p-Coumaroylmalic acid

Details

• Internal ID: 1af3b13d-34eb-425d-9e3e-19c91e94bd37
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives
• IUPAC Name: 2-hydroxy-2-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]butanedioic acid
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)C(CC(=O)O)(C(=O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=O)C(CC(=O)O)(C(=O)O)O)O
• InChI: InChI=1S/C13H12O7/c14-9-4-1-8(2-5-9)3-6-10(15)13(20,12(18)19)7-11(16)17/h1-6,14,20H,7H2,(H,16,17)(H,18,19)/b6-3+
• InChI Key: UZDZNIDGWLPLJL-ZZXKWVIFSA-N
• Popularity: 24 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂O₇
• Molecular Weight: 280.23 g/mol
• Exact Mass: 280.05830272 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.26
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8673	86.73%
Caco-2	-	0.7651	76.51%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6807	68.07%
OATP2B1 inhibitior	-	0.7105	71.05%
OATP1B1 inhibitior	+	0.8638	86.38%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8338	83.38%
BSEP inhibitior	-	0.8254	82.54%
P-glycoprotein inhibitior	-	0.9824	98.24%
P-glycoprotein substrate	-	0.9388	93.88%
CYP3A4 substrate	-	0.6596	65.96%
CYP2C9 substrate	-	0.7798	77.98%
CYP2D6 substrate	-	0.8559	85.59%
CYP3A4 inhibition	-	0.7763	77.63%
CYP2C9 inhibition	-	0.9646	96.46%
CYP2C19 inhibition	-	0.9619	96.19%
CYP2D6 inhibition	-	0.9591	95.91%
CYP1A2 inhibition	-	0.9690	96.90%
CYP2C8 inhibition	-	0.6191	61.91%
CYP inhibitory promiscuity	-	0.9876	98.76%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8170	81.70%
Carcinogenicity (trinary)	Non-required	0.6319	63.19%
Eye corrosion	-	0.9740	97.40%
Eye irritation	-	0.5389	53.89%
Skin irritation	+	0.5478	54.78%
Skin corrosion	-	0.8718	87.18%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9058	90.58%
Micronuclear	+	0.6977	69.77%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	+	0.6169	61.69%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.7678	76.78%
Acute Oral Toxicity (c)	III	0.7305	73.05%
Estrogen receptor binding	+	0.5490	54.90%
Androgen receptor binding	+	0.6882	68.82%
Thyroid receptor binding	-	0.6312	63.12%
Glucocorticoid receptor binding	+	0.6858	68.58%
Aromatase binding	+	0.7386	73.86%
PPAR gamma	+	0.6766	67.66%
Honey bee toxicity	-	0.9275	92.75%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.8640	86.40%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	91.59%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.51%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.41%	86.33%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	86.72%	90.93%
CHEMBL3194	P02766	Transthyretin	85.95%	90.71%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.91%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.01%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.57%	91.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.25%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.80%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.05%	96.00%

Plants that contains it

• Pyrus communis

Cross-Links

• PubChem: 129720114
• LOTUS: LTS0100037
• wikiData: Q105282133