(4R)-4-[(1R,4Z,8Z,10Z,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: 2349
• Molecular Formular: C22H31NO5S
• Molecular Mass: 421.55024
• Monoisotopic Mass: 421.1922941
• SMILES: S1C[C@H](NC1=O)[C@@]1(O[C@@H]2CC[C@@H](/C=C\C=C/CC/C(=C\C(=O)O[C@H](C2)C1)/C)C)O
• 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)/b4-3-,7-5-,16-11-/t15-,17-,18-,19+,22-/m1/s1
• InChIKey: DDVBPZROPPMBLW-ZJBINBEQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1R,4Z,8Z,10Z,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,4Z,8Z,10Z,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: 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

• PubChem SID: 46508901; 160965800
• PubChem CID: 46936439

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 3.0
• LOG S: -4.31
• Solubility (Water): 2.04e-02 g/l

DETAILS

DrugBank - DB02621

• Drug Groups: experimental
• Description: Latrunculin A is an actin binding macrolide purified from the red sea sponge Latrunculia magnifica. It is under investigation for the treatment of cancer. It disrupts actin polymerization, prevents mitotic spindle formation and thus cell replication.
• References: Coue M, Brenner SL, Spector I, Korn ED: Inhibition of actin polymerization by latrunculin A. FEBS Lett. 1987 Mar 23;213(2):316-8. [Pubmed] ; Konishi H, Kikuchi S, Ochiai T, Ikoma H, Kubota T, Ichikawa D, Fujiwara H, Okamoto K, Sakakura C, Sonoyama T, Kokuba Y, Sasaki H, Matsui T, Otsuji E: Latrunculin a has a strong anticancer effect in a peritoneal dissemination model of human gastric cancer in mice. Anticancer Res. 2009 Jun;29(6):2091-7. [Pubmed] ; Foissner I, Wasteneys GO: Wide-ranging effects of eight cytochalasins and latrunculin A and B on intracellular motility and actin filament reorganization in characean internodal cells. Plant Cell Physiol. 2007 Apr;48(4):585-97. Epub 2007 Feb 27. [Pubmed]

REFERENCES

• Coue M, Brenner SL, Spector I, Korn ED: Inhibition of actin polymerization by latrunculin A. FEBS Lett. 1987 Mar 23;213(2):316-8. Pubmed
• Konishi H, Kikuchi S, Ochiai T, Ikoma H, Kubota T, Ichikawa D, Fujiwara H, Okamoto K, Sakakura C, Sonoyama T, Kokuba Y, Sasaki H, Matsui T, Otsuji E: Latrunculin a has a strong anticancer effect in a peritoneal dissemination model of human gastric cancer in mice. Anticancer Res. 2009 Jun;29(6):2091-7. Pubmed
• Foissner I, Wasteneys GO: Wide-ranging effects of eight cytochalasins and latrunculin A and B on intracellular motility and actin filament reorganization in characean internodal cells. Plant Cell Physiol. 2007 Apr;48(4):585-97. Epub 2007 Feb 27. Pubmed