(3S,5S,5aR,6R,9aS,9bS)-5,6-dihydroxy-3,5a-dimethyl-9-methylidene-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2-one

Details

• Internal ID: e4321d41-f66b-4c26-80f0-faa767a25874
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,5S,5aR,6R,9aS,9bS)-5,6-dihydroxy-3,5a-dimethyl-9-methylidene-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2-one
• InChI: InChI=1S/C15H22O4/c1-7-4-5-10(16)15(3)11(17)6-9-8(2)14(18)19-13(9)12(7)15/h8-13,16-17H,1,4-6H2,2-3H3/t8-,9?,10+,11-,12+,13-,15+/m0/s1
• InChI Key: PAWVFYSWUNKMRS-VSVBBCKUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.26
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	-	0.5511	55.11%
Blood Brain Barrier	+	0.5277	52.77%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6303	63.03%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.9025	90.25%
OATP1B3 inhibitior	+	0.8802	88.02%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7420	74.20%
BSEP inhibitior	-	0.9652	96.52%
P-glycoprotein inhibitior	-	0.9372	93.72%
P-glycoprotein substrate	-	0.7905	79.05%
CYP3A4 substrate	+	0.6201	62.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8383	83.83%
CYP3A4 inhibition	-	0.7019	70.19%
CYP2C9 inhibition	-	0.9116	91.16%
CYP2C19 inhibition	-	0.8949	89.49%
CYP2D6 inhibition	-	0.9344	93.44%
CYP1A2 inhibition	-	0.7951	79.51%
CYP2C8 inhibition	-	0.8822	88.22%
CYP inhibitory promiscuity	-	0.8669	86.69%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5167	51.67%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9518	95.18%
Skin irritation	+	0.5243	52.43%
Skin corrosion	-	0.8566	85.66%
Ames mutagenesis	-	0.7501	75.01%
Human Ether-a-go-go-Related Gene inhibition	-	0.7078	70.78%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.8033	80.33%
skin sensitisation	-	0.7337	73.37%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.4894	48.94%
Acute Oral Toxicity (c)	I	0.4417	44.17%
Estrogen receptor binding	+	0.6332	63.32%
Androgen receptor binding	+	0.5311	53.11%
Thyroid receptor binding	+	0.5627	56.27%
Glucocorticoid receptor binding	+	0.7067	70.67%
Aromatase binding	-	0.6159	61.59%
PPAR gamma	-	0.7496	74.96%
Honey bee toxicity	-	0.8214	82.14%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9698	96.98%

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	95.18%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.41%	97.25%
CHEMBL1951	P21397	Monoamine oxidase A	88.74%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.73%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.34%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.18%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.15%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.09%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.53%	93.04%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.34%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.75%	96.38%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.39%	90.24%
CHEMBL340	P08684	Cytochrome P450 3A4	80.17%	91.19%

Plants that contains it

• Artemisia herba-alba

Cross-Links

• PubChem: 162905127
• LOTUS: LTS0248052
• wikiData: Q105204914