3-(3-bromo-4-hydroxyphenyl)-N-[2-({2-[3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide

• ChemBase编号: 153164
• 分子式: C22H24Br2N4O6S2
• 平均质量: 664.38716
• 单一同位素质量: 661.95040051
• SMILES: c1c(cc(c(c1)O)Br)C/C(=N/O)/C(=O)NCCSSCCNC(=O)/C(=N\O)/Cc1cc(c(cc1)O)Br
• Canonical SMILES: O/N=C(\C(=O)NCCSSCCNC(=O)/C(=N\O)/Cc1ccc(c(c1)Br)O)/Cc1ccc(c(c1)Br)O
• InChI: InChI=1S/C22H24Br2N4O6S2/c23-15-9-13(1-3-19(15)29)11-17(27-33)21(31)25-5-7-35-36-8-6-26-22(32)18(28-34)12-14-2-4-20(30)16(24)10-14/h1-4,9-10,29-30,33-34H,5-8,11-12H2,(H,25,31)(H,26,32)
• InChIKey: LMAFSGDNHVBIHU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-(3-bromo-4-hydroxyphenyl)-N-[2-({2-[3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide
• IUPAC传统名: 3-(3-bromo-4-hydroxyphenyl)-N-[2-({2-[3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide
• 别名: Bisprasin, N,N"-(dithiodi-2,1-ethanediyl)bis[3-bromo-4-hydroxy-a-(hydroxyimino)-benzenepropanamide; Psammaplin A

登记号

• CAS号: 110659-91-1
• PubChem SID: 162247303
• PubChem CID: 6399893

理论计算性质

• Acid pKa: 6.273931
• 质子受体: 8
• 质子供体: 6
• LogD (pH = 5.5): 4.0113583
• LogD (pH = 7.4): 2.2065783
• Log P: 4.081383
• 摩尔折射率: 149.0862 cm^3
• 极化性: 56.860638 Å^3
• 极化表面积: 163.84 Å^2
• 可自由旋转的化学键: 13
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO: >10 mg/mL; H2O: insoluble
• 外观: solid

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36/37
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C22H24Br2N4O6S2

详细说明

Sigma Aldrich - P8749

Biochem/physiol Actions
Psammaplin A is an antibiotic, anti-tumor, DNA methyltransferase inhibitor. It is a bromotyrosine-derived, symmetrical conjugate of cystamine, which was first isolated from the Psammaplinaplysilla sponge. Psammaplin A impedes angiogenesis as well as bacterial and tumor cell growth. Psammaplin A inhibits the activities of several key enzymes in prokaryotic and eukaryotic systems including those involved in epigenetic control of gene expression, DNA replication, angiogensis, and microbial detoxification.