CHEBI:167111 - ustiloxin B

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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 ZINC000535385293
Download Molfile XML SDF
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