(2S)-2-[(1E,4R,7E)-4-hydroxy-6-oxo-8-phenylocta-1,7-dienyl]-2,3-dihydropyran-6-one

Details

• Internal ID: 48503a63-732b-44ff-9a0c-f5746699047a
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives
• IUPAC Name: (2S)-2-[(1E,4R,7E)-4-hydroxy-6-oxo-8-phenylocta-1,7-dienyl]-2,3-dihydropyran-6-one
• SMILES (Canonical): C1C=CC(=O)OC1C=CCC(CC(=O)C=CC2=CC=CC=C2)O
• SMILES (Isomeric): C1C=CC(=O)O[C@@H]1/C=C/C[C@H](CC(=O)/C=C/C2=CC=CC=C2)O
• InChI: InChI=1S/C19H20O4/c20-16(8-4-9-18-10-5-11-19(22)23-18)14-17(21)13-12-15-6-2-1-3-7-15/h1-7,9,11-13,16,18,20H,8,10,14H2/b9-4+,13-12+/t16-,18-/m1/s1
• InChI Key: AIRSYDSTHSYQSN-LUTJLFFGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₀O₄
• Molecular Weight: 312.40 g/mol
• Exact Mass: 312.13615911 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.84
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9558	95.58%
Caco-2	-	0.6118	61.18%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7509	75.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9078	90.78%
OATP1B3 inhibitior	+	0.9643	96.43%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6307	63.07%
P-glycoprotein inhibitior	-	0.6604	66.04%
P-glycoprotein substrate	-	0.7250	72.50%
CYP3A4 substrate	+	0.5221	52.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8579	85.79%
CYP3A4 inhibition	-	0.6975	69.75%
CYP2C9 inhibition	-	0.9206	92.06%
CYP2C19 inhibition	-	0.8221	82.21%
CYP2D6 inhibition	-	0.9363	93.63%
CYP1A2 inhibition	-	0.9651	96.51%
CYP2C8 inhibition	-	0.6691	66.91%
CYP inhibitory promiscuity	-	0.9393	93.93%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7841	78.41%
Carcinogenicity (trinary)	Non-required	0.6606	66.06%
Eye corrosion	-	0.9385	93.85%
Eye irritation	-	0.7457	74.57%
Skin irritation	+	0.4918	49.18%
Skin corrosion	-	0.9336	93.36%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5778	57.78%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8226	82.26%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.7552	75.52%
Acute Oral Toxicity (c)	III	0.5533	55.33%
Estrogen receptor binding	+	0.7508	75.08%
Androgen receptor binding	+	0.7398	73.98%
Thyroid receptor binding	-	0.7086	70.86%
Glucocorticoid receptor binding	-	0.5970	59.70%
Aromatase binding	+	0.6791	67.91%
PPAR gamma	+	0.6619	66.19%
Honey bee toxicity	-	0.8858	88.58%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.8122	81.22%

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	95.54%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.94%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.69%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.82%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.18%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.07%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.97%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.33%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.36%	97.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.23%	89.67%
CHEMBL5028	O14672	ADAM10	80.18%	97.50%

Plants that contains it

• Cryptocarya myrtifolia

Cross-Links

• PubChem: 101675711
• LOTUS: LTS0010202
• wikiData: Q104912943