Trichostatin A (racemate)

Details

• Internal ID: f8db2cdd-d99b-44b0-bd56-fd9126650864
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: (2E,4E)-7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide
• InChI: InChI=1S/C17H22N2O3/c1-12(5-10-16(20)18-22)11-13(2)17(21)14-6-8-15(9-7-14)19(3)4/h5-11,13,22H,1-4H3,(H,18,20)/b10-5+,12-11+
• InChI Key: RTKIYFITIVXBLE-WKWSCTOISA-N
• Popularity: 4,543 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂N₂O₃
• Molecular Weight: 302.37 g/mol
• Exact Mass: 302.16304257 g/mol
• Topological Polar Surface Area (TPSA): 69.60 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 7-(4-(dimethylamino)phenyl)-N-hydroxy- 4,6-dimethyl-7-oxo-2,4-heptadienamide
• 1208356-08-4
• Trichostatin A (racemate)
• 2, 7-[4-(dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxo-
• 2, 7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-
• SCHEMBL446806
• CHEBI:91570
• BDBM50410546
• NSC709238
• AKOS030213149
• NSC-709238
• LS-14594
• PD128664
• CS-0021924
• BRD-A19037878-001-01-5
• Hepta-2, 7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl- 7-oxo-, (2E,4E,6R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7367	73.67%
Caco-2	+	0.7002	70.02%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8055	80.55%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9165	91.65%
OATP1B3 inhibitior	+	0.9399	93.99%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6498	64.98%
P-glycoprotein inhibitior	-	0.7590	75.90%
P-glycoprotein substrate	-	0.7076	70.76%
CYP3A4 substrate	-	0.5317	53.17%
CYP2C9 substrate	-	0.7921	79.21%
CYP2D6 substrate	-	0.8410	84.10%
CYP3A4 inhibition	-	0.7435	74.35%
CYP2C9 inhibition	-	0.6977	69.77%
CYP2C19 inhibition	-	0.7953	79.53%
CYP2D6 inhibition	-	0.8863	88.63%
CYP1A2 inhibition	-	0.6158	61.58%
CYP2C8 inhibition	-	0.7098	70.98%
CYP inhibitory promiscuity	-	0.8711	87.11%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.5261	52.61%
Carcinogenicity (trinary)	Non-required	0.4744	47.44%
Eye corrosion	-	0.9727	97.27%
Eye irritation	-	0.8911	89.11%
Skin irritation	-	0.7300	73.00%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4267	42.67%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	+	0.5513	55.13%
skin sensitisation	-	0.8387	83.87%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6565	65.65%
Acute Oral Toxicity (c)	III	0.6453	64.53%
Estrogen receptor binding	+	0.7706	77.06%
Androgen receptor binding	+	0.6722	67.22%
Thyroid receptor binding	+	0.5850	58.50%
Glucocorticoid receptor binding	-	0.5135	51.35%
Aromatase binding	+	0.7456	74.56%
PPAR gamma	+	0.5314	53.14%
Honey bee toxicity	-	0.9043	90.43%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8387	83.87%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4081	P13726	Coagulation factor III	20 nM	IC50	via Super-PRED
CHEMBL325	Q13547	Histone deacetylase 1	11 nM; 0.2 nM	IC50; Ki	via Super-PRED; via Super-PRED
CHEMBL5103	Q969S8	Histone deacetylase 10	1.61 nM; 40 nM	IC50; IC50	via Super-PRED; via Super-PRED
CHEMBL3310	Q96DB2	Histone deacetylase 11	10.6 nM	IC50	via Super-PRED
CHEMBL1937	Q92769	Histone deacetylase 2	16 nM; 0.65 nM	IC50; Ki	via Super-PRED; via Super-PRED
CHEMBL1829	O15379	Histone deacetylase 3	0.5 nM; 10 nM	Ki; IC50	via Super-PRED; via Super-PRED
CHEMBL3038484	O15379	Histone deacetylase 3/NCoR1	0.54 nM	Ki	via Super-PRED
CHEMBL2111363	O15379	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	0.26 nM	Ki	via Super-PRED
CHEMBL3524	P56524	Histone deacetylase 4	2 nM	IC50	via Super-PRED
CHEMBL2563	Q9UQL6	Histone deacetylase 5	8.08 nM	IC50	via Super-PRED
CHEMBL1865	Q9UBN7	Histone deacetylase 6	0.13 nM; 22 nM	Ki; IC50	via Super-PRED; via Super-PRED
CHEMBL2716	Q8WUI4	Histone deacetylase 7	22 nM; 980 nM	IC50; IC50	via Super-PRED; via Super-PRED
CHEMBL3192	Q9BY41	Histone deacetylase 8	25 nM; 790 nM	IC50; IC50	via Super-PRED; via Super-PRED
CHEMBL4145	Q9UKV0	Histone deacetylase 9	20.1 nM	IC50	via Super-PRED
CHEMBL1250378	Q15393	Splicing factor 3B subunit 3	577.6 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	91.71%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	90.97%	94.73%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	90.69%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.08%	96.09%
CHEMBL2039	P27338	Monoamine oxidase B	87.14%	92.51%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.70%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.96%	95.56%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	84.25%	98.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.35%	89.34%
CHEMBL4208	P20618	Proteasome component C5	82.96%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.87%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.79%	90.71%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	81.21%	87.67%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6376322
• LOTUS: LTS0214357
• wikiData: Q77371995