CHEBI:167054 - acrophiarin

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ChEBI Name acrophiarin
ChEBI ID CHEBI:167054
Definition A cyclic hexapeptide echinocandin antibiotic with a myristoyl side chain. It is produced by a specific strain of Penicillium arenicola and exhibits antimycotic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Martin Larralde
Supplier Information
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Formula C49H78N8O17
Net Charge 0
Average Mass 1051.202
Monoisotopic Mass 1050.54849
InChI InChI=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
InChIKey QZRPBFSNQQUAAB-QZXUYJGCSA-N
SMILES [H][C@@]12C[C@@H](O)CN1C(=O)[C@@H](NC(=O)[C@]([H])(C[C@@H](O)[C@@H](O)NC(=O)[C@@H]1[C@@H](O)[C@@H](C)CN1C(=O)[C@@H](NC(=O)[C@@H](NC2=O)[C@H](O)[C@@H](O)C1=CC=C(O)C=C1)[C@H](O)CC(N)=O)NC(=O)CCCCCCCCCCCCC)[C@@H](C)O
Metabolite of Species Details
Penicillium arenicola (NCBI:txid168477) of strain NRRL 8095 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): 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-beta-glucan synthase (EC 2.4.1.34).
(via echinocandin )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via antibiotic antifungal agent )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
antibiotic S31794/F-1 ChEBI
S31794/F-1 SUBMITTER
Manual Xref Database
US4173629 Patent
View more database links
Citations Waiting for Citations Types Sources
27494047 PubMed citation Europe PMC
32239586 PubMed citation SUBMITTER
Last Modified
29 April 2021