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Neamine

AlkaPlorer ID: AK009397

Synonym: 'Neamine'

IUPAC Name: (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxyoxane-3,4-diol

Structure

SMILES: NC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](N)C[C@@H]2N)[C@H](N)[C@@H](O)[C@@H]1O

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InChI: InChI=1S/C12H26N4O6/c13-2-5-8(18)9(19)6(16)12(21-5)22-11-4(15)1-3(14)7(17)10(11)20/h3-12,17-20H,1-2,13-16H2/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-/m1/s1

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InChIKey: SYJXFKPQNSDJLI-HKEUSBCWSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Streptomyces fradiae Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria

Properties Information

Molecule Weight: 322.362

TPSA？: 203.46

MolLogP？: -5.115599999999994

Number of H-Donors: 8

Number of H-Acceptors: 10

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter baumannii Acinetobacter baumannii MIC 32.0 ug.mL-1 10.1021/acs.jmedchem.6b00793
Acinetobacter lwoffii Acinetobacter lwoffii MIC 0.5 ug.mL-1 10.1016/j.ejmech.2018.08.022
Acinetobacter lwoffii Acinetobacter lwoffii MIC 0.5 ug.mL-1 10.1021/acs.jmedchem.6b00818
Acinetobacter lwoffii Acinetobacter lwoffii MIC 2.0 ug.mL-1 10.1021/jm401148j
Acinetobacter lwoffii Acinetobacter lwoffii MIC 2.0 ug.mL-1 10.1021/jm900615h
Acinetobacter lwoffii Acinetobacter lwoffii MIC 128.0 ug.mL-1 10.1016/j.ejmech.2018.08.022
Acinetobacter lwoffii Acinetobacter lwoffii MIC 128.0 ug.mL-1 10.1021/acs.jmedchem.6b00818
Acinetobacter lwoffii Acinetobacter lwoffii MIC 128.0 ug.mL-1 10.1021/jm401148j
Acinetobacter lwoffii Acinetobacter lwoffii MIC 128.0 ug.mL-1 10.1021/jm900615h
Bacillus anthracis Anthrax lethal factor Ki 42900.0 nM 10.1016/j.bmcl.2006.07.005
Bacillus subtilis Bacillus subtilis MIC 1.0 ug.mL-1 10.1039/C6MD00079G
Bacteria Bacterial 70S ribosome IC50 5000.0 nM 10.1016/j.bmc.2013.12.068
Bacteria Bacterial 70S ribosome IC50 5000.0 nM 10.1016/j.bmcl.2010.10.001
Bordetella bronchiseptica Bordetella bronchiseptica MIC 3.3 ug.mL-1 10.1039/C6MD00079G
Burkholderia cepacia Burkholderia cepacia MIC 32.0 ug.mL-1 10.1021/acs.jmedchem.6b00793
Cavia porcellus Cavia porcellus Activity 0.0 % 10.1016/j.bmc.2007.03.056
Cavia porcellus Cavia porcellus Activity 100.0 % 10.1016/j.bmc.2007.03.056
Escherichia coli Escherichia coli Activity nan None 10.1016/j.bmc.2007.03.056
Escherichia coli Escherichia coli MIC 1.0 ug.mL-1 10.1039/C6MD00079G
Escherichia coli Escherichia coli MIC 6.25 ug.mL-1 10.1016/j.bmc.2007.02.009
Escherichia coli Escherichia coli MIC 14.0 ug.mL-1 10.1016/j.bmc.2013.12.068
Escherichia coli Escherichia coli MIC 16.0 ug.mL-1 10.1021/acs.jmedchem.6b00793
Escherichia coli Escherichia coli MIC 32.0 ug.mL-1 10.1016/j.bmc.2010.01.027
Escherichia coli Escherichia coli MIC 32.0 ug.mL-1 10.1016/j.ejmech.2018.08.022
Escherichia coli Escherichia coli MIC 32.0 ug.mL-1 10.1021/acs.jmedchem.6b00793
Escherichia coli Escherichia coli MIC 32.0 ug.mL-1 10.1021/acs.jmedchem.6b00818
Escherichia coli Escherichia coli MIC 32.0 ug.mL-1 10.1021/jm401148j
Escherichia coli Escherichia coli MIC 32.0 ug.mL-1 10.1021/jm900615h
Escherichia coli Escherichia coli MIC 96.0 ug.mL-1 10.1016/j.bmc.2008.08.053
Escherichia coli Escherichia coli MIC 96.0 ug.mL-1 10.1128/aac.01034-06
Escherichia coli Escherichia coli MIC 128.0 ug.mL-1 10.1016/j.ejmech.2018.08.022
Escherichia coli Escherichia coli MIC 128.0 ug.mL-1 10.1021/acs.jmedchem.6b00818
Escherichia coli Escherichia coli MIC 128.0 ug.mL-1 10.1021/jm401148j
Escherichia coli Escherichia coli MIC 128.0 ug.mL-1 10.1021/jm900615h
Escherichia coli Escherichia coli MIC 150.0 ug.mL-1 10.1016/j.bmc.2013.12.068
Escherichia coli Escherichia coli MIC 300.0 ug.mL-1 10.1016/j.bmc.2013.12.068
Escherichia coli Escherichia coli MIC 1536.0 ug.mL-1 10.1128/aac.01034-06
Escherichia coli Escherichia coli MIC 8000.0 nM 10.1016/j.ejmech.2016.10.054
Escherichia coli Escherichia coli MIC 16000.0 nM 10.1016/j.ejmech.2016.10.054
Escherichia coli Escherichia coli MIC 50000.0 nM 10.1016/j.bmcl.2009.03.021
Escherichia coli Escherichia coli MIC 50000.0 nM 10.1039/c2md00253a
Escherichia coli Escherichia coli MIC 128000.0 nM 10.1016/j.ejmech.2016.10.054
Haemophilus influenzae Haemophilus influenzae MIC 32.0 ug.mL-1 10.1021/acs.jmedchem.6b00793
Homo sapiens Phosphatidylcholine-retinol O-acyltransferase IC50 38600.0 nM 10.1016/s0960-894x(02)01073-9
Homo sapiens Phosphatidylcholine-retinol O-acyltransferase IC50 102000.0 nM 10.1016/s0960-894x(02)01073-9
Homo sapiens Phosphatidylcholine-retinol O-acyltransferase IC50 197000.0 nM 10.1016/s0960-894x(02)01073-9
Homo sapiens Phosphatidylcholine-retinol O-acyltransferase IC50 198000.0 nM 10.1016/s0960-894x(02)01073-9
Human immunodeficiency virus 1 Human immunodeficiency virus 1 Inhibition nan % 10.1021/jm049642d
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 REV IC50 21000.0 nM 10.1016/s0960-894x(01)00005-1
Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)(HIV-1) Protein Rev IC50 21000.0 nM 10.1016/j.bmcl.2018.11.004
Human immunodeficiency virus type 1 group M subtype B (isolate PCV12)(HIV-1) Human immunodeficiency virus type 1 Tat protein IC50 28000.0 nM 10.1016/s0960-894x(01)00005-1
Klebsiella aerogenes Klebsiella aerogenes MIC 16000.0 nM 10.1016/j.ejmech.2016.10.054
Klebsiella aerogenes Klebsiella aerogenes MIC 32000.0 nM 10.1016/j.ejmech.2016.10.054
Klebsiella aerogenes Klebsiella aerogenes MIC 128000.0 nM 10.1016/j.ejmech.2016.10.054
Klebsiella pneumoniae Klebsiella pneumoniae MIC 0.5 ug.mL-1 10.1039/C6MD00079G
Klebsiella pneumoniae Klebsiella pneumoniae MIC 2.0 ug.mL-1 10.1016/j.bmc.2010.01.027
Klebsiella pneumoniae Klebsiella pneumoniae MIC 16.0 ug.mL-1 10.1016/j.bmc.2010.01.027
Klebsiella pneumoniae Klebsiella pneumoniae MIC 16.0 ug.mL-1 10.1021/acs.jmedchem.6b00793
Klebsiella pneumoniae Klebsiella pneumoniae MIC 32.0 ug.mL-1 10.1016/j.ejmech.2018.08.022
Klebsiella pneumoniae Klebsiella pneumoniae MIC 32.0 ug.mL-1 10.1021/acs.jmedchem.6b00793
Klebsiella pneumoniae Klebsiella pneumoniae MIC 32.0 ug.mL-1 10.1021/acs.jmedchem.6b00818
Klebsiella pneumoniae Klebsiella pneumoniae MIC 32.0 ug.mL-1 10.1021/jm401148j
Klebsiella pneumoniae Klebsiella pneumoniae MIC 32.0 ug.mL-1 10.1021/jm900615h
Micrococcus luteus Micrococcus luteus Activity nan None 10.1016/j.bmc.2007.03.056
Mus musculus J774 Activity 84.4 % 10.1016/j.ejmech.2018.08.022
Mus musculus J774 Activity 94.8 % 10.1016/j.ejmech.2018.08.022
Mus musculus Mus musculus Activity 84.4 % 10.1021/acs.jmedchem.6b00818
Mus musculus Mus musculus Activity 94.8 % 10.1021/acs.jmedchem.6b00818
Mus musculus Mus musculus LD50 161.0 mg.kg-1 10.1016/j.bmc.2008.08.053
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 5.0 ug.mL-1 10.1039/C6MD00079G
Proteus vulgaris Proteus vulgaris MIC 0.33 ug.mL-1 10.1039/C6MD00079G
Pseudomonas aeruginosa Pseudomonas aeruginosa Activity nan None 10.1016/j.bmc.2007.03.056
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 32.0 ug.mL-1 10.1021/acs.jmedchem.6b00793
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 64.0 ug.mL-1 10.1016/j.bmc.2010.01.027
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 64.0 ug.mL-1 10.1016/j.ejmech.2018.08.022
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 64.0 ug.mL-1 10.1021/acs.jmedchem.6b00818
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 73.0 ug.mL-1 10.1016/j.bmc.2013.12.068
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 128.0 ug.mL-1 10.1016/j.ejmech.2018.08.022
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 128.0 ug.mL-1 10.1021/acs.jmedchem.6b00818
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 128.0 ug.mL-1 10.1021/jm401148j
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 128.0 ug.mL-1 10.1021/jm900615h
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 512.0 ug.mL-1 10.1128/aac.01034-06
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 100000.0 nM 10.1016/j.bmcl.2009.03.021
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) Aminoglycoside 3'-phosphotransferase type IIb Kcat/Km 170000.0 /M/s 10.1128/aac.01034-06
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) Aminoglycoside 3'-phosphotransferase type IIb Km 10300.0 nM 10.1128/aac.01034-06
Salmonella enterica subsp. enterica serovar Paratyphi B Salmonella enterica subsp. enterica serovar Paratyphi B MIC 1.0 ug.mL-1 10.1039/C6MD00079G
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 nan None 10.1016/j.bmc.2007.03.056
Staphylococcus aureus Staphylococcus aureus MIC 0.13 ug.mL-1 10.1039/C6MD00079G
Staphylococcus aureus Staphylococcus aureus MIC 4.0 ug.mL-1 10.1016/j.bmc.2010.01.027
Staphylococcus aureus Staphylococcus aureus MIC 5.0 ug.mL-1 10.1016/j.bmc.2013.12.068
Staphylococcus aureus Staphylococcus aureus MIC 8.0 ug.mL-1 10.1016/j.ejmech.2018.08.022
Staphylococcus aureus Staphylococcus aureus MIC 8.0 ug.mL-1 10.1021/acs.jmedchem.6b00818
Staphylococcus aureus Staphylococcus aureus MIC 16.0 ug.mL-1 10.1016/j.ejmech.2018.08.022
Staphylococcus aureus Staphylococcus aureus MIC 16.0 ug.mL-1 10.1021/acs.jmedchem.6b00818
Staphylococcus aureus Staphylococcus aureus MIC 16.0 ug.mL-1 10.1021/jm401148j
Staphylococcus aureus Staphylococcus aureus MIC 16.0 ug.mL-1 10.1021/jm900615h
Staphylococcus aureus Staphylococcus aureus MIC 32.0 ug.mL-1 10.1021/jm401148j
Staphylococcus aureus Staphylococcus aureus MIC 32.0 ug.mL-1 10.1021/jm900615h
Staphylococcus aureus Staphylococcus aureus MIC 125.0 ug.mL-1 10.1016/j.bmc.2010.01.027
Staphylococcus aureus Staphylococcus aureus MIC 128.0 ug.mL-1 10.1016/j.ejmech.2018.08.022
Staphylococcus aureus Staphylococcus aureus MIC 128.0 ug.mL-1 10.1021/acs.jmedchem.6b00818
Staphylococcus aureus Staphylococcus aureus MIC 128.0 ug.mL-1 10.1021/jm401148j
Staphylococcus aureus Staphylococcus aureus MIC 128.0 ug.mL-1 10.1021/jm900615h
Staphylococcus aureus Staphylococcus aureus MIC 50000.0 nM 10.1016/j.bmcl.2009.03.021
Staphylococcus epidermidis Staphylococcus epidermidis Activity nan None 10.1016/j.bmc.2007.03.056
None ADMET LD50 121.0 mg.kg-1 10.1021/acs.jmedchem.6b00793
None No relevant target Kd 1000.0 nM 10.1021/jm030650o
None Nucleic Acid DNA peak exclusion 40.0 % 10.1016/s0960-894x(01)00115-9
None Nucleic Acid EC50 9500.0 nM 10.1016/j.bmcl.2010.10.001
None Nucleic Acid IC50 50000.0 nM 10.1016/j.bmcl.2005.08.027
None Nucleic Acid Kd 19000.0 nM 10.1016/j.bmcl.2009.03.021
None Nucleic Acid Kd 24000.0 nM 10.1016/j.bmcl.2009.03.021
None Nucleic Acid MIC 100000.0 nM 10.1021/jm970372r
None Nucleic Acid tRNA peak exclusion 47.3 % 10.1016/s0960-894x(01)00115-9
None Ribosomal RNA A-site IC50 460.0 nM 10.1021/acs.jmedchem.6b00793
None Ribosomal RNA A-site Kd 5000.0 nM 10.1016/j.bmcl.2005.08.027
None Ribosomal RNA A-site Kd 7390.0 nM 10.1021/jm060288o
None Ribosomal RNA A-site Kd 7800.0 nM 10.1016/s0960-894x(00)00615-6
None Ribosome IC50 120000.0 nM 10.1016/j.bmcl.2010.10.001
None Unchecked Activity 72.0 % 10.1016/j.bmc.2015.07.062
None Unchecked EC50 9500.0 nM 10.1016/j.bmc.2013.12.068
None Unchecked IC50 10000.0 nM 10.1016/j.bmcl.2005.07.082
None Unchecked IC50 40000.0 nM 10.1016/j.bmcl.2005.07.082
None Unchecked IC50 99030.0 nM 10.1021/acs.jmedchem.6b00793
None Unchecked IC50 298000.0 nM 10.1016/j.bmc.2015.07.062
None Unchecked IC50 751000.0 nM 10.1016/j.bmc.2015.07.062
None Unchecked IC50 nan None 10.1016/j.bmc.2015.07.062
None Unchecked Inhibition 10.0 % 10.1016/j.bmc.2015.07.062
None Unchecked k cat 596.0 min-1 10.1016/s0960-894x(98)00633-7
None Unchecked k cat 1740.0 min-1 10.1016/s0960-894x(98)00633-7
None Unchecked Kcat 0.419 /s 10.1039/c2md00253a
None Unchecked Kcat 1.7 /s 10.1016/j.bmc.2008.08.053
None Unchecked Kcat/Km 7.2 10'4/M/s 10.1039/c2md00253a
None Unchecked Kd 5400.0 nM 10.1016/j.bmc.2015.03.001
None Unchecked Kd 10000.0 nM 10.1039/c2md00253a
None Unchecked Kd 11000.0 nM 10.1016/j.bmcl.2008.09.062
None Unchecked Kd 24900.0 nM 10.1016/j.bmc.2015.07.062
None Unchecked Kd 26000.0 nM 10.1016/j.bmcl.2008.09.062
None Unchecked Kd 160000.0 nM 10.1016/j.bmc.2015.07.062
None Unchecked Kd 187000.0 nM 10.1016/j.bmc.2015.07.062
None Unchecked Kd 248000.0 nM 10.1016/j.bmc.2015.07.062
None Unchecked Kd 394000.0 nM 10.1016/j.bmc.2015.07.062
None Unchecked K m 1.2 uM 10.1016/s0960-894x(98)00633-7
None Unchecked K m 7.9 uM 10.1016/s0960-894x(98)00633-7
None Unchecked Km 5820.0 nM 10.1039/c2md00253a
None Unchecked Km 10300.0 nM 10.1016/j.bmc.2008.08.053
None Unchecked MIC 0.17 ug.mL-1 10.1039/C6MD00079G
None Unchecked Ratio 1.5 None 10.1016/j.bmc.2015.07.062
None Unchecked Ratio 2.36 None 10.1016/j.bmcl.2008.09.062
None Unchecked Ratio 2.5 None 10.1016/j.bmc.2015.07.062
None Unchecked Ratio 1300000.0 M-1 s-1 10.1016/s0960-894x(98)00633-7
None Unchecked Ratio 24000000.0 M-1 s-1 10.1016/s0960-894x(98)00633-7
None Unchecked Ratio IC50 215.28 None 10.1021/acs.jmedchem.6b00793

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT004666 CC(=O)[CoA].NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>CC(=O)NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O enzymemap_32240
AKRT004667 CC(=O)[CoA].NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>CC(=O)N[C@H]1[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)O[C@H](CN)[C@@H](O)[C@@H]1O enzymemap_31549
AKRT018489 NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O.N[C@H]1[C@H](O)[C@@H](CO)O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@@H]1O>>NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O RXN-13147
AKRT018490 NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O.O=P(O)(O)OC[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)O)[C@H](O)[C@@H]1O>>NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O RXN-13203
AKRT018491 NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O RXN-13149
AKRT018492 NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)CC1=O R11275
AKRT018493 NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)[C@@H](OP(=O)(O)O)[C@@H]1O enzymemap_45520
AKRT020425 N[C@H]1C[C@@H](N)[C@H](O)[C@@H](O)[C@@H]1O[C@H]1O[C@H](C=O)[C@@H](O)[C@H](O)[C@H]1N>>NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O RXN-13146