Paeonilactone A

Details

• Internal ID: 1382bd00-8630-444a-b146-be4a64e40778
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: (3R,3aR,6S,7aR)-6-hydroxy-3,6-dimethyl-3a,4,7,7a-tetrahydro-3H-1-benzofuran-2,5-dione
• SMILES (Canonical): CC1C2CC(=O)C(CC2OC1=O)(C)O
• SMILES (Isomeric): C[C@@H]1[C@H]2CC(=O)[C@@](C[C@H]2OC1=O)(C)O
• InChI: InChI=1S/C10H14O4/c1-5-6-3-8(11)10(2,13)4-7(6)14-9(5)12/h5-7,13H,3-4H2,1-2H3/t5-,6-,7-,10+/m1/s1
• InChI Key: NODZICYHUGDVAM-IBNKKVAHSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.22 g/mol
• Exact Mass: 198.08920892 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.28
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 98751-79-2
• (-)-Paeonilactone A
• LQV4N956WD
• (3R,3aR,6S,7aR)-6-hydroxy-3,6-dimethyl-3a,4,7,7a-tetrahydro-3H-1-benzofuran-2,5-dione
• (3R,3aR,6S,7aR)-Tetrahydro-6-hydroxy-3,6-dimethyl-2,5(3H,4H)-benzofurandione
• 2,5(3H,4H)-Benzofurandione, tetrahydro-6-hydroxy-3,6-dimethyl-, (3R,3aR,6S,7aR)-
• (3R,3aR,6S,7aR)-6-hydroxy-3,6-dimethyl-octahydro-1-benzofuran-2,5-dione
• paeonilactone-A
• UNII-LQV4N956WD
• SCHEMBL12002470
• CHEBI:81100
• AKOS032948959
• FS-8646
• C17454
• Q27155056

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9830	98.30%
Caco-2	-	0.6516	65.16%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6371	63.71%
OATP2B1 inhibitior	-	0.8449	84.49%
OATP1B1 inhibitior	+	0.9403	94.03%
OATP1B3 inhibitior	+	0.9393	93.93%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9624	96.24%
P-glycoprotein inhibitior	-	0.9706	97.06%
P-glycoprotein substrate	-	0.8493	84.93%
CYP3A4 substrate	+	0.5144	51.44%
CYP2C9 substrate	-	0.6250	62.50%
CYP2D6 substrate	-	0.8459	84.59%
CYP3A4 inhibition	-	0.7779	77.79%
CYP2C9 inhibition	-	0.9629	96.29%
CYP2C19 inhibition	-	0.9555	95.55%
CYP2D6 inhibition	-	0.9760	97.60%
CYP1A2 inhibition	-	0.8719	87.19%
CYP2C8 inhibition	-	0.9814	98.14%
CYP inhibitory promiscuity	-	0.9926	99.26%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5794	57.94%
Eye corrosion	-	0.9733	97.33%
Eye irritation	-	0.6380	63.80%
Skin irritation	+	0.4942	49.42%
Skin corrosion	-	0.6884	68.84%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7033	70.33%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.8249	82.49%
skin sensitisation	-	0.8061	80.61%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.7635	76.35%
Acute Oral Toxicity (c)	III	0.5236	52.36%
Estrogen receptor binding	-	0.5774	57.74%
Androgen receptor binding	-	0.6034	60.34%
Thyroid receptor binding	-	0.7414	74.14%
Glucocorticoid receptor binding	-	0.6959	69.59%
Aromatase binding	-	0.8678	86.78%
PPAR gamma	-	0.8999	89.99%
Honey bee toxicity	-	0.8888	88.88%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9137	91.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.03%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.60%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.44%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.97%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.13%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.24%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.12%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.73%	92.94%

Plants that contains it

• Paeonia delavayi
• Paeonia lactiflora

Cross-Links

• PubChem: 10081437
• LOTUS: LTS0164953
• wikiData: Q27155056