CID 6438433

Details

• Internal ID: fdcc17e5-d430-4d5d-b0db-de8c3a6489af
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,6R,8S,9R,13S,14S,15R)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-11,15,16-trihydroxy-9,13-dimethyl-4,12-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecane-17-carboxylate
• SMILES (Canonical): CC1CC(C(=O)C2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C(C)C)(OC5)C(=O)OC)O)O)C)O
• SMILES (Isomeric): C[C@@H]1CC(C(=O)[C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H](C(C([C@@H]4C(C(=O)O3)OC(=O)/C=C(\C)/C(C)C)(OC5)C(=O)OC)O)O)C)O
• InChI: InChI=1S/C28H38O11/c1-11(2)12(3)8-17(30)39-19-21-27-10-37-28(21,25(35)36-6)23(33)18(31)20(27)26(5)14(9-16(27)38-24(19)34)13(4)7-15(29)22(26)32/h8,11,13-16,18-21,23,29,31,33H,7,9-10H2,1-6H3/b12-8+/t13-,14+,15?,16-,18-,19?,20-,21-,23?,26+,27-,28?/m1/s1
• InChI Key: OFEQMSZQMBVXLR-ZOJXLSIESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₁₁
• Molecular Weight: 550.60 g/mol
• Exact Mass: 550.24141202 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 0.32
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 168569-27-5
• Methyl (1R,2S,6R,8S,9R,13S,14S,15R)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-11,15,16-trihydroxy-9,13-dimethyl-4,12-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecane-17-carboxylate
• Bruceanol II
• DTXSID801336735
• Methyl 15-((3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-2,11,12-trihydroxy-1,16-dioxopicrasan-21-oate (11beta,12alpha,15beta(E))-
• Picrasan-21-oic acid, 15-((3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-2,11,12-trihydroxy-1,16-dioxo-, methyl ester (11beta,12alpha,15beta(E))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9400	94.00%
Caco-2	-	0.7826	78.26%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7414	74.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8621	86.21%
OATP1B3 inhibitior	+	0.9648	96.48%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6715	67.15%
P-glycoprotein inhibitior	+	0.6777	67.77%
P-glycoprotein substrate	+	0.8232	82.32%
CYP3A4 substrate	+	0.7054	70.54%
CYP2C9 substrate	-	0.8217	82.17%
CYP2D6 substrate	-	0.8936	89.36%
CYP3A4 inhibition	-	0.6779	67.79%
CYP2C9 inhibition	-	0.8454	84.54%
CYP2C19 inhibition	-	0.8668	86.68%
CYP2D6 inhibition	-	0.9242	92.42%
CYP1A2 inhibition	-	0.8495	84.95%
CYP2C8 inhibition	+	0.4829	48.29%
CYP inhibitory promiscuity	-	0.9329	93.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4666	46.66%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9184	91.84%
Skin irritation	-	0.6114	61.14%
Skin corrosion	-	0.9258	92.58%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5265	52.65%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.8286	82.86%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.6081	60.81%
Acute Oral Toxicity (c)	III	0.5067	50.67%
Estrogen receptor binding	+	0.7959	79.59%
Androgen receptor binding	+	0.7180	71.80%
Thyroid receptor binding	-	0.5230	52.30%
Glucocorticoid receptor binding	+	0.7478	74.78%
Aromatase binding	+	0.6596	65.96%
PPAR gamma	+	0.6481	64.81%
Honey bee toxicity	-	0.5268	52.68%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9687	96.87%

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	98.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.65%	96.09%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	94.83%	95.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.78%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.65%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.46%	96.77%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	94.04%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.15%	94.45%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.93%	96.47%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	91.44%	91.07%
CHEMBL2581	P07339	Cathepsin D	91.38%	98.95%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	89.86%	98.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	89.29%	89.50%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	88.04%	97.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.51%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	86.75%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.43%	94.33%
CHEMBL3437	Q16853	Amine oxidase, copper containing	86.04%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.17%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.60%	89.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.23%	96.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.95%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.35%	99.23%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.43%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.92%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.62%	97.14%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.59%	94.80%
CHEMBL299	P17252	Protein kinase C alpha	81.48%	98.03%
CHEMBL5028	O14672	ADAM10	81.29%	97.50%
CHEMBL2535	P11166	Glucose transporter	80.98%	98.75%

Plants that contains it

• Brucea antidysenterica

Cross-Links

• PubChem: 6438433
• LOTUS: LTS0089951
• wikiData: Q105190921