Record Information
Version1.0
Creation Date2016-05-22 04:27:52 UTC
Update Date2026-04-14 18:15:51 UTC
Accession NumberCHEM017561
Identification
Common NameThiostrepton
ClassSmall Molecule
Description
Thiostrepton is a natural cyclic oligopeptide antibiotic, derived from several strains of streptomycetes including Streptomyces azureus and Streptomyces laurentii. Thiostrepton is a natural product of the ribosomally synthesized and post-translationally modified peptide class.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
2-[({2-[(11E)-37-(butan-2-yl)-18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-6,9,16,23,38,41,44,47,59-nonahydroxy-8,60-bis(1-hydroxyethyl)-26,40,46-trimethyl-43-methylidene-28-oxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,30,36,39,42,45,48,52,58,62,63,64-pentadecaazanonacyclo[23.23.9.2²⁹,³².1²,⁵.1¹²,¹⁵.1¹⁹,²².1³¹,³⁵.1⁵⁴,⁵⁷.0¹,⁵³]tetrahexaconta-2(64),4,6,9,12(63),16,19(62),21,23,29,31,33,38,41,44,47,51,54,57,60-icosaen-51-yl]-1,3-thiazol-4-yl}(hydroxy)methylidene)amino]-N-[1-(C-hydroxycarbonimidoyl)eth-1-en-1-yl]prop-2-enimidateGenerator
ThiactinMeSH
BryamycinMeSH
GargonMeSH
Chemical FormulaC72H85N19O18S5
Average Molecular Mass1664.890 g/mol
Monoisotopic Mass1663.492 g/mol
CAS Registry Number1393-48-2
IUPAC Name2-[({2-[(11E)-37-(butan-2-yl)-18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-6,9,16,23,38,41,44,47,59-nonahydroxy-8,60-bis(1-hydroxyethyl)-26,40,46-trimethyl-43-methylidene-28-oxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,30,36,39,42,45,48,52,58,62,63,64-pentadecaazanonacyclo[23.23.9.2²⁹,³².1²,⁵.1¹²,¹⁵.1¹⁹,²².1³¹,³⁵.1⁵⁴,⁵⁷.0¹,⁵³]tetrahexaconta-2(64),4,6,9,12(63),16,19(62),21,23,29,31,33,38,41,44,47,51,54,57,60-icosaen-51-yl]-1,3-thiazol-4-yl}(hydroxy)methylidene)amino]-N-[1-(C-hydroxycarbonimidoyl)eth-1-en-1-yl]prop-2-enimidic acid
Traditional Name2-[({2-[(11E)-18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-6,9,16,23,38,41,44,47,59-nonahydroxy-8,60-bis(1-hydroxyethyl)-26,40,46-trimethyl-43-methylidene-28-oxo-37-(sec-butyl)-27-oxa-3,13,20,56-tetrathia-7,10,17,24,30,36,39,42,45,48,52,58,62,63,64-pentadecaazanonacyclo[23.23.9.2²⁹,³².1²,⁵.1¹²,¹⁵.1¹⁹,²².1³¹,³⁵.1⁵⁴,⁵⁷.0¹,⁵³]tetrahexaconta-2(64),4,6,9,12(63),16,19(62),21,23,29,31,33,38,41,44,47,51,54,57,60-icosaen-51-yl]-1,3-thiazol-4-yl}(hydroxy)methylidene)amino]-N-[1-(C-hydroxycarbonimidoyl)eth-1-en-1-yl]prop-2-enimidic acid
SMILES[H]\C(C)=C1/N=C(O)C(N=C(O)C2=CSC(=N2)C23CCC(=NC2C2=CSC(=N2)C(N=C(O)C2=CSC(=N2)C(N=C(O)C2CSC1=N2)C(C)(O)C(C)O)C(C)OC(=O)C1=NC2=C(C=CC(NC(C(C)CC)C(O)=NC(C)C(O)=NC(=C)C(O)=NC(C)C(O)=N3)C2O)C(=C1)C(C)O)C1=NC(=CS1)C(O)=NC(=C)C(O)=NC(=C)C(O)=N)C(C)O
InChI IdentifierInChI=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+
InChI KeyNSFFHOGKXHRQEW-DVRIZHICSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCyclic peptides
Alternative Parents
Substituents
  • Cyclic alpha peptide
  • Pyridine carboxylic acid
  • 2,4-disubstituted 1,3-thiazole
  • Tetrahydropyridine
  • Aralkylamine
  • Pyridine
  • Imidothiolactone
  • Azole
  • Heteroaromatic compound
  • Tertiary alcohol
  • Thiazole
  • Cyclic carboximidic acid
  • Meta-thiazoline
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Ketimine
  • Lactone
  • Secondary alcohol
  • Oxacycle
  • Secondary amine
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Polyol
  • Azacycle
  • Carboximidic acid
  • Monocarboxylic acid or derivatives
  • Carboximidic acid derivative
  • Secondary aliphatic amine
  • Aromatic alcohol
  • Imine
  • Amine
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
logP3.23ALOGPS
logP7.2ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)2.28ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count36ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area598.63 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity430.74 m³·mol⁻¹ChemAxon
Polarizability164.21 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB11467
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkThiostrepton
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID16129666
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References