7,8-Dihydroxy-3,5,8a-trimethyl-3,3a,4,4a,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: 4cc35555-7aca-4d10-bac2-408ada6bc716
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 7,8-dihydroxy-3,5,8a-trimethyl-3,3a,4,4a,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1C2CC3C(=CC(C(C3(CC2OC1=O)C)O)O)C
• SMILES (Isomeric): CC1C2CC3C(=CC(C(C3(CC2OC1=O)C)O)O)C
• InChI: InChI=1S/C15H22O4/c1-7-4-11(16)13(17)15(3)6-12-9(5-10(7)15)8(2)14(18)19-12/h4,8-13,16-17H,5-6H2,1-3H3
• InChI Key: WTFUIEHNDPETDD-UHFFFAOYSA-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: 1.00
• 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	+	0.9815	98.15%
Caco-2	-	0.5676	56.76%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6688	66.88%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.9150	91.50%
OATP1B3 inhibitior	+	0.9317	93.17%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9256	92.56%
P-glycoprotein inhibitior	-	0.9324	93.24%
P-glycoprotein substrate	-	0.7972	79.72%
CYP3A4 substrate	+	0.5912	59.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8444	84.44%
CYP3A4 inhibition	-	0.5682	56.82%
CYP2C9 inhibition	-	0.8831	88.31%
CYP2C19 inhibition	-	0.8217	82.17%
CYP2D6 inhibition	-	0.9334	93.34%
CYP1A2 inhibition	-	0.6654	66.54%
CYP2C8 inhibition	-	0.9398	93.98%
CYP inhibitory promiscuity	-	0.8188	81.88%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4564	45.64%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9728	97.28%
Skin irritation	+	0.5394	53.94%
Skin corrosion	-	0.9054	90.54%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6194	61.94%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.6677	66.77%
skin sensitisation	-	0.7412	74.12%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5847	58.47%
Acute Oral Toxicity (c)	III	0.5505	55.05%
Estrogen receptor binding	+	0.6105	61.05%
Androgen receptor binding	+	0.5448	54.48%
Thyroid receptor binding	+	0.5352	53.52%
Glucocorticoid receptor binding	-	0.5911	59.11%
Aromatase binding	-	0.8426	84.26%
PPAR gamma	-	0.5588	55.88%
Honey bee toxicity	-	0.7998	79.98%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9916	99.16%

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	92.93%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.56%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.85%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.34%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.06%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.91%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.47%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	85.06%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.55%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.49%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.54%	92.94%

Plants that contains it

• Helianthus tuberosus

Cross-Links

• PubChem: 163083973
• LOTUS: LTS0157213
• wikiData: Q105312494