Bruceoside A

Details

• Internal ID: 89be5224-bab1-4132-990c-cc6e7e18b610
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8S,9S,13S,14R,15R,16S,17S)-15,16-dihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,10-dioxo-11-[(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-11-ene-17-carboxylate
• SMILES (Canonical): CC1C2CC3C45COC(C4C(C(=O)O3)OC(=O)C=C(C)C)(C(C(C5C2(C=C(C1=O)OC6C(C(C(C(O6)CO)O)O)O)C)O)O)C(=O)OC
• SMILES (Isomeric): C[C@H]1[C@@H]2C[C@@H]3[C@@]45CO[C@@]([C@@H]4[C@H](C(=O)O3)OC(=O)C=C(C)C)([C@H]([C@@H]([C@@H]5[C@]2(C=C(C1=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)O)O)C(=O)OC
• InChI: InChI=1S/C32H42O16/c1-11(2)6-17(34)48-23-25-31-10-44-32(25,29(42)43-5)26(40)22(39)24(31)30(4)8-14(18(35)12(3)13(30)7-16(31)47-27(23)41)45-28-21(38)20(37)19(36)15(9-33)46-28/h6,8,12-13,15-16,19-26,28,33,36-40H,7,9-10H2,1-5H3/t12-,13-,15+,16+,19+,20-,21+,22+,23+,24+,25+,26-,28+,30-,31+,32-/m0/s1
• InChI Key: AKSGLPBROCFVSE-TUHDNREHSA-N
• Popularity: 9 references 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: 0.10
• Atomic LogP (AlogP): -2.37
• H-Bond Acceptor: 16
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• Bruceoside-A
• 63306-30-9
• CHEBI:3192
• CHEMBL504960
• bruceosideA
• LS-109750
• AC1L9BNS
• C32H42O16
• DTXSID80979402
• AKSGLPBROCFVSE-TUHDNREHSA-N
• HY-N8995
• AKOS040761433
• CS-0149509
• C08753
• Q27105982
• methyl (1R,2S,3R,6R,8S,9S,13S,14R,15R,16S,17S)-15,16-dihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,10-dioxo-11-[(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-11-ene-17-carboxylate
• Methyl 2-(hexopyranosyloxy)-11,12-dihydroxy-15-[(3-methylbut-2-enoyl)oxy]-3,16-dioxo-13,20-epoxypicras-1-en-21-oate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7012	70.12%
Caco-2	-	0.8733	87.33%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7392	73.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8293	82.93%
OATP1B3 inhibitior	+	0.9346	93.46%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8101	81.01%
P-glycoprotein inhibitior	+	0.7044	70.44%
P-glycoprotein substrate	+	0.7692	76.92%
CYP3A4 substrate	+	0.7124	71.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8918	89.18%
CYP3A4 inhibition	-	0.8951	89.51%
CYP2C9 inhibition	-	0.8400	84.00%
CYP2C19 inhibition	-	0.8450	84.50%
CYP2D6 inhibition	-	0.9304	93.04%
CYP1A2 inhibition	-	0.8917	89.17%
CYP2C8 inhibition	+	0.6118	61.18%
CYP inhibitory promiscuity	-	0.8718	87.18%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5995	59.95%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9167	91.67%
Skin irritation	-	0.7143	71.43%
Skin corrosion	-	0.9347	93.47%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7109	71.09%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5948	59.48%
skin sensitisation	-	0.8488	84.88%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5336	53.36%
Acute Oral Toxicity (c)	III	0.5883	58.83%
Estrogen receptor binding	+	0.7762	77.62%
Androgen receptor binding	+	0.7234	72.34%
Thyroid receptor binding	-	0.5341	53.41%
Glucocorticoid receptor binding	+	0.6725	67.25%
Aromatase binding	+	0.6767	67.67%
PPAR gamma	+	0.7339	73.39%
Honey bee toxicity	-	0.6174	61.74%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9128	91.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.48%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.46%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.28%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.36%	96.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	95.45%	89.34%
CHEMBL2581	P07339	Cathepsin D	90.93%	98.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.33%	91.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.69%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.14%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.95%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.85%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.76%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	87.49%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.27%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.19%	97.28%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.77%	94.33%
CHEMBL5028	O14672	ADAM10	83.27%	97.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.52%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.50%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.22%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.45%	96.61%

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: 441789
• NPASS: NPC190065
• ChEMBL: CHEMBL504960
• LOTUS: LTS0190451
• wikiData: Q27105982