(3R,3aR,5aS,9bS)-3-hydroxy-3,5a,9-trimethyl-3a,4,5,9b-tetrahydrobenzo[g][1]benzofuran-2,8-dione

Details

• Internal ID: d1b087d4-01b4-4f6f-bc82-06498697f44b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3R,3aR,5aS,9bS)-3-hydroxy-3,5a,9-trimethyl-3a,4,5,9b-tetrahydrobenzo[g][1]benzofuran-2,8-dione
• InChI: InChI=1S/C15H18O4/c1-8-10(16)5-7-14(2)6-4-9-12(11(8)14)19-13(17)15(9,3)18/h5,7,9,12,18H,4,6H2,1-3H3/t9-,12+,14+,15-/m1/s1
• InChI Key: GYBXUSIMYWFSFV-WNPSNZDDSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.53
• 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	+	0.9886	98.86%
Caco-2	+	0.5205	52.05%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7332	73.32%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.9309	93.09%
OATP1B3 inhibitior	+	0.8519	85.19%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5374	53.74%
BSEP inhibitior	-	0.8313	83.13%
P-glycoprotein inhibitior	-	0.9225	92.25%
P-glycoprotein substrate	-	0.9108	91.08%
CYP3A4 substrate	+	0.6286	62.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9073	90.73%
CYP3A4 inhibition	-	0.7753	77.53%
CYP2C9 inhibition	-	0.7926	79.26%
CYP2C19 inhibition	-	0.8763	87.63%
CYP2D6 inhibition	-	0.9273	92.73%
CYP1A2 inhibition	+	0.7153	71.53%
CYP2C8 inhibition	-	0.8355	83.55%
CYP inhibitory promiscuity	-	0.8441	84.41%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.3970	39.70%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.8953	89.53%
Skin irritation	+	0.6173	61.73%
Skin corrosion	-	0.8126	81.26%
Ames mutagenesis	-	0.7340	73.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.5620	56.20%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.7837	78.37%
skin sensitisation	-	0.7599	75.99%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.5636	56.36%
Acute Oral Toxicity (c)	III	0.4846	48.46%
Estrogen receptor binding	+	0.5814	58.14%
Androgen receptor binding	-	0.5659	56.59%
Thyroid receptor binding	-	0.5061	50.61%
Glucocorticoid receptor binding	+	0.5902	59.02%
Aromatase binding	-	0.7825	78.25%
PPAR gamma	-	0.5272	52.72%
Honey bee toxicity	-	0.9322	93.22%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5296	52.96%
Fish aquatic toxicity	+	0.9871	98.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.33%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.51%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.49%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.26%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.06%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.90%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.01%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.45%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.27%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.76%	97.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.23%	93.03%
CHEMBL1937	Q92769	Histone deacetylase 2	81.04%	94.75%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.93%	93.04%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 21591793
• LOTUS: LTS0210018
• wikiData: Q105023552