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

Details

• Internal ID: a1bca9f4-e137-40b1-bd4c-1ecd46a5acc9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4S,4aS,5S,8S,8aR)-8-chloro-8a-hydroxy-3,4a,5-trimethyl-9-oxo-5,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-4-yl] (E)-2-methylbut-2-enoate
• InChI: InChI=1S/C20H25ClO5/c1-6-10(2)18(23)26-17-14-11(3)9-25-15(14)16(22)20(24)13(21)8-7-12(4)19(17,20)5/h6,9,12-13,17,24H,7-8H2,1-5H3/b10-6+/t12-,13-,17+,19-,20-/m0/s1
• InChI Key: LIIUXOSINVLFRM-QBZYGJHMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₅ClO₅
• Molecular Weight: 380.90 g/mol
• Exact Mass: 380.1390516 g/mol
• Topological Polar Surface Area (TPSA): 76.70 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.11
• 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	+	0.9927	99.27%
Caco-2	+	0.6760	67.60%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6972	69.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8629	86.29%
OATP1B3 inhibitior	-	0.3375	33.75%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.6321	63.21%
BSEP inhibitior	+	0.6636	66.36%
P-glycoprotein inhibitior	-	0.5267	52.67%
P-glycoprotein substrate	-	0.7440	74.40%
CYP3A4 substrate	+	0.6659	66.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8814	88.14%
CYP3A4 inhibition	-	0.7957	79.57%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	-	0.6188	61.88%
CYP2D6 inhibition	-	0.8142	81.42%
CYP1A2 inhibition	+	0.6704	67.04%
CYP2C8 inhibition	-	0.6206	62.06%
CYP inhibitory promiscuity	-	0.5121	51.21%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8438	84.38%
Carcinogenicity (trinary)	Danger	0.4932	49.32%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9687	96.87%
Skin irritation	-	0.6418	64.18%
Skin corrosion	-	0.8959	89.59%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4149	41.49%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.6178	61.78%
skin sensitisation	-	0.7876	78.76%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6477	64.77%
Acute Oral Toxicity (c)	III	0.4790	47.90%
Estrogen receptor binding	+	0.8844	88.44%
Androgen receptor binding	+	0.6195	61.95%
Thyroid receptor binding	+	0.7350	73.50%
Glucocorticoid receptor binding	+	0.7475	74.75%
Aromatase binding	+	0.7348	73.48%
PPAR gamma	+	0.7999	79.99%
Honey bee toxicity	-	0.6451	64.51%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.42%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.59%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	92.18%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.74%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.80%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.80%	94.45%
CHEMBL4072	P07858	Cathepsin B	86.64%	93.67%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.48%	94.80%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.80%	90.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.47%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.36%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	80.67%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.48%	94.00%

Plants that contains it

• Ligularia fischeri

Cross-Links

• PubChem: 163188998
• LOTUS: LTS0160440
• wikiData: Q105152211