[(4R,4aS,5R,6S,8aR,9aR)-4-hydroxy-9a-methoxy-3,4a,5-trimethyl-2-oxo-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-6-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 7a1746fb-4959-4204-a939-ea9aa6413420
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4R,4aS,5R,6S,8aR,9aR)-4-hydroxy-9a-methoxy-3,4a,5-trimethyl-2-oxo-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-6-yl] (Z)-2-methylbut-2-enoate
• InChI: InChI=1S/C21H30O6/c1-7-11(2)18(23)26-15-9-8-14-10-21(25-6)16(12(3)19(24)27-21)17(22)20(14,5)13(15)4/h7,13-15,17,22H,8-10H2,1-6H3/b11-7-/t13-,14+,15-,17-,20+,21+/m0/s1
• InChI Key: YTKUUOVYXFLJGW-YWPKYKSWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₆
• Molecular Weight: 378.50 g/mol
• Exact Mass: 378.20423867 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9844	98.44%
Caco-2	+	0.6752	67.52%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7892	78.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8792	87.92%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5771	57.71%
BSEP inhibitior	+	0.6781	67.81%
P-glycoprotein inhibitior	-	0.5060	50.60%
P-glycoprotein substrate	-	0.5955	59.55%
CYP3A4 substrate	+	0.6808	68.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8788	87.88%
CYP3A4 inhibition	-	0.6617	66.17%
CYP2C9 inhibition	-	0.8537	85.37%
CYP2C19 inhibition	-	0.9155	91.55%
CYP2D6 inhibition	-	0.9416	94.16%
CYP1A2 inhibition	+	0.6483	64.83%
CYP2C8 inhibition	-	0.5822	58.22%
CYP inhibitory promiscuity	-	0.8320	83.20%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4350	43.50%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.9285	92.85%
Skin irritation	+	0.5101	51.01%
Skin corrosion	-	0.8776	87.76%
Ames mutagenesis	-	0.5364	53.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.7221	72.21%
skin sensitisation	-	0.8376	83.76%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.7486	74.86%
Acute Oral Toxicity (c)	III	0.4568	45.68%
Estrogen receptor binding	+	0.8802	88.02%
Androgen receptor binding	+	0.5903	59.03%
Thyroid receptor binding	+	0.8035	80.35%
Glucocorticoid receptor binding	+	0.7947	79.47%
Aromatase binding	+	0.6459	64.59%
PPAR gamma	+	0.6477	64.77%
Honey bee toxicity	-	0.6896	68.96%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9678	96.78%

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	96.97%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.28%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	90.21%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.25%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.64%	91.07%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.51%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.09%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.99%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.51%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.95%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.47%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.78%	91.24%

Plants that contains it

• Farfugium japonicum

Cross-Links

• PubChem: 163194852
• LOTUS: LTS0022489
• wikiData: Q105361641