bruceosideB

Details

• Internal ID: 0a3ec819-364a-4388-b56c-fe6e265747a3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-15,16-dihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
• SMILES (Canonical): CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C)(OC5)C(=O)OC)O)O)C)OC6C(C(C(C(O6)CO)O)O)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)C=C(C)C)(OC5)C(=O)OC)O)O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C32H42O16/c1-11(2)6-17(35)47-23-25-31-10-44-32(25,29(42)43-5)26(40)21(39)24(31)30(4)8-14(34)22(12(3)13(30)7-16(31)46-27(23)41)48-28-20(38)19(37)18(36)15(9-33)45-28/h6,13,15-16,18-21,23-26,28,33,36-40H,7-10H2,1-5H3/t13-,15+,16+,18+,19-,20+,21+,23+,24+,25+,26-,28-,30-,31+,32-/m0/s1
• InChI Key: JMEAKUYWADWLJX-PKMWWCJOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₂O₁₆
• Molecular Weight: 682.70 g/mol
• Exact Mass: 682.24728525 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -2.22
• H-Bond Acceptor: 16
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• 69687-69-0
• bruceosideB
• SCHEMBL1276836
• LS-109749
• Methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-15,16-dihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7682	76.82%
Caco-2	-	0.8734	87.34%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7661	76.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8377	83.77%
OATP1B3 inhibitior	+	0.9135	91.35%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8310	83.10%
P-glycoprotein inhibitior	+	0.7212	72.12%
P-glycoprotein substrate	+	0.8328	83.28%
CYP3A4 substrate	+	0.7168	71.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8918	89.18%
CYP3A4 inhibition	-	0.8843	88.43%
CYP2C9 inhibition	-	0.8215	82.15%
CYP2C19 inhibition	-	0.8570	85.70%
CYP2D6 inhibition	-	0.9403	94.03%
CYP1A2 inhibition	-	0.8924	89.24%
CYP2C8 inhibition	+	0.6055	60.55%
CYP inhibitory promiscuity	-	0.9127	91.27%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6114	61.14%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9165	91.65%
Skin irritation	-	0.6906	69.06%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.5577	55.77%
Human Ether-a-go-go-Related Gene inhibition	+	0.7319	73.19%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6301	63.01%
skin sensitisation	-	0.8716	87.16%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.7247	72.47%
Acute Oral Toxicity (c)	I	0.4259	42.59%
Estrogen receptor binding	+	0.7702	77.02%
Androgen receptor binding	+	0.7111	71.11%
Thyroid receptor binding	-	0.5430	54.30%
Glucocorticoid receptor binding	+	0.7102	71.02%
Aromatase binding	+	0.6538	65.38%
PPAR gamma	+	0.7063	70.63%
Honey bee toxicity	-	0.5719	57.19%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9727	97.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.57%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.62%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.14%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.24%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.02%	96.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	95.63%	89.34%
CHEMBL2581	P07339	Cathepsin D	94.87%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.74%	96.21%
CHEMBL299	P17252	Protein kinase C alpha	91.50%	98.03%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.34%	91.24%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.02%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.79%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.27%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	88.68%	97.79%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.18%	96.47%
CHEMBL5028	O14672	ADAM10	87.74%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.56%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.17%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.87%	86.33%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	86.81%	81.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.48%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.42%	96.77%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.30%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.75%	94.33%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.38%	98.75%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	84.31%	97.47%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.59%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.15%	95.89%
CHEMBL4072	P07858	Cathepsin B	82.84%	93.67%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.48%	95.71%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.16%	97.28%
CHEMBL1993	P26358	DNA (cytosine-5)-methyltransferase 1	81.99%	95.44%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.99%	97.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.31%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	80.79%	92.50%

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: 3000796
• NPASS: NPC164575
• LOTUS: LTS0055846
• wikiData: Q105131311