[(1R,2R,3S,7R,9R,10S,11R,13R,14R)-2-hydroxy-1,9-dimethyl-4-methylidene-5-oxo-6,12-dioxatetracyclo[8.4.0.03,7.011,13]tetradecan-14-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: b1524a86-e61d-425c-a633-af42921a04dc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: [(1R,2R,3S,7R,9R,10S,11R,13R,14R)-2-hydroxy-1,9-dimethyl-4-methylidene-5-oxo-6,12-dioxatetracyclo[8.4.0.03,7.011,13]tetradecan-14-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C(O2)C3C1(C(C4C(CC3C)OC(=O)C4=C)O)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1[C@H]2[C@H](O2)[C@@H]3[C@@]1([C@@H]([C@H]4[C@@H](C[C@H]3C)OC(=O)C4=C)O)C
• InChI: InChI=1S/C20H26O6/c1-6-8(2)18(22)26-17-15-14(25-15)13-9(3)7-11-12(10(4)19(23)24-11)16(21)20(13,17)5/h6,9,11-17,21H,4,7H2,1-3,5H3/b8-6+/t9-,11-,12-,13-,14-,15-,16-,17+,20-/m1/s1
• InChI Key: UYJDDGUIDPUWHD-SUXGSYMHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.17293854 g/mol
• Topological Polar Surface Area (TPSA): 85.40 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 1.77
• 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	+	0.9296	92.96%
Caco-2	-	0.5409	54.09%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6230	62.30%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8666	86.66%
OATP1B3 inhibitior	+	0.8855	88.55%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8030	80.30%
P-glycoprotein inhibitior	-	0.5616	56.16%
P-glycoprotein substrate	-	0.7568	75.68%
CYP3A4 substrate	+	0.6343	63.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8793	87.93%
CYP3A4 inhibition	+	0.5889	58.89%
CYP2C9 inhibition	-	0.8792	87.92%
CYP2C19 inhibition	-	0.8234	82.34%
CYP2D6 inhibition	-	0.9441	94.41%
CYP1A2 inhibition	-	0.8018	80.18%
CYP2C8 inhibition	-	0.6867	68.67%
CYP inhibitory promiscuity	-	0.8846	88.46%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4636	46.36%
Eye corrosion	-	0.9797	97.97%
Eye irritation	-	0.9265	92.65%
Skin irritation	-	0.6242	62.42%
Skin corrosion	-	0.8872	88.72%
Ames mutagenesis	-	0.5832	58.32%
Human Ether-a-go-go-Related Gene inhibition	-	0.5923	59.23%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	-	0.7204	72.04%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.8354	83.54%
Acute Oral Toxicity (c)	II	0.3690	36.90%
Estrogen receptor binding	+	0.8392	83.92%
Androgen receptor binding	+	0.5350	53.50%
Thyroid receptor binding	-	0.5111	51.11%
Glucocorticoid receptor binding	+	0.7280	72.80%
Aromatase binding	+	0.5965	59.65%
PPAR gamma	+	0.6555	65.55%
Honey bee toxicity	-	0.6258	62.58%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9368	93.68%

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	97.69%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	93.77%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.66%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.15%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.66%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.48%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.50%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	89.39%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.96%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.49%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.83%	89.34%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.53%	92.94%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.33%	91.07%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.65%	93.00%
CHEMBL3401	O75469	Pregnane X receptor	82.99%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.63%	95.50%
CHEMBL299	P17252	Protein kinase C alpha	82.42%	98.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.40%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	81.04%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.45%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.04%	97.36%

Plants that contains it

• Helenium puberulum

Cross-Links

• PubChem: 163047675
• LOTUS: LTS0195535
• wikiData: Q105281512