Largazole

Details

• Internal ID: 538bcf11-aa44-4ac9-b9b9-3ac6378f47ac
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: S-[(E)-4-[(5R,8S,11S)-5-methyl-6,9,13-trioxo-8-propan-2-yl-10-oxa-3,17-dithia-7,14,19,20-tetrazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-trien-11-yl]but-3-enyl] octanethioate
• InChI: InChI=1S/C29H42N4O5S3/c1-5-6-7-8-9-13-24(35)39-14-11-10-12-20-15-22(34)30-16-23-31-21(17-40-23)26-33-29(4,18-41-26)28(37)32-25(19(2)3)27(36)38-20/h10,12,17,19-20,25H,5-9,11,13-16,18H2,1-4H3,(H,30,34)(H,32,37)/b12-10+/t20-,25+,29+/m1/s1
• InChI Key: AXESYCSCGBQJBL-SZPBEECKSA-N
• Popularity: 79 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₂N₄O₅S₃
• Molecular Weight: 622.90 g/mol
• Exact Mass: 622.23173397 g/mol
• Topological Polar Surface Area (TPSA): 206.00 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 5.03
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 11

Synonyms

• 1009815-87-5
• CHEMBL1173445
• S-((E)-4-((5R,8S,11S)-8-Isopropyl-5-methyl-6,9,13-trioxo-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-trien-11-yl)but-3-en-1-yl) octanethioate
• S-[(E)-4-[(5R,8S,11S)-5-methyl-6,9,13-trioxo-8-propan-2-yl-10-oxa-3,17-dithia-7,14,19,20-tetrazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-trien-11-yl]but-3-enyl] octanethioate
• SCHEMBL71330
• DTXSID201043887
• BDBM50322422
• Q59313123
• S-((E)-4-((12Z,22Z,24R,5S,8S)-5-isopropyl-24-methyl-3,6,10-trioxo-24,25-dihydro-7-oxa-4,11-diaza-1(4,2),2(2,4)-dithiazolacyclododecaphane-8-yl)but-3-en-1-yl) octanethioate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9285	92.85%
Caco-2	-	0.8445	84.45%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.3719	37.19%
OATP2B1 inhibitior	-	0.7162	71.62%
OATP1B1 inhibitior	+	0.8221	82.21%
OATP1B3 inhibitior	+	0.9312	93.12%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9841	98.41%
P-glycoprotein inhibitior	+	0.7583	75.83%
P-glycoprotein substrate	+	0.7741	77.41%
CYP3A4 substrate	+	0.6814	68.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8618	86.18%
CYP3A4 inhibition	-	0.7458	74.58%
CYP2C9 inhibition	-	0.8138	81.38%
CYP2C19 inhibition	-	0.6853	68.53%
CYP2D6 inhibition	-	0.8898	88.98%
CYP1A2 inhibition	-	0.7911	79.11%
CYP2C8 inhibition	+	0.7450	74.50%
CYP inhibitory promiscuity	-	0.8721	87.21%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Non-required	0.5560	55.60%
Eye corrosion	-	0.9847	98.47%
Eye irritation	-	0.9387	93.87%
Skin irritation	-	0.7597	75.97%
Skin corrosion	-	0.9085	90.85%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4538	45.38%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7943	79.43%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7331	73.31%
Acute Oral Toxicity (c)	III	0.5913	59.13%
Estrogen receptor binding	+	0.7264	72.64%
Androgen receptor binding	+	0.6019	60.19%
Thyroid receptor binding	-	0.4906	49.06%
Glucocorticoid receptor binding	+	0.6517	65.17%
Aromatase binding	+	0.6526	65.26%
PPAR gamma	+	0.6099	60.99%
Honey bee toxicity	-	0.7875	78.75%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6763	67.63%
Fish aquatic toxicity	+	0.9478	94.78%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL325	Q13547	Histone deacetylase 1	10.09 nM	IC50	via Super-PRED
CHEMBL1937	Q92769	Histone deacetylase 2	18.65 nM	IC50	via Super-PRED
CHEMBL1829	O15379	Histone deacetylase 3	9.09 nM	IC50	via Super-PRED
CHEMBL1865	Q9UBN7	Histone deacetylase 6	165.6 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3310	Q96DB2	Histone deacetylase 11	98.82%	88.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	98.76%	90.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.05%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.74%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	97.33%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.74%	91.11%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	96.26%	92.29%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.67%	94.45%
CHEMBL230	P35354	Cyclooxygenase-2	95.44%	89.63%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.29%	99.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	94.86%	91.24%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	93.80%	85.94%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.06%	97.25%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.22%	89.34%
CHEMBL2996	Q05655	Protein kinase C delta	91.94%	97.79%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.10%	90.71%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.92%	93.03%
CHEMBL5285	Q99683	Mitogen-activated protein kinase kinase kinase 5	89.47%	92.26%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.38%	93.56%
CHEMBL3401	O75469	Pregnane X receptor	87.91%	94.73%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	87.16%	96.90%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.60%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.66%	93.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	84.07%	89.44%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.07%	95.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.01%	92.88%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.84%	100.00%
CHEMBL3891	P07384	Calpain 1	82.80%	93.04%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.59%	86.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.29%	100.00%
CHEMBL299	P17252	Protein kinase C alpha	80.74%	98.03%

Plants that contains it

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Cross-Links

• PubChem: 24757913
• LOTUS: LTS0056793
• wikiData: Q59313123