Surfactin - ≥95% , CAS No.252023-70-4

CAS: 252023-70-4 Cat. No.: S651680 Molecular Weight: 1025.04(Average) EC Number: 607-428-2

GRADE & PURITY ≥95%

Synonyms

CHEBI:71978 | surfactin C | 3-[(3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-3,6,15,18-tetraisobutyl-12-isopropyl-25-(10-methylundecyl)-2,5,8,11,14,17,20,23-octaoxo-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-21-yl]propanoic acid | Surfactin, from Ba

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Surfactin is a potent cyclic lipopeptide biosurfactants consists of four isomers (Surfactin A, B, C and D), which mediates flux of mono-and divalent cations, such as calcium, across lipid bilayer membranes. Surfactin can act as an antimicrobial adjuvant with anti- bacterial , anti- fungal , antimycoplasma and hemolytic effects. Surfactin also has antiviral activity against a variety of enveloped viruses .

In Vitro

Surfactin can increase the activity of NSC277174 against avian pathogenic Escherichia coli (APEC) in vitro with antimicrobial assays such as minimum inhibitory concentrations (MIC) and fractional inhibitory concentration (FIC). For APEC O78 strain, the MIC of NSC277174 and Surfactin are 1000 ug/ml and >1mg/ml, respectively. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

In the model of chick infection (inoculation of E.coli ), Surfactin exerts adjuvant effects with NSC277174 against APEC by lowering the numerical value of mortality and liver bacterial loads, and regulating the expression of inflammatory cytokines et al. Surfactin can act as a novel antimicrobial adjuvant with NSC277174 against AEPC infection in chicken . MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

Specifications

Synonyms

CHEBI:71978 | surfactin C | 3-[(3S, 6R, 9S, 12S, 15R, 18S, 21S, 25R)-9-(carboxymethyl)-3, 6, 15, 18-tetraisobutyl-12-isopropyl-25-(10-methylundecyl)-2, 5, 8, 11, 14, 17, 20, 23-octaoxo-1-oxa-4, 7, 10, 13, 16, 19, 22-heptazacyclopentacos-21-yl]propanoic acid | Surfactin, from Ba

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

Surfactin is a potent cyclic lipopeptide biosurfactants consists of four isomers (Surfactin A, B, C and D), which mediates flux of mono-and divalent cations, such as calcium, across lipid bilayer membranes. Surfactin can act as an antimicrobial adjuvant w

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CC(C)CCCCCCCCCC1CC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O1)CC(C)C)CC(C)C)CC(=O)O)C(C)C)CC(C)C)CC(C)C)CCC(=O)O
• IUPAC Name: 3-[(3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-3,6,15,18-tetrakis(2-methylpropyl)-25-(10-methylundecyl)-2,5,8,11,14,17,20,23-octaoxo-12-propan-2-yl-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-21-yl]propanoic acid
• InChIKey: NJGWOFRZMQRKHT-WGVNQGGSSA-N
• INCHI: 1S/C53H93N7O13/c1-30(2)20-18-16-14-13-15-17-19-21-36-28-43(61)54-37(22-23-44(62)63)47(66)55-38(24-31(3)4)48(67)57-40(26-33(7)8)51(70)60-46(35(11)12)52(71)58-41(29-45(64)65)50(69)56-39(25-32(5)6)49(68)59-42(27-34(9)10)53(72)73-36/h30-42,46H,13-29H2,1-12H3,(H,54,61)(H,55,66)(H,56,69)(H,57,67)(H,58,71)(H,59,68)(H,60,70)(H,62,63)(H,64,65)/t36-,37+,38+,39-,40-,41+,42+,46+/m1/s1
• Isomeric SMILES: CC(C)CCCCCCCCC[C@@H]1CC(=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
• Alternate CAS: 24730-31-2
• MeSH Entry Terms: surfactin C;surfactin peptide
• Molecular Weight: 1025.04(Average)

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Peptidomimetics
      • Subclass Depsipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Peptidomimetics
• Subclass: Depsipeptides
• Intermediate Tree Nodes: Not available
• Direct Parent: Cyclic depsipeptides
• Alternative Parents: Macrolide lactams Alpha amino acid esters Macrolactams Tricarboxylic acids and derivatives Secondary carboxylic acid amides Carboxylic acid esters Lactams Lactones Oxacyclic compounds Azacyclic compounds Carboxylic acids Carbonyl compounds Organopnictogen compounds Hydrocarbon derivatives Organonitrogen compounds Organic oxides
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Cyclic depsipeptide - Macrolide lactam - Alpha-amino acid ester - Macrolactam - Alpha-amino acid or derivatives - Tricarboxylic acid or derivatives - Carboxamide group - Carboxylic acid ester - Lactam - Lactone - Secondary carboxylic acid amide - Carboxylic acid - Carboxylic acid derivative - Oxacycle - Organoheterocyclic compound - Azacycle - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organic oxygen compound - Organopnictogen compound - Organic nitrogen compound - Organooxygen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
• External Descriptors: cyclodepsipeptide - lipopeptide antibiotic - macrocyclic lactone

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

SIRT1 Tchem NAD-dependent deacetylase sirtuin 1 (3505 Activities)

Discover Target: SIRT1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HST2 NAD-dependent deacetylase HST2 (97 Activities)

Discover Target: HST2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Stachybotrys chartarum (30 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 50 mg/mL (Need ultrasonic) H2O : 31.25 mg/mL (Need ultrasonic)
• Molecular Weight: 1036.300 g/mol
• XLogP3: 8.800
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 24
• Exact Mass: 1035.68 Da
• Monoisotopic Mass: 1035.68 Da
• Topological Polar Surface Area: 305.000 Ų
• Heavy Atom Count: 73
• Formal Charge: 0
• Complexity: 1800.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Wei Zhang, Xu Zeng, Jiayi Dong, Yibin Su, Erik Jeppesen, Liqing Wang, Sicheng Yin.  (2025)  The potential of metabolites released by Bacillus subtilis CH21 for the effective Control of the harmful cyanobacterium Raphidiopsis raciborskii.  Journal of Environmental Sciences,      [PMID:] [10.1016/j.jes.2025.08.043]