3-[(2R,5S,8S,11R,14S,17S,20R,23S)-17-(carboxymethyl)-2-(11-methyldodecyl)-8,11,20,23-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24-octaoxo-14-(propan-2-yl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosan-5-yl]propanoic acid

• ChemBase编号: 133344
• 分子式: C53H93N7O13
• 平均质量: 1036.34462
• 单一同位素质量: 1035.68313607
• SMILES: CC(C)CCCCCCCCCC[C@@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)O1)CC(C)C)CC(C)C)CC(=O)O)C(C)C)CC(C)C)CC(C)C)CCC(=O)O
• Canonical SMILES: CC(CCCCCCCCCC[C@H]1OC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CCC(=O)O)CC(C)C)CC(C)C)C(C)C)C
• InChI: InChI=1S/C53H93N7O13/c1-30(2)21-19-17-15-13-14-16-18-20-22-42-51(70)54-36(23-24-43(61)62)46(65)55-37(25-31(3)4)47(66)57-39(27-33(7)8)50(69)60-45(35(11)12)52(71)58-40(29-44(63)64)49(68)56-38(26-32(5)6)48(67)59-41(28-34(9)10)53(72)73-42/h30-42,45H,13-29H2,1-12H3,(H,54,70)(H,55,65)(H,56,68)(H,57,66)(H,58,71)(H,59,67)(H,60,69)(H,61,62)(H,63,64)/t36-,37-,38+,39+,40-,41-,42+,45-/m0/s1
• InChIKey: MCIBIKGNEXKPGE-FOIMPGOESA-N

名称和登记号

名称

• IUPAC标准名: 3-[(2R,5S,8S,11R,14S,17S,20R,23S)-17-(carboxymethyl)-2-(11-methyldodecyl)-8,11,20,23-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24-octaoxo-14-(propan-2-yl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosan-5-yl]propanoic acid
• IUPAC传统名: 3-[(2R,5S,8S,11R,14S,17S,20R,23S)-17-(carboxymethyl)-14-isopropyl-2-(11-methyldodecyl)-8,11,20,23-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24-octaoxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosan-5-yl]propanoic acid
• 别名: Surfactin

登记号

• CAS号: 24730-31-2
• MDL号: MFCD00082048
• PubChem SID: 162227621; 24899562
• PubChem CID: 16219959

理论计算性质

• Acid pKa: 3.6888697
• 质子受体: 12
• 质子供体: 9
• LogD (pH = 5.5): 3.6247888
• LogD (pH = 7.4): 0.3260128
• Log P: 6.60121
• 摩尔折射率: 272.0278 cm^3
• 极化性: 108.021385 Å^3
• 极化表面积: 304.6 Å^2
• 可自由旋转的化学键: 25
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: ethanol: soluble10 mg/mL, clear, slightly yellow
• 临界胶束浓度: 7.5-20 μmol/L (depending on methods)

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC and TLC); ≥98.0% (TLC)
• 简要说明: zwitterionic
• 生物来源: from Bacillus subtilis
• Empirical Formula (Hill Notation): C53H93N7O13

详细说明

Sigma Aldrich - S3523

Application
Surfactin is used as a surfactant to mediate flux of mono-and divalent cations, such as calcium, across lipid bilayer membranes. It is also used to study antitumor activity, activity against enveloped viruses, activity against the protoplast of Bacillus megaterium and the activity against Mycoplasma1.
Biochem/physiol Actions
Surfactin is a lipopeptide antibiotic that is composed of one β-hydroxy fatty acid, which has a long fatty acid moiety, and seven amino acids. Three of them have D configurations. It is a powerful biosurfactant that causes lysis of erythrocytes and bacteria. It is also a clotting inhibitor. Surfactin is thought to disrupt or disintegrate membranes via physicochemical interaction with the membranes1.

Sigma Aldrich - 86196

Other Notes
Powerful biosurfactant. Interfacial properties1; Prototype of a new generation of antitumor compounds. Review2