(4aR,5S,6S,8aS,9aS)-4a,5,6-trihydroxy-3,5,8a-trimethyl-4,6,9,9a-tetrahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: be476781-d3b4-4635-95ef-c50c2299fe05
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (4aR,5S,6S,8aS,9aS)-4a,5,6-trihydroxy-3,5,8a-trimethyl-4,6,9,9a-tetrahydrobenzo[f][1]benzofuran-2-one
• InChI: InChI=1S/C15H20O5/c1-8-9-6-15(19)13(2,7-10(9)20-12(8)17)5-4-11(16)14(15,3)18/h4-5,10-11,16,18-19H,6-7H2,1-3H3/t10-,11-,13+,14-,15+/m0/s1
• InChI Key: RLYOZVIHQJWLDW-ZYDPBQMLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 0.44
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9740	97.40%
Caco-2	-	0.6189	61.89%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6089	60.89%
OATP2B1 inhibitior	-	0.8541	85.41%
OATP1B1 inhibitior	+	0.9117	91.17%
OATP1B3 inhibitior	+	0.9398	93.98%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7280	72.80%
P-glycoprotein inhibitior	-	0.9116	91.16%
P-glycoprotein substrate	-	0.7938	79.38%
CYP3A4 substrate	+	0.6430	64.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8745	87.45%
CYP3A4 inhibition	-	0.6940	69.40%
CYP2C9 inhibition	-	0.8878	88.78%
CYP2C19 inhibition	-	0.8728	87.28%
CYP2D6 inhibition	-	0.9355	93.55%
CYP1A2 inhibition	-	0.7905	79.05%
CYP2C8 inhibition	-	0.9169	91.69%
CYP inhibitory promiscuity	-	0.8867	88.67%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4036	40.36%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9348	93.48%
Skin irritation	+	0.5630	56.30%
Skin corrosion	-	0.9055	90.55%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6479	64.79%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8070	80.70%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5271	52.71%
Acute Oral Toxicity (c)	I	0.3622	36.22%
Estrogen receptor binding	+	0.6274	62.74%
Androgen receptor binding	+	0.6578	65.78%
Thyroid receptor binding	+	0.6140	61.40%
Glucocorticoid receptor binding	+	0.5545	55.45%
Aromatase binding	-	0.5605	56.05%
PPAR gamma	+	0.6538	65.38%
Honey bee toxicity	-	0.8734	87.34%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9841	98.41%

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	94.53%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.63%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.33%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.21%	97.25%
CHEMBL2581	P07339	Cathepsin D	85.57%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.85%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.57%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.61%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.82%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.14%	97.14%
CHEMBL4208	P20618	Proteasome component C5	80.77%	90.00%

Plants that contains it

• Chloranthus serratus

Cross-Links

• PubChem: 101482732
• LOTUS: LTS0245861
• wikiData: Q105348118