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Platencin

AlkaPlorer ID: AK021882

Synonym: None

IUPAC Name: 2,4-dihydroxy-3-[3-[(1S,5S,6R,8S)-5-methyl-9-methylidene-4-oxo-5-tricyclo[6.2.2.01,6]dodec-2-enyl]propanoylamino]benzoic acid

Structure

SMILES: C=C1C[C@@]23C=CC(=O)[C@@](C)(CCC(=O)NC4=C(O)C=CC(C(=O)O)=C4O)[C@@H]2C[C@@H]1CC3

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InChI: InChI=1S/C24H27NO6/c1-13-12-24-9-5-14(13)11-17(24)23(2,18(27)6-10-24)8-7-19(28)25-20-16(26)4-3-15(21(20)29)22(30)31/h3-4,6,10,14,17,26,29H,1,5,7-9,11-12H2,2H3,(H,25,28)(H,30,31)/t14-,17-,23-,24+/m0/s1

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InChIKey: DWUHGPPFFABTIY-RLWZQHMASA-N

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Properties Information

Molecule Weight: 425.48100000000017

TPSA？: 123.93

MolLogP？: 4.022500000000003

Number of H-Donors: 4

Number of H-Acceptors: 5

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis Bacillus subtilis MIC 1.0 ug.mL-1 10.1016/j.bmc.2010.02.030
Candida albicans Candida albicans MIC 64.0 ug.mL-1 10.1016/j.bmc.2010.02.030
Candida albicans Candida albicans MIC 64.0 ug.mL-1 10.1073/pnas.0700746104
Enterococcus faecalis Enterococcus faecalis Activity nan None 10.1021/np100635f
Enterococcus faecalis Enterococcus faecalis MIC 2.0 ug.mL-1 10.1016/j.bmc.2010.02.030
Enterococcus faecalis Enterococcus faecalis MIC 2.0 ug.mL-1 10.1021/acsmedchemlett.0c00653
Enterococcus faecalis Enterococcus faecalis MIC 2.0 ug.mL-1 10.1073/pnas.0700746104
Enterococcus faecium Enterococcus faecium Activity nan None 10.1021/np100635f
Enterococcus faecium Enterococcus faecium MIC 0.06 ug.mL-1 10.1073/pnas.0700746104
Escherichia coli Escherichia coli Activity nan None 10.1021/np100635f
Escherichia coli Escherichia coli MIC 2.0 ug.mL-1 10.1016/j.bmc.2010.02.030
Escherichia coli Escherichia coli MIC 2.0 ug.mL-1 10.1073/pnas.0700746104
Escherichia coli Escherichia coli MIC 4.0 ug.mL-1 10.1021/acsmedchemlett.0c00653
Escherichia coli Escherichia coli MIC 64.0 ug.mL-1 10.1016/j.bmc.2010.02.030
Escherichia coli Escherichia coli MIC 64.0 ug.mL-1 10.1073/pnas.0700746104
Haemophilus influenzae Haemophilus influenzae Activity nan None 10.1021/np100635f
Haemophilus influenzae Haemophilus influenzae MIC 64.0 ug.mL-1 10.1016/j.bmc.2010.02.030
Homo sapiens HeLa IC50 100.0 ug.mL-1 10.1073/pnas.0700746104
Homo sapiens HeLa IC50 86000.0 nM 10.1016/j.bmc.2010.02.030
Mus musculus Brain Stability nan % 10.1016/j.bmc.2017.02.028
Mus musculus Kidney Drug uptake nan None 10.1016/j.bmc.2017.02.028
Mus musculus Kidney Stability nan % 10.1016/j.bmc.2017.02.028
Mus musculus Liver Drug uptake nan None 10.1016/j.bmc.2017.02.028
Mus musculus Liver Stability nan % 10.1016/j.bmc.2017.02.028
Mus musculus Lung Drug uptake nan None 10.1016/j.bmc.2017.02.028
Mus musculus Lung Stability nan % 10.1016/j.bmc.2017.02.028
Mus musculus Mus musculus Activity nan None 10.1073/pnas.0700746104
Mus musculus Mus musculus AUC 978.6 ng.hr.mL-1 10.1016/j.bmc.2017.02.028
Mus musculus Mus musculus AUC 2893.26 ng.hr.mL-1 10.1016/j.bmc.2017.02.028
Mus musculus Mus musculus CL 23.0 mL.min-1.kg-1 10.1016/j.bmc.2017.02.028
Mus musculus Mus musculus Cmax 4000.0 nM 10.1016/j.bmc.2017.02.028
Mus musculus Mus musculus Cmax 11000.0 nM 10.1016/j.bmc.2017.02.028
Mus musculus Mus musculus F 10.0 % 10.1016/j.bmc.2017.02.028
Mus musculus Mus musculus T1/2 0.22 hr 10.1016/j.bmc.2017.02.028
Mus musculus Mus musculus T1/2 1.3 hr 10.1016/j.bmc.2017.02.028
Mus musculus Mus musculus Vd 0.46 L.kg-1 10.1016/j.bmc.2017.02.028
Mus musculus Plasma Drug uptake nan None 10.1016/j.bmc.2017.02.028
Mus musculus Plasma Stability nan % 10.1016/j.bmc.2017.02.028
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 1.0 ug.mL-1 10.1039/C3MD00016H
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 2.0 ug.mL-1 10.1039/C3MD00016H
Mycobacterium tuberculosis Mycobacterium tuberculosis Ratio 64.0 None 10.1039/C3MD00016H
Mycolicibacterium smegmatis Mycolicibacterium smegmatis MIC 0.3 ug.mL-1 10.1039/C3MD00016H
Mycolicibacterium smegmatis Mycolicibacterium smegmatis MIC 0.5 ug.mL-1 10.1039/C3MD00016H
Mycolicibacterium smegmatis Mycolicibacterium smegmatis MIC 1.0 ug.mL-1 10.1039/C3MD00016H
Mycolicibacterium smegmatis Mycolicibacterium smegmatis MIC 8.5 ug.mL-1 10.1039/C3MD00016H
Mycolicibacterium smegmatis Mycolicibacterium smegmatis Ratio 17.0 None 10.1039/C3MD00016H
Staphylococcus aureus 3-oxoacyl-[acyl-carrier-protein] synthase 2 Activity nan None 10.1021/acsmedchemlett.0c00653
Staphylococcus aureus 3-oxoacyl-[acyl-carrier-protein] synthase 2 IC50 4580.0 nM 10.1021/acs.jmedchem.0c02185
Staphylococcus aureus Malonyl-CoA-acyl carrier protein transacylase Activity nan None 10.1073/pnas.0700746104
Staphylococcus aureus Staphylococcus aureus Activity 0.002 ug 10.1073/pnas.0700746104
Staphylococcus aureus Staphylococcus aureus Activity 0.2 ug ml-1 10.1016/j.bmc.2010.02.030
Staphylococcus aureus Staphylococcus aureus Activity 0.2 ug ml-1 10.1016/j.bmcl.2009.06.061
Staphylococcus aureus Staphylococcus aureus Activity 3.0 None 10.1073/pnas.0700746104
Staphylococcus aureus Staphylococcus aureus Activity nan None 10.1021/acsmedchemlett.0c00653
Staphylococcus aureus Staphylococcus aureus Activity nan None 10.1021/np100635f
Staphylococcus aureus Staphylococcus aureus IC50 0.06 ug.mL-1 10.1021/acs.jmedchem.0c02185
Staphylococcus aureus Staphylococcus aureus IC50 0.19 ug.mL-1 10.1073/pnas.0700746104
Staphylococcus aureus Staphylococcus aureus MIC 0.5 ug.mL-1 10.1016/j.bmc.2010.02.030
Staphylococcus aureus Staphylococcus aureus MIC 0.5 ug.mL-1 10.1073/pnas.0700746104
Staphylococcus aureus Staphylococcus aureus MIC 1.0 ug.mL-1 10.1021/acs.jnatprod.7b00745
Staphylococcus aureus Staphylococcus aureus MIC 1.0 ug.mL-1 10.1021/acsmedchemlett.0c00653
Staphylococcus aureus Staphylococcus aureus MIC 1.0 ug.mL-1 10.1039/C8MD00081F
Staphylococcus aureus Staphylococcus aureus MIC 1.0 ug.mL-1 10.1073/pnas.0700746104
Staphylococcus aureus Staphylococcus aureus MIC 8.0 ug.mL-1 10.1016/j.bmc.2010.02.030
Staphylococcus aureus Staphylococcus aureus MIC 8.0 ug.mL-1 10.1021/acsmedchemlett.0c00653
Staphylococcus aureus Staphylococcus aureus MIC 8.0 ug.mL-1 10.1073/pnas.0700746104
Streptococcus pneumoniae Streptococcus pneumoniae Activity nan None 10.1021/np100635f
Streptococcus pneumoniae Streptococcus pneumoniae IC50 0.06 ug.mL-1 10.1021/acs.jmedchem.0c02185
Streptococcus pneumoniae Streptococcus pneumoniae IC50 2.7 ug.mL-1 10.1073/pnas.0700746104
Streptococcus pneumoniae Streptococcus pneumoniae MIC 4.0 ug.mL-1 10.1073/pnas.0700746104
None ADMET Activity 67.0 ug ml-1 10.1073/pnas.0700746104
None ADMET Drug uptake nan None 10.1016/j.bmc.2017.02.028
None ADMET Ratio 0.1 None 10.1016/j.bmc.2017.02.028
None ADMET Ratio 0.4 None 10.1016/j.bmc.2017.02.028
None ADMET Ratio 1.4 None 10.1016/j.bmc.2017.02.028
None ADMET Ratio 3.8 None 10.1016/j.bmc.2017.02.028
None ADMET Stability nan % 10.1016/j.bmc.2017.02.028
None Unchecked Activity nan None 10.1021/acsmedchemlett.0c00653
None Unchecked deltaG -42.97 kJ/mol 10.1021/acsmedchemlett.0c00653
None Unchecked deltaH -11.87 kJ/mol 10.1021/acsmedchemlett.0c00653
None Unchecked IC50 12.0 ug.mL-1 10.1016/j.bmc.2010.02.030
None Unchecked IC50 12.0 ug.mL-1 10.1016/j.bmcl.2009.06.061
None Unchecked IC50 113.0 nM 10.1016/j.bmcl.2009.06.061
None Unchecked IC50 113.0 nM 10.1073/pnas.0700746104
None Unchecked IC50 4580.0 nM 10.1073/pnas.0700746104
None Unchecked IC50 4600.0 nM 10.1021/acsmedchemlett.0c00653
None Unchecked IC50 9170.0 nM 10.1021/acs.jmedchem.0c02185
None Unchecked IC50 9170.0 nM 10.1073/pnas.0700746104
None Unchecked IC50 9200.0 nM 10.1021/acsmedchemlett.0c00653
None Unchecked IC50 16200.0 nM 10.1073/pnas.0700746104
None Unchecked Kd 17.28 nM 10.1021/acsmedchemlett.0c00653
None Unchecked MIC 32.0 ug.mL-1 10.1021/acsmedchemlett.0c00653
None Unchecked Ratio 1.12 None 10.1021/acsmedchemlett.0c00653
None Unchecked -TdeltaS -31.11 kJ/mol 10.1021/acsmedchemlett.0c00653

Metabolism Information