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Clorobiocin

AlkaPlorer ID: AK012942

Synonym: None

IUPAC Name: [(3R,4S,5R,6S)-6-[8-chloro-4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-2-oxochromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate

Structure

SMILES: CO[C@@H]1[C@@H](OC(=O)C2=CC=C(C)N2)[C@@H](O)[C@H](OC2=CC=C3C(O)=C(NC(=O)C4=CC=C(O)C(CC=C(C)C)=C4)C(=O)OC3=C2Cl)OC1(C)C

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InChI: InChI=1S/C35H37ClN2O11/c1-16(2)7-9-18-15-19(10-13-22(18)39)31(42)38-25-26(40)20-11-14-23(24(36)28(20)47-33(25)44)46-34-27(41)29(30(45-6)35(4,5)49-34)48-32(43)21-12-8-17(3)37-21/h7-8,10-15,27,29-30,34,37,39-41H,9H2,1-6H3,(H,38,42)/t27-,29+,30-,34-/m1/s1

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InChIKey: FJAQNRBDVKIIKK-LFLQOBSNSA-N

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Source

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

Properties Information

Molecule Weight: 697.1370000000002

TPSA？: 189.78

MolLogP？: 5.370320000000004

Number of H-Donors: 5

Number of H-Acceptors: 11

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Enterococcus faecalis Enterococcus faecalis MIC 4.0 ug.mL-1 10.1128/aac.01235-07
Enterococcus faecium Enterococcus faecium MIC 0.04 ug.mL-1 10.1016/s0960-894x(00)00304-8
Enterococcus faecium Enterococcus faecium MIC 32.0 ug.mL-1 10.1128/aac.01235-07
Enterococcus faecium Enterococcus faecium MIC nan ug.mL-1 10.1016/s0960-894x(99)00329-7
Enterococcus faecium Enterococcus faecium MIC nan ug.mL-1 10.1016/s0960-894x(99)00492-8
Escherichia coli DNA gyrase IC50 30.0 nM 10.1016/j.bmc.2016.04.043
Escherichia coli DNA gyrase Ratio 1.7 None 10.1016/s0960-894x(99)00329-7
Escherichia coli DNA gyrase subunit B IC50 5.0 nM 10.1128/aac.01235-07
Escherichia coli DNA gyrase subunit B IC50 73.0 nM 10.1128/aac.01235-07
Escherichia coli DNA gyrase subunit B Kd 1.2 nM 10.1021/jm101121s
Escherichia coli DNA gyrase subunit B Ratio 1.7 None 10.1016/s0960-894x(99)00493-x
Escherichia coli DNA gyrase subunit B Ratio IC50 nan None 10.1128/aac.01235-07
Escherichia coli Escherichia coli MIC 2.0 ug.mL-1 10.1128/aac.01235-07
Escherichia coli Escherichia coli MIC 32.0 ug.mL-1 10.1128/aac.01235-07
Escherichia coli K-12 Cell division inhibitor sulA Activity 1.0 uM 10.1128/aac.01235-07
Escherichia coli K-12 DNA gyrase subunit A Activity 1.6 uM 10.1128/aac.01235-07
Homo sapiens DNA topoisomerase II beta Ratio 1.7 None 10.1016/s0960-894x(99)00492-8
Klebsiella pneumoniae Klebsiella pneumoniae MIC 16.0 ug.mL-1 10.1128/aac.01235-07
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 0.06 ug.mL-1 10.1128/aac.01235-07
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 8.0 ug.mL-1 10.1128/aac.01235-07
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 16.0 ug.mL-1 10.1128/aac.01235-07
Staphylococcus aureus DNA gyrase IC50 6.0 nM 10.1016/j.bmc.2016.04.043
Staphylococcus aureus DNA gyrase IC50 8.5 nM 10.1016/j.bmc.2018.05.016
Staphylococcus aureus DNA gyrase Inhibition 86.0 % 10.1016/j.bmc.2018.05.016
Staphylococcus aureus DNA gyrase subunit A IC50 0.648 ug.mL-1 10.1016/j.bmc.2017.01.007
Staphylococcus aureus Staphylococcus aureus MIC 0.04 ug.mL-1 10.1016/s0960-894x(00)00304-8
Staphylococcus aureus Staphylococcus aureus MIC 0.04 ug.mL-1 10.1016/s0960-894x(99)00329-7
Staphylococcus aureus Staphylococcus aureus MIC 0.04 ug.mL-1 10.1016/s0960-894x(99)00492-8
Staphylococcus aureus Staphylococcus aureus MIC 0.04 ug.mL-1 10.1016/s0960-894x(99)00493-x
Staphylococcus aureus Staphylococcus aureus MIC 0.06 ug.mL-1 10.1016/j.bmc.2016.04.043
Staphylococcus aureus Staphylococcus aureus MIC 0.06 ug.mL-1 10.1128/aac.01235-07
Staphylococcus aureus Staphylococcus aureus MIC 0.15 ug.mL-1 10.1016/s0960-894x(99)00329-7
Staphylococcus aureus Staphylococcus aureus MIC 0.15 ug.mL-1 10.1016/s0960-894x(99)00492-8
Staphylococcus aureus Staphylococcus aureus MIC 0.15 ug.mL-1 10.1016/s0960-894x(99)00493-x
Staphylococcus aureus Staphylococcus aureus MIC 0.6 ug.mL-1 10.1016/s0960-894x(00)00304-8
Staphylococcus aureus Staphylococcus aureus MIC 4.0 ug.mL-1 10.1128/aac.01235-07
Staphylococcus aureus Staphylococcus aureus MIC nan ug.mL-1 10.1016/s0960-894x(00)00304-8
Staphylococcus aureus Topoisomerase IV IC50 10000.0 nM 10.1016/j.bmc.2016.04.043
Staphylococcus epidermidis Staphylococcus epidermidis MIC 0.04 ug.mL-1 10.1016/s0960-894x(99)00329-7
Staphylococcus epidermidis Staphylococcus epidermidis MIC 0.04 ug.mL-1 10.1016/s0960-894x(99)00492-8
Staphylococcus epidermidis Staphylococcus epidermidis MIC 0.04 ug.mL-1 10.1016/s0960-894x(99)00493-x
Staphylococcus epidermidis Staphylococcus epidermidis MIC nan ug.mL-1 10.1016/s0960-894x(00)00304-8
Streptococcus pneumoniae Streptococcus pneumoniae MIC 0.25 ug.mL-1 10.1128/aac.01235-07
Streptococcus pneumoniae Streptococcus pneumoniae MIC 1.0 ug.mL-1 10.1128/aac.01235-07
Streptococcus pneumoniae Streptococcus pneumoniae MIC 2.0 ug.mL-1 10.1016/j.bmc.2016.04.043
Streptococcus pyogenes Streptococcus pyogenes MIC 0.04 ug.mL-1 10.1016/s0960-894x(00)00304-8
Streptococcus pyogenes Streptococcus pyogenes MIC 0.04 ug.mL-1 10.1016/s0960-894x(99)00329-7
None Unchecked IC50 30.0 nM 10.1021/acs.jmedchem.7b00315
None Unchecked IC50 3000.0 nM 10.1016/j.bmc.2016.04.043
None Unchecked Ratio 1.7 None 10.1016/s0960-894x(00)00304-8

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT011271 CO[C@@H]1[C@@H](OC(=O)c2ccc(C)[nH]2)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4ccc(O)c(CC=C(C)C)c4)c(=O)oc3c2Cl)OC1(C)C>>*SC(=O)c1ccc(C)[nH]1 MNXR135529
AKRT011272 CO[C@@H]1[C@@H](OC(=O)c2ccc(C)[nH]2)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4ccc(O)c(CC=C(C)C)c4)c(=O)oc3c2Cl)OC1(C)C>>CO[C@@H]1[C@@H](O)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4ccc(O)c(CC=C(C)C)c4)c(=O)oc3c2Cl)OC1(C)C MNXR135529