Tylosin

Details

• Internal ID: 3988792b-0bd6-497d-ab32-dfa2a0e9c4a6
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Aminosaccharides > Aminoglycosides
• 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
• SMILES (Canonical): CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)CC=O)C)C)COC4C(C(C(C(O4)C)O)OC)OC
• SMILES (Isomeric): CC[C@@H]1[C@H](/C=C(/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)O)N(C)C)O)CC=O)C)\C)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC
• 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
• InChI Key: WBPYTXDJUQJLPQ-VMXQISHHSA-N
• Popularity: 2,807 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₇₇NO₁₇
• Molecular Weight: 916.10 g/mol
• Exact Mass: 915.51914999 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.83
• H-Bond Acceptor: 18
• H-Bond Donor: 5
• Rotatable Bonds: 13

Synonyms

• Tylosin A
• Tylosine
• Tylan
• Tylocine
• Fradizine
• Tilosina
• Tylosinum
• 1401-69-0
• Vubityl 200
• UNII-YEF4JXN031
• YEF4JXN031
• CHEBI:17658
• HSDB 7022
• Tylosine [INN-French]
• Tylosinum [INN-Latin]
• Tilosina [INN-Spanish]
• EINECS 215-754-8
• Tylosin [USP:INN:BAN]
• AI3-29799
• DTXSID3043996
• 8026-48-0
• Tylosine (INN-French)
• Tylosinum (INN-Latin)
• Tilosina (INN-Spanish)
• TYLOSIN (MART.)
• TYLOSIN [MART.]
• TYLOSIN (USP-RS)
• TYLOSIN [USP-RS]
• Tylosin (USP:INN:BAN)
• 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
• TYLOSIN (USP IMPURITY)
• TYLOSIN [USP IMPURITY]
• TYLOSIN (USP MONOGRAPH)
• TYLOSIN [USP MONOGRAPH]
• (10E,12E)-(3R,4S,5S,6R,8R,14S,15R)-14-((6-deoxy-2,3-di-O-methyl-beta-D-allopyranosyl)oxymethyl)-5-((3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-dimethylamino-beta-D-glucopyranosyl)oxy)-6-formylmethyl-3-hydroxy-4,8,12-trimethyl-9-oxoheptadeca-10,12-dien-15-olide
• SR-05000002057
• (10E,12E)-(3R,4S,5S,6R,8R,14S,15R)-14-((6-deoxy-2,3-di-O-methyl-beta-D-allopyranosyl)oxymethyl)-5-((3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-l-ribo-hexopyranosyl)-3-dimethylamino-beta-d-glucopyranosyl)oxy)-6-formylmethyl-3-hydroxy-4,8,12-trimet
• Tylosin Base
• Tylosinum (Latin)
• ((2R,3R,4E,6E,9R,11R,12S,13S,14R)-12-(3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranosyloxy)-2-ethyl-14-hydroxy-5,9,13-trimethyl-8,16-dioxo-11-(2-oxoethyl)oxacyclohexadeca-4,6-dien-3-yl)methyl 6-deoxy-2,3-di-O-methyl-beta-D-allopyranoside
• [(2R,3R,4E,6E,9R,11R,12S,13S,14R)-12-[3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranosyloxy]-2-ethyl-14-hydroxy-5,9,13-trimethyl-8,16-dioxo-11-(2-oxoethyl)oxacyclohexadeca-4,6-dien-3-yl]methyl 6-deoxy-2,3-di-O-methyl-beta-D-allopyranoside
• Tylan (TN)
• Tylan 50
• Tylosin A; Fradizine
• Tylosin (USP/INN)
• Tylan 200
• TYLOSIN [INN]
• TYLOSIN [MI]
• SCHEMBL3081
• BSPBio_003548
• TYLOSIN [GREEN BOOK]
• CHEMBL42743
• SPECTRUM1505312
• Tylovet 200 mg/mL Injection
• SCHEMBL16931534
• HY-B0519A
• WBPYTXDJUQJLPQ-VMXQISHHSA-N
• DTXCID001473373
• HMS1922B22
• HMS2093B11
• Pharmakon1600-01505312
• CCG-38343
• LMPK04000004
• NSC758961
• s5108
• AKOS037515746
• CS-3442
• DB11475
• NCGC00263955-02
• E713
• Tylosin A 100 microg/mL in Acetonitrile
• SBI-0206754.P001
• Tylan 200 Injection, Tylan 50 Injection
• C01457
• D02490
• AB00959655_03
• AB00959655_04
• Q411462
• SR-05000002057-1
• SR-05000002057-2
• SR-05000002057-3
• BRD-K37753391-046-03-2
• ((2R,3R,4E,6E,9R,11R,12S,13S,14R)-12-((3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranosyl)oxy)-2-ethyl-14-hydroxy-5, 9,13-trimethyl-8, 16-dioxo-11-(2-oxoethyl)oxacyclohexadeca-4,6-dien-3-yl)methyl 6-deoxy-2,3-di-O-methyl-beta-D-allopyranoside
• [(2R,3R,4E,6E,9R,11R,12S,13S,14R)-12-{[3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranosyl]oxy}-2-ethyl-14-hydroxy-5,9,13-trimethyl-8,16-dioxo-11-(2-oxoethyl)oxacyclohexadeca-4,6-dien-3-yl]methyl 6-deoxy-2,3-di-O-methyl-beta-D-allopyranoside
• 2-[(4R,5S,6S,7R,9R,11E,13Z,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
• Antibiotic obtained from cultures of Streptomyces fradiae, or the same substance produced by any other means

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7902	79.02%
Caco-2	-	0.8677	86.77%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6271	62.71%
OATP2B1 inhibitior	-	0.8646	86.46%
OATP1B1 inhibitior	+	0.9294	92.94%
OATP1B3 inhibitior	+	0.9193	91.93%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9573	95.73%
P-glycoprotein inhibitior	+	0.7508	75.08%
P-glycoprotein substrate	+	0.8239	82.39%
CYP3A4 substrate	+	0.7187	71.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8833	88.33%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9055	90.55%
CYP2C19 inhibition	-	0.8891	88.91%
CYP2D6 inhibition	-	0.9240	92.40%
CYP1A2 inhibition	-	0.8952	89.52%
CYP2C8 inhibition	+	0.6873	68.73%
CYP inhibitory promiscuity	-	0.9643	96.43%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5168	51.68%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9085	90.85%
Skin irritation	-	0.7669	76.69%
Skin corrosion	-	0.9319	93.19%
Ames mutagenesis	-	0.6337	63.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7754	77.54%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.7199	71.99%
skin sensitisation	-	0.8526	85.26%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8781	87.81%
Acute Oral Toxicity (c)	III	0.7906	79.06%
Estrogen receptor binding	+	0.6519	65.19%
Androgen receptor binding	+	0.6724	67.24%
Thyroid receptor binding	+	0.5767	57.67%
Glucocorticoid receptor binding	+	0.7366	73.66%
Aromatase binding	-	0.5788	57.88%
PPAR gamma	+	0.7984	79.84%
Honey bee toxicity	-	0.5984	59.84%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.7200	72.00%
Fish aquatic toxicity	+	0.9451	94.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.74%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.46%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.03%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.34%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.50%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.37%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	90.95%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.88%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.64%	100.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.53%	82.38%
CHEMBL1951	P21397	Monoamine oxidase A	86.80%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.56%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.45%	97.36%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.64%	90.08%
CHEMBL3401	O75469	Pregnane X receptor	84.64%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.63%	92.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.31%	85.14%
CHEMBL4105838	Q96GG9	DCN1-like protein 1	84.08%	95.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.77%	96.90%
CHEMBL1902	P62942	FK506-binding protein 1A	82.74%	97.05%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.45%	83.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.41%	92.94%
CHEMBL5957	P21589	5'-nucleotidase	82.10%	97.78%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.10%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	80.15%	97.79%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5280440
• LOTUS: LTS0082772
• wikiData: Q411462