[(1S,2S,3S,5S,8E,10S,11R)-2-hydroxy-5,9-dimethyl-14-methylidene-13-oxo-4,12-dioxatricyclo[9.3.0.03,5]tetradec-8-en-10-yl] 2-methylpropanoate

Details

• Internal ID: 5c47bfcb-20c6-4cf7-a710-7e8d8a7c0ee1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(1S,2S,3S,5S,8E,10S,11R)-2-hydroxy-5,9-dimethyl-14-methylidene-13-oxo-4,12-dioxatricyclo[9.3.0.03,5]tetradec-8-en-10-yl] 2-methylpropanoate
• SMILES (Canonical): CC1=CCCC2(C(O2)C(C3C(C1OC(=O)C(C)C)OC(=O)C3=C)O)C
• SMILES (Isomeric): C/C/1=C\CC[C@]2([C@@H](O2)[C@H]([C@H]3[C@H]([C@H]1OC(=O)C(C)C)OC(=O)C3=C)O)C
• InChI: InChI=1S/C19H26O6/c1-9(2)17(21)23-14-10(3)7-6-8-19(5)16(25-19)13(20)12-11(4)18(22)24-15(12)14/h7,9,12-16,20H,4,6,8H2,1-3,5H3/b10-7+/t12-,13-,14-,15+,16-,19-/m0/s1
• InChI Key: FKAXTWSRTCKBKT-VPPQWMCISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₆
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.17293854 g/mol
• Topological Polar Surface Area (TPSA): 85.40 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.91
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9573	95.73%
Caco-2	-	0.5389	53.89%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6494	64.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9073	90.73%
OATP1B3 inhibitior	+	0.8305	83.05%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.8413	84.13%
P-glycoprotein inhibitior	-	0.6289	62.89%
P-glycoprotein substrate	-	0.6419	64.19%
CYP3A4 substrate	+	0.6546	65.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8811	88.11%
CYP3A4 inhibition	-	0.5933	59.33%
CYP2C9 inhibition	-	0.7571	75.71%
CYP2C19 inhibition	-	0.8092	80.92%
CYP2D6 inhibition	-	0.9229	92.29%
CYP1A2 inhibition	+	0.5292	52.92%
CYP2C8 inhibition	-	0.6556	65.56%
CYP inhibitory promiscuity	-	0.9132	91.32%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4509	45.09%
Eye corrosion	-	0.9793	97.93%
Eye irritation	-	0.8749	87.49%
Skin irritation	-	0.5353	53.53%
Skin corrosion	-	0.8332	83.32%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6699	66.99%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.5066	50.66%
skin sensitisation	-	0.7083	70.83%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6713	67.13%
Acute Oral Toxicity (c)	III	0.5091	50.91%
Estrogen receptor binding	+	0.7293	72.93%
Androgen receptor binding	+	0.6149	61.49%
Thyroid receptor binding	+	0.6043	60.43%
Glucocorticoid receptor binding	+	0.7290	72.90%
Aromatase binding	+	0.5581	55.81%
PPAR gamma	+	0.6585	65.85%
Honey bee toxicity	-	0.6254	62.54%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9589	95.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	96.72%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.67%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.86%	94.45%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.84%	96.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.84%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.11%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.84%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.18%	89.00%
CHEMBL2581	P07339	Cathepsin D	87.51%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.46%	99.23%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.63%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.20%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.02%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.19%	95.50%
CHEMBL230	P35354	Cyclooxygenase-2	83.14%	89.63%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.68%	97.14%
CHEMBL5028	O14672	ADAM10	82.62%	97.50%
CHEMBL3401	O75469	Pregnane X receptor	82.20%	94.73%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.75%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.68%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.53%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.62%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.37%	95.89%

Plants that contains it

• Schistostephium crataegifolium

Cross-Links

• PubChem: 163190856
• LOTUS: LTS0046596
• wikiData: Q104996473