Bruceanol G

Details

• Internal ID: 60250041-fccf-44ab-86f4-917aa37ee7eb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8S,9R,12S,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecane-17-carboxylate
• SMILES (Canonical): CC1CC(=O)C(C2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C(C)(C)OC(=O)C)(OC5)C(=O)OC)O)O)C)O
• SMILES (Isomeric): C[C@@H]1CC(=O)[C@H]([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(C)(C)OC(=O)C)(OC5)C(=O)OC)O)O)C)O
• InChI: InChI=1S/C30H40O13/c1-12-8-16(32)23(35)28(6)15(12)10-17-29-11-40-30(26(38)39-7,24(36)19(34)21(28)29)22(29)20(25(37)41-17)42-18(33)9-13(2)27(4,5)43-14(3)31/h9,12,15,17,19-24,34-36H,8,10-11H2,1-7H3/b13-9+/t12-,15+,17-,19-,20-,21-,22-,23-,24+,28+,29-,30+/m1/s1
• InChI Key: LNFLSPAGUXRAML-GLQLFLDVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₀O₁₃
• Molecular Weight: 608.60 g/mol
• Exact Mass: 608.24689133 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.00
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 168301-20-0
• Methyl (1beta,11beta,12alpha,15beta(E))-15-((4-(acetyloxy)-3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-1,11,12-trihydroxy-2,16-dioxopicrasan-21-oate
• CHEMBL445045
• DTXSID101336734
• methyl (1R,2S,3R,6R,8S,9R,12S,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecane-17-carboxylate
• Picrasan-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	+	0.9422	94.22%
Caco-2	-	0.8276	82.76%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7866	78.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8603	86.03%
OATP1B3 inhibitior	+	0.9292	92.92%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9068	90.68%
P-glycoprotein inhibitior	+	0.7631	76.31%
P-glycoprotein substrate	+	0.8380	83.80%
CYP3A4 substrate	+	0.7285	72.85%
CYP2C9 substrate	-	0.8253	82.53%
CYP2D6 substrate	-	0.8954	89.54%
CYP3A4 inhibition	-	0.7186	71.86%
CYP2C9 inhibition	-	0.7836	78.36%
CYP2C19 inhibition	-	0.8348	83.48%
CYP2D6 inhibition	-	0.9331	93.31%
CYP1A2 inhibition	-	0.8286	82.86%
CYP2C8 inhibition	+	0.5854	58.54%
CYP inhibitory promiscuity	-	0.9045	90.45%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5305	53.05%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9179	91.79%
Skin irritation	-	0.6577	65.77%
Skin corrosion	-	0.9286	92.86%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5311	53.11%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6806	68.06%
skin sensitisation	-	0.8406	84.06%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5719	57.19%
Acute Oral Toxicity (c)	III	0.5975	59.75%
Estrogen receptor binding	+	0.7634	76.34%
Androgen receptor binding	+	0.7288	72.88%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7844	78.44%
Aromatase binding	+	0.7117	71.17%
PPAR gamma	+	0.6996	69.96%
Honey bee toxicity	-	0.5428	54.28%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9813	98.13%

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	98.62%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.30%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.52%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.10%	97.25%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	95.43%	95.71%
CHEMBL2581	P07339	Cathepsin D	94.81%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	91.63%	89.34%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.26%	96.77%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.28%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.46%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.05%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.98%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.52%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.28%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.84%	94.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.91%	95.71%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.62%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.58%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.44%	99.23%
CHEMBL5028	O14672	ADAM10	83.27%	97.50%
CHEMBL1902	P62942	FK506-binding protein 1A	83.10%	97.05%
CHEMBL340	P08684	Cytochrome P450 3A4	82.78%	91.19%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.66%	89.50%
CHEMBL1951	P21397	Monoamine oxidase A	82.43%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.41%	94.45%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.91%	92.88%
CHEMBL2996	Q05655	Protein kinase C delta	81.77%	97.79%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.50%	90.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.47%	97.09%

Plants that contains it

• Brucea antidysenterica

Cross-Links

• PubChem: 6440620
• LOTUS: LTS0069800
• wikiData: Q105091123