Surfactin(mixture of isomers) - Moligand™, ≥95%, mixture of isomers , CAS No.252023-70-4

CAS: 252023-70-4 Cat. No.: S329585 Molecular Weight: 1025.04(Average) EC Number: 607-428-2

GRADE & PURITY Moligand™, ≥95%, mixture of isomers

Synonyms

surfactin C | 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

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Surfactin is lipopeptide antibiotic. Powerful biosurfactant resulting in the lysis of erythrocytes and bacteria. Also a clotting inhibitor.

Specifications

Synonyms

surfactin C | 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

Specifications & Purity

Moligand™, ≥95%, mixture of isomers

Biochemical and Physiological Mechanisms

Surfactin is a potent cyclic lipopeptide biosurfactants consists of multiple isomers , 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, a

Source

Bacillus subtilis

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

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

Grade

Moligand™

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504758805
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504758805
• 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)

Explore this target

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in ethanol (9.80 - 10.20 mg/ml).
• 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]