Picrasan-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: 0f2a3953-2794-4144-941d-d2f837af0099
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (2R,3R,6R,8S,9R,12S,13S,14S,15R,16R,17R)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,19-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)(CO5)C(=O)OC)O)O)C)O
• SMILES (Isomeric): C[C@@H]1CC(=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)OC(=O)/C=C(\C)/C(C)C)(CO5)C(=O)OC)O)O)C)O
• InChI: InChI=1S/C28H38O11/c1-11(2)12(3)8-17(30)39-19-21-27(25(35)36-6)10-37-28(21)16(38-24(19)34)9-14-13(4)7-15(29)22(32)26(14,5)20(28)18(31)23(27)33/h8,11,13-14,16,18-23,31-33H,7,9-10H2,1-6H3/b12-8+/t13-,14+,16-,18-,19-,20-,21+,22-,23+,26+,27+,28?/m1/s1
• InChI Key: QUFIQQXAIBYXLR-HEVMZGAASA-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: 1.70
• Atomic LogP (AlogP): 0.32
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• DTXSID601100978
• Picrasan-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))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9461	94.61%
Caco-2	-	0.7977	79.77%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8150	81.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8623	86.23%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8739	87.39%
P-glycoprotein inhibitior	+	0.6989	69.89%
P-glycoprotein substrate	+	0.7634	76.34%
CYP3A4 substrate	+	0.7105	71.05%
CYP2C9 substrate	-	0.8253	82.53%
CYP2D6 substrate	-	0.8954	89.54%
CYP3A4 inhibition	-	0.7852	78.52%
CYP2C9 inhibition	-	0.7951	79.51%
CYP2C19 inhibition	-	0.8467	84.67%
CYP2D6 inhibition	-	0.9413	94.13%
CYP1A2 inhibition	-	0.8327	83.27%
CYP2C8 inhibition	+	0.5274	52.74%
CYP inhibitory promiscuity	-	0.9291	92.91%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5617	56.17%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9217	92.17%
Skin irritation	-	0.6481	64.81%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	+	0.5099	50.99%
Human Ether-a-go-go-Related Gene inhibition	-	0.6678	66.78%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.5908	59.08%
skin sensitisation	-	0.8465	84.65%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6635	66.35%
Acute Oral Toxicity (c)	I	0.4133	41.33%
Estrogen receptor binding	+	0.7706	77.06%
Androgen receptor binding	+	0.7176	71.76%
Thyroid receptor binding	-	0.5073	50.73%
Glucocorticoid receptor binding	+	0.7607	76.07%
Aromatase binding	+	0.6804	68.04%
PPAR gamma	+	0.6802	68.02%
Honey bee toxicity	-	0.5540	55.40%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9895	98.95%

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	98.67%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.31%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.08%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.39%	85.14%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	94.45%	89.34%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	92.63%	95.71%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.73%	96.47%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	91.42%	85.30%
CHEMBL3437	Q16853	Amine oxidase, copper containing	90.03%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.71%	96.77%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.87%	96.00%
CHEMBL340	P08684	Cytochrome P450 3A4	88.01%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.56%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.05%	91.07%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.02%	97.25%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.14%	85.31%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.98%	98.75%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.53%	92.88%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.46%	97.14%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.07%	94.33%
CHEMBL3837	P07711	Cathepsin L	83.71%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.44%	95.89%
CHEMBL2581	P07339	Cathepsin D	83.29%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.12%	97.09%
CHEMBL2535	P11166	Glucose transporter	82.82%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.35%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.99%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.94%	89.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.89%	89.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.34%	95.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.35%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.28%	90.71%

Plants that contains it

• Brucea antidysenterica

Cross-Links

• PubChem: 6444293
• LOTUS: LTS0034204
• wikiData: Q105228133