17-Ethyl-1,14-dihydroxy-12-[1-(4-hydroxy-3-methoxycyclohexyl)prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone

Details

• Internal ID: a7080980-64d0-4d55-8e90-f54fc8c96fb1
• Taxonomy: Phenylpropanoids and polyketides > Macrolide lactams
• IUPAC Name: 17-ethyl-1,14-dihydroxy-12-[1-(4-hydroxy-3-methoxycyclohexyl)prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
• InChI: InChI=1S/C43H69NO12/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)44-16-12-11-13-31(44)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(22-29)52-7/h18,20,25,27-33,35-39,45-46,51H,10-17,19,21-23H2,1-9H3
• InChI Key: ZDQSOHOQTUFQEM-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₉NO₁₂
• Molecular Weight: 792.00 g/mol
• Exact Mass: 791.48197664 g/mol
• Topological Polar Surface Area (TPSA): 178.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 4.47
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 11011-38-4
• 17-ethyl-1,14-dihydroxy-12-[1-(4-hydroxy-3-methoxycyclohexyl)prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
• Ascomycin (Immunomycin,FK-520)
• 104987-12-4
• ZDQSOHOQTUFQEM-UHFFFAOYSA-N
• BCP28504
• Immunomycin; FK520; FR 900520
• FT-0662303
• 1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-17-ethyl-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo [22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1, 14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclo-hexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1, 14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1 '-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy -3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy -13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo-[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclo-hexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]-octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl] -23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23, 25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa -4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25 -dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,-27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl -11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo [22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo-[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]-octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,-10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetrone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone
• 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone
• 17-Ethyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxycyclo hexyl)-1-methylvinyl)-23,25-dimethoxy-13,19,21,27-tetra methyl-11,28-dioxa-4-azatricyclo(22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6890	68.90%
Caco-2	-	0.8482	84.82%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5747	57.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8325	83.25%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9387	93.87%
P-glycoprotein inhibitior	+	0.7820	78.20%
P-glycoprotein substrate	+	0.9090	90.90%
CYP3A4 substrate	+	0.7692	76.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8882	88.82%
CYP3A4 inhibition	-	0.9058	90.58%
CYP2C9 inhibition	-	0.9184	91.84%
CYP2C19 inhibition	-	0.9050	90.50%
CYP2D6 inhibition	-	0.9336	93.36%
CYP1A2 inhibition	-	0.8921	89.21%
CYP2C8 inhibition	+	0.6252	62.52%
CYP inhibitory promiscuity	-	0.9694	96.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4849	48.49%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9147	91.47%
Skin irritation	-	0.7522	75.22%
Skin corrosion	-	0.9335	93.35%
Ames mutagenesis	-	0.5270	52.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3829	38.29%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.7243	72.43%
skin sensitisation	-	0.8711	87.11%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	+	0.4825	48.25%
Acute Oral Toxicity (c)	III	0.6459	64.59%
Estrogen receptor binding	+	0.8616	86.16%
Androgen receptor binding	+	0.8564	85.64%
Thyroid receptor binding	+	0.5229	52.29%
Glucocorticoid receptor binding	+	0.7527	75.27%
Aromatase binding	+	0.6450	64.50%
PPAR gamma	+	0.7526	75.26%
Honey bee toxicity	-	0.6597	65.97%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.7827	78.27%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	39.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1902	P62942	FK506-binding protein 1A	99.88%	97.05%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.94%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.58%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.93%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.16%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.67%	85.14%
CHEMBL2052031	Q13451	Peptidyl-prolyl cis-trans isomerase FKBP5	92.67%	88.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.12%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.09%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.51%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.62%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.77%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.20%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.76%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.91%	93.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.49%	94.00%
CHEMBL1871	P10275	Androgen Receptor	84.19%	96.43%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.87%	90.08%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.70%	96.95%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.58%	82.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.41%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.08%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	82.30%	91.49%
CHEMBL4072	P07858	Cathepsin B	81.28%	93.67%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.06%	93.65%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.54%	100.00%

Plants that contains it

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Cross-Links

• PubChem: 2241
• LOTUS: LTS0204853
• wikiData: Q104202315