Bruceanol C

Details

• Internal ID: 228509f9-3449-4d0f-896d-21a2ab81d1e5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (2R,3S,6R,8S,12S,13S,14R,15R,16S,17R)-3-[(E)-5-acetyloxy-4,5-dimethyl-2-oxohex-3-enoyl]-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
• SMILES (Canonical): CC1=CC(=O)C(C2(C1CC3C45C2C(C(C(C4C(C(=O)O3)C(=O)C(=O)C=C(C)C(C)(C)OC(=O)C)(OC5)C(=O)OC)O)O)C)O
• SMILES (Isomeric): CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@@H]3C45[C@@H]2[C@H]([C@@H]([C@@]([C@@H]4[C@H](C(=O)O3)C(=O)C(=O)/C=C(\C)/C(C)(C)OC(=O)C)(OC5)C(=O)OC)O)O)C)O
• InChI: InChI=1S/C31H38O13/c1-12-8-17(34)24(37)29(6)15(12)10-18-30-11-42-31(27(40)41-7,25(38)21(36)23(29)30)22(30)19(26(39)43-18)20(35)16(33)9-13(2)28(4,5)44-14(3)32/h8-9,15,18-19,21-25,36-38H,10-11H2,1-7H3/b13-9+/t15-,18+,19+,21+,22+,23+,24+,25-,29-,30?,31+/m0/s1
• InChI Key: ZIQXGRZNRFCISN-OFGJEKSYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₈O₁₃
• Molecular Weight: 618.60 g/mol
• Exact Mass: 618.23124126 g/mol
• Topological Polar Surface Area (TPSA): 200.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.23
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 114586-21-9
• DTXSID401336733
• Methyl (2R,3S,6R,8S,12S,13S,14R,15R,16S,17R)-3-[(E)-5-acetyloxy-4,5-dimethyl-2-oxohex-3-enoyl]-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
• Picras-3-en-21-oic acid, 15-((4-(acetyloxy)-3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-1,11,12-trihydroxy-2,16-dioxo-, methyl ester, (1beta,11beta,12alpha,15beta(E))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9094	90.94%
Caco-2	-	0.8247	82.47%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8028	80.28%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.8226	82.26%
OATP1B3 inhibitior	+	0.9545	95.45%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9436	94.36%
P-glycoprotein inhibitior	+	0.7631	76.31%
P-glycoprotein substrate	+	0.8599	85.99%
CYP3A4 substrate	+	0.7328	73.28%
CYP2C9 substrate	-	0.8217	82.17%
CYP2D6 substrate	-	0.8913	89.13%
CYP3A4 inhibition	-	0.7964	79.64%
CYP2C9 inhibition	-	0.8531	85.31%
CYP2C19 inhibition	-	0.8300	83.00%
CYP2D6 inhibition	-	0.9193	91.93%
CYP1A2 inhibition	-	0.8397	83.97%
CYP2C8 inhibition	+	0.5831	58.31%
CYP inhibitory promiscuity	-	0.8827	88.27%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5006	50.06%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.9140	91.40%
Skin irritation	-	0.6643	66.43%
Skin corrosion	-	0.9246	92.46%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5232	52.32%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5515	55.15%
skin sensitisation	-	0.8168	81.68%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.8027	80.27%
Acute Oral Toxicity (c)	III	0.5269	52.69%
Estrogen receptor binding	+	0.7570	75.70%
Androgen receptor binding	+	0.7358	73.58%
Thyroid receptor binding	+	0.5335	53.35%
Glucocorticoid receptor binding	+	0.8004	80.04%
Aromatase binding	+	0.6677	66.77%
PPAR gamma	+	0.7294	72.94%
Honey bee toxicity	-	0.6776	67.76%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9606	96.06%

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	98.55%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.40%	85.14%
CHEMBL2581	P07339	Cathepsin D	95.56%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.81%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.67%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	92.04%	91.07%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.52%	97.25%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	89.83%	95.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.32%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.46%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.89%	96.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	87.57%	90.93%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.47%	94.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.52%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.44%	95.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.37%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.97%	97.14%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	85.82%	97.47%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.73%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.49%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.68%	96.95%
CHEMBL5028	O14672	ADAM10	84.32%	97.50%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.87%	89.34%
CHEMBL340	P08684	Cytochrome P450 3A4	83.52%	91.19%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.49%	97.21%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.97%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.96%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.19%	97.09%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.61%	100.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.49%	97.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.02%	91.24%

Plants that contains it

• Brucea antidysenterica

Cross-Links

• PubChem: 6440833
• LOTUS: LTS0154963
• wikiData: Q105091116