(3aS,6R,6aR,9aR,9bR)-6-hydroxy-6,9a-dimethyl-3-methylidene-4,5,6a,7,8,9b-hexahydro-3aH-azuleno[8,7-b]furan-2,9-dione

Details

• Internal ID: 4efdf221-9387-408e-8583-4352e47fbe2b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (3aS,6R,6aR,9aR,9bR)-6-hydroxy-6,9a-dimethyl-3-methylidene-4,5,6a,7,8,9b-hexahydro-3aH-azuleno[8,7-b]furan-2,9-dione
• InChI: InChI=1S/C15H20O4/c1-8-9-6-7-14(2,18)10-4-5-11(16)15(10,3)12(9)19-13(8)17/h9-10,12,18H,1,4-7H2,2-3H3/t9-,10-,12+,14+,15-/m0/s1
• InChI Key: AVYCHSJMWUJUQZ-JPXUEEETSA-N
• Popularity: 2 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): 63.60 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9819	98.19%
Caco-2	+	0.5479	54.79%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6643	66.43%
OATP2B1 inhibitior	-	0.8532	85.32%
OATP1B1 inhibitior	+	0.8774	87.74%
OATP1B3 inhibitior	+	0.8906	89.06%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5842	58.42%
BSEP inhibitior	-	0.9521	95.21%
P-glycoprotein inhibitior	-	0.8940	89.40%
P-glycoprotein substrate	-	0.8977	89.77%
CYP3A4 substrate	+	0.5906	59.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8919	89.19%
CYP3A4 inhibition	-	0.7590	75.90%
CYP2C9 inhibition	-	0.8322	83.22%
CYP2C19 inhibition	-	0.8356	83.56%
CYP2D6 inhibition	-	0.9546	95.46%
CYP1A2 inhibition	+	0.5423	54.23%
CYP2C8 inhibition	-	0.7535	75.35%
CYP inhibitory promiscuity	-	0.9772	97.72%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5828	58.28%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.8539	85.39%
Skin irritation	+	0.5613	56.13%
Skin corrosion	-	0.8671	86.71%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8314	83.14%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.7823	78.23%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5686	56.86%
Acute Oral Toxicity (c)	II	0.4677	46.77%
Estrogen receptor binding	+	0.6984	69.84%
Androgen receptor binding	+	0.5508	55.08%
Thyroid receptor binding	-	0.6788	67.88%
Glucocorticoid receptor binding	+	0.5711	57.11%
Aromatase binding	-	0.5295	52.95%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9039	90.39%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9901	99.01%

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	95.03%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.02%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.71%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.37%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.34%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.57%	92.94%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.87%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.54%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.23%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	80.85%	97.79%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.29%	93.04%
CHEMBL1937	Q92769	Histone deacetylase 2	80.18%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.08%	94.45%

Plants that contains it

• Ambrosia arborescens

Cross-Links

• PubChem: 163017996
• LOTUS: LTS0142842
• wikiData: Q104919902