7-Ethylidene-4,21-di(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetrazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone

Details

• Internal ID: 13f561ba-d657-4fae-b383-b44fa44aab47
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: 7-ethylidene-4,21-di(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetrazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone
• InChI: InChI=1S/C24H36N4O6S2/c1-6-16-21(30)28-20(14(4)5)24(33)34-15-9-7-8-10-35-36-12-17(22(31)25-16)26-23(32)19(13(2)3)27-18(29)11-15/h6-7,9,13-15,17,19-20H,8,10-12H2,1-5H3,(H,25,31)(H,26,32)(H,27,29)(H,28,30)
• InChI Key: OHRURASPPZQGQM-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₆N₄O₆S₂
• Molecular Weight: 540.70 g/mol
• Exact Mass: 540.20762723 g/mol
• Topological Polar Surface Area (TPSA): 193.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.43
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 7-ethylidene-4,21-di(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetrazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone
• Romidepsin (FK228; Depsipeptide)
• FK 228;FR 901228;NSC 630176
• Neuro_000275
• CHEMBL2130995
• HMS3656D16
• AKOS032960428
• NCI60_009796
• FT-0674421
• Cyclo[(2Z)-2-amino-2-butenoyl-L-valyl-(3S,4E)-3-hydroxy-7-mercapto-4-heptenoyl-D-valyl-D-cysteinyl] Cyclic (35)-Disulfide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8678	86.78%
Caco-2	-	0.8199	81.99%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7416	74.16%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.8543	85.43%
OATP1B3 inhibitior	+	0.9315	93.15%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9352	93.52%
P-glycoprotein inhibitior	+	0.6698	66.98%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.6230	62.30%
CYP2C9 substrate	-	0.6217	62.17%
CYP2D6 substrate	-	0.8885	88.85%
CYP3A4 inhibition	-	0.8635	86.35%
CYP2C9 inhibition	-	0.8480	84.80%
CYP2C19 inhibition	-	0.7897	78.97%
CYP2D6 inhibition	-	0.9103	91.03%
CYP1A2 inhibition	-	0.8014	80.14%
CYP2C8 inhibition	-	0.6520	65.20%
CYP inhibitory promiscuity	-	0.9809	98.09%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7400	74.00%
Carcinogenicity (trinary)	Non-required	0.5594	55.94%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9697	96.97%
Skin irritation	-	0.7651	76.51%
Skin corrosion	-	0.9258	92.58%
Ames mutagenesis	-	0.5491	54.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.6741	67.41%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8439	84.39%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5866	58.66%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.6210	62.10%
Thyroid receptor binding	+	0.5597	55.97%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.6394	63.94%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.7915	79.15%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1163125	O60885	Bromodomain-containing protein 4	36 nM	IC50	via Super-PRED
CHEMBL325	Q13547	Histone deacetylase 1	0.0015 nM; 1.6 nM	Ki; IC50	via Super-PRED; via Super-PRED
CHEMBL5103	Q969S8	Histone deacetylase 10	0.9 nM	IC50	via Super-PRED
CHEMBL3310	Q96DB2	Histone deacetylase 11	0.3 nM	IC50	via Super-PRED
CHEMBL1937	Q92769	Histone deacetylase 2	0.038 nM; 3.9 nM	Ki; IC50	via Super-PRED; via Super-PRED
CHEMBL1829	O15379	Histone deacetylase 3	0.15 nM	Ki	via Super-PRED
CHEMBL3038484	O15379	Histone deacetylase 3/NCoR1	0.15 nM	Ki	via Super-PRED
CHEMBL2111363	O15379	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	3 nM	IC50	via Super-PRED
CHEMBL3524	P56524	Histone deacetylase 4	510 nM	IC50	via Super-PRED
CHEMBL2563	Q9UQL6	Histone deacetylase 5	550 nM	Ki	via Super-PRED
CHEMBL1865	Q9UBN7	Histone deacetylase 6	9.5 nM; 9.1 nM	Ki; IC50	via Super-PRED; via Super-PRED
CHEMBL4600	Q13153	Serine/threonine-protein kinase PAK 1	1 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.12%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.62%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.53%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.51%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.64%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	88.08%	89.63%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.45%	89.00%
CHEMBL2581	P07339	Cathepsin D	87.12%	98.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.91%	92.88%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.50%	99.23%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.89%	89.34%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.80%	97.09%
CHEMBL1949	P62937	Cyclophilin A	82.67%	98.57%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.49%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.90%	90.71%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.51%	83.10%
CHEMBL299	P17252	Protein kinase C alpha	81.12%	98.03%
CHEMBL255	P29275	Adenosine A2b receptor	80.95%	98.59%
CHEMBL3401	O75469	Pregnane X receptor	80.83%	94.73%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.72%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.42%	100.00%

Plants that contains it

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Cross-Links

• PubChem: 3425
• LOTUS: LTS0069295
• wikiData: Q104193374