1-Feruloyloxy cinnamic acid

Details

• Internal ID: 7f5c5c44-326e-41bc-bbba-b673a00c951f
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: 3-[1-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxycyclohexa-2,4-dien-1-yl]prop-2-enoic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OC2(CC=CC=C2)C=CC(=O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC2(CC=CC=C2)C=CC(=O)O)O
• InChI: InChI=1S/C19H18O6/c1-24-16-13-14(5-7-15(16)20)6-8-18(23)25-19(12-9-17(21)22)10-3-2-4-11-19/h2-10,12-13,20H,11H2,1H3,(H,21,22)/b8-6+,12-9?
• InChI Key: LEVFFSWUVNUHNB-ZFFFOARKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₆
• Molecular Weight: 342.30 g/mol
• Exact Mass: 342.11033829 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.85
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9789	97.89%
Caco-2	-	0.7875	78.75%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8771	87.71%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.9181	91.81%
OATP1B3 inhibitior	+	0.9575	95.75%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9345	93.45%
P-glycoprotein inhibitior	-	0.6814	68.14%
P-glycoprotein substrate	-	0.8046	80.46%
CYP3A4 substrate	+	0.5730	57.30%
CYP2C9 substrate	-	0.5979	59.79%
CYP2D6 substrate	-	0.8436	84.36%
CYP3A4 inhibition	-	0.7865	78.65%
CYP2C9 inhibition	+	0.5622	56.22%
CYP2C19 inhibition	-	0.6043	60.43%
CYP2D6 inhibition	-	0.8911	89.11%
CYP1A2 inhibition	-	0.6480	64.80%
CYP2C8 inhibition	+	0.7409	74.09%
CYP inhibitory promiscuity	-	0.8408	84.08%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7599	75.99%
Carcinogenicity (trinary)	Non-required	0.5235	52.35%
Eye corrosion	-	0.9639	96.39%
Eye irritation	-	0.6154	61.54%
Skin irritation	-	0.6344	63.44%
Skin corrosion	-	0.9051	90.51%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4687	46.87%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8014	80.14%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.7500	75.00%
Nephrotoxicity	-	0.7577	75.77%
Acute Oral Toxicity (c)	III	0.6237	62.37%
Estrogen receptor binding	+	0.9054	90.54%
Androgen receptor binding	+	0.6639	66.39%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7628	76.28%
Aromatase binding	+	0.7907	79.07%
PPAR gamma	+	0.6511	65.11%
Honey bee toxicity	-	0.8483	84.83%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5545	55.45%
Fish aquatic toxicity	+	0.9695	96.95%

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	99.08%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.85%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.16%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.01%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.74%	96.00%
CHEMBL3194	P02766	Transthyretin	91.40%	90.71%
CHEMBL4208	P20618	Proteasome component C5	90.60%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.62%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.49%	89.62%
CHEMBL1951	P21397	Monoamine oxidase A	88.45%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.38%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.54%	95.50%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.69%	80.78%

Plants that contains it

• Curcuma chuanyujin

Cross-Links

• PubChem: 156613243
• LOTUS: LTS0049996
• wikiData: Q105150803