(4R)-4-[(1R,4Z,8Z,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: 5708
• Molecular Formular: C20H29NO5S
• Molecular Mass: 395.51296
• Monoisotopic Mass: 395.17664403
• SMILES: O=C1N[C@@H](CS1)[C@@]1(O)C[C@@H]2OC(=O)/C=C(\CC/C=C\[C@H](CC[C@H](C2)O1)C)/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)/b5-3-,14-9-/t13-,15-,16-,17+,20-/m1/s1
• InChIKey: NSHPHXHGRHSMIK-JRIKCGFMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1R,4Z,8Z,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,4Z,8Z,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: LATRUNCULIN B

Database IDs

• PubChem SID: 160969135; 99444551
• PubChem CID: 6436219

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 1.98
• LOG S: -3.74
• Solubility (Water): 7.13e-02 g/l

DETAILS

DrugBank - DB08080

Drug information: experimental