Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2142)
Drug Name
Daptomycin
Synonyms
Dapcin; Daptomicina; Daptomycine; Daptomycinum; LY 146032; LY-146032; LY146032; (2S)-daptomycin; 103060-53-3; C72H101N17O26; Cidecin; Cubicin; DAPTOMYCIN; CHEBI:600103; 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-alpha-asparagine; SCHEMBL28102
Indication Methicillin-resistant staphylococcus infection [ICD11: 1D01] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 1620.7 Topological Polar Surface Area 702
Heavy Atom Count 115 Rotatable Bond Count 35
Hydrogen Bond Donor Count 22 Hydrogen Bond Acceptor Count 28
Cross-matching ID
PubChem CID
16134395
ChEBI ID
CHEBI:600103
CAS Number
103060-53-3
Formula
C72H101N17O26
Canonical SMILES
CCCCCCCCCC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC3C(OC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC3=O)CCCN)CC(=O)O)C)CC(=O)O)CO)C(C)CC(=O)O)CC(=O)C4=CC=CC=C4N)C
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
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
CDP-alcohol phosphatidyltransferase (pgsA) DME1149 Streptococcus mitis
A0A081Q830_STRMT
2.7.8.5
[2]
CDP-alcohol phosphatidyltransferase (pgsA) DME1150 Streptococcus oralis
A0A081R409_STROR
2.7.8.5
[2]
References
1 Daptomycin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Mutations in cdsA and pgsA correlate with daptomycin resistance in Streptococcus mitis and S. oralis. Antimicrob Agents Chemother. 2019 Jan 29;63(2). pii: e01531-18.

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