Paneolic acid

Details

• Internal ID: e8464bcd-47f5-4b88-94a9-c4fa72d5c619
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Cyclic ketones > Cyclohexenones
• IUPAC Name: (2S,3aR,5R)-5-acetyl-2,5,7-trimethyl-6-oxo-1,3,3a,4-tetrahydroindene-2-carboxylic acid
• SMILES (Canonical): CC1=C2CC(CC2CC(C1=O)(C)C(=O)C)(C)C(=O)O
• SMILES (Isomeric): CC1=C2C[C@@](C[C@H]2C[C@](C1=O)(C)C(=O)C)(C)C(=O)O
• InChI: InChI=1S/C15H20O4/c1-8-11-7-14(3,13(18)19)5-10(11)6-15(4,9(2)16)12(8)17/h10H,5-7H2,1-4H3,(H,18,19)/t10-,14-,15+/m0/s1
• InChI Key: VFTMSVNDYVXTOG-NZVBXONLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• (2S,3aR,5R)-5-acetyl-2,5,7-trimethyl-6-oxo-1,3,3a,4-tetrahydroindene-2-carboxylic Acid
• RefChem:169864
• CHEBI:197928

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.7644	76.44%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7695	76.95%
OATP2B1 inhibitior	-	0.8504	85.04%
OATP1B1 inhibitior	+	0.9396	93.96%
OATP1B3 inhibitior	+	0.8896	88.96%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.8405	84.05%
P-glycoprotein inhibitior	-	0.9591	95.91%
P-glycoprotein substrate	-	0.8595	85.95%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.9114	91.14%
CYP3A4 inhibition	-	0.8385	83.85%
CYP2C9 inhibition	-	0.8785	87.85%
CYP2C19 inhibition	-	0.9495	94.95%
CYP2D6 inhibition	-	0.9686	96.86%
CYP1A2 inhibition	-	0.7908	79.08%
CYP2C8 inhibition	-	0.8948	89.48%
CYP inhibitory promiscuity	-	0.9683	96.83%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8913	89.13%
Carcinogenicity (trinary)	Non-required	0.5483	54.83%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.8235	82.35%
Skin irritation	+	0.6374	63.74%
Skin corrosion	-	0.9495	94.95%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5968	59.68%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.6199	61.99%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.7372	73.72%
Acute Oral Toxicity (c)	II	0.3641	36.41%
Estrogen receptor binding	+	0.6033	60.33%
Androgen receptor binding	-	0.5093	50.93%
Thyroid receptor binding	-	0.6097	60.97%
Glucocorticoid receptor binding	-	0.7195	71.95%
Aromatase binding	-	0.6843	68.43%
PPAR gamma	-	0.6446	64.46%
Honey bee toxicity	-	0.9396	93.96%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.05%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.23%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	90.07%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.40%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.00%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.70%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.66%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	82.35%	83.82%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.37%	93.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.79%	93.04%
CHEMBL340	P08684	Cytochrome P450 3A4	80.34%	91.19%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11230843
• LOTUS: LTS0181380
• wikiData: Q75057119