Molecule

spiramycin I

AlkaPlorer ID: AK004729

Synonym: 'Spiramycin', 'Foromacidine A', 'foromacidin A', 'Demycarosylturimycin H', 'Spiramycin A', 'Spiramycin 1', 'Not named', 'Spiramycin I', 'spiramycin'

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

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](O)[C@H](C)O3)[C@H](N(C)C)[C@H]2O)[C@@H](CC=O)C[C@@H](C)[C@@H](O[C@H]2CC[C@H](N(C)C)[C@@H](C)O2)/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]1O

InChI: InChI=1S/C43H74N2O14/c1-24-21-29(19-20-46)39(59-42-37(49)36(45(9)10)38(27(4)56-42)58-35-23-43(6,51)41(50)28(5)55-35)40(52-11)31(47)22-33(48)53-25(2)15-13-12-14-16-32(24)57-34-18-17-30(44(7)8)26(3)54-34/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27-,28+,29+,30+,31-,32+,34+,35+,36-,37-,38-,39+,40+,41+,42+,43-/m1/s1

InChIKey: ACTOXUHEUCPTEW-CEUOBAOPSA-N

Reference

PubChem CID: 5289394

LOTUS: LTS0019437

Source

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

Properties Information

Molecule Weight: 843.0649999999999

TPSA？: 195.38

MolLogP？: 2.3251000000000093

Number of H-Donors: 4

Number of H-Acceptors: 16

RingCount: 4

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bacillus spizizenii	Bacillus spizizenii	MIC	590.0	nM	10.1021/acs.jmedchem.6b00764
Chlamydia psittaci 6BC	Chlamydia psittaci 6BC	MIC	1.0	ug.mL-1	10.1128/aac.00962-07
Chlamydia psittaci 6BC	Chlamydia psittaci 6BC	MIC	200.0	ug.mL-1	10.1128/aac.00962-07
Chlamydia trachomatis	Chlamydia trachomatis	MIC	0.8	ug.mL-1	10.1128/aac.00962-07
Chlamydia trachomatis	Chlamydia trachomatis	MIC	4.0	ug.mL-1	10.1128/aac.00962-07
Enterococcus faecalis	Enterococcus faecalis	MIC	0.5	ug.mL-1	10.1128/aac.00481-08
Enterococcus faecalis	Enterococcus faecalis	MIC	2.0	ug.mL-1	10.1128/aac.00481-08
Enterococcus faecalis	Enterococcus faecalis	MIC	8.0	ug.mL-1	10.1128/aac.00481-08
Enterococcus faecalis	Enterococcus faecalis	MIC	64.0	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	8.0	ug.mL-1	10.1128/aac.00481-08
Escherichia coli	Escherichia coli	MIC	9.0	ug.mL-1	10.1016/j.bmcl.2013.01.004
Escherichia coli	Escherichia coli	MIC	200.0	ug.mL-1	10.1128/aac.00481-08
Escherichia coli	Escherichia coli	MIC	400.0	ug.mL-1	10.1128/aac.00481-08
Escherichia coli	Escherichia coli	MIC	1000.0	ug.mL-1	10.1128/aac.00481-08
Homo sapiens	Bile salt export pump	IC50	133000.0	nM	10.1093/toxsci/kft176
Homo sapiens	Canalicular multispecific organic anion transporter 1	IC50	133000.0	nM	10.1093/toxsci/kft176
Homo sapiens	Canalicular multispecific organic anion transporter 2	IC50	133000.0	nM	10.1093/toxsci/kft176
Homo sapiens	HeLa	IC50	34410.0	nM	10.1021/acs.jmedchem.6b00764
Homo sapiens	HeLa	IC50	189000.0	nM	10.1021/acs.jmedchem.1c01569
Homo sapiens	HepG2	IC50	30510.0	nM	10.1021/acs.jmedchem.6b00764
Homo sapiens	KB	IC50	31260.0	nM	10.1021/acs.jmedchem.6b00764
Homo sapiens	MCF7	IC50	33110.0	nM	10.1021/acs.jmedchem.6b00764
Homo sapiens	Multidrug resistance-associated protein 4	IC50	133000.0	nM	10.1093/toxsci/kft176
Homo sapiens	NHDF	IC50	31100.0	nM	10.1021/acs.jmedchem.6b00764
Homo sapiens	Proteinase-activated receptor 2	Inhibition	nan	%	10.1128/aac.00140-07
Homo sapiens	Solute carrier organic anion transporter family member 1B1	Inhibition	64.77	%	10.1124/mol.112.084152
Homo sapiens	Solute carrier organic anion transporter family member 1B3	Inhibition	86.18	%	10.1124/mol.112.084152
Micrococcus luteus	Micrococcus luteus	MIC	300.0	nM	10.1021/acs.jmedchem.6b00764
Mus musculus	Mus musculus	Activity	24.0	%	10.1128/aac.00082-07
Mus musculus	Mus musculus	Activity	25.2	%	10.1128/aac.00082-07
Mus musculus	Mus musculus	Activity	28.1	%	10.1128/aac.00082-07
Mus musculus	Mus musculus	Activity	29.5	%	10.1128/aac.00082-07
Mus musculus	Mus musculus	Activity	32.5	%	10.1128/aac.00082-07
Mus musculus	Mus musculus	Activity	34.1	%	10.1128/aac.00082-07
Mus musculus	Mus musculus	Activity	82.4	%ID	10.1128/aac.00082-07
Mus musculus	Mus musculus	Activity	86.5	%ID	10.1128/aac.00082-07
Mus musculus	Mus musculus	Activity	90.5	%ID	10.1128/aac.00082-07
Mus musculus	Mus musculus	CLup	4.55	ml/min	10.1128/aac.00082-07
Mus musculus	Mus musculus	CLup	4.63	ml/min	10.1128/aac.00082-07
Mus musculus	Mus musculus	CLup	4.64	ml/min	10.1128/aac.00082-07
Mus musculus	Mus musculus	CLup	4.7	ml/min	10.1128/aac.00082-07
Mus musculus	Mus musculus	CLup	5.03	ml/min	10.1128/aac.00082-07
Mus musculus	Mus musculus	CLup	5.15	ml/min	10.1128/aac.00082-07
Mycoplasma putrefaciens	Mycoplasma putrefaciens	MIC	0.25	ug.mL-1	10.1128/aac.00420-07
Mycoplasma putrefaciens	Mycoplasma putrefaciens	MIC50	0.125	ug.mL-1	10.1128/aac.00420-07
Mycoplasma putrefaciens	Mycoplasma putrefaciens	MIC50	0.25	ug.mL-1	10.1128/aac.00420-07
Mycoplasma putrefaciens	Mycoplasma putrefaciens	MIC90	0.25	ug.mL-1	10.1128/aac.00420-07
Mycoplasma putrefaciens	Mycoplasma putrefaciens	MIC90	0.5	ug.mL-1	10.1128/aac.00420-07
Pasteurella multocida	Pasteurella multocida	MIC	12.5	ug.mL-1	10.1128/aac.00245-08
Pasteurella multocida	Pasteurella multocida	MIC	25.0	ug.mL-1	10.1128/aac.00245-08
Pasteurella multocida	Pasteurella multocida	Ratio	1.0	None	10.1128/aac.00245-08
Pasteurella multocida	Pasteurella multocida	Ratio	2.0	None	10.1128/aac.00245-08
Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	0.0	ug.mL-1	10.1016/j.bmcl.2013.01.004
Salmonella enterica subsp. enterica serovar Typhimurium	Salmonella typhimurium	MIC	9.0	ug.mL-1	10.1016/j.bmcl.2013.01.004
Severe acute respiratory syndrome coronavirus 2	Replicase polyprotein 1ab	Inhibition	2.778	%	10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Hit score	0.1355	None	10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Hit score	0.1388	None	10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	-0.05	%	10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	3.45	%	10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition index	0.02813	None	10.1101/2020.04.03.023846
Staphylococcus aureus	Staphylococcus aureus	MIC	4.0	ug.mL-1	10.1128/aac.00481-08
Staphylococcus aureus	Staphylococcus aureus	MIC	8.0	ug.mL-1	10.1128/aac.00481-08
Staphylococcus aureus	Staphylococcus aureus	MIC	8.0	ug.mL-1	10.1128/aac.01583-07
Staphylococcus aureus	Staphylococcus aureus	MIC	22.0	ug.mL-1	10.1016/j.bmcl.2013.01.004
Staphylococcus aureus	Staphylococcus aureus	MIC	32.0	ug.mL-1	10.1128/aac.00481-08
Staphylococcus aureus	Staphylococcus aureus	MIC	128.0	ug.mL-1	10.1128/aac.01583-07
Staphylococcus aureus	Staphylococcus aureus	MIC	256.0	ug.mL-1	10.1016/j.ejmech.2019.02.055
Staphylococcus aureus	Staphylococcus aureus	MIC	4000.0	ug.mL-1	10.1128/aac.01583-07
Staphylococcus aureus	Staphylococcus aureus	MIC	4740.0	nM	10.1021/acs.jmedchem.6b00764
Staphylococcus aureus	Staphylococcus aureus	MIC	9490.0	nM	10.1021/acs.jmedchem.6b00764
Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	2370.0	nM	10.1021/acs.jmedchem.6b00764
Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	300.0	nM	10.1021/acs.jmedchem.6b00764
Toxoplasma gondii	Toxoplasma gondii	IC50	262200.0	nM	10.1021/acs.jmedchem.1c01569
Toxoplasma gondii	Toxoplasma gondii	Ratio	3.0	None	10.1021/jm101593u
Toxoplasma gondii	Toxoplasma gondii	Ratio	5.0	None	10.1021/jm101593u
Toxoplasma gondii	Toxoplasma gondii	Ratio	8.0	None	10.1021/jm101593u
None	ADMET	Activity	0.58	%	10.1128/aac.00082-07
None	ADMET	Activity	1.21	%	10.1128/aac.00082-07
None	ADMET	Activity	4.36	%	10.1128/aac.00082-07
None	ADMET	Activity	8.28	%	10.1128/aac.00082-07
None	ADMET	Activity	9.15	%	10.1128/aac.00082-07
None	ADMET	Activity	14.1	%	10.1128/aac.00082-07
None	ADMET	AUC	10116.72	ng.hr.mL-1	10.1021/acs.jmedchem.0c01177
None	ADMET	CL	1.14	L/min	10.1021/acs.jmedchem.0c01177
None	ADMET	CL	144.2	ml/min	10.1021/acs.jmedchem.0c01177
None	ADMET	CL	887.0	ml/min	10.1021/acs.jmedchem.0c01177
None	ADMET	Cmax	2000.0	nM	10.1021/acs.jmedchem.0c01177
None	ADMET	Cmax	2700.0	nM	10.1021/acs.jmedchem.0c01177
None	ADMET	Cmax	3700.0	nM	10.1021/acs.jmedchem.0c01177
None	ADMET	Drugexcretion	4.4	%	10.1021/acs.jmedchem.0c01177
None	ADMET	Drugexcretion	13.9	%	10.1021/acs.jmedchem.0c01177
None	ADMET	Drug uptake	1.77	ug ml-1	10.1128/aac.00082-07
None	ADMET	Drug uptake	3.45	ug ml-1	10.1128/aac.00082-07
None	ADMET	Drug uptake	7.82	ug ml-1	10.1128/aac.00082-07
None	ADMET	Drug uptake	8.65	ug ml-1	10.1128/aac.00082-07
None	ADMET	Drug uptake	14.0	ug ml-1	10.1128/aac.00082-07
None	ADMET	Drug uptake	19.1	ug ml-1	10.1128/aac.00082-07
None	ADMET	F	10.0	%	10.1021/acs.jmedchem.0c01177
None	ADMET	PPB	48.0	%	10.1021/acs.jmedchem.0c01177
None	ADMET	Ratio IC50	0.72	None	10.1021/acs.jmedchem.1c01569
None	ADMET	T1/2	5.54	hr	10.1021/acs.jmedchem.0c01177
None	ADMET	T1/2	6.23	hr	10.1021/acs.jmedchem.0c01177
None	ADMET	Tmax	3.3	hr	10.1021/acs.jmedchem.0c01177
None	ADMET	Tmax	4.0	hr	10.1021/acs.jmedchem.0c01177
None	ADMET	Vdss	5.5	L.kg-1	10.1021/acs.jmedchem.0c01177
None	Hepatotoxicity	Hepatotoxicity	nan	None	10.1021/tx900326k
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)	0.0	%	10.1016/s0399-8320(04)95062-2
None	NON-PROTEIN TARGET	Hepatotoxicity (moderate)	0.0	None	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	0.5	ug.mL-1	10.1128/aac.00481-08
None	NON-PROTEIN TARGET	MIC	8.0	ug.mL-1	10.1128/aac.00481-08
None	No relevant target	LogP	0.58	None	10.1021/acs.jmedchem.6b00764
None	No relevant target	Solubility	4500.0	ug.mL-1	10.1021/acs.jmedchem.6b00764
None	Nucleic Acid	Inhibition	48.0	%	10.1021/jm00129a027
None	Nucleic Acid	Inhibition	53.0	%	10.1021/jm00129a027
None	Nucleic Acid	Inhibition	85.0	%	10.1021/jm00129a027
None	Unchecked	Hepatotoxicity (acute)	4.0	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)	3.0	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)	0.0	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	Kcat	0.2	/s	10.1128/aac.01570-09
None	Unchecked	Kcat/Km	4.19	10'2/s/M	10.1128/aac.01570-09
None	Unchecked	Km	478000.0	nM	10.1128/aac.01570-09
None	Unchecked	Ratio IC50	0.9	None	10.1021/acs.jmedchem.6b00764
None	Unchecked	Ratio IC50	0.94	None	10.1021/acs.jmedchem.6b00764
None	Unchecked	Ratio IC50	1.02	None	10.1021/acs.jmedchem.6b00764

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT011273	CO[C@@H]1[C@@H](O[C@@H]2O[C@H](C)[C@@H](O[C@H]3C[C@@](C)(O)[C@@H](O)[C@H](C)O3)[C@H](N(C)C)[C@H]2O)[C@@H](CC=O)C[C@@H](C)[C@@H](O[C@H]2CC[C@H](N(C)C)[C@@H](C)O2)/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]1O>>CO[C@@H]1[C@@H](O[C@@H]2O[C@H](C)[C@@H](O[C@H]3C[C@@](C)(O)[C@@H](O)[C@H](C)O3)[C@H](N(C)C)[C@H]2OP(=O)(O)O)[C@@H](CC=O)C[C@@H](C)[C@@H](O[C@H]2CC[C@H](N(C)C)[C@@H](C)O2)C=CC=CC[C@@H](C)OC(=O)C[C@H]1O	enzymemap_43350
AKRT011360	CO[C@H]1[C@H](O)CC(=O)O[C@H](C)C/C=C/C=C/[C@H](O[C@H]2CC[C@H](N(C)C)[C@@H](C)O2)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]1O[C@H](C)[C@@H](O[C@H]2C[C@@](C)(O)[C@@H](O)[C@H](C)O2)[C@H](N(C)C)[C@H]1O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>CO[C@H]1[C@H](O)CC(=O)O[C@H](C)CC=CC=C[C@H](O[C@H]2CC[C@H](N(C)C)[C@@H](C)O2)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]1O[C@H](C)[C@@H](O[C@H]2C[C@@](C)(O)[C@@H](O)[C@H](C)O2)[C@H](N(C)C)[C@H]1OP(=O)(O)O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O	None