(4aR,9aR)-9a-hydroxy-3,4a,5-trimethyl-4,7-dihydrobenzo[f][1]benzofuran-2,8-dione

Details

• Internal ID: b00d4c5c-e337-4571-a737-6f4c8ee850ef
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4aR,9aR)-9a-hydroxy-3,4a,5-trimethyl-4,7-dihydrobenzo[f][1]benzofuran-2,8-dione
• SMILES (Canonical): CC1=CCC(=O)C2=CC3(C(=C(C(=O)O3)C)CC12C)O
• SMILES (Isomeric): CC1=CCC(=O)C2=C[C@@]3(C(=C(C(=O)O3)C)C[C@]12C)O
• InChI: InChI=1S/C15H16O4/c1-8-4-5-12(16)11-7-15(18)10(6-14(8,11)3)9(2)13(17)19-15/h4,7,18H,5-6H2,1-3H3/t14-,15-/m1/s1
• InChI Key: JBAINTSOJBDJDS-HUUCEWRRSA-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: 0.80
• Atomic LogP (AlogP): 1.80
• 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	+	0.9962	99.62%
Caco-2	+	0.8549	85.49%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6962	69.62%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.9047	90.47%
OATP1B3 inhibitior	+	0.8647	86.47%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.8343	83.43%
P-glycoprotein inhibitior	-	0.9299	92.99%
P-glycoprotein substrate	-	0.8502	85.02%
CYP3A4 substrate	+	0.5822	58.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8856	88.56%
CYP3A4 inhibition	-	0.8425	84.25%
CYP2C9 inhibition	-	0.8857	88.57%
CYP2C19 inhibition	-	0.9444	94.44%
CYP2D6 inhibition	-	0.9749	97.49%
CYP1A2 inhibition	-	0.7281	72.81%
CYP2C8 inhibition	-	0.8668	86.68%
CYP inhibitory promiscuity	-	0.9301	93.01%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4487	44.87%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.5983	59.83%
Skin irritation	+	0.5640	56.40%
Skin corrosion	-	0.8853	88.53%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7816	78.16%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6658	66.58%
skin sensitisation	-	0.7191	71.91%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.7484	74.84%
Acute Oral Toxicity (c)	III	0.3402	34.02%
Estrogen receptor binding	-	0.7950	79.50%
Androgen receptor binding	-	0.5297	52.97%
Thyroid receptor binding	-	0.6219	62.19%
Glucocorticoid receptor binding	-	0.5815	58.15%
Aromatase binding	-	0.6496	64.96%
PPAR gamma	-	0.6115	61.15%
Honey bee toxicity	-	0.8298	82.98%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9922	99.22%

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	96.55%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.21%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.44%	98.95%
CHEMBL4208	P20618	Proteasome component C5	85.43%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.07%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.29%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.65%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.55%	85.14%

Plants that contains it

• Smyrnium creticum

Cross-Links

• PubChem: 162845276
• LOTUS: LTS0140580
• wikiData: Q105124181