CHEBI:71978 - surfactin C

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name surfactin C
ChEBI ID CHEBI:71978
Definition A cyclodepsipeptide that is N-[(3R)-3-hydroxy-13-methyltetradecanoyl]-L-α-glutamyl-L-leucyl-D-leucyl-L-valyl-L-α-aspartyl-D-leucyl-L-leucine in which the C-terminal carboxy group has been lactonised by condensation with the alcoholic hydroxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C53H93N7O13
Net Charge 0
Average Mass 1036.34460
Monoisotopic Mass 1035.68314
InChI 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
InChIKey NJGWOFRZMQRKHT-WGVNQGGSSA-N
SMILES [H][C@@]1(CCCCCCCCCC(C)C)CC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)O1
Roles Classification
Chemical Role(s): surfactant
A substance which lowers the surface tension of the medium in which it is dissolved, and/or the interfacial tension with other phases, and, accordingly, is positively adsorbed at the liquid/vapour and/or at other interfaces.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antiviral agent
A substance that destroys or inhibits replication of viruses.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via peptide antibiotic )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
platelet aggregation inhibitor
A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing surfactin C (CHEBI:71978) has role antibacterial agent (CHEBI:33282)
surfactin C (CHEBI:71978) has role antifungal agent (CHEBI:35718)
surfactin C (CHEBI:71978) has role antineoplastic agent (CHEBI:35610)
surfactin C (CHEBI:71978) has role antiviral agent (CHEBI:22587)
surfactin C (CHEBI:71978) has role metabolite (CHEBI:25212)
surfactin C (CHEBI:71978) has role platelet aggregation inhibitor (CHEBI:50427)
surfactin C (CHEBI:71978) has role surfactant (CHEBI:35195)
surfactin C (CHEBI:71978) is a cyclodepsipeptide (CHEBI:35213)
surfactin C (CHEBI:71978) is a lipopeptide antibiotic (CHEBI:25061)
surfactin C (CHEBI:71978) is a macrocyclic lactone (CHEBI:63944)
Incoming surfactin (CHEBI:29681) has part surfactin C (CHEBI:71978)
IUPAC Name
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
Manual Xref Database
C12043 KEGG COMPOUND
View more database links
Registry Number Type Source
24730-31-2
Note: (2013-01-31) Both Kegg Compound and ChemIDplus use this CAS number and the structure of surfactin C for 'surfactin'.
 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12007605 PubMed citation Europe PMC
16245181 PubMed citation Europe PMC
16734989 PubMed citation Europe PMC
17126323 PubMed citation Europe PMC
17928958 PubMed citation Europe PMC
Last Modified
31 January 2013