2-Hydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]butanedioic acid

Details

• Internal ID: cc10b735-bbc4-48a3-8e60-eceac1e84c2b
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: 2-hydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]butanedioic acid
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OCC(CC(=O)O)(C(=O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C=CC(=O)OCC(CC(=O)O)(C(=O)O)O)O
• InChI: InChI=1S/C14H14O8/c15-10-4-1-9(2-5-10)3-6-12(18)22-8-14(21,13(19)20)7-11(16)17/h1-6,15,21H,7-8H2,(H,16,17)(H,19,20)
• InChI Key: HYKWTTSTHYCYEH-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₈
• Molecular Weight: 310.26 g/mol
• Exact Mass: 310.06886740 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.24
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7703	77.03%
Caco-2	-	0.8595	85.95%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7720	77.20%
OATP2B1 inhibitior	-	0.7206	72.06%
OATP1B1 inhibitior	+	0.8956	89.56%
OATP1B3 inhibitior	+	0.9533	95.33%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8588	85.88%
BSEP inhibitior	-	0.5395	53.95%
P-glycoprotein inhibitior	-	0.9516	95.16%
P-glycoprotein substrate	-	0.9336	93.36%
CYP3A4 substrate	-	0.5600	56.00%
CYP2C9 substrate	-	0.5983	59.83%
CYP2D6 substrate	-	0.8618	86.18%
CYP3A4 inhibition	-	0.8990	89.90%
CYP2C9 inhibition	-	0.9219	92.19%
CYP2C19 inhibition	-	0.9122	91.22%
CYP2D6 inhibition	-	0.9316	93.16%
CYP1A2 inhibition	-	0.8950	89.50%
CYP2C8 inhibition	+	0.5845	58.45%
CYP inhibitory promiscuity	-	0.9690	96.90%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8932	89.32%
Carcinogenicity (trinary)	Non-required	0.6410	64.10%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.5717	57.17%
Skin irritation	-	0.7092	70.92%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4834	48.34%
Micronuclear	+	0.5606	56.06%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.5781	57.81%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.7461	74.61%
Acute Oral Toxicity (c)	III	0.7810	78.10%
Estrogen receptor binding	+	0.8705	87.05%
Androgen receptor binding	+	0.7769	77.69%
Thyroid receptor binding	-	0.6990	69.90%
Glucocorticoid receptor binding	+	0.6982	69.82%
Aromatase binding	+	0.6920	69.20%
PPAR gamma	+	0.5953	59.53%
Honey bee toxicity	-	0.8744	87.44%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7656	76.56%
Fish aquatic toxicity	+	0.8742	87.42%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.13%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.82%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	92.11%	83.82%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.82%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.72%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.50%	95.56%
CHEMBL3194	P02766	Transthyretin	88.09%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.86%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.05%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.82%	94.62%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.22%	91.71%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	83.13%	90.93%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.68%	89.67%

Plants that contains it

• Lilium longiflorum

Cross-Links

• PubChem: 162882831
• LOTUS: LTS0119378
• wikiData: Q105035357