Paeonilide

Details

• Internal ID: 39fc2bf7-0659-4390-b98f-0f48964cc89a
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Benzoic acid esters
• IUPAC Name: [(3R,3aR,6aR)-5-oxo-6a-(2-oxopropyl)-2,3,3a,4-tetrahydrofuro[2,3-b]furan-3-yl]methyl benzoate
• SMILES (Canonical): CC(=O)CC12C(CC(=O)O1)C(CO2)COC(=O)C3=CC=CC=C3
• SMILES (Isomeric): CC(=O)C[C@]12[C@H](CC(=O)O1)[C@H](CO2)COC(=O)C3=CC=CC=C3
• InChI: InChI=1S/C17H18O6/c1-11(18)8-17-14(7-15(19)23-17)13(10-22-17)9-21-16(20)12-5-3-2-4-6-12/h2-6,13-14H,7-10H2,1H3/t13-,14+,17+/m0/s1
• InChI Key: KPLJENFVVZWBMN-JJRVBVJISA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₆
• Molecular Weight: 318.32 g/mol
• Exact Mass: 318.11033829 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.73
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• CHEBI:66718
• Q27135341
• [(3R,3aR,6aR)-5-oxo-6a-(2-oxopropyl)-2,3,3a,4-tetrahydrofuro[2,3-b]furan-3-yl]methyl benzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9783	97.83%
Caco-2	+	0.5323	53.23%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7484	74.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8952	89.52%
OATP1B3 inhibitior	+	0.9616	96.16%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6706	67.06%
P-glycoprotein inhibitior	-	0.6912	69.12%
P-glycoprotein substrate	-	0.6916	69.16%
CYP3A4 substrate	+	0.5434	54.34%
CYP2C9 substrate	+	0.6104	61.04%
CYP2D6 substrate	-	0.8536	85.36%
CYP3A4 inhibition	-	0.8831	88.31%
CYP2C9 inhibition	-	0.6537	65.37%
CYP2C19 inhibition	+	0.5358	53.58%
CYP2D6 inhibition	-	0.8880	88.80%
CYP1A2 inhibition	-	0.7946	79.46%
CYP2C8 inhibition	+	0.5359	53.59%
CYP inhibitory promiscuity	-	0.8190	81.90%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8843	88.43%
Carcinogenicity (trinary)	Non-required	0.5056	50.56%
Eye corrosion	-	0.9247	92.47%
Eye irritation	-	0.7984	79.84%
Skin irritation	-	0.8489	84.89%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7515	75.15%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.5106	51.06%
skin sensitisation	-	0.7460	74.60%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	-	0.5923	59.23%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6869	68.69%
Acute Oral Toxicity (c)	III	0.7418	74.18%
Estrogen receptor binding	+	0.7462	74.62%
Androgen receptor binding	+	0.5516	55.16%
Thyroid receptor binding	-	0.6696	66.96%
Glucocorticoid receptor binding	-	0.6815	68.15%
Aromatase binding	-	0.6971	69.71%
PPAR gamma	-	0.6290	62.90%
Honey bee toxicity	-	0.9176	91.76%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9630	96.30%

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	96.78%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.17%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.01%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.60%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	91.69%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.46%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.78%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.70%	95.56%
CHEMBL4208	P20618	Proteasome component C5	84.98%	90.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.40%	83.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.37%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	80.24%	94.73%

Plants that contains it

• Paeonia delavayi

Cross-Links

• PubChem: 10448571
• LOTUS: LTS0270039
• wikiData: Q27135341