(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编号: 2349
• 分子式: C22H31NO5S
• 平均质量: 421.55024
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: (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
• 别名: 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

登记号

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

理论计算性质

JChem

• Acid pKa: 11.356813
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 4.314082
• LogD (pH = 7.4): 4.3140354
• Log P: 4.314083
• 摩尔折射率: 115.9611 cm^3
• 极化性: 44.748425 Å^3
• 极化表面积: 84.86 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.0
• LOG S: -4.31
• 溶解度: 2.04e-02 g/l

详细说明

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]

参考文献

• 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