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Josamycin

AlkaPlorer ID: AK000584

Synonym: None

IUPAC Name: [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate

Structure

SMILES: CO[C@@H]1[C@@H](O[C@@H]2O[C@H](C)[C@@H](O[C@H]3C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O3)[C@H](N(C)C)[C@H]2O)[C@@H](CC=O)C[C@@H](C)[C@@H](O)/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]1OC(C)=O

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InChI: InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1

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InChIKey: XJSFLOJWULLJQS-NGVXBBESSA-N

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Reference

PubChem CID: 5282165

CAS: 11033-18-4

NPASS: NPC314451

Properties Information

Molecule Weight: 828.0060000000002

TPSA？: 206.05

MolLogP？: 3.013400000000005

Number of H-Donors: 3

Number of H-Acceptors: 16

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus spizizenii Bacillus spizizenii MIC 0.4 ug.mL-1 10.1021/jm00215a025
Bacteria Bacterial 70S ribosome IC50 1200.0 nM 10.1021/jm00215a025
Bacteria Bacterial 70S ribosome pK50 5.9 None 10.1021/jm00215a025
Chlamydia psittaci 6BC Chlamydia psittaci 6BC MIC 0.05 ug.mL-1 10.1128/aac.00962-07
Chlamydia psittaci 6BC Chlamydia psittaci 6BC MIC 10.0 ug.mL-1 10.1128/aac.00962-07
Chlamydia trachomatis Chlamydia trachomatis MIC 0.05 ug.mL-1 10.1128/aac.00962-07
Chlamydia trachomatis Chlamydia trachomatis MIC 0.2 ug.mL-1 10.1128/aac.00962-07
Enterococcus faecalis Enterococcus faecalis MIC 1.0 ug.mL-1 10.1128/aac.00481-08
Escherichia coli Escherichia coli Activity nan None 10.1128/aac.01266-07
Escherichia coli Escherichia coli MIC 4.0 ug.mL-1 10.1128/aac.01048-06
Escherichia coli Escherichia coli MIC 8.0 ug.mL-1 10.1128/aac.00481-08
Escherichia coli Escherichia coli MIC 16.0 ug.mL-1 10.1128/aac.00481-08
Escherichia coli Escherichia coli MIC 32.0 ug.mL-1 10.1128/aac.01048-06
Escherichia coli Escherichia coli MIC 512.0 ug.mL-1 10.1128/aac.01048-06
Homo sapiens Adenosine A1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A2a receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2b adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2c adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-1 adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-2 adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bradykinin B2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cannabinoid CB1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cholecystokinin A receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-2 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Delta opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D2 receptor AC50 10000.0 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Equilibrative nucleoside transporter 1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Estrogen receptor alpha AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Ghrelin receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Glucocorticoid receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens IB3-1 Activity nan None 10.1128/aac.01142-06
Homo sapiens Kappa opioid receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Melanocortin receptor 3 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Melanocortin receptor 4 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Monoamine oxidase A AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Motilin receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M3 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuronal acetylcholine receptor protein alpha-4 subunit AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuropeptide Y receptor type 1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Norepinephrine transporter AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4D AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Pregnane X receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Progesterone receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Proteinase-activated receptor 2 Inhibition nan % 10.1128/aac.00140-07
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2a (5-HT2a) receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2c (5-HT2c) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 3a (5-HT3a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin transporter AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thromboxane A2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Type-1 angiotensin II receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vasopressin V1a receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vasopressin V2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Klebsiella pneumoniae Klebsiella pneumoniae MIC 25.0 ug.mL-1 10.1021/jm00215a025
Mus musculus P-glycoprotein 3 Activity nan None 10.1046/j.1440-1681.2000.03308.x
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC 0.007 ug.mL-1 10.1128/aac.01684-08
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC 0.01 ug.mL-1 10.1128/aac.01563-08
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC 0.0156 ug.mL-1 10.1128/aac.00779-07
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC 0.0625 ug.mL-1 10.1128/aac.00779-07
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC 0.1 ug.mL-1 10.1128/aac.01563-08
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC 64.0 ug.mL-1 10.1128/aac.00779-07
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC50 0.0313 ug.mL-1 10.1128/aac.00779-07
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC50 2.0 ug.mL-1 10.1128/aac.01684-08
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC50 8.0 ug.mL-1 10.1128/aac.00779-07
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC50 32.0 ug.mL-1 10.1128/aac.01563-08
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC50 64.0 ug.mL-1 10.1128/aac.00779-07
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC90 0.0625 ug.mL-1 10.1128/aac.00779-07
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC90 4.0 ug.mL-1 10.1128/aac.01684-08
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC90 16.0 ug.mL-1 10.1128/aac.00779-07
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC90 64.0 ug.mL-1 10.1128/aac.00779-07
Mycoplasmoides pneumoniae Mycoplasmoides pneumoniae MIC90 64.0 ug.mL-1 10.1128/aac.01563-08
Rattus norvegicus Androgen Receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Cyclooxygenase-1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus GABA receptor alpha-1 subunit AC50 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Glutamate (NMDA) receptor subunit zeta 1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Voltage-gated L-type calcium channel alpha-1C subunit AC50 10000.0 nM 10.1038/s41467-023-40064-9
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 8.86 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.08039 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.05 % 10.6019/CHEMBL4495565
Staphylococcus aureus Staphylococcus aureus MIC 1.0 ug.mL-1 10.1016/j.bmcl.2013.12.029
Staphylococcus aureus Staphylococcus aureus MIC 1.0 ug.mL-1 10.1128/aac.00481-08
Staphylococcus aureus Staphylococcus aureus MIC 1.0 ug.mL-1 10.1128/aac.01583-07
Staphylococcus aureus Staphylococcus aureus MIC 1.6 ug.mL-1 10.1021/jm00215a025
Staphylococcus aureus Staphylococcus aureus MIC 2.0 ug.mL-1 10.1016/j.bmcl.2013.12.029
Staphylococcus aureus Staphylococcus aureus MIC 32.0 ug.mL-1 10.1016/j.bmcl.2013.12.029
Staphylococcus aureus Staphylococcus aureus MIC 64.0 ug.mL-1 10.1128/aac.01583-07
Staphylococcus aureus Staphylococcus aureus MIC 2000.0 ug.mL-1 10.1128/aac.01583-07
Staphylococcus epidermidis Staphylococcus epidermidis MIC 1.0 ug.mL-1 10.1016/j.bmcl.2013.12.029
Staphylococcus epidermidis Staphylococcus epidermidis MIC 2.0 ug.mL-1 10.1016/j.bmcl.2013.12.029
Staphylococcus epidermidis Staphylococcus epidermidis MIC 32.0 ug.mL-1 10.1016/j.bmcl.2013.12.029
Streptococcus pneumoniae Streptococcus pneumoniae Activity 1.0 ug ml-1 10.1128/aac.00157-07
Streptococcus pneumoniae Streptococcus pneumoniae Activity 4.0 ug ml-1 10.1128/aac.00157-07
Streptococcus pneumoniae Streptococcus pneumoniae Activity 87.2 % 10.1128/aac.00157-07
Streptococcus pneumoniae Streptococcus pneumoniae MIC 0.5 ug.mL-1 10.1128/aac.00157-07
Streptococcus pneumoniae Streptococcus pneumoniae MIC 2.0 ug.mL-1 10.1128/aac.00157-07
Streptococcus pneumoniae Streptococcus pneumoniae MIC50 2.0 ug.mL-1 10.1128/aac.00157-07
Streptococcus pneumoniae Streptococcus pneumoniae MIC90 2.0 ug.mL-1 10.1128/aac.00157-07
Streptomyces acidiscabies Streptomyces acidiscabies DIZ nan None 10.1584/jpestics.28.183
Streptomyces acidiscabies Streptomyces acidiscabies IZ 10.0 mm 10.1584/jpestics.28.183
Streptomyces acidiscabies Streptomyces acidiscabies IZ 13.0 mm 10.1584/jpestics.28.183
Streptomyces acidiscabies Streptomyces acidiscabies IZ 17.0 mm 10.1584/jpestics.28.183
Streptomyces alboniger Streptomyces alboniger DIZ nan None 10.1584/jpestics.28.183
Streptomyces alboniger Streptomyces alboniger IZ 14.0 mm 10.1584/jpestics.28.183
Streptomyces alboniger Streptomyces alboniger IZ 15.0 mm 10.1584/jpestics.28.183
Streptomyces scabiei Streptomyces scabiei IZ 11.0 mm 10.1584/jpestics.28.183
Streptomyces scabiei Streptomyces scabiei IZ 15.0 mm 10.1584/jpestics.28.183
Streptomyces scabiei Streptomyces scabiei IZ 17.0 mm 10.1584/jpestics.28.183
Streptomyces scabiei Streptomyces scabiei IZ 21.0 mm 10.1584/jpestics.28.183
Streptomyces scabiei Streptomyces scabiei IZ 29.0 mm 10.1584/jpestics.28.183
None NON-PROTEIN TARGET Hepatotoxicity (acute) 0.0 % 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) 20.0 % 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 MIC 0.25 ug.mL-1 10.1128/aac.00481-08
None Ribosome Activity nan None 10.1021/acs.jnatprod.7b00133
None Unchecked Activity nan None 10.1128/aac.01142-06
None Unchecked Hepatotoxicity (acute) 9.0 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) 5.0 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) 6.0 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 Inhibition nan % 10.1021/acs.jnatprod.7b00133

Metabolism Information