(4aR,5R,6R,9aR)-6,9a-dihydroxy-3,4a,5-trimethyl-5,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: a546acb1-0531-469f-acff-65fd0eb57208
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4aR,5R,6R,9aR)-6,9a-dihydroxy-3,4a,5-trimethyl-5,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-2-one
• InChI: InChI=1S/C15H20O4/c1-8-11-7-14(3)9(2)12(16)5-4-10(14)6-15(11,18)19-13(8)17/h6,9,12,16,18H,4-5,7H2,1-3H3/t9-,12+,14+,15+/m0/s1
• InChI Key: OQAZFOILNZZZRF-ZEQHWRKHSA-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): 66.80 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.68
• 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	+	0.9938	99.38%
Caco-2	+	0.8755	87.55%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7371	73.71%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.9079	90.79%
OATP1B3 inhibitior	+	0.9296	92.96%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5321	53.21%
BSEP inhibitior	-	0.8504	85.04%
P-glycoprotein inhibitior	-	0.9315	93.15%
P-glycoprotein substrate	-	0.8609	86.09%
CYP3A4 substrate	+	0.6392	63.92%
CYP2C9 substrate	-	0.7943	79.43%
CYP2D6 substrate	-	0.8686	86.86%
CYP3A4 inhibition	-	0.6314	63.14%
CYP2C9 inhibition	-	0.9074	90.74%
CYP2C19 inhibition	-	0.9135	91.35%
CYP2D6 inhibition	-	0.9583	95.83%
CYP1A2 inhibition	-	0.6469	64.69%
CYP2C8 inhibition	-	0.8838	88.38%
CYP inhibitory promiscuity	-	0.9152	91.52%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4418	44.18%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9748	97.48%
Skin irritation	+	0.7082	70.82%
Skin corrosion	-	0.9170	91.70%
Ames mutagenesis	-	0.6670	66.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5936	59.36%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5368	53.68%
skin sensitisation	-	0.8043	80.43%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.5242	52.42%
Acute Oral Toxicity (c)	I	0.5041	50.41%
Estrogen receptor binding	-	0.7389	73.89%
Androgen receptor binding	+	0.5594	55.94%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4662	46.62%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.5802	58.02%
Honey bee toxicity	-	0.8745	87.45%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9910	99.10%

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	94.34%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.25%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.41%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.95%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.92%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.69%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.16%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.53%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.67%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.27%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.48%	86.33%

Plants that contains it

• Senecio praecox

Cross-Links

• PubChem: 44138803
• LOTUS: LTS0089111
• wikiData: Q105196689