5,8-dihydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 4003a388-a4ac-4e4e-8998-e2f444fcd27a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 5,8-dihydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one
• InChI: InChI=1S/C15H20O4/c1-6-9-4-12(17)8(3)13(9)14-10(5-11(6)16)7(2)15(18)19-14/h8-14,16-17H,1-2,4-5H2,3H3
• InChI Key: WHEHTIGCPBNOIX-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.04
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9853	98.53%
Caco-2	-	0.5421	54.21%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.4913	49.13%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.8564	85.64%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9707	97.07%
P-glycoprotein inhibitior	-	0.9351	93.51%
P-glycoprotein substrate	-	0.8403	84.03%
CYP3A4 substrate	+	0.5286	52.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.8814	88.14%
CYP2C9 inhibition	-	0.8899	88.99%
CYP2C19 inhibition	-	0.8067	80.67%
CYP2D6 inhibition	-	0.9282	92.82%
CYP1A2 inhibition	-	0.6476	64.76%
CYP2C8 inhibition	-	0.8990	89.90%
CYP inhibitory promiscuity	-	0.9025	90.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9342	93.42%
Carcinogenicity (trinary)	Non-required	0.5601	56.01%
Eye corrosion	-	0.9635	96.35%
Eye irritation	+	0.5408	54.08%
Skin irritation	-	0.5577	55.77%
Skin corrosion	-	0.8687	86.87%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6902	69.02%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.8375	83.75%
skin sensitisation	-	0.7080	70.80%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4607	46.07%
Estrogen receptor binding	+	0.5570	55.70%
Androgen receptor binding	-	0.4905	49.05%
Thyroid receptor binding	-	0.5352	53.52%
Glucocorticoid receptor binding	+	0.7072	70.72%
Aromatase binding	-	0.6982	69.82%
PPAR gamma	-	0.7930	79.30%
Honey bee toxicity	-	0.7528	75.28%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9494	94.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	93.08%	91.49%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.14%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.03%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.38%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.20%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.52%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.43%	85.14%
CHEMBL2581	P07339	Cathepsin D	84.48%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.34%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.28%	89.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.64%	96.00%

Plants that contains it

• Launaea arborescens

Cross-Links

• PubChem: 74400554
• LOTUS: LTS0269370
• wikiData: Q105305258