(Z)-3-[2-(carboxymethyl)-3,4-dihydroxy-phenyl]prop-2-enoic acid

Details

• Internal ID: 108139b2-7825-4825-aa17-3e24efe01972
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acids
• IUPAC Name: (Z)-3-[2-(carboxymethyl)-3,4-dihydroxyphenyl]prop-2-enoic acid
• SMILES (Canonical): C1=CC(=C(C(=C1C=CC(=O)O)CC(=O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C(=C1/C=C\C(=O)O)CC(=O)O)O)O
• InChI: InChI=1S/C11H10O6/c12-8-3-1-6(2-4-9(13)14)7(11(8)17)5-10(15)16/h1-4,12,17H,5H2,(H,13,14)(H,15,16)/b4-2-
• InChI Key: KUONJHGPPAGOFL-RQOWECAXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₀O₆
• Molecular Weight: 238.19 g/mol
• Exact Mass: 238.04773803 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.82
• H-Bond Acceptor: 4
• 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	+	0.8901	89.01%
Caco-2	-	0.8326	83.26%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7383	73.83%
OATP2B1 inhibitior	-	0.7093	70.93%
OATP1B1 inhibitior	+	0.8264	82.64%
OATP1B3 inhibitior	+	0.9665	96.65%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9278	92.78%
P-glycoprotein inhibitior	-	0.9863	98.63%
P-glycoprotein substrate	-	0.9631	96.31%
CYP3A4 substrate	-	0.7001	70.01%
CYP2C9 substrate	-	0.5976	59.76%
CYP2D6 substrate	-	0.8517	85.17%
CYP3A4 inhibition	-	0.9112	91.12%
CYP2C9 inhibition	-	0.9737	97.37%
CYP2C19 inhibition	-	0.9786	97.86%
CYP2D6 inhibition	-	0.9395	93.95%
CYP1A2 inhibition	-	0.9566	95.66%
CYP2C8 inhibition	-	0.6648	66.48%
CYP inhibitory promiscuity	-	0.9795	97.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8132	81.32%
Carcinogenicity (trinary)	Non-required	0.6742	67.42%
Eye corrosion	-	0.9435	94.35%
Eye irritation	+	0.9686	96.86%
Skin irritation	+	0.6196	61.96%
Skin corrosion	-	0.7444	74.44%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8870	88.70%
Micronuclear	+	0.7918	79.18%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	+	0.8044	80.44%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8143	81.43%
Acute Oral Toxicity (c)	III	0.7045	70.45%
Estrogen receptor binding	-	0.7382	73.82%
Androgen receptor binding	-	0.5376	53.76%
Thyroid receptor binding	-	0.7465	74.65%
Glucocorticoid receptor binding	+	0.6902	69.02%
Aromatase binding	-	0.7121	71.21%
PPAR gamma	+	0.6145	61.45%
Honey bee toxicity	-	0.9621	96.21%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.8600	86.00%
Fish aquatic toxicity	+	0.9635	96.35%

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	98.40%	91.11%
CHEMBL3194	P02766	Transthyretin	90.68%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.40%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.65%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	86.23%	90.17%
CHEMBL2581	P07339	Cathepsin D	85.91%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.55%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	83.37%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.17%	99.15%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.71%	91.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.08%	89.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.62%	94.62%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	81.26%	98.11%

Plants that contains it

• Salvia przewalskii

Cross-Links

• PubChem: 49770696
• NPASS: NPC148438