(4R)-4-[(1R,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-one

• ChemBase ID: 155620
• Molecular Formular: C22H31NO5S
• Molecular Mass: 421.55024
• Monoisotopic Mass: 421.1922941
• 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/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\C=C\CC/C(=C\C(=O)O2)/C
• InChI: InChI=1S/C22H31NO5S/c1-15-7-5-3-4-6-8-16(2)11-20(24)27-18-12-17(10-9-15)28-22(26,13-18)19-14-29-21(25)23-19/h3-5,7,11,15,17-19,26H,6,8-10,12-14H2,1-2H3,(H,23,25)/t15-,17-,18-,19+,22-/m1/s1
• InChIKey: DDVBPZROPPMBLW-SDLUEBNPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1R,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-one
• IUPAC Traditional name: (4R)-4-[(1R,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-one
• Synonyms: LAT-A; [1R-[1R*, 4Z, 8E, 10Z, 12S*, 15R*, 17R*(R*)]]-4-(17-Hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl)-2-thiazolidinone; Latrunculin A

Database IDs

• CAS Number: 76343-93-6
• PubChem SID: 162249758
• PubChem CID: 445420

CALCULATED PROPERTIES

• Acid pKa: 11.356813
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.314082
• LogD (pH = 7.4): 4.3140354
• Log P: 4.314083
• Molar Refractivity: 115.9611 cm^3
• Polarizability: 44.748425 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble
• Apperance: waxy 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: ≥85% (HPLC)
• Biological Source: from Negombata magnifica
• Mol. Weight: mol wt 421.6
• Empirical Formula (Hill Notation): C22H31NO5S

DETAILS

Sigma Aldrich - L5163

Biochem/physiol Actions
Latrunculin A inhibits actin polymerization by a different mechanism than cytochalasins. Latrunculin A disrupts microfilament-mediated processes.