[(4aS,5R,6S,8aR,9aR)-9a-hydroxy-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: d506ddcc-b1f2-43da-997a-46ef11db8e9d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4aS,5R,6S,8aR,9aR)-9a-hydroxy-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/C20H28O5/c1-6-11(2)17(21)24-16-8-7-14-9-20(23)15(12(3)18(22)25-20)10-19(14,5)13(16)4/h6,13-14,16,23H,7-10H2,1-5H3/b11-6-/t13-,14+,16-,19+,20+/m0/s1
• InChI Key: QHIDRSDWHHORCC-VYKLVJNKSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.27
• H-Bond Acceptor: 5
• 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	+	0.9937	99.37%
Caco-2	+	0.8068	80.68%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8071	80.71%
OATP2B1 inhibitior	-	0.8671	86.71%
OATP1B1 inhibitior	+	0.8869	88.69%
OATP1B3 inhibitior	+	0.8481	84.81%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.6124	61.24%
BSEP inhibitior	+	0.6463	64.63%
P-glycoprotein inhibitior	-	0.4646	46.46%
P-glycoprotein substrate	-	0.6878	68.78%
CYP3A4 substrate	+	0.6862	68.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8818	88.18%
CYP3A4 inhibition	-	0.6049	60.49%
CYP2C9 inhibition	-	0.8018	80.18%
CYP2C19 inhibition	-	0.8574	85.74%
CYP2D6 inhibition	-	0.9565	95.65%
CYP1A2 inhibition	-	0.5215	52.15%
CYP2C8 inhibition	-	0.7967	79.67%
CYP inhibitory promiscuity	-	0.9214	92.14%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5292	52.92%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9468	94.68%
Skin irritation	+	0.6684	66.84%
Skin corrosion	-	0.9062	90.62%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7377	73.77%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5428	54.28%
skin sensitisation	-	0.8506	85.06%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.7673	76.73%
Acute Oral Toxicity (c)	I	0.3031	30.31%
Estrogen receptor binding	+	0.6633	66.33%
Androgen receptor binding	-	0.4866	48.66%
Thyroid receptor binding	+	0.6906	69.06%
Glucocorticoid receptor binding	+	0.7165	71.65%
Aromatase binding	+	0.5564	55.64%
PPAR gamma	+	0.5426	54.26%
Honey bee toxicity	-	0.7867	78.67%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9943	99.43%

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	98.57%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.85%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.30%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.32%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.49%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.30%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.67%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.54%	97.14%
CHEMBL2581	P07339	Cathepsin D	83.18%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.86%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.29%	86.33%

Plants that contains it

• Farfugium japonicum

Cross-Links

• PubChem: 101517792
• LOTUS: LTS0246005
• wikiData: Q105220938