Details of the Drug

General Information of Drug (ID: DM159U2)

Drug Name

Evernimicin

Synonyms

Everninomicin; Everninomycin; Everninomycins; Ziracin; Evernimicin [USAN:INN]; Sch-27899; Antibiotic 13-384-1

Indication

Disease Entry	ICD 11	Status	REF
Bacterial infection	1A00-1C4Z	Discontinued in Phase 3	[1]

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 4

Molecular Weight (mw)

1631.4

Topological Polar Surface Area (xlogp)

1.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C70H97Cl2NO38
IUPAC Name: [(2R,3R,4R,6S)-6-[(2R,2'R,3'S,3aR,4R,4'R,6S,7S,7aR)-6-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6S)-6-[(3aR,3'aS,4R,6'S,7R,7'R,7aS,7'aS)-7-(2,4-dihydroxy-6-methylbenzoyl)oxy-7'-hydroxyspiro[3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4,2'-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran]-6'-yl]oxy-4-hydroxy-5-methoxy-2-(methoxymethyl)oxan-3-yl]oxy-3-hydroxy-5-methoxy-6-methyloxan-4-yl]oxy-4',7-dihydroxy-2',4,7a-trimethylspiro[3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2,6'-oxane]-3'-yl]oxy-4-[(2S,4S,5R,6S)-5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl]oxy-2-methyloxan-3-yl] 3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoate
Canonical SMILES: C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@]3(C[C@H]2O)O[C@@H]4[C@H](O[C@H]([C@H]([C@]4(O3)C)O)O[C@@H]5[C@H]([C@@H](O[C@@H]([C@@H]5OC)C)O[C@@H]6[C@H](O[C@H]([C@H]([C@H]6O)OC)O[C@H]7[C@@H]([C@H]8[C@H](CO7)O[C@@]9(O8)[C@H]1[C@H]([C@@H](CO9)OC(=O)C2=C(C=C(C=C2C)O)O)OCO1)O)COC)O)C)C)O[C@H]1C[C@]([C@H]([C@@H](O1)C)OC)(C)[N+](=O)[O-])OC(=O)C1=C(C(=C(C(=C1OC)Cl)O)Cl)C
InChI: InChI=1S/C70H97Cl2NO38/c1-24-15-31(74)16-32(75)40(24)61(82)100-36-22-94-70(60-53(36)92-23-93-60)108-37-21-91-63(46(79)52(37)109-70)106-65-56(89-13)45(78)51(35(101-65)20-86-10)104-64-47(80)55(50(87-11)27(4)97-64)105-66-57(81)68(9)59(30(7)98-66)110-69(111-68)18-33(76)48(28(5)107-69)102-38-17-34(99-39-19-67(8,73(84)85)58(90-14)29(6)96-39)49(26(3)95-38)103-62(83)41-25(2)42(71)44(77)43(72)54(41)88-12/h15-16,26-30,33-39,45-53,55-60,63-66,74-81H,17-23H2,1-14H3/t26-,27-,28-,29+,30-,33-,34-,35-,36-,37+,38+,39+,45+,46-,47-,48-,49-,50+,51-,52-,53+,55-,56+,57-,58+,59-,60-,63+,64+,65+,66+,67+,68-,69-,70-/m1/s1
InChIKey: UPADRKHAIMTUCC-OWALTSPQSA-N

Cross-matching ID

PubChem CID: 6917933
CAS Number: 109545-84-8
DrugBank ID: DB06431
TTD ID: D0LA5G

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial 50S ribosomal RNA (Bact 50S rRNA)	TTUWYEA	NOUNIPROTAC	Modulator	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800002696)
2	Evernimicin binds exclusively to the 50S ribosomal subunit and inhibits translation in cell-free systems derived from both gram-positive and gram-n... Antimicrob Agents Chemother. 2000 May;44(5):1121-6.
3	A synthetic alanyl-initiator tRNA with initiator tRNA properties as determined by fluorescence measurements: comparison to a synthetic alanyl-elongator tRNA. Nucleic Acids Res. 1991 Oct 25;19(20):5749-54.
4	An examination of the differential sensitivity to ketolide antibiotics in ermB strains of Streptococcus pyogenes and Streptococcus pneumoniae. Curr Microbiol. 2004 Oct;49(4):239-47.
5	Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature. 2001 Oct 25;413(6858):814-21.
6	Review of macrolides and ketolides: focus on respiratory tract infections. Drugs. 2001;61(4):443-98.
7	The ChEMBL database in 2017. Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954.
8	Depression of colony formation by human thymus-derived lymphocytes with rifampin and other antimicrobial agents. J Infect Dis. 1981 Jun;143(6):832-5.
9	Retapamulin inhibition of translation and 50S ribosomal subunit formation in Staphylococcus aureus cells. Antimicrob Agents Chemother. 2007 Sep;51(9):3385-7.
10	The streptogramin antibiotics: update on their mechanism of action. Expert Opin Investig Drugs. 1998 Apr;7(4):591-9.
11	2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.