[(3aR,5S,5aS,8S,8aS,9aR)-8-hydroxy-5-methyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-8a-yl]methyl acetate

Details

• Internal ID: d7a5ef41-ada6-46c8-9dd2-4c561eeea38d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: [(3aR,5S,5aS,8S,8aS,9aR)-8-hydroxy-5-methyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-8a-yl]methyl acetate
• InChI: InChI=1S/C17H24O5/c1-9-6-14-12(10(2)16(20)22-14)7-17(8-21-11(3)18)13(9)4-5-15(17)19/h9,12-15,19H,2,4-8H2,1,3H3/t9-,12+,13-,14+,15-,17+/m0/s1
• InChI Key: YPJDNPTZPPPTEV-AZQFOKQKSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.40 g/mol
• Exact Mass: 308.16237386 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.83
• 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	+	0.9825	98.25%
Caco-2	+	0.7244	72.44%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7354	73.54%
OATP2B1 inhibitior	-	0.8606	86.06%
OATP1B1 inhibitior	+	0.8842	88.42%
OATP1B3 inhibitior	+	0.9550	95.50%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6456	64.56%
BSEP inhibitior	-	0.9071	90.71%
P-glycoprotein inhibitior	-	0.8638	86.38%
P-glycoprotein substrate	-	0.6768	67.68%
CYP3A4 substrate	+	0.6716	67.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	-	0.6719	67.19%
CYP2C9 inhibition	-	0.6802	68.02%
CYP2C19 inhibition	-	0.8187	81.87%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.5936	59.36%
CYP2C8 inhibition	-	0.6199	61.99%
CYP inhibitory promiscuity	-	0.9287	92.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6443	64.43%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.8935	89.35%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9247	92.47%
Ames mutagenesis	-	0.6337	63.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6522	65.22%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8672	86.72%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.4599	45.99%
Acute Oral Toxicity (c)	III	0.3586	35.86%
Estrogen receptor binding	+	0.7191	71.91%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5488	54.88%
Glucocorticoid receptor binding	+	0.7890	78.90%
Aromatase binding	-	0.5671	56.71%
PPAR gamma	-	0.5770	57.70%
Honey bee toxicity	-	0.7710	77.10%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9910	99.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.50%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.49%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.77%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.74%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.80%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.71%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	86.97%	98.03%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.68%	94.80%
CHEMBL2581	P07339	Cathepsin D	82.02%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.98%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.61%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.18%	96.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.07%	95.89%

Plants that contains it

• Rudbeckia mollis

Cross-Links

• PubChem: 21634229
• LOTUS: LTS0025511
• wikiData: Q104402043