(3aR,4aS,5S,8aR,9aR)-4a-hydroxy-8a-methyl-3-methylidenespiro[4,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-5,2'-oxirane]-2-one

Details

• Internal ID: f5c7efaf-4174-4950-af50-a4447d191e52
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4aS,5S,8aR,9aR)-4a-hydroxy-8a-methyl-3-methylidenespiro[4,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-5,2'-oxirane]-2-one
• InChI: InChI=1S/C15H20O4/c1-9-10-6-15(17)13(2,7-11(10)19-12(9)16)4-3-5-14(15)8-18-14/h10-11,17H,1,3-8H2,2H3/t10-,11-,13-,14+,15+/m1/s1
• InChI Key: UFRJLTNQNNHRPM-YXRJLALLSA-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): 59.10 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.57
• 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	+	0.9892	98.92%
Caco-2	+	0.6577	65.77%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7824	78.24%
OATP2B1 inhibitior	-	0.8511	85.11%
OATP1B1 inhibitior	+	0.8823	88.23%
OATP1B3 inhibitior	+	0.9494	94.94%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5102	51.02%
BSEP inhibitior	-	0.9448	94.48%
P-glycoprotein inhibitior	-	0.9418	94.18%
P-glycoprotein substrate	-	0.8118	81.18%
CYP3A4 substrate	+	0.5963	59.63%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8550	85.50%
CYP3A4 inhibition	-	0.8261	82.61%
CYP2C9 inhibition	-	0.8143	81.43%
CYP2C19 inhibition	-	0.8189	81.89%
CYP2D6 inhibition	-	0.9320	93.20%
CYP1A2 inhibition	-	0.7316	73.16%
CYP2C8 inhibition	-	0.8268	82.68%
CYP inhibitory promiscuity	-	0.9552	95.52%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4672	46.72%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.8066	80.66%
Skin irritation	+	0.5195	51.95%
Skin corrosion	-	0.9167	91.67%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.8377	83.77%
skin sensitisation	-	0.8373	83.73%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5707	57.07%
Acute Oral Toxicity (c)	III	0.4627	46.27%
Estrogen receptor binding	+	0.7233	72.33%
Androgen receptor binding	+	0.6466	64.66%
Thyroid receptor binding	-	0.5197	51.97%
Glucocorticoid receptor binding	+	0.7902	79.02%
Aromatase binding	+	0.6781	67.81%
PPAR gamma	-	0.6159	61.59%
Honey bee toxicity	-	0.8210	82.10%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9889	98.89%

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	97.21%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.02%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.51%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	92.27%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.04%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.77%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.14%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.78%	93.03%
CHEMBL2581	P07339	Cathepsin D	84.84%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.74%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.07%	86.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.03%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.00%	96.09%

Plants that contains it

• Inula racemosa

Cross-Links

• PubChem: 14633209
• LOTUS: LTS0163958
• wikiData: Q105272055