2-({2-[(1R,8S,18S,25S,26R,37S,40S,46S,59S)-37-[(2S)-butan-2-yl]-18-[(2S,3R)-2,3-dihydroxybutan-2-yl]-11-ethylidene-59-hydroxy-8-[(1R)-1-hydroxyethyl]-60-[(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-7,10,17,24,30,36,39,42,45,48,52,58,62,63,64-pentadecaazanonacyclo[23.23.9.229,32.12,5.112,15.119,22.131,35.154,57.01,53]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazol-4-yl}formamido)-N-(1-carbamoyleth-1-en-1-yl)prop-2-enamide

• ChemBase ID: 129876
• Molecular Formular: C72H85N19O18S5
• Molecular Mass: 1664.8868
• Monoisotopic Mass: 1663.49235198
• SMILES: C[C@@H](O)[C@@](C)(O)[C@H]1c2nc(cs2)C(=O)N[C@@H]2c3scc(C4[C@](c5scc(C(=O)N[C@H](C(=O)N/C(=C\C)/C6=NC(C(=O)N1)CS6)[C@@H](C)O)n5)(NC(=O)[C@@H](NC(=O)C(=C)NC(=O)[C@H](C)NC(=O)[C@@H](NC1C=Cc5c(cc(C(=O)O[C@@H]2C)nc5[C@H]1O)[C@H](C)O)[C@H](CC)C)C)CCC(=N4)c1nc(C(=O)NC(=C)C(=O)NC(=C)C(=O)N)cs1)n3
• Canonical SMILES: C/C=C/1\NC(=O)[C@@H](NC(=O)c2csc(n2)[C@]23CCC(=NC3c3csc(n3)[C@@H](NC(=O)c3nc([C@@H](NC(=O)C4N=C1SC4)[C@@]([C@H](O)C)(O)C)sc3)[C@@H](C)OC(=O)c1cc([C@@H](O)C)c3c(n1)[C@@H](O)C(C=C3)N[C@H](C(=O)N[C@H](C(=O)NC(=C)C(=O)N[C@H](C(=O)N2)C)C)[C@H](CC)C)c1scc(n1)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)[C@H](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)/t26-,30-,31-,32-,33+,34+,35+,39?,45?,47-,48-,49-,51-,52?,53+,71+,72+/m0/s1
• InChIKey: NSFFHOGKXHRQEW-YDIHMWRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({2-[(1R,8S,18S,25S,26R,37S,40S,46S,59S)-37-[(2S)-butan-2-yl]-18-[(2S,3R)-2,3-dihydroxybutan-2-yl]-11-ethylidene-59-hydroxy-8-[(1R)-1-hydroxyethyl]-60-[(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-7,10,17,24,30,36,39,42,45,48,52,58,62,63,64-pentadecaazanonacyclo[23.23.9.2^2^9,^3^2.1^2,^5.1^1^2,^1^5.1^1^9,^2^2.1^3^1,^3^5.1^5^4,^5^7.0^1,^5^3]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazol-4-yl}formamido)-N-(1-carbamoyleth-1-en-1-yl)prop-2-enamide
• IUPAC Traditional name: 2-({2-[(1R,8S,18S,25S,26R,37S,40S,46S,59S)-37-[(2S)-butan-2-yl]-18-[(2S,3R)-2,3-dihydroxybutan-2-yl]-11-ethylidene-59-hydroxy-8-[(1R)-1-hydroxyethyl]-60-[(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-7,10,17,24,30,36,39,42,45,48,52,58,62,63,64-pentadecaazanonacyclo[23.23.9.2^2^9,^3^2.1^2,^5.1^1^2,^1^5.1^1^9,^2^2.1^3^1,^3^5.1^5^4,^5^7.0^1,^5^3]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazol-4-yl}formamido)-N-(1-carbamoyleth-1-en-1-yl)prop-2-enamide
• Synonyms: Alaninamide; Bryamycie; Thiactin; Thiostrepton

Database IDs

• CAS Number: 1393-48-2
• PubChem SID: 162224162
• PubChem CID: 57473100; 16130278
• CHEMBL: 468719
• Wikipedia Title: Thiostrepton

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

Physical Property

• Solubility: Insoluble in water; 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.
• Apperance: White to off-white powder
• Melting Point: 246-256 °C