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Rifamycin

AlkaPlorer ID: AK000376

Synonym: None

IUPAC Name: [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate

Structure

SMILES: CO[C@H]1/C=C/O[C@@]2(C)OC3=C(C)C(O)=C4C(O)=C(C=C(O)C4=C3C2=O)N=C(O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C

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InChI: InChI=1S/C37H47NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1

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InChIKey: HJYYPODYNSCCOU-ODRIEIDWSA-N

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Properties Information

Molecule Weight: 697.7780000000002

TPSA？: 204.8

MolLogP？: 5.403620000000006

Number of H-Donors: 6

Number of H-Acceptors: 12

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Chlorocebus sabaeus Vero CC50 62.46 ug.mL-1 10.1016/j.bmcl.2013.02.030
Enterococcus faecalis Enterococcus faecalis MIC 1.0 ug.mL-1 10.1021/jm00167a029
Escherichia coli Escherichia coli MIC 3.0 ug.mL-1 10.1021/jm970791o
Escherichia coli Escherichia coli MIC 16.0 ug.mL-1 10.1021/jm00167a029
Escherichia coli Escherichia coli MIC 25.0 ug.mL-1 10.1021/jm970791o
Escherichia coli Escherichia coli MIC 100.0 ug.mL-1 10.1021/jm00143a010
Escherichia coli Escherichia coli MIC 100.0 ug.mL-1 10.1021/jm00220a012
Haemophilus influenzae Haemophilus influenzae MIC 0.125 ug.mL-1 10.1021/jm00167a029
Homo sapiens Acetylcholinesterase AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-1a adrenergic receptor AC50 8130.9 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens B-cell lymphoma 6 protein Kd 1000000.0 nM 10.1021/acs.jmedchem.7b00313
Homo sapiens Bile salt export pump IC50 6300.0 nM 10.1124/dmd.111.040758
Homo sapiens Bile salt export pump IC50 9500.0 nM 10.1002/hep.27206
Homo sapiens Bile salt export pump IC50 12200.0 nM 10.1023/a:1023278211849
Homo sapiens Bile salt export pump IC50 206500.0 nM 10.1023/a:1023278211849
Homo sapiens Bile salt export pump Ki 31000.0 nM 10.1053/gast.2002.36591
Homo sapiens Cyclooxygenase-1 AC50 28699.9 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Estrogen receptor alpha AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Homo sapiens Activity nan None 10.1002/hep.27206
Homo sapiens Homo sapiens Cmax 2780.0 nM 10.1002/hep.27206
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Multidrug resistance-associated protein 1 Activity 110.0 % 10.1016/s0304-3835(99)00024-5
Homo sapiens Mu opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 11639.4 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Norepinephrine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Plasma fCmax 3.153 uM 10.1124/dmd.111.040758
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Solute carrier organic anion transporter family member 1A2 Ki 11000.0 nM 10.1053/jhep.2002.34133
Homo sapiens Solute carrier organic anion transporter family member 1B1 Activity nan None 10.1074/jbc.m004968200
Homo sapiens Solute carrier organic anion transporter family member 1B1 IC50 230.0 nM 10.1124/dmd.104.002477
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 95.4 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 1B1 Ki 2000.0 nM 10.1053/jhep.2002.34133
Homo sapiens Solute carrier organic anion transporter family member 1B3 Activity nan None 10.1074/jbc.m004968200
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 101.4 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 1B3 Ki 3000.0 nM 10.1053/jhep.2002.34133
Homo sapiens Solute carrier organic anion transporter family member 2B1 Inhibition 74.8 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 2B1 Ki 3000.0 nM 10.1053/jhep.2002.34133
Homo sapiens Thrombin AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thromboxane A2 receptor AC50 8767.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vascular endothelial growth factor receptor 2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Klebsiella pneumoniae Klebsiella pneumoniae MIC 32.0 ug.mL-1 10.1021/jm00167a029
Klebsiella pneumoniae Klebsiella pneumoniae MIC 100.0 ug.mL-1 10.1021/jm00143a010
Klebsiella pneumoniae Klebsiella pneumoniae MIC 100.0 ug.mL-1 10.1021/jm00220a012
Leishmania donovani Leishmania donovani IC50 1500.0 nM 10.6019/CHEMBL3392926
Leishmania donovani Leishmania donovani IC50 13870.0 nM 10.6019/CHEMBL3392926
Mus musculus Bile salt export pump Activity 29.8 % 10.1053/jhep.2001.24171
Mycobacterium avium Mycobacterium avium MIC 32.0 ug.mL-1 10.1021/jm00167a029
Mycobacterium avium Mycobacterium avium MIC50 128.0 ug.mL-1 10.1021/jm00167a029
Mycobacterium avium Mycobacterium avium MIC90 nan ug.mL-1 10.1021/jm00167a029
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 0.39 ug.mL-1 10.1016/j.bmcl.2013.02.030
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 0.5 ug.mL-1 10.1021/jm00167a029
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 2.0 nM 10.1021/jm500571f
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 4.0 nM 10.1021/jm500571f
Neisseria gonorrhoeae Neisseria gonorrhoeae MIC 0.032 ug.mL-1 10.1021/jm00167a029
Plasmodium falciparum Plasmodium falciparum IC50 550.0 nM 10.6019/CHEMBL3392926
Proteus vulgaris Proteus vulgaris MIC 1.0 ug.mL-1 10.1021/jm00167a029
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 8.0 ug.mL-1 10.1021/jm00167a029
Rattus norvegicus Bile salt export pump IC50 3100.0 nM 10.1124/dmd.111.040758
Rattus norvegicus Bile salt export pump Ki 3800.0 nM 10.1016/s0016-5085(00)70224-1
Rattus norvegicus Liver IC50 nan None 10.1002/hep.27206
Rattus norvegicus Multidrug resistance protein 1a Activity nan None 10.1016/0006-2952(95)00045-2
Rattus norvegicus Rattus norvegicus Activity 1.0 % 10.1021/jm00164a013
Rattus norvegicus Rattus norvegicus Activity 4.0 % 10.1021/jm00164a013
Rattus norvegicus Rattus norvegicus Activity 21.0 % 10.1021/jm00164a013
Rattus norvegicus Solute carrier organic anion transporter family member 1A1 Activity nan None None
Rattus norvegicus Solute carrier organic anion transporter family member 1A1 Ki 6600.0 nM 10.1053/jhep.2000.8539
Rattus norvegicus Solute carrier organic anion transporter family member 1A4 Ki 7300.0 nM 10.1053/jhep.2000.8539
Salmonella enterica subsp. enterica serovar Paratyphi A Salmonella paratyphi MIC 100.0 ug.mL-1 10.1021/jm00143a010
Salmonella enterica subsp. enterica serovar Paratyphi B Salmonella enterica subsp. enterica serovar Paratyphi B MIC 100.0 ug.mL-1 10.1021/jm00220a012
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 24.03 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.1815 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -1.23 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.02 % 10.6019/CHEMBL4495565
Staphylococcus aureus Staphylococcus aureus ED50 0.38 mg.kg-1 10.1021/jm00167a029
Staphylococcus aureus Staphylococcus aureus ED50 0.93 mg.kg-1 10.1021/jm00167a029
Staphylococcus aureus Staphylococcus aureus MIC 0.001 ug.mL-1 10.1021/jm00164a013
Staphylococcus aureus Staphylococcus aureus MIC 0.004 ug.mL-1 10.1021/jm00167a029
Staphylococcus aureus Staphylococcus aureus MIC 0.005 ug.mL-1 10.1021/jm00143a010
Staphylococcus aureus Staphylococcus aureus MIC 0.005 ug.mL-1 10.1021/jm00220a012
Staphylococcus aureus Staphylococcus aureus MIC 0.016 ug.mL-1 10.1016/j.bmcl.2007.08.048
Staphylococcus aureus Staphylococcus aureus MIC 2.0 ug.mL-1 10.1016/j.bmcl.2007.08.048
Staphylococcus aureus Staphylococcus aureus MIC 64.0 ug.mL-1 10.1016/j.bmcl.2007.08.048
Staphylococcus epidermidis Staphylococcus epidermidis MIC 0.002 ug.mL-1 10.1021/jm00167a029
Streptococcus pneumoniae Streptococcus pneumoniae MIC 0.008 ug.mL-1 10.1021/jm00167a029
Streptococcus pyogenes Streptococcus pyogenes MIC 0.032 ug.mL-1 10.1021/jm00167a029
Streptomyces acidiscabies Streptomyces acidiscabies DIZ nan None 10.1584/jpestics.28.183
Streptomyces acidiscabies Streptomyces acidiscabies IZ 12.0 mm 10.1584/jpestics.28.183
Streptomyces alboniger Streptomyces alboniger DIZ nan None 10.1584/jpestics.28.183
Streptomyces alboniger Streptomyces alboniger IZ 11.0 mm 10.1584/jpestics.28.183
Streptomyces alboniger Streptomyces alboniger IZ 21.0 mm 10.1584/jpestics.28.183
Streptomyces scabiei Streptomyces scabiei DIZ nan None 10.1584/jpestics.28.183
Streptomyces scabiei Streptomyces scabiei IZ 11.0 mm 10.1584/jpestics.28.183
Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 990.0 nM 10.6019/CHEMBL3392926
Trypanosoma cruzi Trypanosoma cruzi IC50 49950.0 nM 10.6019/CHEMBL3392926
None ADMET CL 3.0 uL.min-1.(10^6cells)-1 10.6019/CHEMBL3301361
None ADMET CL 80.0 mL.min-1.kg-1 10.1021/jm000407e
None ADMET T1/2 0.33 hr 10.1021/jm000407e
None ADMET Vd 1.2 L.kg-1 10.1021/jm000407e
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
None NON-PROTEIN TARGET GI50 3200.0 nM 10.1016/j.bmcl.2014.08.032
None NON-PROTEIN TARGET GI50 10000.0 nM 10.1016/j.bmcl.2014.08.032
None NON-PROTEIN TARGET GI50 14500.0 nM 10.1016/j.bmcl.2014.08.032
None NON-PROTEIN TARGET GI50 15500.0 nM 10.1016/j.bmcl.2014.08.032
None NON-PROTEIN TARGET GI50 15900.0 nM 10.1016/j.bmcl.2014.08.032
None NON-PROTEIN TARGET GI50 16600.0 nM 10.1016/j.bmcl.2014.08.032
None NON-PROTEIN TARGET GI50 18600.0 nM 10.1016/j.bmcl.2014.08.032
None NON-PROTEIN TARGET GI50 21400.0 nM 10.1016/j.bmcl.2014.08.032
None NON-PROTEIN TARGET Hepatotoxicity (acute) 2.3 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (animal toxicity known) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (benign tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (granulomatous hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (mechanism) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 5.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 10.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (time to onset) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET IC50 15680.0 nM 10.6019/CHEMBL3392926
None NON-PROTEIN TARGET IC50 41620.0 nM 10.6019/CHEMBL3392926
None No relevant target LogD7.4 1.19 None 10.6019/CHEMBL3301361
None No relevant target LogP 3.71 None 10.1016/j.bmcl.2013.02.030
None Nucleic Acid IC50 15.0 nM/unit 10.1021/jm970791o
None Nucleic Acid IC50 85.0 nM/unit 10.1021/jm970791o
None Unchecked Activity nan None 10.1021/np0604580
None Unchecked Activity nan None 10.1074/jbc.m608207200
None Unchecked Hepatotoxicity (acute) 3.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (association with vascular disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (choleostasis) 2.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (chronic liver disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cirrhosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (comment) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cytolytic) 2.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (malignant tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (severe hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (steatosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (successful reintroduction) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked IC50 8.6 nM 10.1128/aac.00753-10
None Unchecked IC50 31640.0 nM 10.1074/jbc.m608207200
None Unchecked Inhibition 0.7 % 10.1074/jbc.m608207200
None Unchecked Selectivity Index 160.1 None 10.1016/j.bmcl.2013.02.030

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT004305 CC(=O)O[C@@H]1[C@H](C)[C@@H](O)/C=C/OC2(C)Oc3c(C)c(O)c4c(O)c(cc(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@H]1C.C[SAH]>>CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C R06998
AKRT004306 CC(=O)O[C@@H]1[C@H](C)[C@@H](O)/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@H]1C.C[SAH]>>CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C RXN-9611
AKRT011286 CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C>>CO[C@@H](/C=C/O[C@@]1(C)Oc2c(C)c(O)c3c(c2C1=O)C(=O)C=C(O)C3=O)[C@@H](C)[C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)/C=C/C=C(/C)C(N)=O 58676
AKRT011287 CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C>>CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C(=O)C=C(NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)C(C)[C@H](OC(C)=O)[C@@H]1C)C4=O MNXR149735
AKRT011288 CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C>>CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C(=O)C=C(NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C4=O RXN-20243
AKRT011289 CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C>>CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C(O)=CC(O)(NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C4=O 58628
AKRT011293 CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C(=O)C=C(NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C4=O>>CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C R06999