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 ID: 133344
• Molecular Formular: C53H93N7O13
• Molecular Mass: 1036.34462
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: 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
• Synonyms: Surfactin

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 3.6888697
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): 3.6247888
• LogD (pH = 7.4): 0.3260128
• Log P: 6.60121
• Molar Refractivity: 272.0278 cm^3
• Polarizability: 108.021385 Å^3
• Polar Surface Area: 304.6 Å^2
• Rotatable Bonds: 25
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: soluble10 mg/mL, clear, slightly yellow
• Critical Micelle Concentration: 7.5-20 μmol/L (depending on methods)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC and TLC); ≥98.0% (TLC)
• Description: zwitterionic
• Biological Source: from Bacillus subtilis
• Empirical Formula (Hill Notation): C53H93N7O13

DETAILS

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