2-({2-[(1R,8S,11Z,18S,25S,26R,37R,40S,46S,53S,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: 178584
• Molecular Formular: C72H85N19O18S5
• Molecular Mass: 1664.8868
• Monoisotopic Mass: 1663.49235198
• SMILES: c12cc(c3c(n1)[C@H](C(C=C3)N[C@H]([C@H](CC)C)C(=O)N[C@H](C(=O)NC(=C)C(=O)N[C@H](C(=O)N[C@@]13[C@H](N=C(CC1)c1nc(cs1)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)c1nc([C@H]([C@H](OC2=O)C)NC(=O)c2nc(sc2)[C@H]([C@](O)([C@H](O)C)C)NC(=O)C2N=C(SC2)/C(=C/C)/NC(=O)[C@H]([C@H](O)C)NC(=O)c2nc3sc2)sc1)C)C)O)[C@@H](O)C
• Canonical SMILES: C/C=C/1\NC(=O)[C@@H](NC(=O)c2csc(n2)[C@]23CCC(=N[C@@H]3c3csc(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)/b38-15-/t26-,30-,31-,32-,33+,34+,35+,39?,45?,47+,48-,49-,51-,52+,53+,71+,72+/m0/s1
• InChIKey: NSFFHOGKXHRQEW-SKAGQBDNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({2-[(1R,8S,11Z,18S,25S,26R,37R,40S,46S,53S,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,11Z,18S,25S,26R,37R,40S,46S,53S,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: Thiostrepton

Database IDs

• CAS Number: 1393-48-2
• PubChem SID: 164234494
• PubChem CID: 71752542

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: Acetic Acid; Chloroform
• Apperance: Off-White Solid
• Melting Point: 248-257°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T375150

Natural antibiotic derived from Streptomyces.

REFERENCES

• Starosta, A., et al.; Chem. Biol., 16, 1087 (2009)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)
• Kwok, J., et al.: Mol. Cancer Res., 8, 24 (2009)