[(3aR,4S,5aR,6R,8R,9bS)-6,8-dihydroxy-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl] 2-methylprop-2-enoate

Details

• Internal ID: a5f81b77-4fc6-4bef-9106-895be3bb31c2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aR,4S,5aR,6R,8R,9bS)-6,8-dihydroxy-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl] 2-methylprop-2-enoate
• InChI: InChI=1S/C19H24O6/c1-8(2)17(22)24-12-7-19(5)13(21)6-11(20)9(3)15(19)16-14(12)10(4)18(23)25-16/h11-14,16,20-21H,1,4,6-7H2,2-3,5H3/t11-,12+,13-,14-,16+,19+/m1/s1
• InChI Key: NTCSHISKGXYZGN-GWZPNUFXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.15728848 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.42
• 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	+	0.9886	98.86%
Caco-2	+	0.5645	56.45%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6262	62.62%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.9206	92.06%
OATP1B3 inhibitior	+	0.8747	87.47%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9185	91.85%
P-glycoprotein inhibitior	-	0.7663	76.63%
P-glycoprotein substrate	-	0.6060	60.60%
CYP3A4 substrate	+	0.6608	66.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8532	85.32%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8366	83.66%
CYP2C19 inhibition	-	0.9326	93.26%
CYP2D6 inhibition	-	0.9574	95.74%
CYP1A2 inhibition	-	0.7897	78.97%
CYP2C8 inhibition	-	0.7249	72.49%
CYP inhibitory promiscuity	-	0.8573	85.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4532	45.32%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.7875	78.75%
Skin irritation	+	0.4907	49.07%
Skin corrosion	-	0.9087	90.87%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3814	38.14%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.6783	67.83%
skin sensitisation	-	0.7659	76.59%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.7913	79.13%
Acute Oral Toxicity (c)	I	0.3595	35.95%
Estrogen receptor binding	+	0.6511	65.11%
Androgen receptor binding	+	0.5426	54.26%
Thyroid receptor binding	+	0.5475	54.75%
Glucocorticoid receptor binding	+	0.5403	54.03%
Aromatase binding	-	0.6247	62.47%
PPAR gamma	+	0.5806	58.06%
Honey bee toxicity	-	0.4823	48.23%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9955	99.55%

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	95.30%	91.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.11%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	91.82%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.47%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.44%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.21%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.46%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.55%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.19%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.42%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.97%	96.09%

Plants that contains it

• Chamaemelum fuscatum

Cross-Links

• PubChem: 162938263
• LOTUS: LTS0167668
• wikiData: Q105185371