Picras-3-en-21-oic acid, 15-((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))-

Details

• Internal ID: 8465c906-faa4-47c2-b825-74a5c294112e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-3-[(E)-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]nonadec-9-ene-17-carboxylate
• SMILES (Canonical): CC1=CC(=O)C(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): CC1=CC(=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)(OC5)C(=O)OC)O)O)C)O
• InChI: InChI=1S/C28H36O11/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/h7-8,11,14,16,18-23,31-33H,9-10H2,1-6H3/b12-8+/t14-,16+,18+,19+,20+,21+,22+,23-,26-,27+,28-/m0/s1
• InChI Key: BOUBPFYATGCWDW-UENHEUQBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₁₁
• Molecular Weight: 548.60 g/mol
• Exact Mass: 548.22576196 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.24
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• methyl (1beta,11beta,12alpha,15beta)-15-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-1,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-21-oate
• Picras-3-en-21-oic acid, 15-((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))-
• CHEBI:65526
• Q27133975

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9094	90.94%
Caco-2	-	0.7938	79.38%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8028	80.28%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8495	84.95%
OATP1B3 inhibitior	+	0.9545	95.45%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8745	87.45%
P-glycoprotein inhibitior	+	0.7296	72.96%
P-glycoprotein substrate	+	0.9085	90.85%
CYP3A4 substrate	+	0.7098	70.98%
CYP2C9 substrate	-	0.8217	82.17%
CYP2D6 substrate	-	0.8936	89.36%
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	+	0.4673	46.73%
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	-	0.9185	91.85%
Skin irritation	-	0.6643	66.43%
Skin corrosion	-	0.9246	92.46%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5779	57.79%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8168	81.68%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6263	62.63%
Acute Oral Toxicity (c)	III	0.5269	52.69%
Estrogen receptor binding	+	0.7907	79.07%
Androgen receptor binding	+	0.6833	68.33%
Thyroid receptor binding	+	0.5565	55.65%
Glucocorticoid receptor binding	+	0.7705	77.05%
Aromatase binding	+	0.6727	67.27%
PPAR gamma	+	0.7010	70.10%
Honey bee toxicity	-	0.5770	57.70%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
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	99.35%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.95%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.65%	96.00%
CHEMBL2581	P07339	Cathepsin D	95.42%	98.95%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	94.44%	95.71%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	93.40%	96.47%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.22%	94.45%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	91.64%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	91.13%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.01%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.64%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.18%	85.14%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	88.89%	97.47%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.99%	94.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.89%	97.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.77%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.57%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.34%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.36%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.34%	97.28%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.78%	97.25%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.33%	89.34%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.95%	96.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.66%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.43%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.85%	86.33%
CHEMBL5028	O14672	ADAM10	81.73%	97.50%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.41%	94.80%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.10%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.05%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.97%	95.50%
CHEMBL1937	Q92769	Histone deacetylase 2	80.74%	94.75%

Plants that contains it

• Brucea antidysenterica

Cross-Links

• PubChem: 70697724
• LOTUS: LTS0164842
• wikiData: Q27133975