(2E)-but-2-enedioic acid (1R,2R,3S,4S,6R,7R,8R,14S)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.01,8]tetradecan-6-yl 2-{[2-(diethylamino)ethyl]sulfanyl}acetate

• ChemBase ID: 178617
• Molecular Formular: C32H51NO8S
• Molecular Mass: 609.81424
• Monoisotopic Mass: 609.3335386
• SMILES: C1[C@]([C@H]([C@@H]([C@]23[C@H]([C@]([C@@H]1OC(=O)CSCCN(CC)CC)([C@@H](CC3)C)C)C(=O)CC2)C)O)(C=C)C.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: OC(=O)/C=C/C(=O)O.CCN(CCSCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@@H]([C@@]23[C@H]([C@@]1(C)[C@H](C)CC2)C(=O)CC3)C)CC
• InChI: InChI=1S/C28H47NO4S.C4H4O4/c1-8-26(6)17-22(33-23(31)18-34-16-15-29(9-2)10-3)27(7)19(4)11-13-28(20(5)25(26)32)14-12-21(30)24(27)28;5-3(6)1-2-4(7)8/h8,19-20,22,24-25,32H,1,9-18H2,2-7H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t19-,20-,22+,24-,25-,26+,27-,28+;/m0./s1
• InChIKey: YXQXDXAHCSEVSD-OEMYKGCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid (1R,2R,3S,4S,6R,7R,8R,14S)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^1,^8]tetradecan-6-yl 2-{[2-(diethylamino)ethyl]sulfanyl}acetate
• IUPAC Traditional name: fumaric acid (1R,2R,3S,4S,6R,7R,8R,14S)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^1,^8]tetradecan-6-yl 2-{[2-(diethylamino)ethyl]sulfanyl}acetate
• Synonyms: (3aS,4R,5S,6S,8R,9S,9aR,10R)-2-[[2-(Diethylamino)ethyl]thio]acetic Acid 6-Ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl Ester (2E)-2-Butenedioate; SQ-22947; Denagard; Dynamutilin; Tiamutin; Tiavet; Tiamulin Fumarate

Database IDs

• CAS Number: 55297-96-6
• PubChem SID: 164234527
• PubChem CID: 71752558

CALCULATED PROPERTIES

• Acid pKa: 14.425536
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.1178626
• LogD (pH = 7.4): 2.407737
• Log P: 4.5014277
• Molar Refractivity: 140.7401 cm^3
• Polarizability: 55.918926 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 139-141°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T436600

A derivative of Pleuromutilin. Antibacterial.

REFERENCES

• Aarestrup, F., et al.: Vet. Microbiol.
• Egger, H., et al.: J. Antibiot., 29, 923 (1976)
• Baughn, C.O., et al.: Avian Dis., 22, 620 (1976)
• Goodwin, R.F., et al.: Vet. Rec., 104, 194 (1976)
• Kitai, K., et al.: Antimicrob. Agents Chemother., 31, 1935 (1976)