N-Coumaroyl serotonin

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	1e212a19-60b9-451a-8b14-dd8b857566c7
Taxonomy	Organoheterocyclic compounds > Indoles and derivatives > Tryptamines and derivatives > Serotonins > N-acylserotonins
IUPAC Name	(E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
SMILES (Canonical)	C1=CC(=CC=C1C=CC(=O)NCCC2=CNC3=C2C=C(C=C3)O)O
SMILES (Isomeric)	C1=CC(=CC=C1/C=C/C(=O)NCCC2=CNC3=C2C=C(C=C3)O)O
InChI	InChI=1S/C19H18N2O3/c22-15-4-1-13(2-5-15)3-8-19(24)20-10-9-14-12-21-18-7-6-16(23)11-17(14)18/h1-8,11-12,21-23H,9-10H2,(H,20,24)/b8-3+
InChI Key	WLZPAFGVOWCVMG-FPYGCLRLSA-N
Popularity	29 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₉H₁₈N₂O₃
Molecular Weight	322.40 g/mol
Exact Mass	322.13174244 g/mol
Topological Polar Surface Area (TPSA)	85.40 Å²
XlogP	2.20
Atomic LogP (AlogP)	2.95
H-Bond Acceptor	3
H-Bond Donor	4
Rotatable Bonds	5

Synonyms

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N-Coumaroyl serotonin

68573-24-0

p-coumaroylserotonin

4-Coumaroylserotonin

Coumaroylserotonin 98

201301-83-9

N6-cis-p-Coumaroylserotonin

trans-N-(p-Coumaroyl)serotonin

(E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide

n-(p-coumaroyl)serotonin

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.6594	65.94%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7999	79.99%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.8905	89.05%
OATP1B3 inhibitior	+	0.9464	94.64%
MATE1 inhibitior	-	0.8609	86.09%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.8346	83.46%
P-glycoprotein inhibitior	-	0.7208	72.08%
P-glycoprotein substrate	+	0.6560	65.60%
CYP3A4 substrate	+	0.5273	52.73%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.8180	81.80%
CYP3A4 inhibition	+	0.5870	58.70%
CYP2C9 inhibition	-	0.6384	63.84%
CYP2C19 inhibition	-	0.7920	79.20%
CYP2D6 inhibition	-	0.5537	55.37%
CYP1A2 inhibition	+	0.7745	77.45%
CYP2C8 inhibition	+	0.6588	65.88%
CYP inhibitory promiscuity	+	0.7550	75.50%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5921	59.21%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.8556	85.56%
Skin irritation	-	0.8077	80.77%
Skin corrosion	-	0.9603	96.03%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7392	73.92%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.8948	89.48%
skin sensitisation	-	0.8821	88.21%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.9019	90.19%
Acute Oral Toxicity (c)	III	0.5722	57.22%
Estrogen receptor binding	+	0.8725	87.25%
Androgen receptor binding	+	0.6741	67.41%
Thyroid receptor binding	-	0.5161	51.61%
Glucocorticoid receptor binding	+	0.6533	65.33%
Aromatase binding	+	0.7016	70.16%
PPAR gamma	+	0.7972	79.72%
Honey bee toxicity	-	0.8981	89.81%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	-	0.6067	60.67%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	99.56%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	94.43%	94.75%
CHEMBL2581	P07339	Cathepsin D	94.09%	98.95%
CHEMBL3959	P16083	Quinone reductase 2	93.54%	89.49%
CHEMBL255	P29275	Adenosine A2b receptor	93.36%	98.59%
CHEMBL1914	P06276	Butyrylcholinesterase	92.88%	95.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.14%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.84%	89.00%
CHEMBL325	Q13547	Histone deacetylase 1	90.08%	95.92%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	89.28%	83.10%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.99%	91.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.61%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	88.51%	98.35%
CHEMBL2535	P11166	Glucose transporter	88.20%	98.75%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	87.35%	89.67%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	86.66%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.23%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.94%	95.56%
CHEMBL206	P03372	Estrogen receptor alpha	84.60%	97.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.33%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.33%	96.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.25%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.61%	86.33%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	82.02%	89.33%
CHEMBL1829	O15379	Histone deacetylase 3	81.72%	95.00%
CHEMBL3385	P27361	MAP kinase ERK1	81.69%	96.29%
CHEMBL3194	P02766	Transthyretin	80.33%	90.71%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	80.31%	96.39%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Amorphophallus konjac

Carthamus tinctorius

Centaurea nigra

Echinochloa esculenta

Ipomoea obscura

Phragmites australis