Ascomycin

Details

• Internal ID: 1445f4eb-6df6-4adf-8856-e15807e93780
• Taxonomy: Phenylpropanoids and polyketides > Macrolide lactams
• IUPAC Name: (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-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
• SMILES (Canonical): CCC1C=C(CC(CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC1=O)O)C)C(=CC4CCC(C(C4)OC)O)C)O)C)OC)OC)C)C
• SMILES (Isomeric): CC[C@@H]1/C=C(/C[C@@H](C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]4CC[C@H]([C@@H](C4)OC)O)/C)O)C)OC)OC)C)\C
• 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/b24-18+,26-20+/t25-,27+,28+,29-,30+,31-,32+,33-,35+,36-,37-,38+,39+,43+/m0/s1
• InChI Key: ZDQSOHOQTUFQEM-NURRSENYSA-N
• Popularity: 435 references 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

• Immunomycin
• 104987-12-4
• FK520
• FR 900520
• FK 520
• L-683590
• AUF4U5NSJK
• FK-520
• L 683590
• CHEMBL8597
• CHEBI:29582
• FR-900520
• Ascomycin from Streptomyces hygroscopicus var. ascomyceticus
• Changchuanmycin
• (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,22R,26aS)-8-ethyl-5,19-dihydroxy-3-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4H,23H)-tetrone
• C43H69NO12
• UNII-AUF4U5NSJK
• FR 520
• MFCD06198665
• NSC 106410
• NSC-106410
• Ascomycin (FK520)
• SCHEMBL25512
• BSPBio_001318
• L 683,590
• L-683,590
• CHEBI:94818
• DTXSID80894126
• ZDQSOHOQTUFQEM-NURRSENYSA-N
• HMS1361B20
• HMS1791B20
• HMS1989B20
• HMS3402B20
• EX-A1796
• BDBM50068939
• FR-520
• HB0123
• s7411
• AKOS015916691
• CCG-270483
• CS-1516
• IDI1_033788
• NCGC00163418-01
• NCGC00163418-02
• 15,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-4,10,12,18-tetram
• HY-13557
• Ascomycin (FK 520, FR 900520, Imm
• Q4803998
• BRD-K88998544-001-02-4
• BRD-K99369265-001-01-4
• TACROLIMUS IMPURITY, ASCOMYCIN- [USP IMPURITY]
• TACROLIMUS MONOHYDRATE IMPURITY A [EP IMPURITY]
• (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0?,?]octacos-18-ene-2,3,10,16-tetrone
• (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-Hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone
• (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-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
• (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R ,19R,26aS)-8-Ethyl-5,6,8,11,12,13,14,15,16,17,18,1 9,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E )-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetrameth yl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)tetrone
• (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-ethyl-5,19-dihydroxy-3-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4H,23H)-tetrone
• (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-Ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)tetrone
• (ascomycin)17-Ethyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]octacos-18-ene-2,3,10,16-tetraone
• (E)-(9S,12S,13R,14S,17R,21S,23S,24R,25S,27S)-17-Ethyl-1,14-dihydroxy-12-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]octacos-18-ene-2,3,10,16-tetraone
• (E)-(S)-17-Ethyl-1,14-dihydroxy-12-[(E)-2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]oct acos-18-ene-2,3,10,16-tetraone
• (E)-17-Ethyl-1,14-dihydroxy-12-[(E)-2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]octacos-18-ene-2,3,10,16-tetraone
• 135635-46-0
• 15,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-8-ethyl-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-4,10,12,18-tetramethyl-, (3S-(3R*(E(1S*,3S*,4S*)),4S*,19S*,26aR*))-
• 17-Ethyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]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

There are no matching plants.

Cross-Links

• PubChem: 5282071
• LOTUS: LTS0036043
• wikiData: Q4803998