Debromoaplysiatoxin

Details

• Internal ID: 11026ec5-d130-4063-910f-3d89e8aef950
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (1S,3R,4S,5S,9R,13S,14R)-13-hydroxy-9-[(1R)-1-hydroxyethyl]-3-[(2S,5S)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-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=CC(=CC=C4)O)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=CC(=CC=C4)O)OC)C)OC(=O)C[C@@H](OC(=O)C[C@@]1(O3)O)[C@@H](C)O)(C)C
• InChI: InChI=1S/C32H48O10/c1-18(11-12-24(38-7)22-9-8-10-23(34)13-22)29-20(3)26-16-32(41-29)30(5,6)15-19(2)31(37,42-32)17-28(36)39-25(21(4)33)14-27(35)40-26/h8-10,13,18-21,24-26,29,33-34,37H,11-12,14-17H2,1-7H3/t18-,19+,20-,21+,24-,25+,26-,29+,31-,32-/m0/s1
• InChI Key: REAZZDPREXHWNV-HJUJCDCNSA-N
• Popularity: 41 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₈O₁₀
• Molecular Weight: 592.70 g/mol
• Exact Mass: 592.32474772 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.39
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• CHEMBL2148106
• 52423-28-6
• NSC 271679
• BRN 4624539
• G-2408
• SCHEMBL22736825
• BDBM50391386
• J10.963K
• (1S,3R,4S,5S,9R,13S,14R)-13-hydroxy-9-[(1R)-1-hydroxyethyl]-3-[(2S,5S)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-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	+	0.9341	93.41%
Caco-2	-	0.8190	81.90%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7727	77.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8538	85.38%
OATP1B3 inhibitior	-	0.3456	34.56%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8731	87.31%
P-glycoprotein inhibitior	+	0.7220	72.20%
P-glycoprotein substrate	+	0.7538	75.38%
CYP3A4 substrate	+	0.7162	71.62%
CYP2C9 substrate	-	0.8072	80.72%
CYP2D6 substrate	-	0.8558	85.58%
CYP3A4 inhibition	-	0.6717	67.17%
CYP2C9 inhibition	-	0.8949	89.49%
CYP2C19 inhibition	-	0.8792	87.92%
CYP2D6 inhibition	-	0.9486	94.86%
CYP1A2 inhibition	-	0.7378	73.78%
CYP2C8 inhibition	+	0.5771	57.71%
CYP inhibitory promiscuity	-	0.9651	96.51%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6529	65.29%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.9317	93.17%
Skin irritation	-	0.7067	70.67%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4568	45.68%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5489	54.89%
skin sensitisation	-	0.9124	91.24%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7404	74.04%
Acute Oral Toxicity (c)	III	0.3458	34.58%
Estrogen receptor binding	+	0.7593	75.93%
Androgen receptor binding	+	0.6761	67.61%
Thyroid receptor binding	+	0.5599	55.99%
Glucocorticoid receptor binding	+	0.7867	78.67%
Aromatase binding	+	0.7299	72.99%
PPAR gamma	+	0.7786	77.86%
Honey bee toxicity	-	0.6998	69.98%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9737	97.37%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL299	P17252	Protein kinase C alpha	0.26 nM	Ki	PMID: 22625994
CHEMBL3045	P05771	Protein kinase C beta	0.17 nM	Ki	PMID: 22625994
CHEMBL2996	Q05655	Protein kinase C delta	9.7 nM; 0.2 nM; 9.7 nM	Ki; Ki; Ki	via Super-PRED; PMID: 22625994; PMID: 23582444
CHEMBL3582	Q02156	Protein kinase C epsilon	0.63 nM	Ki	PMID: 22625994
CHEMBL3616	P24723	Protein kinase C eta	0.11 nM	Ki	PMID: 22625994
CHEMBL2938	P05129	Protein kinase C gamma	0.38 nM	Ki	PMID: 22625994
CHEMBL3920	Q04759	Protein kinase C theta	0.11 nM	Ki	PMID: 22625994

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.20%	98.95%
CHEMBL240	Q12809	HERG	97.68%	89.76%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.47%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.97%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.91%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.41%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.20%	85.14%
CHEMBL236	P41143	Delta opioid receptor	94.90%	99.35%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.51%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.57%	89.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.35%	93.40%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.05%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.53%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.44%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.32%	97.09%
CHEMBL1907	P15144	Aminopeptidase N	86.62%	93.31%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	85.23%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.40%	93.56%
CHEMBL299	P17252	Protein kinase C alpha	84.18%	98.03%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.77%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	81.18%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.09%	99.23%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.90%	94.80%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.71%	95.89%
CHEMBL4208	P20618	Proteasome component C5	80.58%	90.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.54%	93.03%

Plants that contains it

• Cinnamomum camphora

Cross-Links

• PubChem: 5352033
• NPASS: NPC62800
• ChEMBL: CHEMBL2148106
• LOTUS: LTS0190868
• wikiData: Q104246299