Thiostrepton information

Thiostrepton^[1]
Names
	IUPAC name N-[3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl]-2-[(1R,8S,11Z,18S,25S,26R,53S,59S)-37-butan-2-yl-18-[(2S,3R)-2,3-dihydroxybutan-2-yl]-11-ethylidene-59-hydroxy-8-[(1R)-1-hydroxyethyl]-31-[(1S)-1-hydroxyethyl]-26,40,46-trimethyl-43-methylidene-6,9,16,23,28,38,41,44,47-nonaoxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,36,39,42,45,48,52,58,61,62,63,64-pentadecazanonacyclo[23.23.9.329,35.12,5.112,15.119,22.154,57.01,53.032,60]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazole-4-carboxamide
	Other names Alaninamide, Bryamycin, Thiactin
Identifiers
CAS Number	1393-48-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL468719 ;
ChemSpider	24603973;
ECHA InfoCard	100.014.304
EC Number	215-734-9;
PubChem CID	16130278;
UNII	HR4S203Y18 ;
CompTox Dashboard (EPA)	DTXSID5040625 ;
	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 Key: NSFFHOGKXHRQEW-AIHSUZKVSA-N;
	SMILES C[C@@H](O)[C@@](C)(O)[C@@H](C2=NC6=CS2)NC(C1CSC(/C(NC([C@@H](NC(C3=CS[C@]([C@]4(NC([C@@H](NC(C(NC([C@H](C)NC%10=O)=O)=C)=O)C)=O)C(C5=CSC([C@H]([C@@H](C)OC(C8=CC([C@H](C)O)=C(C=CC(N[C@]([H])%10[C@H](CC)C)[C@@H]9O)C9=N8)=O)NC6=O)=N5)N=C(C7=NC(C(NC(C(NC(C(N)=O)=C)=O)=C)=O)=CS7)CC4)=N3)=O)[C@@H](C)O)=O)=C/C)=N1)=O;
Properties
Chemical formula	C72H85N19O18S5
Molar mass	1664.83 g/mol
Appearance	White to off-white powder
Melting point	246 to 256 °C (475 to 493 °F; 519 to 529 K)
Solubility in water	Insoluble
Solubility in other solvents	Soluble in CHCl3, CH2Cl2, dioxane, pyridine, glacial acetic acid, DMF. Practically insoluble in the lower alcohols, nonpolar organic solvents, diluted aqueous acids or bases. May be dissolved by methanolic acid or base, but with decomposition.
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P312, P330, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Thiostrepton is a natural cyclic oligopeptide antibiotic of the thiopeptide class, derived from several strains of streptomycetes, such as Streptomyces azureus and Streptomyces laurentii. Thiostrepton is a natural product of the ribosomally synthesized and post-translationally modified peptide (RiPP) class.

^ Merck Index, 11th Edition, 9295.
^ Thiostrepton product page at Fermentek

[1] Merck Index, 11th Edition, 9295.

[2] Thiostrepton product page at Fermentek

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