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

Details

• Internal ID: 491e41dc-9840-40b0-8ad1-fb4a12db5401
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: 3,5-dihydroxy-4-[3-(4-hydroxyphenyl)prop-2-enoyloxy]cyclohexene-1-carboxylic acid
• InChI: InChI=1S/C16H16O7/c17-11-4-1-9(2-5-11)3-6-14(20)23-15-12(18)7-10(16(21)22)8-13(15)19/h1-7,12-13,15,17-19H,8H2,(H,21,22)
• InChI Key: HLTJQPFRKIIQGY-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	+	0.9132	91.32%
Caco-2	-	0.9260	92.60%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6497	64.97%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8942	89.42%
OATP1B3 inhibitior	+	0.9207	92.07%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9588	95.88%
BSEP inhibitior	-	0.7730	77.30%
P-glycoprotein inhibitior	-	0.9257	92.57%
P-glycoprotein substrate	-	0.8814	88.14%
CYP3A4 substrate	+	0.5102	51.02%
CYP2C9 substrate	-	0.5915	59.15%
CYP2D6 substrate	-	0.8660	86.60%
CYP3A4 inhibition	-	0.9298	92.98%
CYP2C9 inhibition	-	0.7884	78.84%
CYP2C19 inhibition	-	0.8576	85.76%
CYP2D6 inhibition	-	0.9216	92.16%
CYP1A2 inhibition	-	0.8542	85.42%
CYP2C8 inhibition	+	0.5220	52.20%
CYP inhibitory promiscuity	-	0.7889	78.89%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8582	85.82%
Carcinogenicity (trinary)	Non-required	0.5964	59.64%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.7423	74.23%
Skin irritation	-	0.6577	65.77%
Skin corrosion	-	0.9377	93.77%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5493	54.93%
Micronuclear	+	0.6959	69.59%
Hepatotoxicity	-	0.6132	61.32%
skin sensitisation	+	0.5133	51.33%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6878	68.78%
Acute Oral Toxicity (c)	III	0.5333	53.33%
Estrogen receptor binding	+	0.5840	58.40%
Androgen receptor binding	+	0.6007	60.07%
Thyroid receptor binding	-	0.6152	61.52%
Glucocorticoid receptor binding	-	0.4809	48.09%
Aromatase binding	-	0.6920	69.20%
PPAR gamma	-	0.5350	53.50%
Honey bee toxicity	-	0.7783	77.83%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9734	97.34%

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	95.59%	91.11%
CHEMBL3194	P02766	Transthyretin	92.69%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.26%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.22%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.08%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.65%	94.62%
CHEMBL4040	P28482	MAP kinase ERK2	87.86%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.87%	97.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.40%	94.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.99%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.96%	93.00%
CHEMBL2581	P07339	Cathepsin D	82.57%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.54%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.52%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.04%	95.50%

Plants that contains it

• Dicksonia antarctica

Cross-Links

• PubChem: 4477520
• LOTUS: LTS0084354
• wikiData: Q105030289