Kavapyrone

Details

• Internal ID: 0ea11a07-702b-4e89-8d90-97fa0c1ee2e4
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives
• IUPAC Name: 4-methoxy-6-[(2R,3S)-3-phenyloxiran-2-yl]pyran-2-one
• SMILES (Canonical): COC1=CC(=O)OC(=C1)C2C(O2)C3=CC=CC=C3
• SMILES (Isomeric): COC1=CC(=O)OC(=C1)[C@H]2[C@@H](O2)C3=CC=CC=C3
• InChI: InChI=1S/C14H12O4/c1-16-10-7-11(17-12(15)8-10)14-13(18-14)9-5-3-2-4-6-9/h2-8,13-14H,1H3/t13-,14-/m0/s1
• InChI Key: MLGUXXSGWWCJQW-KBPBESRZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24 g/mol
• Exact Mass: 244.07355886 g/mol
• Topological Polar Surface Area (TPSA): 48.10 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.46
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 4-methoxy-6-[(2R,3S)-3-phenyloxiran-2-yl]-2H-pyran-2-one
• CHEBI:6116
• (+)-(7R,8S)-epoxy-5,6-didehydrokavain
• Q27089357

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9696	96.96%
Caco-2	+	0.8703	87.03%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8220	82.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8989	89.89%
OATP1B3 inhibitior	+	0.9742	97.42%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.5884	58.84%
P-glycoprotein inhibitior	-	0.5880	58.80%
P-glycoprotein substrate	-	0.9644	96.44%
CYP3A4 substrate	-	0.5974	59.74%
CYP2C9 substrate	-	0.8026	80.26%
CYP2D6 substrate	-	0.8636	86.36%
CYP3A4 inhibition	-	0.5339	53.39%
CYP2C9 inhibition	-	0.7162	71.62%
CYP2C19 inhibition	+	0.7822	78.22%
CYP2D6 inhibition	-	0.8903	89.03%
CYP1A2 inhibition	-	0.5460	54.60%
CYP2C8 inhibition	-	0.6972	69.72%
CYP inhibitory promiscuity	+	0.7157	71.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Danger	0.3786	37.86%
Eye corrosion	-	0.9535	95.35%
Eye irritation	-	0.6443	64.43%
Skin irritation	-	0.6398	63.98%
Skin corrosion	-	0.9715	97.15%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3879	38.79%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.5085	50.85%
skin sensitisation	-	0.9000	90.00%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	+	0.5952	59.52%
Acute Oral Toxicity (c)	III	0.7044	70.44%
Estrogen receptor binding	+	0.6723	67.23%
Androgen receptor binding	+	0.7100	71.00%
Thyroid receptor binding	-	0.6321	63.21%
Glucocorticoid receptor binding	-	0.7061	70.61%
Aromatase binding	+	0.5719	57.19%
PPAR gamma	-	0.5371	53.71%
Honey bee toxicity	-	0.8986	89.86%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.8870	88.70%

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	96.59%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.56%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.79%	86.33%
CHEMBL2581	P07339	Cathepsin D	89.62%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	89.54%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.03%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.75%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.53%	96.09%

Plants that contains it

• Artocarpus altilis
• Piper rusbyi

Cross-Links

• PubChem: 71296128
• NPASS: NPC17834
• LOTUS: LTS0175779
• wikiData: Q27089357