4,5-Dihydroxy-3-[3-(4-hydroxyphenyl)prop-2-enoyloxy]cyclohexene-1-carboxylic acid

Details

• Internal ID: 48892dca-8cd3-4883-a309-58175d497d67
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: 4,5-dihydroxy-3-[3-(4-hydroxyphenyl)prop-2-enoyloxy]cyclohexene-1-carboxylic acid
• SMILES (Canonical): C1C(C(C(C=C1C(=O)O)OC(=O)C=CC2=CC=C(C=C2)O)O)O
• SMILES (Isomeric): C1C(C(C(C=C1C(=O)O)OC(=O)C=CC2=CC=C(C=C2)O)O)O
• InChI: InChI=1S/C16H16O7/c17-11-4-1-9(2-5-11)3-6-14(19)23-13-8-10(16(21)22)7-12(18)15(13)20/h1-6,8,12-13,15,17-18,20H,7H2,(H,21,22)
• InChI Key: LKLFKFQUYFROPV-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆O₇
• Molecular Weight: 320.29 g/mol
• Exact Mass: 320.08960285 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.45
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9688	96.88%
Caco-2	-	0.9062	90.62%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7666	76.66%
OATP2B1 inhibitior	-	0.7210	72.10%
OATP1B1 inhibitior	+	0.9178	91.78%
OATP1B3 inhibitior	+	0.9361	93.61%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8387	83.87%
P-glycoprotein inhibitior	-	0.9156	91.56%
P-glycoprotein substrate	-	0.8467	84.67%
CYP3A4 substrate	-	0.5099	50.99%
CYP2C9 substrate	-	0.5923	59.23%
CYP2D6 substrate	-	0.8652	86.52%
CYP3A4 inhibition	-	0.9492	94.92%
CYP2C9 inhibition	-	0.8851	88.51%
CYP2C19 inhibition	-	0.9106	91.06%
CYP2D6 inhibition	-	0.9412	94.12%
CYP1A2 inhibition	-	0.8279	82.79%
CYP2C8 inhibition	+	0.4825	48.25%
CYP inhibitory promiscuity	-	0.9178	91.78%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8154	81.54%
Carcinogenicity (trinary)	Non-required	0.5681	56.81%
Eye corrosion	-	0.9816	98.16%
Eye irritation	-	0.6519	65.19%
Skin irritation	-	0.6532	65.32%
Skin corrosion	-	0.9337	93.37%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5629	56.29%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.6382	63.82%
skin sensitisation	+	0.6134	61.34%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.7364	73.64%
Acute Oral Toxicity (c)	III	0.4852	48.52%
Estrogen receptor binding	-	0.4927	49.27%
Androgen receptor binding	+	0.5895	58.95%
Thyroid receptor binding	-	0.6114	61.14%
Glucocorticoid receptor binding	+	0.5403	54.03%
Aromatase binding	-	0.6287	62.87%
PPAR gamma	-	0.5656	56.56%
Honey bee toxicity	-	0.8486	84.86%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9819	98.19%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.29%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.43%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.04%	95.56%
CHEMBL3194	P02766	Transthyretin	90.02%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.90%	86.33%
CHEMBL2581	P07339	Cathepsin D	89.12%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.12%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.93%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.39%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.25%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.72%	96.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.24%	94.62%
CHEMBL4208	P20618	Proteasome component C5	80.16%	90.00%

Plants that contains it

• Phegopteris connectilis

Cross-Links

• PubChem: 78070785
• LOTUS: LTS0240027
• wikiData: Q105153109