Aplysiatoxin

Details

• Internal ID: 35df7c43-0358-4f3b-9b67-4b45a0d90085
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (1S,3R,4S,5S,9R,13S,14R)-3-[(2S,5S)-5-(2-bromo-5-hydroxyphenyl)-5-methoxypentan-2-yl]-13-hydroxy-9-[(1R)-1-hydroxyethyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione
• SMILES (Canonical): CC1CC(C23CC(C(C(O2)C(C)CCC(C4=C(C=CC(=C4)O)Br)OC)C)OC(=O)CC(OC(=O)CC1(O3)O)C(C)O)(C)C
• SMILES (Isomeric): C[C@@H]1CC([C@@]23C[C@@H]([C@@H]([C@H](O2)[C@@H](C)CC[C@@H](C4=C(C=CC(=C4)O)Br)OC)C)OC(=O)C[C@@H](OC(=O)C[C@@]1(O3)O)[C@@H](C)O)(C)C
• InChI: InChI=1S/C32H47BrO10/c1-17(8-11-24(39-7)22-12-21(35)9-10-23(22)33)29-19(3)26-15-32(42-29)30(5,6)14-18(2)31(38,43-32)16-28(37)40-25(20(4)34)13-27(36)41-26/h9-10,12,17-20,24-26,29,34-35,38H,8,11,13-16H2,1-7H3/t17-,18+,19-,20+,24-,25+,26-,29+,31-,32-/m0/s1
• InChI Key: RHJPBGWFGOAEID-BEDNPZBZSA-N
• Popularity: 73 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₇BrO₁₀
• Molecular Weight: 671.60 g/mol
• Exact Mass: 670.23526 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 5.15
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• CHEMBL1256416
• C32H47BrO10
• C32-H47-Br-O10
• BRN 1675020
• SCHEMBL2020276
• DTXSID60880082
• BDBM50327943
• (1S,3R,4S,5S,9R,13S,14R)-3-[(2S,5S)-5-(2-bromo-5-hydroxyphenyl)-5-methoxypentan-2-yl]-13-hydroxy-9-[(1R)-1-hydroxyethyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9588	95.88%
Caco-2	-	0.8303	83.03%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6671	66.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8383	83.83%
OATP1B3 inhibitior	-	0.2236	22.36%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.8900	89.00%
P-glycoprotein inhibitior	+	0.7153	71.53%
P-glycoprotein substrate	+	0.7361	73.61%
CYP3A4 substrate	+	0.7187	71.87%
CYP2C9 substrate	-	0.8066	80.66%
CYP2D6 substrate	-	0.8542	85.42%
CYP3A4 inhibition	-	0.8400	84.00%
CYP2C9 inhibition	-	0.7765	77.65%
CYP2C19 inhibition	-	0.8667	86.67%
CYP2D6 inhibition	-	0.9195	91.95%
CYP1A2 inhibition	-	0.7152	71.52%
CYP2C8 inhibition	+	0.6885	68.85%
CYP inhibitory promiscuity	-	0.9181	91.81%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8683	86.83%
Carcinogenicity (trinary)	Non-required	0.5042	50.42%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9279	92.79%
Skin irritation	-	0.7343	73.43%
Skin corrosion	-	0.9370	93.70%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4317	43.17%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5918	59.18%
skin sensitisation	-	0.8858	88.58%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.7302	73.02%
Acute Oral Toxicity (c)	III	0.4394	43.94%
Estrogen receptor binding	+	0.7754	77.54%
Androgen receptor binding	+	0.7159	71.59%
Thyroid receptor binding	+	0.5417	54.17%
Glucocorticoid receptor binding	+	0.7923	79.23%
Aromatase binding	+	0.7410	74.10%
PPAR gamma	+	0.7825	78.25%
Honey bee toxicity	-	0.7242	72.42%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9932	99.32%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL299	P17252	Protein kinase C alpha	0.4 nM	Ki	PMID: 20817520
CHEMBL3045	P05771	Protein kinase C beta	0.45 nM	Ki	PMID: 20817520
CHEMBL2996	Q05655	Protein kinase C delta	12 nM; 0.41 nM	Ki; Ki	PMID: 20817520; PMID: 20817520
CHEMBL3582	Q02156	Protein kinase C epsilon	1.3 nM	Ki	PMID: 20817520
CHEMBL3616	P24723	Protein kinase C eta	0.36 nM	Ki	PMID: 20817520
CHEMBL2938	P05129	Protein kinase C gamma	0.63 nM	Ki	PMID: 20817520
CHEMBL3920	Q04759	Protein kinase C theta	0.16 nM	Ki	PMID: 20817520

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.82%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.80%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	96.53%	97.79%
CHEMBL240	Q12809	HERG	96.15%	89.76%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.45%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.67%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.38%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.97%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.65%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.92%	95.89%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	87.63%	89.67%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	87.09%	85.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.93%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.68%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.99%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	84.64%	98.03%
CHEMBL242	Q92731	Estrogen receptor beta	84.34%	98.35%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	83.62%	80.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.42%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.12%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.25%	97.25%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.78%	93.56%
CHEMBL1907	P15144	Aminopeptidase N	81.44%	93.31%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.21%	82.38%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.35%	91.07%
CHEMBL4208	P20618	Proteasome component C5	80.16%	90.00%

Plants that contains it

• Cinnamomum camphora

Cross-Links

• PubChem: 21672114
• NPASS: NPC51198
• ChEMBL: CHEMBL1256416
• LOTUS: LTS0059840
• wikiData: Q104246301