2-({2-[37-(butan-2-yl)-18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-59-hydroxy-8,60-bis(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-7,10,17,24,30,36,39,42,45,48,52,58,62,63,64-pentadecaazanonacyclo[23.23.9.2??,??.1?,?.1??,??.1??,??.1??,??.1??,??.0?,??]tetrahexaconta-2(64),4,12(63),19(62),21,29,31,33,51,54,57,60-dodecaen-51-yl]-1,3-thiazol-4-yl}formamido)-N-(1-carbamoyleth-1-en-1-yl)prop-2-enamide

• ChemBase ID: 104709
• Molecular Formular: C72H85N19O18S5
• Molecular Mass: 1664.8868
• Monoisotopic Mass: 1663.49235198
• SMILES: CCC(C)C1NC2C=Cc3c(nc(cc3C(C)O)C(=O)OC(C)C3NC(=O)c4csc(n4)C(NC(=O)C4CSC(=N4)/C(=C/C)/NC(=O)C(NC(=O)c4csc(n4)C4(CCC(=NC4c4csc3n4)c3nc(cs3)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)NC(=O)C(C)NC(=O)C(=C)NC(=O)C(C)NC1=O)C(C)O)C(C)(O)C(C)O)C2O
• Canonical SMILES: C/C=C/1\NC(=O)C(NC(=O)c2csc(n2)C23CCC(=NC3c3csc(n3)C(NC(=O)c3nc(C(NC(=O)C4N=C1SC4)C(C(O)C)(O)C)sc3)C(C)OC(=O)c1cc(C(O)C)c3c(n1)C(O)C(C=C3)NC(C(=O)NC(C(=O)NC(=C)C(=O)NC(C(=O)N2)C)C)C(CC)C)c1scc(n1)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C(O)C
• 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)
• InChIKey: NSFFHOGKXHRQEW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({2-[37-(butan-2-yl)-18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-59-hydroxy-8,60-bis(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-7,10,17,24,30,36,39,42,45,48,52,58,62,63,64-pentadecaazanonacyclo[23.23.9.2??,??.1?,?.1??,??.1??,??.1??,??.1??,??.0?,??]tetrahexaconta-2(64),4,12(63),19(62),21,29,31,33,51,54,57,60-dodecaen-51-yl]-1,3-thiazol-4-yl}formamido)-N-(1-carbamoyleth-1-en-1-yl)prop-2-enamide
• IUPAC Traditional name: N-(1-carbamoyleth-1-en-1-yl)-2-({2-[18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-59-hydroxy-8,60-bis(1-hydroxyethyl)-26,40,46-trimethyl-43-methylidene-6,9,16,23,28,38,41,44,47-nonaoxo-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[23.23.9.2??,??.1?,?.1??,??.1??,??.1??,??.1??,??.0?,??]tetrahexaconta-2(64),4,12(63),19(62),21,29,31,33,51,54,57,60-dodecaen-51-yl]-1,3-thiazol-4-yl}formamido)prop-2-enamide
• Synonyms: THIOSTREPTON

Database IDs

• CAS Number: 1393-48-2
• EC Number: 215-734-9
• PubChem SID: 162091916
• PubChem CID: 16220061

CALCULATED PROPERTIES

• Acid pKa: 10.5668
• H Acceptors: 25
• H Donor: 17
• LogD (pH = 5.5): -3.4530418
• LogD (pH = 7.4): -2.002715
• Log P: -1.8114586
• Molar Refractivity: 414.5894 cm^3
• Polarizability: 158.71379 Å^3
• Polar Surface Area: 562.74 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 0°C, Desiccate, Protect from light
• RTECS: XN6300100

Product Information

• Purity: 90%

DETAILS

MP Biomedicals - 02156893

Purity: 90%
Peptide antibiotic that inhibits binding of EF-G and GTP to the 50S ribosomal subunit.

REFERENCES

• Garratt, R., Trends in Biol. Sciences, 189: June, (1983).