2-[(3aR,4R,6S,7R,7aR)-6-ethenyl-6-methyl-4-[(E)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-4,5,7,7a-tetrahydro-3aH-1-benzofuran-7-yl]prop-2-enoic acid

Details

• Internal ID: af31d803-d387-4bfe-851e-600d44ca665c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 2-[(3aR,4R,6S,7R,7aR)-6-ethenyl-6-methyl-4-[(E)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-4,5,7,7a-tetrahydro-3aH-1-benzofuran-7-yl]prop-2-enoic acid
• InChI: InChI=1S/C20H24O6/c1-7-10(3)18(23)25-13-9-20(6,8-2)15(12(5)17(21)22)16-14(13)11(4)19(24)26-16/h7-8,13-16H,2,4-5,9H2,1,3,6H3,(H,21,22)/b10-7+/t13-,14-,15-,16+,20-/m1/s1
• InChI Key: LTXDJOCJYDKONK-JJSQXJCYSA-N
• Popularity: 61 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.15728848 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 2.82
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9859	98.59%
Caco-2	-	0.5616	56.16%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6000	60.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8833	88.33%
OATP1B3 inhibitior	+	0.8733	87.33%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6820	68.20%
P-glycoprotein inhibitior	-	0.5834	58.34%
P-glycoprotein substrate	-	0.7385	73.85%
CYP3A4 substrate	+	0.6244	62.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9197	91.97%
CYP3A4 inhibition	-	0.6559	65.59%
CYP2C9 inhibition	-	0.9266	92.66%
CYP2C19 inhibition	-	0.9197	91.97%
CYP2D6 inhibition	-	0.9693	96.93%
CYP1A2 inhibition	-	0.8244	82.44%
CYP2C8 inhibition	-	0.7289	72.89%
CYP inhibitory promiscuity	-	0.8906	89.06%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9043	90.43%
Carcinogenicity (trinary)	Non-required	0.4343	43.43%
Eye corrosion	-	0.9564	95.64%
Eye irritation	-	0.8866	88.66%
Skin irritation	-	0.5726	57.26%
Skin corrosion	-	0.9063	90.63%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6443	64.43%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.7336	73.36%
skin sensitisation	-	0.5759	57.59%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.8810	88.10%
Acute Oral Toxicity (c)	III	0.3818	38.18%
Estrogen receptor binding	+	0.6188	61.88%
Androgen receptor binding	+	0.6165	61.65%
Thyroid receptor binding	+	0.5381	53.81%
Glucocorticoid receptor binding	-	0.4820	48.20%
Aromatase binding	-	0.6202	62.02%
PPAR gamma	-	0.5054	50.54%
Honey bee toxicity	-	0.6244	62.44%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9727	97.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.49%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.38%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	92.72%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.39%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.38%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.28%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.43%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.74%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.52%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.10%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.04%	96.09%

Plants that contains it

• Ageratina palmeri
• Cronquistianthus chachapoyensis

Cross-Links

• PubChem: 13895543
• LOTUS: LTS0057930
• wikiData: Q105157250