CHEBI:29693 - thiostrepton

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ChEBI Name thiostrepton
ChEBI ID CHEBI:29693
Definition A heterodetic cyclic peptide, in which the cyclisation step involves a formal lactonisation between the carboxy group of a quinaldic acid-based residue and a secondary alcohol. An antibiotic that inhibits bacterial protein synthesis. Also acts as an antitumor agent.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C72H85N19O18S5
Net Charge 0
Average Mass 1664.88700
Monoisotopic Mass 1663.49235
InChI InChI=1S/C72H85N19O18S5/c1-14-26(3)47-63(105)78-30(7)57(99)75-28(5)56(98)76-31(8)58(100)91-72-19-18-40(66-85-43(22-111-66)59(101)77-29(6)55(97)74-27(4)54(73)96)81-52(72)42-21-112-67(83-42)49(34(11)109-69(107)41-20-37(32(9)92)36-16-17-39(79-47)51(95)50(36)80-41)89-60(102)44-24-113-68(86-44)53(71(13,108)35(12)94)90-62(104)45-23-110-65(84-45)38(15-2)82-64(106)48(33(10)93)88-61(103)46-25-114-70(72)87-46/h15-17,20-22,24-26,30-35,39,45,47-49,51-53,79,92-95,108H,4-6,14,18-19,23H2,1-3,7-13H3,(H2,73,96)(H,74,97)(H,75,99)(H,76,98)(H,77,101)(H,78,105)(H,82,106)(H,88,103)(H,89,102)(H,90,104)(H,91,100)/b38-15-/t26-,30-,31-,32-,33+,34+,35+,39+,45+,47-,48-,49-,51-,52+,53+,71+,72+/m0/s1
InChIKey NSFFHOGKXHRQEW-AIHSUZKVSA-N
SMILES [H][C@]12N=C(CC[C@@]11NC(=O)[C@H](C)NC(=O)C(=C)NC(=O)[C@H](C)NC(=O)[C@@H](N[C@@H]3C=Cc4c(cc(nc4[C@H]3O)C(=O)O[C@H](C)[C@H](NC(=O)c3csc(n3)[C@@H](NC(=O)[C@H]3CSC(=N3)\C(NC(=O)[C@@H](NC(=O)c3csc1n3)[C@@H](C)O)=C\C)[C@](C)(O)[C@@H](C)O)c1nc2cs1)[C@H](C)O)[C@@H](C)CC)c1nc(cs1)C(=O)NC(=C)C(=O)NC(=C)C(N)=O
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): antibacterial drug
A drug used to treat or prevent bacterial infections.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
protein synthesis inhibitor
A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing thiostrepton (CHEBI:29693) has role antibacterial drug (CHEBI:36047)
thiostrepton (CHEBI:29693) has role antineoplastic agent (CHEBI:35610)
thiostrepton (CHEBI:29693) has role metabolite (CHEBI:25212)
thiostrepton (CHEBI:29693) has role protein synthesis inhibitor (CHEBI:48001)
thiostrepton (CHEBI:29693) is a heterodetic cyclic peptide (CHEBI:24533)
Synonym Source
Thiostrepton KEGG COMPOUND
Manual Xrefs Databases
3007 VSDB
C00000753 KNApSAcK
C12054 KEGG COMPOUND
D06111 KEGG DRUG
Thiostrepton Wikipedia
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Registry Numbers Types Sources
1393-48-2 CAS Registry Number ChemIDplus
7390758 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
04 August 2014