[(3aS,6S,9S,9aR,9bR)-9-hydroxy-6-methyl-3-methylidene-2-oxo-4,5,6,8,9,9b-hexahydro-3aH-azuleno[4,5-b]furan-9a-yl]methyl acetate

Details

• Internal ID: 51d46b9f-03f8-4f5e-be89-76b21d394853
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: [(3aS,6S,9S,9aR,9bR)-9-hydroxy-6-methyl-3-methylidene-2-oxo-4,5,6,8,9,9b-hexahydro-3aH-azuleno[4,5-b]furan-9a-yl]methyl acetate
• InChI: InChI=1S/C17H22O5/c1-9-4-5-12-10(2)16(20)22-15(12)17(8-21-11(3)18)13(9)6-7-14(17)19/h6,9,12,14-15,19H,2,4-5,7-8H2,1,3H3/t9-,12-,14-,15+,17-/m0/s1
• InChI Key: JIHJFJDIALKJHP-VSAMXWFBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.75
• 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	+	0.9909	99.09%
Caco-2	+	0.5348	53.48%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7636	76.36%
OATP2B1 inhibitior	-	0.8610	86.10%
OATP1B1 inhibitior	+	0.8761	87.61%
OATP1B3 inhibitior	+	0.9454	94.54%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5956	59.56%
BSEP inhibitior	-	0.8718	87.18%
P-glycoprotein inhibitior	-	0.8179	81.79%
P-glycoprotein substrate	-	0.7850	78.50%
CYP3A4 substrate	+	0.6335	63.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	-	0.6446	64.46%
CYP2C9 inhibition	-	0.6772	67.72%
CYP2C19 inhibition	-	0.8699	86.99%
CYP2D6 inhibition	-	0.9465	94.65%
CYP1A2 inhibition	-	0.6157	61.57%
CYP2C8 inhibition	-	0.6187	61.87%
CYP inhibitory promiscuity	-	0.9501	95.01%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6296	62.96%
Eye corrosion	-	0.9819	98.19%
Eye irritation	-	0.8636	86.36%
Skin irritation	+	0.4949	49.49%
Skin corrosion	-	0.9198	91.98%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7459	74.59%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5843	58.43%
skin sensitisation	-	0.8564	85.64%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5901	59.01%
Acute Oral Toxicity (c)	III	0.4128	41.28%
Estrogen receptor binding	+	0.6957	69.57%
Androgen receptor binding	+	0.6092	60.92%
Thyroid receptor binding	+	0.5363	53.63%
Glucocorticoid receptor binding	+	0.7486	74.86%
Aromatase binding	+	0.5496	54.96%
PPAR gamma	+	0.6596	65.96%
Honey bee toxicity	-	0.8471	84.71%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5250	52.50%
Fish aquatic toxicity	+	0.9909	99.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.97%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.67%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.44%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.75%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.70%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.00%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.60%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.77%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.14%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.88%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	80.87%	91.19%
CHEMBL4040	P28482	MAP kinase ERK2	80.41%	83.82%
CHEMBL5028	O14672	ADAM10	80.14%	97.50%

Plants that contains it

• Parthenium tomentosum

Cross-Links

• PubChem: 162953853
• LOTUS: LTS0239063
• wikiData: Q105129045