CHEBI:600103 - daptomycin

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ChEBI Name daptomycin
ChEBI ID CHEBI:600103
Definition A polypeptide comprising N-decanoyltryptophan, asparagine, aspartic acid, threonine, glycine, ornithine, aspartic acid, D-alanine, aspartic acid, glycine, D-serine, threo-3-methylglutamic acid and 3-anthraniloylalanine (also known as kynurinine) coupled in sequence and lactonised by condensation of the carboxylic acid group of the 3-anthraniloylalanine with the alcohol group of the threonine residue.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:29570, CHEBI:321017, CHEBI:478132, CHEBI:478255
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Formula C72H101N17O26
Net Charge 0
Average Mass 1620.67060
Monoisotopic Mass 1619.710
InChI InChI=1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35-,36-,37-,43+,44+,45+,46+,47+,48+,49+,50-,60+,61+/m1/s1
InChIKey DOAKLVKFURWEDJ-RWDRXURGSA-N
SMILES CCCCCCCCCC(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H]1[C@@H](C)OC(=O)[C@H](CC(=O)c2ccccc2N)NC(=O)[C@@H](NC(=O)[C@@H](CO)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCN)NC(=O)CNC1=O)[C@H](C)CC(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
calcium-dependent antibiotics
Any antimicrobial agent whose activity is dependent on the presence of calcium ions.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via peptide antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing daptomycin (CHEBI:600103) has role antibacterial drug (CHEBI:36047)
daptomycin (CHEBI:600103) has role bacterial metabolite (CHEBI:76969)
daptomycin (CHEBI:600103) has role calcium-dependent antibiotics (CHEBI:140190)
daptomycin (CHEBI:600103) is a heterodetic cyclic peptide (CHEBI:24533)
daptomycin (CHEBI:600103) is a lipopeptide (CHEBI:46895)
daptomycin (CHEBI:600103) is a lipopeptide antibiotic (CHEBI:25061)
daptomycin (CHEBI:600103) is a macrocycle (CHEBI:51026)
daptomycin (CHEBI:600103) is a macrolide (CHEBI:25106)
IUPAC Name
N-decanoyl-L-tryptophyl-L-asparaginyl-N-[(3S,6S,9R,15S,18R,21S,24S,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriacontan-30-yl]-L-α-asparagine
INNs Sources
daptomicina ChemIDplus
daptomycin ChemIDplus
daptomycine ChemIDplus
daptomycinum ChemIDplus
Synonyms Sources
daptomycin ChEMBL
Daptomycin KEGG COMPOUND
LY 146032 ChemIDplus
N-decanoyl-L-tryptophyl-L-asparaginyl-L-aspartyl-L-threonylglycyl-L-ornithyl-L-aspartyl-D-alanyl-L-aspartylglycyl-D-seryl-threo-3-methyl-L-glutamyl-3-anthraniloyl-L-alanine 1.13-3.4-lactone ChEBI
N-decanoyl-L-tryptophyl-L-asparaginyl-L-aspartyl-L-threonylglycyl-L-ornithyl-L-aspartyl-D-alanyl-L-aspartylglycyl-D-seryl-threo-3-methyl-L-glutamyl-3-anthraniloyl-L-alanine ε1-lactone ChemIDplus
Brand Names Sources
Cidecin ChemIDplus
Cubicin ChemIDplus
Manual Xrefs Databases
C12013 KEGG COMPOUND
D01080 KEGG DRUG
Daptomycin Wikipedia
DB00080 DrugBank
View more database links
Registry Numbers Types Sources
103060-53-3 CAS Registry Number KEGG COMPOUND
103060-53-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14622998 PubMed citation ChEMBL
15227539 PubMed citation Europe PMC
15271343 PubMed citation Europe PMC
15500379 PubMed citation Europe PMC
15815985 PubMed citation Europe PMC
15870461 PubMed citation Europe PMC
16311632 PubMed citation Europe PMC
17402833 PubMed citation Europe PMC
18360590 PubMed citation Europe PMC
18989686 PubMed citation Europe PMC
19015332 PubMed citation Europe PMC
19303806 PubMed citation Europe PMC
19875242 PubMed citation Europe PMC
20522545 PubMed citation Europe PMC
Last Modified
20 February 2018
General Comment
2011-03-17 A naturally-occurring compound found in the soil saprotroph Streptomyces roseosporus, daptomycin is effective against Gram-positive bacteria and is used in the treatment of complicated Gram-positive infections of the skin and soft tissues. It has also been investigated for the treatment of vancomycin-resistant enterococcal infections, complicated urinary tract infections, and community-acquired pneumonia.