Prenylcaffeic acid

Details

• Internal ID: fea121f8-9e84-461d-aa3d-420c82fe8d72
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acids
• IUPAC Name: (2E)-2-[(3,4-dihydroxyphenyl)methylidene]-5-methylhex-4-enoic acid
• SMILES (Canonical): CC(=CCC(=CC1=CC(=C(C=C1)O)O)C(=O)O)C
• SMILES (Isomeric): CC(=CC/C(=C\C1=CC(=C(C=C1)O)O)/C(=O)O)C
• InChI: InChI=1S/C14H16O4/c1-9(2)3-5-11(14(17)18)7-10-4-6-12(15)13(16)8-10/h3-4,6-8,15-16H,5H2,1-2H3,(H,17,18)/b11-7+
• InChI Key: YQMRJFZDFYWSRI-YRNVUSSQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.27 g/mol
• Exact Mass: 248.10485899 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.92
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9900	99.00%
Caco-2	+	0.5663	56.63%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8419	84.19%
OATP2B1 inhibitior	-	0.5764	57.64%
OATP1B1 inhibitior	+	0.9528	95.28%
OATP1B3 inhibitior	+	0.9506	95.06%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6016	60.16%
P-glycoprotein inhibitior	-	0.9771	97.71%
P-glycoprotein substrate	-	0.9495	94.95%
CYP3A4 substrate	-	0.6468	64.68%
CYP2C9 substrate	-	0.5992	59.92%
CYP2D6 substrate	-	0.8781	87.81%
CYP3A4 inhibition	-	0.8756	87.56%
CYP2C9 inhibition	+	0.6615	66.15%
CYP2C19 inhibition	-	0.5610	56.10%
CYP2D6 inhibition	-	0.7312	73.12%
CYP1A2 inhibition	-	0.5252	52.52%
CYP2C8 inhibition	-	0.8866	88.66%
CYP inhibitory promiscuity	-	0.6736	67.36%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7430	74.30%
Carcinogenicity (trinary)	Non-required	0.7209	72.09%
Eye corrosion	-	0.9522	95.22%
Eye irritation	+	0.9701	97.01%
Skin irritation	-	0.5132	51.32%
Skin corrosion	-	0.7307	73.07%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7724	77.24%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	+	0.7499	74.99%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.6585	65.85%
Acute Oral Toxicity (c)	III	0.6601	66.01%
Estrogen receptor binding	+	0.5347	53.47%
Androgen receptor binding	+	0.7290	72.90%
Thyroid receptor binding	+	0.5616	56.16%
Glucocorticoid receptor binding	+	0.6603	66.03%
Aromatase binding	-	0.5063	50.63%
PPAR gamma	+	0.7479	74.79%
Honey bee toxicity	-	0.9609	96.09%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9968	99.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.45%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.39%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.28%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	89.01%	94.73%
CHEMBL2581	P07339	Cathepsin D	88.63%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.20%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.37%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.53%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.94%	99.17%
CHEMBL4208	P20618	Proteasome component C5	82.37%	90.00%
CHEMBL3194	P02766	Transthyretin	82.04%	90.71%

Plants that contains it

• Populus ciliata
• Populus yunnanensis

Cross-Links

• PubChem: 129723082
• LOTUS: LTS0271012
• wikiData: Q104375509