5,8,9a-Trihydroxy-3,5,8a-trimethyl-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: e46c81ac-1e21-438f-8ae0-71fc14203a6b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 5,8,9a-trihydroxy-3,5,8a-trimethyl-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2CC3C(CCC(C3(CC2(OC1=O)O)C)O)(C)O
• SMILES (Isomeric): CC1=C2CC3C(CCC(C3(CC2(OC1=O)O)C)O)(C)O
• InChI: InChI=1S/C15H22O5/c1-8-9-6-10-13(2,7-15(9,19)20-12(8)17)11(16)4-5-14(10,3)18/h10-11,16,18-19H,4-7H2,1-3H3
• InChI Key: BWOFLNFAFOQHRS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₅
• Molecular Weight: 282.33 g/mol
• Exact Mass: 282.14672380 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.87
• 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	+	0.9938	99.38%
Caco-2	+	0.6897	68.97%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7371	73.71%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.9134	91.34%
OATP1B3 inhibitior	+	0.9296	92.96%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5321	53.21%
BSEP inhibitior	-	0.7101	71.01%
P-glycoprotein inhibitior	-	0.9387	93.87%
P-glycoprotein substrate	-	0.8943	89.43%
CYP3A4 substrate	+	0.6462	64.62%
CYP2C9 substrate	-	0.7948	79.48%
CYP2D6 substrate	-	0.8745	87.45%
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	-	0.8368	83.68%
CYP inhibitory promiscuity	-	0.9152	91.52%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4418	44.18%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8291	82.91%
Skin irritation	+	0.7082	70.82%
Skin corrosion	-	0.9170	91.70%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5633	56.33%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5091	50.91%
skin sensitisation	-	0.8043	80.43%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.6712	67.12%
Acute Oral Toxicity (c)	I	0.5041	50.41%
Estrogen receptor binding	+	0.6077	60.77%
Androgen receptor binding	+	0.5814	58.14%
Thyroid receptor binding	+	0.6978	69.78%
Glucocorticoid receptor binding	+	0.6200	62.00%
Aromatase binding	+	0.5604	56.04%
PPAR gamma	+	0.6559	65.59%
Honey bee toxicity	-	0.9041	90.41%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
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
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.48%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.74%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.89%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.35%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.71%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.41%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.53%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.51%	100.00%
CHEMBL1871	P10275	Androgen Receptor	84.67%	96.43%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.07%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.92%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.33%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.28%	82.69%

Plants that contains it

• Chloranthus serratus

Cross-Links

• PubChem: 75597610
• LOTUS: LTS0067246
• wikiData: Q104947415