA cyclic hexapeptide echinocandin antibiotic with a myristoyl side chain. It is produced by a specific strain of Penicillium arenicola and exhibits antimycotic activity.
Last Modified29 April 2021
SubmitterMartin Larralde
DownloadsMolfile
FormulaC49H78N8O17
Net Charge0
Average Mass1051.202
Monoisotopic Mass1050.54849
SMILES[H][C@@]12C[C@@H](O)CN1C(=O)[C@H]([C@@H](C)O)NC(=O)[C@@]([H])(NC(=O)CCCCCCCCCCCCC)C[C@@H](O)[C@@H](O)NC(=O)[C@@H]1[C@@H](O)[C@@H](C)CN1C(=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/C49H78N8O17/c1-4-5-6-7-8-9-10-11-12-13-14-15-35(64)51-30-21-33(62)45(70)55-47(72)39-40(65)25(2)23-57(39)49(74)37(32(61)22-34(50)63)53-46(71)38(42(67)41(66)27-16-18-28(59)19-17-27)54-44(69)31-20-29(60)24-56(31)48(73)36(26(3)58)52-43(30)68/h16-19,25-26,29-33,36-42,45,58-62,65-67,70H,4-15,20-24H2,1-3H3,(H2,50,63)(H,51,64)(H,52,68)(H,53,71)(H,54,69)(H,55,72)/t25-,26+,29+,30-,31-,32+,33+,36-,37-,38-,39-,40-,41-,42-,45+/m0/s1
InChIKeyQZRPBFSNQQUAAB-QZXUYJGCSA-N
Species of MetaboliteComponentSourceComments
Penicillium arenicola (ncbitaxon:168477) - PubMed (32239586) Strain: NRRL 8095
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:
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
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)
acrophiarin (CHEBI:167054) has role Penicillium metabolite (CHEBI:76964)
acrophiarin (CHEBI:167054) is a antibiotic antifungal agent (CHEBI:86478)
acrophiarin (CHEBI:167054) is a echinocandin (CHEBI:57248)
acrophiarin (CHEBI:167054) is a homodetic cyclic peptide (CHEBI:24613)
IUPAC Name 
N-{(2R,6S,9S,11R,12R,14aS,15S,16S,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]-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl}tetradecanamide
Synonyms  Source
S31794/F-1SUBMITTER
antibiotic S31794/F-1ChEBI
Manual XrefsDatabases
US4173629Patent
Citations