(3R,3aR,8aR,9aR)-5-(hydroxymethyl)-3,8a-dimethyl-3,3a,4,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: 7d6f5723-f6bc-422d-a01e-bbfbec189efd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3R,3aR,8aR,9aR)-5-(hydroxymethyl)-3,8a-dimethyl-3,3a,4,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
• InChI: InChI=1S/C15H22O3/c1-9-11-6-12-10(8-16)4-3-5-15(12,2)7-13(11)18-14(9)17/h9,11,13,16H,3-8H2,1-2H3/t9-,11-,13-,15-/m1/s1
• InChI Key: BDHZZVFUIUYLNJ-ZTYOMDHBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.44
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9955	99.55%
Caco-2	+	0.8819	88.19%
Blood Brain Barrier	+	0.5605	56.05%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8106	81.06%
OATP2B1 inhibitior	-	0.8475	84.75%
OATP1B1 inhibitior	+	0.8720	87.20%
OATP1B3 inhibitior	+	0.9623	96.23%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	+	0.6827	68.27%
BSEP inhibitior	-	0.8293	82.93%
P-glycoprotein inhibitior	-	0.9063	90.63%
P-glycoprotein substrate	-	0.7978	79.78%
CYP3A4 substrate	+	0.5741	57.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8573	85.73%
CYP3A4 inhibition	-	0.5256	52.56%
CYP2C9 inhibition	-	0.8636	86.36%
CYP2C19 inhibition	-	0.8034	80.34%
CYP2D6 inhibition	-	0.9217	92.17%
CYP1A2 inhibition	-	0.7880	78.80%
CYP2C8 inhibition	-	0.9225	92.25%
CYP inhibitory promiscuity	-	0.7425	74.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5472	54.72%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.7257	72.57%
Skin irritation	-	0.5497	54.97%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.5554	55.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4795	47.95%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5408	54.08%
skin sensitisation	-	0.8422	84.22%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5437	54.37%
Acute Oral Toxicity (c)	III	0.5997	59.97%
Estrogen receptor binding	-	0.5395	53.95%
Androgen receptor binding	-	0.5872	58.72%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4684	46.84%
Aromatase binding	-	0.5829	58.29%
PPAR gamma	-	0.7482	74.82%
Honey bee toxicity	-	0.8821	88.21%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9873	98.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.53%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.02%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.71%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.86%	94.45%
CHEMBL2581	P07339	Cathepsin D	88.22%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.10%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.62%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.94%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.67%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.99%	94.75%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.56%	93.04%
CHEMBL299	P17252	Protein kinase C alpha	82.04%	98.03%

Plants that contains it

• Inula helenium

Cross-Links

• PubChem: 162903786
• LOTUS: LTS0158306
• wikiData: Q104924212