Compound: Surfactin
SMILES: O=C1O[C@@H](CC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](CC(C)C)C(N[C@H](C(N[C@H](C(N[C@@H](C(N[C@H]1CC(C)C)=O)CC(C)C)=O)CC(=O)O)=O)C(C)C)=O)CC(C)C)CCC(=O)O)CCCCCCCCCC(C)C
InChIKey: NJGWOFRZMQRKHT-WGVNQGGSSA-N
Synonyms: Surfactin, 24730-31-2, 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, DTXSID20893274, 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, RefChem:1099297, ZU5L4DKH78, CHEBI:29681, DTXCID501323212, 3-(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, surfactin C, 252023-70-4, 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-heptaazacyclopentacosan-21-yl)propanoic acid, 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-heptaazacyclopentacosan-21-yl]propanoic acid, 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, Leu7-Surfactin, iso-C15-Surfactin, E6T3DJ8ZVE, Surfactin(mixture of isomers), CHEMBL508272, SCHEMBL1434743, CHEBI:71978, NJGWOFRZMQRKHT-WGVNQGGSSA-N, BDBM50378583, Cyclo(L-a-aspartyl-D-leucyl-L-leucyl-3-hydroxy-13-methyltetradecanoyl-L-a-glutamyl-L-leucyl-D-leucyl-L-valyl), FS172608, NS00094931, Q3132229, Surfactin, from Bacillus subtilis, >=98.0% (HPLC), 1393353-89-3, 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-heptaazacyclopentacosan-21-yl]propanoic acid, Cyclo[L-alpha-aspartyl-D-leucyl-L-leucyl-(3R)-3-hydroxy-13-methyltetradecanoyl-L-alpha-glutamyl-L-leucyl-D-leucyl-L-valyl], Leucine, N-[N-[N-[N-[N-[N-[N-(3-hydroxy-13-methyltetradecanoyl)-L-alpha-glutamyl]-L-leucyl]-D-leucyl]-L-valyl]-L-alpha-aspartyl]-D-leucyl]-, psi-lactone, L-
Theoretical properties:
molecular_formula: C53H93N7O13
molecular_weight: 1036.3 g/mol
exact_mass: 1035.68313605 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 9
hydrogen_bond_acceptor_count: 13
rotatable_bond_count: 24
heavy_atom_count: 73
topological_polar_surface_area: 305 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Surfactin C is a cyclodepsipeptide that is N-[(3R)-3-hydroxy-13-methyltetradecanoyl]-L-alpha-glutamyl-L-leucyl-D-leucyl-L-valyl-L-alpha-aspartyl-D-leucyl-L-leucine in which the C-terminal carboxy group has been lactonised by condensation with the alcoholic hydroxy group. It has a role as an antiviral agent, a metabolite, an antibacterial agent, a surfactant, an antineoplastic agent, an antifungal agent and a platelet aggregation inhibitor. It is a lipopeptide antibiotic, a cyclodepsipeptide and a macrocyclic lactone.
chebi: A cyclodepsipeptide that is <em>N</em>-[(3<i>R</i>)-3-hydroxy-13-methyltetradecanoyl]-<small>L</small>-α-glutamyl-<small>L</small>-leucyl-<small>D</small>-leucyl-<small>L</small>-valyl-<small>L</small>-α-aspartyl-<small>D</small>-leucyl-<small>L</small>-leucine in which the C-terminal carboxy group has been lactonised by condensation with the alcoholic hydroxy group.
chembl: SURFACTIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Surfactin is a cyclic lipopeptide, commonly used as an antibiotic for its capacity as a surfactant. It is an amphiphile capable of withstanding hydrophilic and hydrophobic environments. The Gram-positive bacterial species Bacillus subtilis produces surfactin for its antibiotic effects against competitors. Surfactin showcases antibacterial, antiviral, antifungal, and hemolytic effects.