daptomycin (CHEBI:600103)

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CHEBI:600103 - daptomycin

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ChEBI ID	CHEBI:600103
ChEBI Name	daptomycin
Stars
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.
Secondary ChEBI IDs	CHEBI:29570, CHEBI:321017, CHEBI:478132, CHEBI:478255
Last Modified	20 February 2018
Downloads	Molfile

Formula	C72H101N17O26
Net Charge	0
Average Mass	1620.693
Monoisotopic Mass	1619.71037
SMILES	CCCCCCCCCC(=O)N[C@@H](Cc1cnc2ccccc12)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H]1C(=O)NCC(=O)N[C@@H](CCCN)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)NCC(=O)N[C@H](CO)C(=O)N[C@@H]([C@H](C)CC(=O)O)C(=O)N[C@@H](CC(=O)c2ccccc2N)C(=O)O[C@@H]1C
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

Wikipedia

Roles Classification

Chemical Roles:	Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:	bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. antibacterial drug A drug used to treat or prevent bacterial infections. 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.
Application:	antibacterial drug A drug used to treat or prevent bacterial infections.

ChEBI Ontology

Outgoing Relation(s)
	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	Source
daptomycine	ChemIDplus
daptomicina	ChemIDplus
daptomycin	ChemIDplus
daptomycinum	ChemIDplus

Synonyms	Source
Daptomycin	KEGG COMPOUND
daptomycin	ChEMBL
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
LY 146032	ChemIDplus

Brand Names	Source
Cidecin	ChemIDplus
Cubicin	ChemIDplus

Manual Xrefs	Databases
C12013	KEGG COMPOUND
D01080	KEGG DRUG
DB00080	DrugBank
Daptomycin	Wikipedia

Registry Numbers	Sources
CAS:103060-53-3	KEGG COMPOUND
CAS:103060-53-3	ChemIDplus

Citations