Molecule

Tylosin

AlkaPlorer ID: AK001372

Synonym: None

IUPAC Name: 2-[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-[(2R,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-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde

Structure

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

InChI: InChI=1S/C46H77NO17/c1-13-33-30(22-58-45-42(57-12)41(56-11)37(52)26(5)60-45)18-23(2)14-15-31(49)24(3)19-29(16-17-48)39(25(4)32(50)20-34(51)62-33)64-44-38(53)36(47(9)10)40(27(6)61-44)63-35-21-46(8,55)43(54)28(7)59-35/h14-15,17-18,24-30,32-33,35-45,50,52-55H,13,16,19-22H2,1-12H3/b15-14+,23-18+/t24-,25+,26-,27-,28+,29+,30-,32-,33-,35+,36-,37-,38-,39-,40-,41-,42-,43+,44+,45-,46-/m1/s1

InChIKey: WBPYTXDJUQJLPQ-VMXQISHHSA-N

Reference

Threonine dehydratases in different strains of Streptomyces fradiae

PubChem CID: 5280440

CAS: 108050-54-0

LOTUS: LTS0082772

NPASS: NPC316205

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Penicillium fuscum	Penicillium	Aspergillaceae	Eurotiales	Eurotiomycetes	Ascomycota	Fungi	Eukaryota
Penicillium clavigerum	Penicillium	Aspergillaceae	Eurotiales	Eurotiomycetes	Ascomycota	Fungi	Eukaryota

Properties Information

Molecule Weight: 916.112

TPSA？: 238.67

MolLogP？: 1.8335000000000103

Number of H-Donors: 5

Number of H-Acceptors: 18

RingCount: 4

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Anaerococcus prevotii	Anaerococcus prevotii	MIC	8.0	ug.mL-1	10.1021/jm00403a025
Bacillus subtilis	Bacillus subtilis	MIC	0.78	ug.mL-1	10.1021/jm00345a014
Bacteroides fragilis	Bacteroides fragilis	MIC	0.5	ug.mL-1	10.1021/jm00403a025
Bacteroides fragilis	Bacteroides fragilis	MIC	1.0	ug.mL-1	10.1021/jm00403a025
Bacteroides thetaiotaomicron	Bacteroides thetaiotaomicron	MIC	1.0	ug.mL-1	10.1021/jm00403a025
Campylobacter jejuni	Campylobacter jejuni	Activity	nan	None	10.1128/aac.00450-08
Campylobacter jejuni	Campylobacter jejuni	MIC	64.0	ug.mL-1	10.1128/aac.00450-08
Campylobacter jejuni	Campylobacter jejuni	MIC	128.0	ug.mL-1	10.1128/aac.00450-08
Campylobacter jejuni	Campylobacter jejuni	MIC	512.0	ug.mL-1	10.1128/aac.00450-08
Chlamydia trachomatis	Chlamydia trachomatis	MIC	0.25	ug.mL-1	10.1021/jm00403a025
Clostridioides difficile	Clostridioides difficile	MIC	1.0	ug.mL-1	10.1021/jm00403a025
Clostridium perfringens	Clostridium perfringens	MIC	0.25	ug.mL-1	10.1021/jm00403a025
Clostridium septicum	Clostridium septicum	MIC	0.5	ug.mL-1	10.1021/jm00403a025
Collinsella aerofaciens	Collinsella aerofaciens	MIC	0.12	ug.mL-1	10.1021/jm00403a025
Cronobacter sakazakii	Cronobacter sakazakii	MIC	32.0	ug.mL-1	10.1016/j.ejmech.2022.114495
Cutibacterium acnes	Cutibacterium acnes	MIC	0.5	ug.mL-1	10.1021/jm00403a025
Eikenella corrodens	Eikenella corrodens	MIC	1.0	ug.mL-1	10.1021/jm00403a025
Enterococcus faecalis	Enterococcus faecalis	MIC	1.0	ug.mL-1	10.1021/jm0308951
Enterococcus faecalis	Enterococcus faecalis	MIC	1.0	ug.mL-1	10.1128/aac.00481-08
Enterococcus faecalis	Enterococcus faecalis	MIC	12.5	ug.mL-1	10.1016/j.bmcl.2005.11.061
Enterococcus faecalis	Enterococcus faecalis	MIC	16.0	ug.mL-1	10.1128/aac.00481-08
Enterococcus faecium	Enterococcus faecium	MIC	1.0	ug.mL-1	10.1016/j.ejmech.2022.114495
Enterococcus faecium	Enterococcus faecium	MIC	2.0	ug.mL-1	10.1021/jm00403a025
Escherichia coli	Escherichia coli	Activity	nan	None	10.1128/aac.01266-07
Escherichia coli	Escherichia coli	ID50	4.0	mg ml-1	10.1021/jm00345a014
Escherichia coli	Escherichia coli	MIC	16.0	ug.mL-1	10.1128/aac.00481-08
Escherichia coli	Escherichia coli	MIC	16.0	ug.mL-1	10.1128/aac.01126-09
Escherichia coli	Escherichia coli	MIC	32.0	ug.mL-1	10.1016/j.ejmech.2022.114495
Escherichia coli	Escherichia coli	MIC	50.0	ug.mL-1	10.1021/jm00345a014
Escherichia coli	Escherichia coli	MIC	64.0	ug.mL-1	10.1021/jm0308951
Escherichia coli	Escherichia coli	MIC	64.0	ug.mL-1	10.1128/aac.01048-06
Escherichia coli	Escherichia coli	MIC	128.0	ug.mL-1	10.1128/aac.00481-08
Escherichia coli	Escherichia coli	MIC	128.0	ug.mL-1	10.1128/aac.01048-06
Escherichia coli	Escherichia coli	MIC	128.0	ug.mL-1	10.1128/aac.01126-09
Escherichia coli	Escherichia coli	MIC	512.0	ug.mL-1	10.1128/aac.01048-06
Escherichia coli	Escherichia coli	MIC	1024.0	ug.mL-1	10.1128/aac.01126-09
Fusobacterium	Fusobacterium	MIC	0.03	ug.mL-1	10.1021/jm00403a025
Fusobacterium necrophorum	Fusobacterium necrophorum	MIC	0.5	ug.mL-1	10.1021/jm00403a025
Haemophilus influenzae	Haemophilus influenzae	MIC	8.0	ug.mL-1	10.1021/jm0308951
Haemophilus influenzae	Haemophilus influenzae	MIC	8.0	ug.mL-1	10.1021/jm034233n
Haemophilus influenzae	Haemophilus influenzae	MIC	16.0	ug.mL-1	10.1021/jm00403a025
Haemophilus influenzae	Haemophilus influenzae	MIC	32.0	ug.mL-1	10.1021/jm00403a025
Haemophilus parainfluenzae	Haemophilus parainfluenzae	MIC	16.0	ug.mL-1	10.1021/jm00403a025
Homo sapiens	Histone deacetylase 6	Inhibition	4.17	%	10.6019/CHEMBL4808148
Homo sapiens	Histone deacetylase 6	Inhibition	13.31	%	10.6019/CHEMBL4808148
Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	32.0	ug.mL-1	10.1016/j.ejmech.2022.114495
Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	100.0	ug.mL-1	10.1021/jm00345a014
Micrococcus luteus	Micrococcus luteus	MIC	0.1	ug.mL-1	10.1021/jm00345a014
Mus musculus	Mus musculus	Concentration	nan	None	10.1021/jm00403a025
Mus musculus	Mus musculus	PD50	86.0	mg kg-1	10.1021/jm960435q
Mus musculus	Mus musculus	PD50	86.0	mg kg-1	10.1021/jm960436i
Mycoplasma putrefaciens	Mycoplasma putrefaciens	MIC	0.06	ug.mL-1	10.1128/aac.00420-07
Mycoplasma putrefaciens	Mycoplasma putrefaciens	MIC50	0.015	ug.mL-1	10.1128/aac.00420-07
Mycoplasma putrefaciens	Mycoplasma putrefaciens	MIC50	0.03	ug.mL-1	10.1128/aac.00420-07
Mycoplasma putrefaciens	Mycoplasma putrefaciens	MIC90	0.015	ug.mL-1	10.1128/aac.00420-07
Mycoplasma putrefaciens	Mycoplasma putrefaciens	MIC90	0.06	ug.mL-1	10.1128/aac.00420-07
Mycoplasmoides gallisepticum	Mycoplasmoides gallisepticum	MIC	100.0	nM	10.1021/jm00107a045
Mycoplasmoides gallisepticum	Mycoplasmoides gallisepticum	MIC	100.0	nM	10.1021/jm00122a033
Mycoplasmoides gallisepticum	Mycoplasmoides gallisepticum	MIC	100.0	nM	10.1021/jm00399a005
Pasteurella multocida	Pasteurella multocida	MIC	25.0	ug.mL-1	10.1021/jm960435q
Pasteurella multocida	Pasteurella multocida	MIC	25.0	ug.mL-1	10.1021/jm960436i
Peptoniphilus asaccharolyticus	Peptoniphilus asaccharolyticus	MIC	0.06	ug.mL-1	10.1021/jm00403a025
Peptostreptococcus anaerobius	Peptostreptococcus anaerobius	MIC	8.0	ug.mL-1	10.1021/jm00403a025
Phocaeicola vulgatus	Phocaeicola vulgatus	MIC	1.0	ug.mL-1	10.1021/jm00403a025
Prevotella melaninogenica	Prevotella melaninogenica	MIC	0.03	ug.mL-1	10.1021/jm00403a025
Prevotella melaninogenica	Prevotella melaninogenica	MIC	0.25	ug.mL-1	10.1021/jm00403a025
Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	32.0	ug.mL-1	10.1016/j.ejmech.2022.114495
Pseudomonas sp.	Pseudomonas sp.	MIC	150.0	ug.mL-1	10.1128/aac.00802-06
Pseudomonas sp.	Pseudomonas sp.	MIC	400.0	ug.mL-1	10.1128/aac.00802-06
Rattus norvegicus	Rattus norvegicus	Concentration	nan	None	10.1021/jm00403a025
Severe acute respiratory syndrome coronavirus 2	Replicase polyprotein 1ab	Inhibition	2.323	%	10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	0.36	%	10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	3.54	%	10.21203/rs.3.rs-23951/v1
Staphylococcus aureus	Staphylococcus aureus	MIC	0.2	ug.mL-1	10.1016/j.bmcl.2005.11.061
Staphylococcus aureus	Staphylococcus aureus	MIC	0.25	ug.mL-1	10.1016/j.ejmech.2022.114495
Staphylococcus aureus	Staphylococcus aureus	MIC	0.5	ug.mL-1	10.1016/j.ejmech.2022.114495
Staphylococcus aureus	Staphylococcus aureus	MIC	0.5	ug.mL-1	10.1021/jm00403a025
Staphylococcus aureus	Staphylococcus aureus	MIC	0.5	ug.mL-1	10.1021/jm0308951
Staphylococcus aureus	Staphylococcus aureus	MIC	0.78	ug.mL-1	10.1021/jm00345a014
Staphylococcus aureus	Staphylococcus aureus	MIC	1.0	ug.mL-1	10.1016/j.ejmech.2022.114495
Staphylococcus aureus	Staphylococcus aureus	MIC	1.0	ug.mL-1	10.1021/jm00403a025
Staphylococcus aureus	Staphylococcus aureus	MIC	1.0	ug.mL-1	10.1021/jm0308951
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	1.56	ug.mL-1	10.1016/j.bmcl.2005.11.061
Staphylococcus aureus	Staphylococcus aureus	MIC	2.0	ug.mL-1	10.1016/j.ejmech.2022.114495
Staphylococcus aureus	Staphylococcus aureus	MIC	2.0	ug.mL-1	10.1021/jm034233n
Staphylococcus aureus	Staphylococcus aureus	MIC	2.0	ug.mL-1	10.1128/aac.01583-07
Staphylococcus aureus	Staphylococcus aureus	MIC	12.5	ug.mL-1	10.1016/j.bmcl.2005.11.061
Staphylococcus aureus	Staphylococcus aureus	MIC	16.0	ug.mL-1	10.1128/aac.00481-08
Staphylococcus aureus	Staphylococcus aureus	MIC	32.0	ug.mL-1	10.1016/j.ejmech.2022.114495
Staphylococcus aureus	Staphylococcus aureus	MIC	128.0	ug.mL-1	10.1021/jm0308951
Staphylococcus aureus	Staphylococcus aureus	MIC	1024.0	ug.mL-1	10.1128/aac.01583-07
Staphylococcus aureus	Staphylococcus aureus	MIC	2000.0	ug.mL-1	10.1128/aac.01583-07
Staphylococcus aureus	Staphylococcus aureus	MIC	6000.0	ug.mL-1	10.1128/aac.01583-07
Staphylococcus aureus	Staphylococcus aureus	MIC	nan	None	10.1128/aac.01583-07
Staphylococcus chromogenes	Staphylococcus chromogenes	MIC	0.5	ug.mL-1	10.1016/j.ejmech.2022.114495
Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	0.25	ug.mL-1	10.1021/jm00403a025
Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	0.39	ug.mL-1	10.1016/j.bmcl.2005.11.061
Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	1.0	ug.mL-1	10.1021/jm00403a025
Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	128.0	ug.mL-1	10.1021/jm00403a025
Streptococcus	Streptococcus	MIC	0.25	ug.mL-1	10.1021/jm00403a025
Streptococcus	Streptococcus	MIC	1.0	ug.mL-1	10.1021/jm00403a025
Streptococcus dysgalactiae	Streptococcus dysgalactiae	MIC	1.0	ug.mL-1	10.1016/j.ejmech.2022.114495
Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	0.098	ug.mL-1	10.1016/j.bmcl.2005.11.061
Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	0.2	ug.mL-1	10.1016/j.bmcl.2005.11.061
Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	0.25	ug.mL-1	10.1021/jm00403a025
Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	0.25	ug.mL-1	10.1021/jm034233n
Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	0.5	ug.mL-1	10.1021/jm0308951
Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	12.5	ug.mL-1	10.1016/j.bmcl.2005.11.061
Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	64.0	ug.mL-1	10.1021/jm034233n
Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	128.0	ug.mL-1	10.1021/jm00403a025
Streptococcus pyogenes	Streptococcus pyogenes	ED50	0.5	mg.kg-1	10.1021/jm00403a025
Streptococcus pyogenes	Streptococcus pyogenes	ED50	1.3	mg.kg-1	10.1021/jm00403a025
Streptococcus pyogenes	Streptococcus pyogenes	ED50	42.0	mg.kg-1	10.1021/jm00403a025
Streptococcus pyogenes	Streptococcus pyogenes	MIC	0.25	ug.mL-1	10.1021/jm00403a025
Streptococcus pyogenes	Streptococcus pyogenes	MIC	0.25	ug.mL-1	10.1021/jm034233n
Streptococcus pyogenes	Streptococcus pyogenes	MIC	0.5	ug.mL-1	10.1021/jm0308951
Streptococcus pyogenes	Streptococcus pyogenes	MIC	1.0	ug.mL-1	10.1021/jm0308951
Streptococcus pyogenes	Streptococcus pyogenes	MIC	64.0	ug.mL-1	10.1021/jm034233n
Streptococcus sanguinis	Streptococcus sanguinis	MIC	0.5	ug.mL-1	10.1021/jm00403a025
Streptococcus viridans	Streptococcus viridans	MIC	128.0	ug.mL-1	10.1021/jm00403a025
None	ADMET	Log K	0.68	None	10.1021/jm960436i
None	ADMET	pCF	0.167	None	10.1021/jm960436i
None	ADMET	pNF	0.497	None	10.1021/jm960436i
None	NON-PROTEIN TARGET	MIC	0.5	ug.mL-1	10.1128/aac.00481-08
None	No relevant target	CLogP	-0.786	None	10.1021/jm960436i
None	No relevant target	CLogP	0.0	None	10.1021/jm960436i
None	No relevant target	CLogP	1.63	None	10.1021/jm960436i
None	No relevant target	LogD	1.15	None	10.1021/jm960436i
None	No relevant target	pKa	7.73	None	10.1007/s11095-013-1232-z
None	No relevant target	pKa1	7.73	None	10.1021/jm960436i
None	Nucleic Acid	Kd	2.75	nM	10.1021/jm9000659
None	Ribosome	Activity	nan	None	10.1021/acs.jnatprod.7b00133
None	Unchecked	Activity	nan	None	10.1021/acsmedchemlett.8b00472
None	Unchecked	Activity	nan	None	10.1128/aac.01425-08
None	Unchecked	Inhibition	nan	%	10.1021/acs.jnatprod.7b00133
None	Unchecked	Kcat	0.174	/s	10.1128/aac.01570-09
None	Unchecked	Kcat/Km	1.33	10'3/s/M	10.1128/aac.01570-09
None	Unchecked	Km	131000.0	nM	10.1128/aac.01570-09
None	Unchecked	MIC	0.5	ug.mL-1	10.1021/jm00403a025

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT010256	CC[C@H]1OC(=O)C[C@@H](O)[C@H](C)[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(=O)/C=C/C(C)=C/[C@@H]1CO[C@@H]1O[C@H](C)[C@@H](O)[C@@H](O)[C@H]1OC.C[SAH]>>CC[C@H]1OC(=O)C[C@@H](O)[C@H](C)[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(=O)/C=C/C(C)=C/[C@@H]1CO[C@@H]1O[C@H](C)[C@@H](O)[C@@H](OC)[C@H]1OC	MACROCIN-O-METHYLTRANSFERASE-RXN
AKRT010258	CC[C@H]1OC(=O)C[C@@H](O)[C@H](C)[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(=O)/C=C/C(C)=C/[C@@H]1CO[C@@H]1O[C@H](C)[C@@H](O)[C@@H](OC)[C@H]1OC.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>CC[C@H]1OC(=O)C[C@@H](O)[C@H](C)[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]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](CC=O)C[C@@H](C)C(=O)/C=C/C(C)=C/[C@@H]1CO[C@@H]1O[C@H](C)[C@@H](O)[C@@H](OC)[C@H]1OC	RXN-15073
AKRT010259	CC[C@H]1OC(=O)C[C@@H](O)[C@H](C)[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(=O)/C=C/C(C)=C/[C@@H]1CO[C@@H]1O[C@H](C)[C@@H](O)[C@@H](OC)[C@H]1OC>>CC[C@H]1OC(=O)C[C@@H](O)[C@H](C)[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](CCO)C[C@@H](C)C(=O)/C=C/C(C)=C/[C@@H]1CO[C@@H]1O[C@H](C)[C@@H](O)[C@@H](OC)[C@H]1OC	RXN-15072