Nb-p-Coumaroyltryptamine

Details

• Internal ID: d0ce9054-2bac-4199-973c-bcf5ca406ba3
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: (E)-3-(4-hydroxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]prop-2-enamide
• SMILES (Canonical): C1=CC=C2C(=C1)C(=CN2)CCNC(=O)C=CC3=CC=C(C=C3)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=CN2)CCNC(=O)/C=C/C3=CC=C(C=C3)O
• InChI: InChI=1S/C19H18N2O2/c22-16-8-5-14(6-9-16)7-10-19(23)20-12-11-15-13-21-18-4-2-1-3-17(15)18/h1-10,13,21-22H,11-12H2,(H,20,23)/b10-7+
• InChI Key: CDMGLLBADMBULG-JXMROGBWSA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈N₂O₂
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.136827821 g/mol
• Topological Polar Surface Area (TPSA): 65.10 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.25
• H-Bond Acceptor: 2
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• Nb-p-Coumaroyltryptamine
• (E)-N-[2-(3-Indolyl)ethyl]-3-(4-hydroxyphenyl)acrylamide
• 2-Propenamide, 3-(4-hydroxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]-, (2E)-
• N-Feruloyltryptamine
• p-coumaroyltryptamine
• N-(p-Coumaroyl)-tryptamine
• SCHEMBL798186
• SCHEMBL798226
• CHEMBL488849
• CDMGLLBADMBULG-JXMROGBWSA-N
• CHEBI:174932
• (E)-3-(4-hydroxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]prop-2-enamide
• AC5561
• AKOS016811508
• AC-29783
• CS-12365
• A918875
• (E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxyphenyl) acrylamide
• (E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)acrylamide
• (2E)-3-(4-hydroxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]prop-2-enamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.5898	58.98%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7457	74.57%
OATP2B1 inhibitior	-	0.8566	85.66%
OATP1B1 inhibitior	+	0.9042	90.42%
OATP1B3 inhibitior	+	0.9467	94.67%
MATE1 inhibitior	-	0.8609	86.09%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.9141	91.41%
P-glycoprotein inhibitior	-	0.7126	71.26%
P-glycoprotein substrate	-	0.5346	53.46%
CYP3A4 substrate	+	0.5650	56.50%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.8180	81.80%
CYP3A4 inhibition	+	0.5994	59.94%
CYP2C9 inhibition	-	0.5880	58.80%
CYP2C19 inhibition	-	0.7788	77.88%
CYP2D6 inhibition	+	0.5188	51.88%
CYP1A2 inhibition	+	0.8264	82.64%
CYP2C8 inhibition	+	0.7498	74.98%
CYP inhibitory promiscuity	+	0.8128	81.28%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5734	57.34%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.8819	88.19%
Skin irritation	-	0.8104	81.04%
Skin corrosion	-	0.9602	96.02%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7475	74.75%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.8323	83.23%
skin sensitisation	-	0.8771	87.71%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8444	84.44%
Acute Oral Toxicity (c)	III	0.5644	56.44%
Estrogen receptor binding	+	0.9462	94.62%
Androgen receptor binding	+	0.7654	76.54%
Thyroid receptor binding	-	0.6042	60.42%
Glucocorticoid receptor binding	+	0.5615	56.15%
Aromatase binding	+	0.7961	79.61%
PPAR gamma	+	0.8349	83.49%
Honey bee toxicity	-	0.8826	88.26%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.7056	70.56%

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	99.64%	91.11%
CHEMBL1914	P06276	Butyrylcholinesterase	95.36%	95.00%
CHEMBL1937	Q92769	Histone deacetylase 2	94.82%	94.75%
CHEMBL2581	P07339	Cathepsin D	94.75%	98.95%
CHEMBL3959	P16083	Quinone reductase 2	93.57%	89.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.63%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.82%	89.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	91.48%	83.10%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.87%	93.99%
CHEMBL255	P29275	Adenosine A2b receptor	89.38%	98.59%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	88.31%	89.67%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	87.64%	96.67%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	87.28%	89.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.80%	96.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.89%	91.71%
CHEMBL2535	P11166	Glucose transporter	85.32%	98.75%
CHEMBL3310	Q96DB2	Histone deacetylase 11	84.91%	88.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.70%	96.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	83.35%	96.39%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.11%	99.23%
CHEMBL4208	P20618	Proteasome component C5	81.76%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.76%	89.62%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.84%	94.62%
CHEMBL3401	O75469	Pregnane X receptor	80.59%	94.73%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	80.13%	89.44%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.06%	86.33%

Plants that contains it

• Carthamus tinctorius
• Cinnamosma madagascariensis
• Zea mays

Cross-Links

• PubChem: 5458878
• LOTUS: LTS0176591
• wikiData: Q76306433