Name: Feglymycin
Rating: 5 (10 reviews)

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HIT ID:HIT212038905
Cas No:209335-49-9
常用名:Feglymycin
IUPAC:(2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-2-(3,5-dihydroxyphenyl)acetamido]-3-methylbutanamido]-2-(3,5-dihydroxyphenyl)acetamido]-2-(4-hydroxyphenyl)acetamido]-2-(3,5-dihydroxyphenyl)acetamido]-2-(4-hydroxyphenyl)acetamido]-2-(3,5-dihydroxyphenyl)acetamido]-3-methylbutanamido]-2-(3,5-dihydroxyphenyl)acetamido]-2-(4-hydroxyphenyl)acetamido]-3-phenylpropanamido]butanedioic acid
IUPAC:(2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-2-(3,5-dihydroxyphenyl)acetamido]-3-methylbutanamido]-2-(3,5-dihydroxyphenyl)acetamido]-2-(4-hydroxyphenyl)acetamido]-2-(3,5-dihydroxyphenyl)acetamido]-2-(4-hydroxyphenyl)acetamido]-2-(3,5-dihydroxyphenyl)acetamido]-3-methylbutanamido]-2-(3,5-dihydroxyphenyl)acetamido]-2-(4-hydroxyphenyl)acetamido]-3-phenylpropanamido]butanedioic acid
InChI key:QJQKBRUTBCTBKE-OVYRLPCXSA-N

分子式:C95H97N13O30
分子量:1900.882
氢键供体数 (HBD):29
氢键受体数 (HBA):31
LogP:1.4809853
SMILES:CC(C)[C@H](NC(=O)[C@H](NC(=O)[C@H](N)c1ccc(O)cc1)c1cc(O)cc(O)c1)C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CC(O)=O)C(O)=O)c1ccc(O)cc1)c1cc(O)cc(O)c1)c1cc(O)cc(O)c1)c1ccc(O)cc1)c1cc(O)cc(O)c1)c1ccc(O)cc1)c1cc(O)cc(O)c1
SMILES:CC(C)[C@H](NC(=O)[C@H](NC(=O)[C@H](N)c1ccc(O)cc1)c1cc(O)cc(O)c1)C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CC(O)=O)C(O)=O)c1ccc(O)cc1)c1cc(O)cc(O)c1)c1cc(O)cc(O)c1)c1ccc(O)cc1)c1cc(O)cc(O)c1)c1ccc(O)cc1)c1cc(O)cc(O)c1

Feglymycin is a 13-amino acid peptide originally isolated from Streptomyces that has antibacterial and antiviral activities. It is active against Gram-positive bacteria (MICs = 32-64 μg/ml) and inhibits HIV viral replication in H9 cells (IC50 = ~5 μM). Feglymycin is also active against clinical isolates of HIV-1 from clades A-D, A/E, and G (EC50s = 0.5-6.7 μM). It interacts with gp120 and inhibits HIV-1 NL4.3 binding to human soluble CD4 (EC50 = 4.4 μM) and to CD4+ SupT1 T cells by 74.5% when used at a concentration of 10.5 μM. Feglymycin inhibits the E. coli peptidoglycan biosynthesis enzymes MurA and MurC (Kis = 3.4 and 0.3 μM, respectively) in a noncompetitive manner.

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