3-[(E)-3-(3,5-dihydroxyphenyl)prop-2-enoyl]-5-hydroxy-3,4-dihydropyran-2-one

Details

• Internal ID: 8704cf91-98d2-4420-b404-3db51ba75f03
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives
• IUPAC Name: 3-[(E)-3-(3,5-dihydroxyphenyl)prop-2-enoyl]-5-hydroxy-3,4-dihydropyran-2-one
• SMILES (Canonical): C1C(C(=O)OC=C1O)C(=O)C=CC2=CC(=CC(=C2)O)O
• SMILES (Isomeric): C1C(C(=O)OC=C1O)C(=O)/C=C/C2=CC(=CC(=C2)O)O
• InChI: InChI=1S/C14H12O6/c15-9-3-8(4-10(16)5-9)1-2-13(18)12-6-11(17)7-20-14(12)19/h1-5,7,12,15-17H,6H2/b2-1+
• InChI Key: QTRTXOAPDVHYMO-OWOJBTEDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₆
• Molecular Weight: 276.24 g/mol
• Exact Mass: 276.06338810 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.64
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8468	84.68%
Caco-2	-	0.5479	54.79%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5550	55.50%
OATP2B1 inhibitior	-	0.7205	72.05%
OATP1B1 inhibitior	+	0.9087	90.87%
OATP1B3 inhibitior	+	0.9203	92.03%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8468	84.68%
P-glycoprotein inhibitior	-	0.9566	95.66%
P-glycoprotein substrate	-	0.9401	94.01%
CYP3A4 substrate	-	0.5175	51.75%
CYP2C9 substrate	+	0.5904	59.04%
CYP2D6 substrate	-	0.8506	85.06%
CYP3A4 inhibition	-	0.7643	76.43%
CYP2C9 inhibition	-	0.8713	87.13%
CYP2C19 inhibition	-	0.9182	91.82%
CYP2D6 inhibition	-	0.9475	94.75%
CYP1A2 inhibition	-	0.9685	96.85%
CYP2C8 inhibition	-	0.6890	68.90%
CYP inhibitory promiscuity	-	0.8331	83.31%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9146	91.46%
Carcinogenicity (trinary)	Non-required	0.5314	53.14%
Eye corrosion	-	0.9779	97.79%
Eye irritation	+	0.7686	76.86%
Skin irritation	-	0.5181	51.81%
Skin corrosion	-	0.9073	90.73%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7910	79.10%
Micronuclear	+	0.7459	74.59%
Hepatotoxicity	+	0.5322	53.22%
skin sensitisation	-	0.6280	62.80%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.5551	55.51%
Acute Oral Toxicity (c)	III	0.4352	43.52%
Estrogen receptor binding	+	0.7159	71.59%
Androgen receptor binding	+	0.6657	66.57%
Thyroid receptor binding	-	0.5916	59.16%
Glucocorticoid receptor binding	-	0.4844	48.44%
Aromatase binding	+	0.7224	72.24%
PPAR gamma	+	0.6361	63.61%
Honey bee toxicity	-	0.8003	80.03%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8459	84.59%

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	97.98%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	94.96%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.03%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.92%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.45%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.72%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.79%	99.17%
CHEMBL2581	P07339	Cathepsin D	84.00%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.64%	92.94%
CHEMBL3194	P02766	Transthyretin	82.07%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.69%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.55%	96.00%

Plants that contains it

• Rheum australe
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum

Cross-Links

• PubChem: 5320968
• NPASS: NPC253124