4,4''-bis(N-feruloyl)serotonin

Details

• Internal ID: e2dcda34-9bef-458e-ab1d-763b72e0e7b6
• Taxonomy: Benzenoids > Phenols > Methoxyphenols
• IUPAC Name: (E)-N-[2-[5-hydroxy-4-[5-hydroxy-3-[2-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]amino]ethyl]-1H-indol-4-yl]-1H-indol-3-yl]ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)NCCC2=CNC3=C2C(=C(C=C3)O)C4=C(C=CC5=C4C(=CN5)CCNC(=O)C=CC6=CC(=C(C=C6)O)OC)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)NCCC2=CNC3=C2C(=C(C=C3)O)C4=C(C=CC5=C4C(=CN5)CCNC(=O)/C=C/C6=CC(=C(C=C6)O)OC)O)O
• InChI: InChI=1S/C40H38N4O8/c1-51-33-19-23(3-9-29(33)45)5-13-35(49)41-17-15-25-21-43-27-7-11-31(47)39(37(25)27)40-32(48)12-8-28-38(40)26(22-44-28)16-18-42-36(50)14-6-24-4-10-30(46)34(20-24)52-2/h3-14,19-22,43-48H,15-18H2,1-2H3,(H,41,49)(H,42,50)/b13-5+,14-6+
• InChI Key: URHRFQQPWDNDQE-ACFHMISVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₃₈N₄O₈
• Molecular Weight: 702.70 g/mol
• Exact Mass: 702.26896418 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.90
• H-Bond Acceptor: 8
• H-Bond Donor: 8
• Rotatable Bonds: 13

Synonyms

• 4,4'-Bis(N-feruloyl)serotonin
• CHEMBL4206909
• (p-chlorophenyl)-Sulfamoyl azide
• (4-chlorophenyl)-Sulfamoyl azide
• CHEBI:184799
• DTXSID201307899
• 175702-03-1
• Sulfamoyl azide, (4-chlorophenyl)- (9CI)
• 4,4''-Bi[N-(4-hydroxy-3-methoxycinnamoyl)serotonin]
• (2E)-3-(4-hydroxy-3-methoxyphenyl)-N-{2-[5-hydroxy-4-(5-hydroxy-3-{2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]ethyl}-1H-indol-4-yl)-1H-indol-3-yl]ethyl}prop-2-enamide
• (2E)-N-{2-[5,5'-dihydroxy-3'-(2-{[(2E)-1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-ylidene]amino}ethyl)-1H,1'H-[4,4'-biindole]-3-yl]ethyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid
• (E)-N-[2-[5-hydroxy-4-[5-hydroxy-3-[2-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]amino]ethyl]-1H-indol-4-yl]-1H-indol-3-yl]ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9828	98.28%
Caco-2	-	0.8775	87.75%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7260	72.60%
OATP2B1 inhibitior	+	0.7184	71.84%
OATP1B1 inhibitior	+	0.8974	89.74%
OATP1B3 inhibitior	+	0.9353	93.53%
MATE1 inhibitior	-	0.9009	90.09%
OCT2 inhibitior	-	0.6611	66.11%
BSEP inhibitior	+	0.9901	99.01%
P-glycoprotein inhibitior	+	0.8160	81.60%
P-glycoprotein substrate	+	0.5293	52.93%
CYP3A4 substrate	+	0.5831	58.31%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	-	0.8002	80.02%
CYP3A4 inhibition	+	0.8541	85.41%
CYP2C9 inhibition	+	0.7094	70.94%
CYP2C19 inhibition	+	0.5583	55.83%
CYP2D6 inhibition	-	0.8539	85.39%
CYP1A2 inhibition	-	0.5954	59.54%
CYP2C8 inhibition	+	0.7901	79.01%
CYP inhibitory promiscuity	+	0.6461	64.61%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5808	58.08%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9123	91.23%
Skin irritation	-	0.7747	77.47%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6857	68.57%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.8198	81.98%
skin sensitisation	-	0.9007	90.07%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8642	86.42%
Acute Oral Toxicity (c)	III	0.6543	65.43%
Estrogen receptor binding	+	0.8081	80.81%
Androgen receptor binding	+	0.8130	81.30%
Thyroid receptor binding	+	0.6231	62.31%
Glucocorticoid receptor binding	+	0.6732	67.32%
Aromatase binding	+	0.6009	60.09%
PPAR gamma	+	0.7417	74.17%
Honey bee toxicity	-	0.8585	85.85%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	-	0.4319	43.19%

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	99.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.66%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.93%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.97%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.70%	86.33%
CHEMBL2581	P07339	Cathepsin D	92.74%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.26%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.25%	89.00%
CHEMBL4208	P20618	Proteasome component C5	92.07%	90.00%
CHEMBL2535	P11166	Glucose transporter	90.96%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.07%	95.56%
CHEMBL1255126	O15151	Protein Mdm4	88.88%	90.20%
CHEMBL255	P29275	Adenosine A2b receptor	88.53%	98.59%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.33%	99.17%
CHEMBL3194	P02766	Transthyretin	88.06%	90.71%
CHEMBL1914	P06276	Butyrylcholinesterase	85.06%	95.00%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	84.44%	97.03%
CHEMBL3788	O00444	Serine/threonine-protein kinase PLK4	83.28%	83.65%
CHEMBL1937	Q92769	Histone deacetylase 2	83.17%	94.75%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	81.42%	95.48%

Plants that contains it

• Carthamus tinctorius

Cross-Links

• PubChem: 10484893
• LOTUS: LTS0220267
• wikiData: Q76415737