[(4R,4aS,5R,6S,8aR,9aS)-4,9a-dihydroxy-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: bf858c19-b8d1-4e24-88d7-867de8164bb4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4R,4aS,5R,6S,8aR,9aS)-4,9a-dihydroxy-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/C20H28O6/c1-6-10(2)17(22)25-14-8-7-13-9-20(24)15(11(3)18(23)26-20)16(21)19(13,5)12(14)4/h6,12-14,16,21,24H,7-9H2,1-5H3/b10-6-/t12-,13+,14-,16-,19+,20-/m0/s1
• InChI Key: NFAZPKOZGQLFNL-VCKJCAQWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.40 g/mol
• Exact Mass: 364.18858861 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.24
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9690	96.90%
Caco-2	+	0.6636	66.36%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7318	73.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9021	90.21%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5771	57.71%
BSEP inhibitior	+	0.5594	55.94%
P-glycoprotein inhibitior	-	0.6162	61.62%
P-glycoprotein substrate	-	0.6450	64.50%
CYP3A4 substrate	+	0.6692	66.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8763	87.63%
CYP3A4 inhibition	-	0.5532	55.32%
CYP2C9 inhibition	-	0.8514	85.14%
CYP2C19 inhibition	-	0.9399	93.99%
CYP2D6 inhibition	-	0.9263	92.63%
CYP1A2 inhibition	-	0.5986	59.86%
CYP2C8 inhibition	-	0.7137	71.37%
CYP inhibitory promiscuity	-	0.7768	77.68%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Danger	0.4399	43.99%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9548	95.48%
Skin irritation	+	0.5960	59.60%
Skin corrosion	-	0.8706	87.06%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7208	72.08%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6650	66.50%
skin sensitisation	-	0.8247	82.47%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.7795	77.95%
Acute Oral Toxicity (c)	III	0.3864	38.64%
Estrogen receptor binding	+	0.7939	79.39%
Androgen receptor binding	+	0.5585	55.85%
Thyroid receptor binding	+	0.7358	73.58%
Glucocorticoid receptor binding	+	0.7377	73.77%
Aromatase binding	+	0.6263	62.63%
PPAR gamma	+	0.5402	54.02%
Honey bee toxicity	-	0.7328	73.28%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9707	97.07%

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	97.51%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.59%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.91%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.89%	99.23%
CHEMBL2581	P07339	Cathepsin D	86.95%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.44%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.26%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.88%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.58%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.77%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.32%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.75%	100.00%

Plants that contains it

• Farfugium japonicum

Cross-Links

• PubChem: 163190358
• LOTUS: LTS0021718
• wikiData: Q105178358