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CHEBI:167111 - ustiloxin B

ChEBI IDCHEBI:167111
ChEBI Nameustiloxin B
Stars
DefinitionA heterodetic cyclic peptide with formula C26H39N5O12S produced by Ustilaginoidea virens fungi. It is an inhibitor of microtubule assembly.
Last Modified15 September 2021
SubmitterAnne Morgat
DownloadsMolfile
FormulaC26H39N5O12S
Net Charge0
Average Mass645.688
Monoisotopic Mass645.23159
SMILESCC[C@@]1(C)Oc2cc(c(S(=O)C[C@@H](O)C[C@H](N)C(=O)O)cc2O)[C@@H](O)[C@H](NC)C(=O)N[C@@H](C)C(=O)N[C@@H]1C(=O)NCC(=O)O
InChIInChI=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
InChIKeyBISPUFPESHDUKH-CEALTDAMSA-N
Species of MetaboliteComponentSourceComments
Ustilaginoidea virens (ncbitaxon:1159556) - PubMed (8071121) Isolated from the false smut balls caused by Ustilaginoidea virens on rice.
Aspergillus flavus (ncbitaxon:5059) - PubMed (24841822)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
mycotoxin  Poisonous substance produced by fungi.
microtubule-destabilising agent  Any substance that interacts with tubulin to inhibit polymerisation of microtubules.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
ChEBI Ontology
Outgoing Relation(s)
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 XrefsDatabases
FDB021299FooDB
C00016647KNApSAcK
HMDB0041373HMDB
8093149ChemSpider
Registry NumbersSources
CAS:151841-41-7ChemIDplus
Citations