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Apramycin

AlkaPlorer ID: AK013951

Synonym: None

IUPAC Name: (2R,3R,4S,5S,6S)-2-[[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-4-hydroxy-3-(methylamino)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol

Structure

SMILES: CN[C@@H]1[C@@H](O[C@H]2O[C@H](CO)[C@@H](N)[C@H](O)[C@H]2O)O[C@H]2C[C@@H](N)[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](N)C[C@@H]3N)O[C@@H]2[C@@H]1O

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InChI: InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1

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InChIKey: XZNUGFQTQHRASN-XQENGBIVSA-N

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Properties Information

Molecule Weight: 539.5830000000003

TPSA？: 283.64000000000004

MolLogP？: -6.949300000000007

Number of H-Donors: 11

Number of H-Acceptors: 16

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter baumannii Acinetobacter baumannii Activity 4.0 ug ml-1 10.1039/C9MD00093C
Bacillus subtilis Bacillus subtilis MIC nan None 10.1021/acs.jnatprod.5b00752
Bacteria Bacterial 70S ribosome IC50 0.078 ug.mL-1 10.1039/C9MD00093C
Enterobacter cloacae Enterobacter cloacae Activity 2.0 ug ml-1 10.1039/C9MD00093C
Escherichia coli Escherichia coli Activity 4.0 ug ml-1 10.1039/C9MD00093C
Escherichia coli Escherichia coli Activity nan None 10.1016/j.ejmech.2022.114342
Escherichia coli Escherichia coli MIC 50.0 ug.mL-1 10.1021/acs.jnatprod.6b00621
Escherichia coli Escherichia coli MIC nan None 10.1021/acs.jnatprod.5b00752
Klebsiella pneumoniae Klebsiella pneumoniae Activity 1.0 ug ml-1 10.1039/C9MD00093C
Mycolicibacterium smegmatis Mycolicibacterium smegmatis MIC 0.39 ug.mL-1 10.1021/acs.jnatprod.5b00752
Mycolicibacterium smegmatis Mycolicibacterium smegmatis MIC 2.5 ug.mL-1 10.1021/acs.jnatprod.6b00621
Pseudomonas aeruginosa Pseudomonas aeruginosa Activity 4.0 ug ml-1 10.1039/C9MD00093C
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 50.0 ug.mL-1 10.1021/acs.jnatprod.6b00621
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC nan None 10.1021/acs.jnatprod.5b00752
Rhodococcus fascians Rhodococcus fascians MIC 50.0 ug.mL-1 10.1021/acs.jnatprod.6b00621
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Staphylococcus aureus Staphylococcus aureus Activity 4.0 ug ml-1 10.1039/C9MD00093C
Staphylococcus aureus Staphylococcus aureus MIC 30.0 ug.mL-1 10.1021/acs.jnatprod.6b00621
Staphylococcus aureus Staphylococcus aureus MIC nan None 10.1021/acs.jnatprod.5b00752
None Unchecked IC50 40.0 ug.mL-1 10.1039/C9MD00093C
None Unchecked IC50 67.0 ug.mL-1 10.1039/C9MD00093C
None Unchecked IC50 69.0 ug.mL-1 10.1039/C9MD00093C
None Unchecked Ratio IC50 513.0 None 10.1039/C9MD00093C
None Unchecked Ratio IC50 859.0 None 10.1039/C9MD00093C
None Unchecked Ratio IC50 885.0 None 10.1039/C9MD00093C

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT004382 CC(=O)[32S].CN[C@@H]1[C@@H](O[C@H]2O[C@H](CO)[C@@H](N)[C@H](O)[C@H]2O)O[C@H]2C[C@@H](N)[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](N)C[C@@H]3N)O[C@@H]2[C@@H]1O>>CN[C@@H]1[C@@H](O[C@H]2O[C@H](CO)[C@@H](N)[C@H](O)[C@H]2O)O[C@H]2C[C@@H](N)[C@@H](OC3C(NC(C)=O)CC(N)C(O)C3O)O[C@@H]2[C@@H]1O None
AKRT004544 CC(=O)[CoA].CN[C@@H]1[C@@H](O[C@H]2O[C@H](CO)[C@@H](N)[C@H](O)[C@H]2O)O[C@H]2C[C@@H](N)[C@@H](O[C@@H]3[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)O[C@@H]2[C@@H]1O>>CN[C@@H]1[C@@H](O[C@H]2O[C@H](CO)[C@@H](N)[C@H](O)[C@H]2O)O[C@H]2C[C@@H](N)[C@@H](OC3C(NC(C)=O)CC(N)C(O)C3O)O[C@@H]2[C@@H]1O enzymemap_32212