Paecilotoxin

Details

• Internal ID: 9921cade-432a-4d61-9460-661d01699aac
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: (2S)-N-[(2S)-1-[[(2S)-1-[[1-[[(2S)-1-[[(2S)-1-[[1-[[1-[(4-amino-4-oxobutyl)amino]-2-methyl-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-3-hydroxy-4-methyl-1-oxopentan-2-yl]amino]-6-hydroxy-4-methyl-1,8-dioxodecan-2-yl]-4-methyl-1-[(E,4S)-4-methylhex-2-enoyl]pyrrolidine-2-carboxamide
• InChI: InChI=1S/C58H102N10O13/c1-18-35(9)22-23-45(72)68-31-37(11)29-43(68)51(77)62-42(28-36(10)27-39(70)30-38(69)19-2)49(75)64-46(47(73)34(7)8)52(78)66-57(14,15)54(80)63-40(25-32(3)4)48(74)61-41(26-33(5)6)50(76)65-58(16,17)55(81)67-56(12,13)53(79)60-24-20-21-44(59)71/h22-23,32-37,39-43,46-47,70,73H,18-21,24-31H2,1-17H3,(H2,59,71)(H,60,79)(H,61,74)(H,62,77)(H,63,80)(H,64,75)(H,65,76)(H,66,78)(H,67,81)/b23-22+/t35-,36?,37?,39?,40-,41-,42-,43-,46-,47?/m0/s1
• InChI Key: GWAKUJDAJHEQBU-CXMBYJBLSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₈H₁₀₂N₁₀O₁₃
• Molecular Weight: 1147.50 g/mol
• Exact Mass: 1146.76278335 g/mol
• Topological Polar Surface Area (TPSA): 354.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 2.09
• H-Bond Acceptor: 13
• H-Bond Donor: 11
• Rotatable Bonds: 35

Synonyms

• Antibiotic A 20668
• A 20668 (antibiotic)
• NSC 608984
• orb1986911
• SCHEMBL30098845
• AKOS040748737
• A 20668
• (2S)-N-((13S,16S,22S,25S)-1-amino-29-hydroxy-22-(1-hydroxy-2-methylpropyl)-13,16-diisobutyl-7,7,10,10,19,19,27-heptamethyl-1,6,9,12,15,18,21,24,31-nonaoxo-5,8,11,14,17,20,23-heptaazatritriacontan-25-yl)-4-methyl-1-((S,E)-4-methylhex-2-enoyl)pyrrolidine-2-carboxamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7580	75.80%
Caco-2	-	0.8623	86.23%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Lysosomes	0.5323	53.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8391	83.91%
OATP1B3 inhibitior	+	0.9143	91.43%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9789	97.89%
P-glycoprotein inhibitior	+	0.7432	74.32%
P-glycoprotein substrate	+	0.8754	87.54%
CYP3A4 substrate	+	0.7379	73.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8763	87.63%
CYP3A4 inhibition	-	0.8378	83.78%
CYP2C9 inhibition	-	0.8699	86.99%
CYP2C19 inhibition	-	0.7954	79.54%
CYP2D6 inhibition	-	0.8966	89.66%
CYP1A2 inhibition	-	0.8877	88.77%
CYP2C8 inhibition	+	0.6791	67.91%
CYP inhibitory promiscuity	-	0.9586	95.86%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5963	59.63%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.8968	89.68%
Skin irritation	-	0.7692	76.92%
Skin corrosion	-	0.8819	88.19%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6632	66.32%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.5427	54.27%
skin sensitisation	-	0.8688	86.88%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6829	68.29%
Acute Oral Toxicity (c)	III	0.6645	66.45%
Estrogen receptor binding	+	0.6747	67.47%
Androgen receptor binding	+	0.7257	72.57%
Thyroid receptor binding	+	0.6362	63.62%
Glucocorticoid receptor binding	+	0.7315	73.15%
Aromatase binding	+	0.7433	74.33%
PPAR gamma	+	0.7874	78.74%
Honey bee toxicity	-	0.7098	70.98%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5376	53.76%
Fish aquatic toxicity	+	0.6843	68.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3837	P07711	Cathepsin L	99.92%	96.61%
CHEMBL2581	P07339	Cathepsin D	99.72%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.96%	96.09%
CHEMBL4801	P29466	Caspase-1	98.49%	96.85%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.46%	97.25%
CHEMBL3359	P21462	Formyl peptide receptor 1	98.28%	93.56%
CHEMBL4018	P49146	Neuropeptide Y receptor type 2	97.97%	98.94%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	97.58%	98.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	97.19%	97.21%
CHEMBL4227	P25090	Lipoxin A4 receptor	97.00%	100.00%
CHEMBL2514	O95665	Neurotensin receptor 2	96.87%	100.00%
CHEMBL4072	P07858	Cathepsin B	96.06%	93.67%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	95.72%	97.29%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	95.47%	90.71%
CHEMBL299	P17252	Protein kinase C alpha	95.43%	98.03%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	95.14%	96.47%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.00%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.99%	99.17%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	94.70%	92.86%
CHEMBL221	P23219	Cyclooxygenase-1	94.69%	90.17%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	94.62%	83.10%
CHEMBL237	P41145	Kappa opioid receptor	94.41%	98.10%
CHEMBL2094135	Q96BI3	Gamma-secretase	94.23%	98.05%
CHEMBL4123	P30989	Neurotensin receptor 1	94.22%	96.67%
CHEMBL4660	P28907	Lymphocyte differentiation antigen CD38	94.11%	95.27%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	93.82%	95.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.72%	96.95%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	91.77%	100.00%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	91.30%	87.16%
CHEMBL236	P41143	Delta opioid receptor	91.27%	99.35%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	91.09%	92.38%
CHEMBL4588	P22894	Matrix metalloproteinase 8	90.99%	94.66%
CHEMBL2413	P32246	C-C chemokine receptor type 1	90.85%	89.50%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	90.52%	91.81%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.41%	97.09%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	89.87%	97.50%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	89.17%	89.34%
CHEMBL220	P22303	Acetylcholinesterase	89.12%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.04%	96.00%
CHEMBL2431	P31751	Serine/threonine-protein kinase AKT2	89.02%	98.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.67%	97.14%
CHEMBL2996	Q05655	Protein kinase C delta	88.57%	97.79%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.44%	93.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.14%	98.75%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	87.86%	95.36%
CHEMBL3437	Q16853	Amine oxidase, copper containing	87.79%	94.00%
CHEMBL3176	O43603	Galanin receptor 2	87.55%	98.89%
CHEMBL206	P03372	Estrogen receptor alpha	87.48%	97.64%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.23%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.02%	91.19%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.02%	95.17%
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	86.99%	95.52%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.97%	85.31%
CHEMBL4777	P25929	Neuropeptide Y receptor type 1	86.94%	96.67%
CHEMBL3776	Q14790	Caspase-8	86.87%	97.06%
CHEMBL4015	P41597	C-C chemokine receptor type 2	86.60%	98.57%
CHEMBL3238	P23786	Carnitine palmitoyltransferase 2	86.59%	94.05%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	86.31%	99.00%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	86.25%	96.25%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	86.02%	97.47%
CHEMBL283	P08254	Matrix metalloproteinase 3	85.76%	97.29%
CHEMBL255	P29275	Adenosine A2b receptor	85.25%	98.59%
CHEMBL5028	O14672	ADAM10	85.15%	97.50%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	85.01%	95.00%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	84.95%	92.50%
CHEMBL4816	Q9Y243	Serine/threonine-protein kinase AKT3	84.54%	96.28%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	84.33%	97.50%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.24%	89.62%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	83.82%	97.23%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.81%	96.90%
CHEMBL4506	Q96EB6	NAD-dependent deacetylase sirtuin 1	83.37%	88.33%
CHEMBL1075317	P61964	WD repeat-containing protein 5	83.26%	96.33%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	83.23%	88.42%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	82.87%	96.03%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	82.16%	98.24%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.81%	91.03%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.51%	94.33%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	80.77%	83.14%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	80.67%	97.64%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.41%	89.00%
CHEMBL3468	P55210	Caspase-7	80.38%	95.68%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.36%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.36%	82.69%
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	80.36%	81.29%
CHEMBL333	P08253	Matrix metalloproteinase-2	80.20%	96.31%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6450280
• LOTUS: LTS0011403
• wikiData: Q105107460