Tricoumaroyl spermidine

Details

• Internal ID: cb0f5d35-7c4b-47eb-8010-a1affb46961c
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: (E)-3-(4-hydroxyphenyl)-N-[4-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-[3-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]propyl]amino]butyl]prop-2-enamide
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)NCCCCN(CCCNC(=O)C=CC2=CC=C(C=C2)O)C(=O)C=CC3=CC=C(C=C3)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=O)NCCCCN(CCCNC(=O)/C=C/C2=CC=C(C=C2)O)C(=O)/C=C/C3=CC=C(C=C3)O)O
• InChI: InChI=1S/C34H37N3O6/c38-29-13-4-26(5-14-29)10-19-32(41)35-22-1-2-24-37(34(43)21-12-28-8-17-31(40)18-9-28)25-3-23-36-33(42)20-11-27-6-15-30(39)16-7-27/h4-21,38-40H,1-3,22-25H2,(H,35,41)(H,36,42)/b19-10+,20-11+,21-12+
• InChI Key: PFDVWJCSCYDRMZ-AUCPOXKISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₃₇N₃O₆
• Molecular Weight: 583.70 g/mol
• Exact Mass: 583.26823591 g/mol
• Topological Polar Surface Area (TPSA): 139.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.47
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 15

Synonyms

• N1,N5,N10-(E)-tri-p-coumaroylspermidine
• 131086-78-7
• 364368-18-3
• N1,N5,N10-tricoumaroyl spermidine
• N(1),N(5),N(10)-tricoumaroylspermidine
• N(1),N(5),N(10)-tricoumaroyl spermidine
• N(1),N(5),N(10)-tri-(4-coumaroyl)spermidine
• 2-Propenamide, 3-(4-hydroxyphenyl)-N-[4-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]amino]butyl]-N-[3-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]amino]propyl]-, (2E)-
• N(1),N(5),N(10)-tri-[(E)-p-coumaroyl]spermidine
• (2E)-3-(4-hydroxyphenyl)-N-(4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino}butyl)-N-(3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino}propyl)prop-2-enamide
• (E)-3-(4-Hydroxyphenyl)-N-(4-((E)-3-(4-hydroxyphenyl)acrylamido)butyl)-N-(3-((E)-3-(4-hydroxyphenyl)acrylamido)propyl)acrylamide
• tri-Coumaroyl spermidine
• MEGxp0_000365
• CHEMBL4470577
• SCHEMBL12880180
• CHEBI:61514
• DTXSID001279428
• AKOS040763150
• FS-8349
• N,N',N''-tris-(p-coumaroyl)spermidine
• C18069
• Q27131117
• (E)-3-(4-hydroxyphenyl)-N-[4-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-[3-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]propyl]amino]butyl]prop-2-enamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8604	86.04%
Caco-2	-	0.8750	87.50%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8562	85.62%
OATP2B1 inhibitior	-	0.7130	71.30%
OATP1B1 inhibitior	+	0.8588	85.88%
OATP1B3 inhibitior	+	0.9392	93.92%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8547	85.47%
P-glycoprotein inhibitior	+	0.8629	86.29%
P-glycoprotein substrate	-	0.5000	50.00%
CYP3A4 substrate	+	0.5377	53.77%
CYP2C9 substrate	-	0.8063	80.63%
CYP2D6 substrate	-	0.8250	82.50%
CYP3A4 inhibition	+	0.7793	77.93%
CYP2C9 inhibition	-	0.8691	86.91%
CYP2C19 inhibition	-	0.8132	81.32%
CYP2D6 inhibition	-	0.7355	73.55%
CYP1A2 inhibition	-	0.9107	91.07%
CYP2C8 inhibition	-	0.6878	68.78%
CYP inhibitory promiscuity	-	0.8516	85.16%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8228	82.28%
Carcinogenicity (trinary)	Non-required	0.6164	61.64%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9295	92.95%
Skin irritation	-	0.7708	77.08%
Skin corrosion	-	0.9549	95.49%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3874	38.74%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9129	91.29%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6843	68.43%
Acute Oral Toxicity (c)	III	0.6324	63.24%
Estrogen receptor binding	+	0.7190	71.90%
Androgen receptor binding	+	0.8819	88.19%
Thyroid receptor binding	+	0.5654	56.54%
Glucocorticoid receptor binding	+	0.5639	56.39%
Aromatase binding	-	0.5366	53.66%
PPAR gamma	+	0.7339	73.39%
Honey bee toxicity	-	0.9254	92.54%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9275	92.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.55%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.96%	91.11%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	91.98%	89.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.34%	99.17%
CHEMBL2179	P04062	Beta-glucocerebrosidase	91.02%	85.31%
CHEMBL4040	P28482	MAP kinase ERK2	90.77%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.20%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.23%	96.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	85.29%	93.10%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.56%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	84.07%	94.73%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	83.02%	96.67%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.94%	90.71%
CHEMBL4208	P20618	Proteasome component C5	81.84%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.78%	95.56%
CHEMBL2514	O95665	Neurotensin receptor 2	81.71%	100.00%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	80.58%	89.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.28%	86.33%

Plants that contains it

• Aphelandra chamissoniana
• Arachis hypogaea
• Coleogyne ramosissima
• Quercus dentata

Cross-Links

• PubChem: 14777879
• LOTUS: LTS0028397
• wikiData: Q27131117