bruceine J

Details

• Internal ID: 201ee4a3-1cc8-42ac-b2c5-79ad2a4bb457
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbutanoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylic acid
• SMILES (Canonical): CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)CC(C)C)(OC5)C(=O)O)O)O)C)O
• SMILES (Isomeric): CC1=C(C(=O)C[C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)OC(=O)CC(C)C)(OC5)C(=O)O)O)O)C)O
• InChI: InChI=1S/C25H32O11/c1-9(2)5-14(27)36-17-19-24-8-34-25(19,22(32)33)20(30)16(29)18(24)23(4)7-12(26)15(28)10(3)11(23)6-13(24)35-21(17)31/h9,11,13,16-20,28-30H,5-8H2,1-4H3,(H,32,33)/t11-,13+,16+,17+,18+,19+,20-,23-,24+,25-/m0/s1
• InChI Key: COWHTTGEYSMEQL-IELPQYESSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₁
• Molecular Weight: 508.50 g/mol
• Exact Mass: 508.19446183 g/mol
• Topological Polar Surface Area (TPSA): 177.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.51
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• 948038-38-8
• CHEMBL399970
• HY-N10899
• CS-0637466
• (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbutanoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8822	88.22%
Caco-2	-	0.8058	80.58%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8185	81.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8324	83.24%
OATP1B3 inhibitior	+	0.9001	90.01%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6404	64.04%
P-glycoprotein inhibitior	-	0.4911	49.11%
P-glycoprotein substrate	+	0.8467	84.67%
CYP3A4 substrate	+	0.6917	69.17%
CYP2C9 substrate	-	0.8170	81.70%
CYP2D6 substrate	-	0.8883	88.83%
CYP3A4 inhibition	-	0.8695	86.95%
CYP2C9 inhibition	-	0.7633	76.33%
CYP2C19 inhibition	-	0.8662	86.62%
CYP2D6 inhibition	-	0.9419	94.19%
CYP1A2 inhibition	-	0.8708	87.08%
CYP2C8 inhibition	-	0.5572	55.72%
CYP inhibitory promiscuity	-	0.8619	86.19%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6211	62.11%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9204	92.04%
Skin irritation	-	0.6059	60.59%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5840	58.40%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5658	56.58%
skin sensitisation	-	0.8646	86.46%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8382	83.82%
Acute Oral Toxicity (c)	III	0.5038	50.38%
Estrogen receptor binding	+	0.6513	65.13%
Androgen receptor binding	+	0.6893	68.93%
Thyroid receptor binding	-	0.5251	52.51%
Glucocorticoid receptor binding	+	0.6563	65.63%
Aromatase binding	+	0.6958	69.58%
PPAR gamma	+	0.6090	60.90%
Honey bee toxicity	-	0.6598	65.98%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9935	99.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	97.33%	95.17%
CHEMBL4040	P28482	MAP kinase ERK2	96.90%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.73%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.12%	96.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	95.09%	96.47%
CHEMBL2581	P07339	Cathepsin D	94.97%	98.95%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	94.76%	96.38%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.89%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.55%	85.14%
CHEMBL299	P17252	Protein kinase C alpha	92.27%	98.03%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.15%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.11%	96.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.62%	96.21%
CHEMBL2996	Q05655	Protein kinase C delta	90.44%	97.79%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.03%	97.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.50%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.84%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.33%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.48%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.24%	95.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.13%	89.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.95%	93.04%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.42%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	83.84%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.68%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.00%	97.28%
CHEMBL5028	O14672	ADAM10	82.78%	97.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.30%	93.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.88%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	81.71%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.30%	97.09%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.02%	82.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.90%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.79%	95.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.73%	90.71%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	80.14%	97.47%

Plants that contains it

• Asplenium normale
• Brucea javanica
• Carpobrotus edulis
• Castanea crenata
• Centrolobium tomentosum
• Ceratophyllum submersum
• Dracocephalum kotschyi
• Lippia carviodora
• Myrica nana
• Psilostrophe cooperi
• Sideritis tragoriganum
• Solanum jamaicense
• Trifolium alexandrinum

Cross-Links

• PubChem: 23656476
• NPASS: NPC173686
• LOTUS: LTS0224487
• wikiData: Q104967341