Muraymycin C1
AlkaPlorer ID: AK007741
Synonym: None
IUPAC Name: (2S)-2-[[(1S)-2-[[(2S,3S)-1-[3-[[(1S,2S)-2-[(2S,3R,4R,5R)-5-(aminomethyl)-4-hydroxy-3-methoxyoxolan-2-yl]oxy-1-carboxy-2-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]ethyl]amino]propylamino]-3-hydroxy-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: CO[C@H]1[C@H](O[C@H]([C@H]2O[C@@H](N3C=CC(O)=NC3=O)[C@H](O)[C@@H]2O)[C@H](NCCCN=C(O)[C@@H](N=C(O)[C@@H](NC(O)=N[C@H](C(=O)O)C(C)C)[C@@H]2CCNC(=N)N2)[C@@H](O)C(C)C)C(=O)O)O[C@H](CN)[C@H]1O
InChI: InChI=1S/C38H63N11O17/c1-14(2)19(33(57)58)47-37(61)48-20(16-7-11-43-36(40)44-16)31(56)46-21(23(51)15(3)4)30(55)42-10-6-9-41-22(34(59)60)27(66-35-29(63-5)24(52)17(13-39)64-35)28-25(53)26(54)32(65-28)49-12-8-18(50)45-38(49)62/h8,12,14-17,19-29,32,35,41,51-54H,6-7,9-11,13,39H2,1-5H3,(H,42,55)(H,46,56)(H,57,58)(H,59,60)(H3,40,43,44)(H,45,50,62)(H2,47,48,61)/t16-,17+,19-,20-,21-,22-,23-,24+,25-,26+,27-,28-,29+,32+,35-/m0/s1
InChIKey: GOFOFDWFFIGTML-IZAYEQDHSA-N
Reference
Structures of the Muraymycins, Novel Peptidoglycan Biosynthesis Inhibitors
PubChem CID: 145991805
LOTUS: LTS0152175
NPASS: NPC487099
{NPAtlas: NPA006302
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Streptomyces sp. | Streptomyces | Streptomycetaceae | Kitasatosporales | Actinomycetes | Actinomycetota | None | Bacteria |
| Streptomyces sp. NRRL 30471 | Streptomyces | Streptomycetaceae | Kitasatosporales | Actinomycetes | Actinomycetota | None | Bacteria |
Properties Information
Molecule Weight: 945.982
TPSA？: 443.32
MolLogP？: -4.388130000000008
Number of H-Donors: 16
Number of H-Acceptors: 20
RingCount: 4
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Aquifex aeolicus (strain VF5) | Phospho-N-acetylmuramoyl-pentapeptide-transferase | IC50 | 0.35 | nM | 10.1021/acs.jnatprod.7b01054 |
| Escherichia coli | Escherichia coli | MIC | 1.0 | ug.mL-1 | 10.1021/acs.jnatprod.7b01054 |
| Escherichia coli | Escherichia coli | MIC | 8.0 | ug.mL-1 | 10.1021/acs.jnatprod.7b01054 |
| Staphylococcus aureus | Phospho-N-acetylmuramoyl-pentapeptide-transferase | IC50 | 0.0157 | nM | 10.1021/acs.jnatprod.7b01054 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 32.0 | ug.mL-1 | 10.1021/acs.jnatprod.7b01054 |