(4R)-4-[(1R,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one

• ChemBase ID: 155621
• Molecular Formular: C20H29NO5S
• Molecular Mass: 395.51296
• Monoisotopic Mass: 395.17664403
• SMILES: C[C@H]1CC[C@@H]2C[C@H](C[C@@](O2)([C@@H]2CSC(=O)N2)O)OC(=O)/C=C(\CC/C=C\1)/C
• Canonical SMILES: O=C1SC[C@H](N1)[C@@]1(O)C[C@H]2C[C@H](O1)CC[C@H](C)/C=C\CC/C(=C\C(=O)O2)/C
• InChI: InChI=1S/C20H29NO5S/c1-13-5-3-4-6-14(2)9-18(22)25-16-10-15(8-7-13)26-20(24,11-16)17-12-27-19(23)21-17/h3,5,9,13,15-17,24H,4,6-8,10-12H2,1-2H3,(H,21,23)/t13-,15-,16-,17+,20-/m1/s1
• InChIKey: NSHPHXHGRHSMIK-ZHKLBRLOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1R,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one
• IUPAC Traditional name: (4R)-4-[(1R,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one
• Synonyms: LAT-B; Latrunculin B from Latruncula magnifica

Database IDs

• CAS Number: 76343-94-7
• MDL Number: MFCD00270879
• PubChem SID: 162249759
• PubChem CID: 6436219

CALCULATED PROPERTIES

• Acid pKa: 11.357242
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.7868667
• LogD (pH = 7.4): 3.7868195
• Log P: 3.7868671
• Molar Refractivity: 105.6425 cm^3
• Polarizability: 41.321865 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble
• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥80% (HPLC)
• Mol. Weight: mol wt 395.5
• Empirical Formula (Hill Notation): C20H29NSO5

DETAILS

Sigma Aldrich - L5288

Biochem/physiol Actions
Latrunculin B inhibits actin polymerization in vitro. Latrunculin B disrupts microfilament-mediated processes.