[(1R,2R,4S,7E,9R,10R,11R)-10-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-9-yl] 3-methylbut-2-enoate

Details

• Internal ID: 9a68c370-ea87-468a-83e3-017e1d4ed519
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(1R,2R,4S,7E,9R,10R,11R)-10-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-9-yl] 3-methylbut-2-enoate
• SMILES (Canonical): CC1=CCCC2(C(O2)C3C(C(C1OC(=O)C=C(C)C)O)C(=C)C(=O)O3)C
• SMILES (Isomeric): C/C/1=C\CC[C@]2([C@H](O2)[C@H]3[C@@H]([C@H]([C@@H]1OC(=O)C=C(C)C)O)C(=C)C(=O)O3)C
• InChI: InChI=1S/C20H26O6/c1-10(2)9-13(21)24-16-11(3)7-6-8-20(5)18(26-20)17-14(15(16)22)12(4)19(23)25-17/h7,9,14-18,22H,4,6,8H2,1-3,5H3/b11-7+/t14-,15-,16-,17-,18-,20+/m1/s1
• InChI Key: XYEXFSWBSVHZOV-PDYHQHBKSA-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: 2.30
• Atomic LogP (AlogP): 2.22
• 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	+	0.9720	97.20%
Caco-2	+	0.5310	53.10%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6436	64.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9184	91.84%
OATP1B3 inhibitior	+	0.8341	83.41%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.5510	55.10%
P-glycoprotein inhibitior	-	0.5110	51.10%
P-glycoprotein substrate	-	0.5932	59.32%
CYP3A4 substrate	+	0.6671	66.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8941	89.41%
CYP3A4 inhibition	-	0.5517	55.17%
CYP2C9 inhibition	-	0.7887	78.87%
CYP2C19 inhibition	-	0.8489	84.89%
CYP2D6 inhibition	-	0.9270	92.70%
CYP1A2 inhibition	-	0.5152	51.52%
CYP2C8 inhibition	+	0.4607	46.07%
CYP inhibitory promiscuity	-	0.9471	94.71%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4629	46.29%
Eye corrosion	-	0.9782	97.82%
Eye irritation	-	0.9185	91.85%
Skin irritation	-	0.5413	54.13%
Skin corrosion	-	0.8225	82.25%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5839	58.39%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.5033	50.33%
skin sensitisation	-	0.6689	66.89%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7142	71.42%
Acute Oral Toxicity (c)	III	0.5328	53.28%
Estrogen receptor binding	+	0.7035	70.35%
Androgen receptor binding	+	0.5909	59.09%
Thyroid receptor binding	+	0.5494	54.94%
Glucocorticoid receptor binding	+	0.5928	59.28%
Aromatase binding	-	0.5701	57.01%
PPAR gamma	+	0.5979	59.79%
Honey bee toxicity	-	0.5186	51.86%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9546	95.46%

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	96.88%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.74%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	94.91%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.48%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.65%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.59%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.86%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.03%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.78%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.19%	94.08%
CHEMBL2581	P07339	Cathepsin D	85.31%	98.95%
CHEMBL5028	O14672	ADAM10	84.14%	97.50%
CHEMBL3401	O75469	Pregnane X receptor	84.09%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.45%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.96%	97.14%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.91%	97.28%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.52%	91.07%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.84%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.25%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.39%	94.00%

Plants that contains it

• Montanoa karwinskii

Cross-Links

• PubChem: 162871282
• LOTUS: LTS0057544
• wikiData: Q105344453