Muraymycin D2
AlkaPlorer ID: AK008856
Synonym: None
IUPAC Name: (2S)-2-[[(1S)-2-[[(2S)-1-[3-[[(1S,2S)-2-[(2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxyoxolan-2-yl]oxy-1-carboxy-2-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]ethyl]amino]propylamino]-4-methyl-1-oxopentan-2-yl]amino]-1-[(6S)-2-amino-1,4,5,6-tetrahydropyrimidin-6-yl]-2-oxoethyl]carbamoylamino]-3-methylbutanoic acid
Structure
SMILES: CC(C)C[C@H](N=C(O)[C@@H](NC(O)=N[C@H](C(=O)O)C(C)C)[C@@H]1CCNC(=N)N1)C(O)=NCCCN[C@H](C(=O)O)[C@H](O[C@@H]1O[C@H](CN)[C@@H](O)[C@H]1O)[C@H]1O[C@@H](N2C=CC(O)=NC2=O)[C@H](O)[C@@H]1O
InChI: InChI=1S/C37H61N11O16/c1-14(2)12-17(43-30(55)21(16-6-10-42-35(39)44-16)47-36(60)46-20(15(3)4)32(56)57)29(54)41-9-5-8-40-22(33(58)59)27(64-34-26(53)23(50)18(13-38)62-34)28-24(51)25(52)31(63-28)48-11-7-19(49)45-37(48)61/h7,11,14-18,20-28,31,34,40,50-53H,5-6,8-10,12-13,38H2,1-4H3,(H,41,54)(H,43,55)(H,56,57)(H,58,59)(H3,39,42,44)(H,45,49,61)(H2,46,47,60)/t16-,17-,18+,20-,21-,22-,23+,24-,25+,26+,27-,28-,31+,34-/m0/s1
InChIKey: RRTIONDZEJYWBN-VDXVSALRSA-N
Reference
Structures of the Muraymycins, Novel Peptidoglycan Biosynthesis Inhibitors
PubChem CID: 136000717
LOTUS: LTS0094567
{NPAtlas: NPA007567
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Streptomyces sp. | Streptomyces | Streptomycetaceae | Kitasatosporales | Actinomycetes | Actinomycetota | None | Bacteria |
Properties Information
Molecule Weight: 915.9560000000004
TPSA？: 434.09
MolLogP？: -4.013030000000007
Number of H-Donors: 16
Number of H-Acceptors: 19
RingCount: 4
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Bacillus subtilis | Bacillus subtilis | Activity | nan | None | 10.1021/jm200906r |
| Bacillus subtilis (strain 168) | Phospho-N-acetylmuramoyl-pentapeptide-transferase | IC50 | 10.0 | nM | 10.1021/jm200906r |
| Bacillus subtilis (strain 168) | Phospho-N-acetylmuramoyl-pentapeptide-transferase | IC50 | 10.0 | nM | 10.1021/ml100057z |
| Bacillus subtilis (strain 168) | Phospho-N-acetylmuramoyl-pentapeptide-transferase | Ki | 7.6 | nM | 10.1021/jm200906r |
| Enterococcus faecalis | Enterococcus faecalis | MIC | 64.0 | ug.mL-1 | 10.1021/jm200906r |
| Enterococcus faecalis | Enterococcus faecalis | MIC | 64.0 | ug.mL-1 | 10.1021/jm2009343 |
| Enterococcus faecalis | Enterococcus faecalis | MIC | 64.0 | ug.mL-1 | 10.1021/ml100057z |
| Enterococcus faecium | Enterococcus faecium | MIC | 64.0 | ug.mL-1 | 10.1021/jm200906r |
| Enterococcus faecium | Enterococcus faecium | MIC | 64.0 | ug.mL-1 | 10.1021/jm2009343 |
| Enterococcus faecium | Enterococcus faecium | MIC | 64.0 | ug.mL-1 | 10.1021/ml100057z |
| Pseudomonas aeruginosa | Pseudomonas aeruginosa | MIC | 32.0 | ug.mL-1 | 10.1021/ml5000096 |
| Pseudomonas aeruginosa | Pseudomonas aeruginosa | MIC | 64.0 | ug.mL-1 | 10.1021/ml5000096 |
| Staphylococcus aureus | Staphylococcus aureus | ED50 | 1.1 | mg.kg-1 | 10.1021/jm2009343 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 64.0 | ug.mL-1 | 10.1021/jm200906r |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 64.0 | ug.mL-1 | 10.1021/jm2009343 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 64.0 | ug.mL-1 | 10.1021/ml100057z |
| Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099) | Undecaprenyl-phosphate alpha-N-acetylglucosaminyl 1-phosphate transferase | IC50 | 1230000.0 | nM | 10.1021/jm200906r |
| None | Unchecked | IC50 | 2.8 | nM | 10.1021/acs.jmedchem.0c00973 |
| None | Unchecked | IC50 | 2.8 | nM | 10.1021/ml5000096 |
| None | Unchecked | IC50 | 25.0 | nM | 10.1016/j.bmc.2021.116556 |