(4aR,5R,9aR)-9a-hydroxy-3,4a,5-trimethyl-4,5-dihydrobenzo[f][1]benzofuran-2,6-dione

Details

• Internal ID: 15b10361-4624-4e8c-9693-48554f39ff37
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4aR,5R,9aR)-9a-hydroxy-3,4a,5-trimethyl-4,5-dihydrobenzo[f][1]benzofuran-2,6-dione
• SMILES (Canonical): CC1C(=O)C=CC2=CC3(C(=C(C(=O)O3)C)CC12C)O
• SMILES (Isomeric): C[C@H]1C(=O)C=CC2=C[C@@]3(C(=C(C(=O)O3)C)C[C@]12C)O
• InChI: InChI=1S/C15H16O4/c1-8-11-7-14(3)9(2)12(16)5-4-10(14)6-15(11,18)19-13(8)17/h4-6,9,18H,7H2,1-3H3/t9-,14+,15+/m0/s1
• InChI Key: KCJJMMITMIZHFI-TZTCFGBESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.28 g/mol
• Exact Mass: 260.10485899 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.66
• 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	+	0.9966	99.66%
Caco-2	+	0.7002	70.02%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6553	65.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9091	90.91%
OATP1B3 inhibitior	+	0.9010	90.10%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7740	77.40%
P-glycoprotein inhibitior	-	0.9539	95.39%
P-glycoprotein substrate	-	0.8281	82.81%
CYP3A4 substrate	+	0.6023	60.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8904	89.04%
CYP3A4 inhibition	-	0.8487	84.87%
CYP2C9 inhibition	-	0.8396	83.96%
CYP2C19 inhibition	-	0.9467	94.67%
CYP2D6 inhibition	-	0.9599	95.99%
CYP1A2 inhibition	-	0.5951	59.51%
CYP2C8 inhibition	-	0.8886	88.86%
CYP inhibitory promiscuity	-	0.8293	82.93%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.3781	37.81%
Eye corrosion	-	0.9774	97.74%
Eye irritation	-	0.9108	91.08%
Skin irritation	+	0.5478	54.78%
Skin corrosion	-	0.8849	88.49%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6464	64.64%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.6860	68.60%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7069	70.69%
Acute Oral Toxicity (c)	III	0.4008	40.08%
Estrogen receptor binding	-	0.7103	71.03%
Androgen receptor binding	+	0.5727	57.27%
Thyroid receptor binding	-	0.5721	57.21%
Glucocorticoid receptor binding	-	0.7627	76.27%
Aromatase binding	-	0.7534	75.34%
PPAR gamma	-	0.5769	57.69%
Honey bee toxicity	-	0.8549	85.49%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9929	99.29%

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	95.83%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.79%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.24%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.97%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.34%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.18%	89.00%
CHEMBL4208	P20618	Proteasome component C5	82.33%	90.00%

Plants that contains it

• Ligulariopsis shichuana
• Ziziphus jujuba

Cross-Links

• PubChem: 163049634
• LOTUS: LTS0138622
• wikiData: Q105346704