[(3aS,4S,5R,6aR,9aR,9bS)-5-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: f86b80f3-808e-41c1-98ee-5f83bec6e3e7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aS,4S,5R,6aR,9aR,9bS)-5-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-2-methylbut-2-enoate
• InChI: InChI=1S/C20H24O5/c1-6-9(2)19(22)25-18-15-12(5)20(23)24-17(15)14-10(3)7-8-13(14)11(4)16(18)21/h6-7,13-18,21H,4-5,8H2,1-3H3/b9-6+/t13-,14-,15-,16+,17-,18-/m0/s1
• InChI Key: MXNYEYDKNYIYGB-WSKWLIBYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.40 g/mol
• Exact Mass: 344.16237386 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.48
• 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	+	0.9684	96.84%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5177	51.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8706	87.06%
OATP1B3 inhibitior	+	0.8897	88.97%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6408	64.08%
P-glycoprotein inhibitior	-	0.6433	64.33%
P-glycoprotein substrate	-	0.7937	79.37%
CYP3A4 substrate	+	0.5941	59.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8778	87.78%
CYP3A4 inhibition	-	0.7158	71.58%
CYP2C9 inhibition	-	0.8400	84.00%
CYP2C19 inhibition	-	0.7009	70.09%
CYP2D6 inhibition	-	0.9360	93.60%
CYP1A2 inhibition	-	0.5189	51.89%
CYP2C8 inhibition	-	0.8061	80.61%
CYP inhibitory promiscuity	-	0.8403	84.03%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5014	50.14%
Eye corrosion	-	0.9531	95.31%
Eye irritation	-	0.8376	83.76%
Skin irritation	-	0.6078	60.78%
Skin corrosion	-	0.9213	92.13%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.6533	65.33%
skin sensitisation	-	0.7390	73.90%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5915	59.15%
Acute Oral Toxicity (c)	II	0.4459	44.59%
Estrogen receptor binding	+	0.6028	60.28%
Androgen receptor binding	+	0.5356	53.56%
Thyroid receptor binding	+	0.5376	53.76%
Glucocorticoid receptor binding	+	0.5679	56.79%
Aromatase binding	-	0.5751	57.51%
PPAR gamma	-	0.5252	52.52%
Honey bee toxicity	-	0.7106	71.06%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9753	97.53%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.67%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.93%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.66%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.29%	99.23%
CHEMBL2581	P07339	Cathepsin D	88.77%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.60%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	87.17%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.76%	94.45%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.28%	97.21%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.50%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.45%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.49%	93.03%

Plants that contains it

• Lasiolaena santosii

Cross-Links

• PubChem: 162949594
• LOTUS: LTS0265262
• wikiData: Q105174408