CHEBI:167111 - ustiloxin B

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ChEBI Name ustiloxin B ChEBI ID CHEBI:167111 Definition A heterodetic cyclic peptide with formula C26H39N5O12S produced by Ustilaginoidea virens fungi. It is an inhibitor of microtubule assembly. Stars This entity has been manually annotated by the ChEBI Team. Submitter Anne Morgat Supplier Information Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C26H39N5O12S Net Charge 0 Average Mass 645.680 Monoisotopic Mass 645.23159 InChI InChI=1S/C26H39N5O12S/c1-5-26(3)21(24(39)29-9-18(34)35)31-22(37)11(2)30-23(38)19(28-4)20(36)13-7-16(43-26)15(33)8-17(13)44(42)10-12(32)6-14(27)25(40)41/h7-8,11-12,14,19-21,28,32-33,36H,5-6,9-10,27H2,1-4H3,(H,29,39)(H,30,38)(H,31,37)(H,34,35)(H,40,41)/t11-,12-,14-,19-,20+,21+,26+,44?/m0/s1 InChIKey BISPUFPESHDUKH-CEALTDAMSA-N SMILES CC[C@@]1(C)OC2=CC([C@@H](O)[C@H](NC)C(=O)N[C@@H](C)C(=O)N[C@@H]1C(=O)NCC(O)=O)=C(C=C2O)S(=O)C[C@@H](O)C[C@H](N)C(O)=O Metabolite of Species Details Ustilaginoidea virens (NCBI:txid1159556) Isolated from the false smut balls caused by Ustilaginoidea virens on rice. See: PubMed Aspergillus flavus (NCBI:txid5059) 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): microtubule-destabilising agent Any substance that interacts with tubulin to inhibit polymerisation of microtubules. mycotoxin Poisonous substance produced by fungi. Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus . View more via ChEBI Ontology ChEBI Ontology Outgoing ustiloxin B (CHEBI:167111) has role Aspergillus metabolite (CHEBI:76956) ustiloxin B (CHEBI:167111) has role microtubule-destabilising agent (CHEBI:61951) ustiloxin B (CHEBI:167111) has role mycotoxin (CHEBI:25442) ustiloxin B (CHEBI:167111) is a aromatic ether (CHEBI:35618) ustiloxin B (CHEBI:167111) is a heterodetic cyclic peptide (CHEBI:24533) ustiloxin B (CHEBI:167111) is a macrocycle (CHEBI:51026) ustiloxin B (CHEBI:167111) is a phenols (CHEBI:33853) ustiloxin B (CHEBI:167111) is a secondary alcohol (CHEBI:35681) ustiloxin B (CHEBI:167111) is a secondary carboxamide (CHEBI:140325) ustiloxin B (CHEBI:167111) is a sulfoxide (CHEBI:22063) IUPAC Name (4S)-5-{[(3R,4S,7S,10S,11R)-4-[(carboxymethyl)carbamoyl]-3-ethyl-11,15-dihydroxy-3,7-dimethyl-10-(methylamino)-6,9-dioxo-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-trien-13-yl]sulfinyl}-4-hydroxy-L-norvaline Manual Xrefs Databases 8093149 ChemSpider C00016647 KNApSAcK FDB021299 FooDB HMDB0041373 HMDB View more database links Registry Number Type Source 151841-41-7 CAS Registry Number ChemIDplus Citations Types Sources 24841822 PubMed citation Europe PMC 25414363 PubMed citation Europe PMC 26343725 PubMed citation Europe PMC 26842395 PubMed citation Europe PMC 27166860 PubMed citation Europe PMC 28208606 PubMed citation Europe PMC 28245594 PubMed citation Europe PMC 32211196 PubMed citation Europe PMC 32679089 PubMed citation Europe PMC 8071121 PubMed citation SUBMITTER 9630863 PubMed citation Europe PMC Last Modified 15 September 2021