(4aR,8R,8aS,9aR)-8-hydroxy-3,5,8a-trimethyl-4a,8,9,9a-tetrahydro-4H-benzo[f][1]benzofuran-2,7-dione

Details

• Internal ID: 064af473-d141-44d8-be48-6cb7b02d0a85
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (4aR,8R,8aS,9aR)-8-hydroxy-3,5,8a-trimethyl-4a,8,9,9a-tetrahydro-4H-benzo[f][1]benzofuran-2,7-dione
• SMILES (Canonical): CC1=CC(=O)C(C2(C1CC3=C(C(=O)OC3C2)C)C)O
• SMILES (Isomeric): CC1=CC(=O)[C@@H]([C@@]2([C@@H]1CC3=C(C(=O)O[C@@H]3C2)C)C)O
• InChI: InChI=1S/C15H18O4/c1-7-4-11(16)13(17)15(3)6-12-9(5-10(7)15)8(2)14(18)19-12/h4,10,12-13,17H,5-6H2,1-3H3/t10-,12-,13+,15+/m1/s1
• InChI Key: PUPNTYBHFLLOBZ-PBOSXPJTSA-N
• Popularity: 1 reference 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: 0.70
• 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	+	0.9920	99.20%
Caco-2	+	0.5146	51.46%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7567	75.67%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.8943	89.43%
OATP1B3 inhibitior	+	0.8939	89.39%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8619	86.19%
P-glycoprotein inhibitior	-	0.9272	92.72%
P-glycoprotein substrate	-	0.8226	82.26%
CYP3A4 substrate	+	0.6018	60.18%
CYP2C9 substrate	-	0.7829	78.29%
CYP2D6 substrate	-	0.8959	89.59%
CYP3A4 inhibition	-	0.5366	53.66%
CYP2C9 inhibition	-	0.8869	88.69%
CYP2C19 inhibition	-	0.8921	89.21%
CYP2D6 inhibition	-	0.9462	94.62%
CYP1A2 inhibition	-	0.6500	65.00%
CYP2C8 inhibition	-	0.9115	91.15%
CYP inhibitory promiscuity	-	0.8664	86.64%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4271	42.71%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8446	84.46%
Skin irritation	+	0.5785	57.85%
Skin corrosion	-	0.8873	88.73%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5852	58.52%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.6033	60.33%
skin sensitisation	-	0.7678	76.78%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5135	51.35%
Acute Oral Toxicity (c)	III	0.5571	55.71%
Estrogen receptor binding	+	0.6056	60.56%
Androgen receptor binding	+	0.5456	54.56%
Thyroid receptor binding	-	0.6154	61.54%
Glucocorticoid receptor binding	-	0.6090	60.90%
Aromatase binding	-	0.8087	80.87%
PPAR gamma	+	0.5364	53.64%
Honey bee toxicity	-	0.9086	90.86%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9937	99.37%

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	96.10%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.67%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.73%	85.14%
CHEMBL2581	P07339	Cathepsin D	86.61%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	85.05%	90.17%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.68%	86.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.84%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.53%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.48%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.31%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.17%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.09%	86.33%

Plants that contains it

• Salvia palaefolia

Cross-Links

• PubChem: 162912521
• LOTUS: LTS0256634
• wikiData: Q105215217