Moschamine

Details

• Internal ID: 1dbba0aa-bfad-43d9-b0e2-895f758493a7
• 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-hydroxy-3-methoxyphenyl)prop-2-enamide
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)NCCC2=CNC3=C2C=C(C=C3)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)NCCC2=CNC3=C2C=C(C=C3)O)O
• InChI: InChI=1S/C20H20N2O4/c1-26-19-10-13(2-6-18(19)24)3-7-20(25)21-9-8-14-12-22-17-5-4-15(23)11-16(14)17/h2-7,10-12,22-24H,8-9H2,1H3,(H,21,25)/b7-3+
• InChI Key: WGHKJYWENWLOMY-XVNBXDOJSA-N
• Popularity: 28 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀N₂O₄
• Molecular Weight: 352.40 g/mol
• Exact Mass: 352.14230712 g/mol
• Topological Polar Surface Area (TPSA): 94.60 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.96
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• N-Feruloylserotonin
• N-Feruloyl Serotonin
• 68573-23-9
• feruloylserotonin
• 193224-22-5
• Feruloylserotonin 98
• (E)-N-(2-(5-Hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide
• TRYPTAMINE, N-FERULOYL
• CHEMBL564482
• CHEBI:85158
• UNII-2PP8322487
• (E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
• 2PP8322487
• (2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
• 2-Propenamide, N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)-, (2E)-
• 2-Propenamide, N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)-, (E)-
• N-[2-(5-HYDROXY-1H-INDOL-3-YL)ETHYL]-3-(4-HYDROXY-3-METHOXY-PHENYL)PROP-2-ENAMIDE
• (E/Z)-Moschamine
• SEROTONIN (I), N-(FERULOYL)-
• Nb-(E)-Feruloylserotonin
• ferulic acid serotonin amide
• N-(Feruloyl)-Serotonin (I)
• SCHEMBL12063415
• DTXSID70172925
• N-FERULOYL SEROTONIN [INCI]
• BDBM50296246
• HY-118824A
• NSC-369502
• N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide
• MS-25464
• CS-0131111
• Q25099720
• (e)-N-(3-methoxy-4-hydroxycinnamoyl)-5-hydroxytryptamine
• N-(2-(5-Hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9910	99.10%
Caco-2	-	0.7105	71.05%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6996	69.96%
OATP2B1 inhibitior	-	0.7121	71.21%
OATP1B1 inhibitior	+	0.9088	90.88%
OATP1B3 inhibitior	+	0.9473	94.73%
MATE1 inhibitior	-	0.9009	90.09%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9555	95.55%
P-glycoprotein inhibitior	-	0.4867	48.67%
P-glycoprotein substrate	+	0.6937	69.37%
CYP3A4 substrate	+	0.6018	60.18%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	-	0.8002	80.02%
CYP3A4 inhibition	+	0.8347	83.47%
CYP2C9 inhibition	+	0.5588	55.88%
CYP2C19 inhibition	-	0.5804	58.04%
CYP2D6 inhibition	-	0.8127	81.27%
CYP1A2 inhibition	+	0.6866	68.66%
CYP2C8 inhibition	+	0.8244	82.44%
CYP inhibitory promiscuity	+	0.8262	82.62%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6016	60.16%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9381	93.81%
Skin irritation	-	0.7571	75.71%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8623	86.23%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.8948	89.48%
skin sensitisation	-	0.8980	89.80%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.9315	93.15%
Acute Oral Toxicity (c)	III	0.6450	64.50%
Estrogen receptor binding	+	0.7813	78.13%
Androgen receptor binding	+	0.5620	56.20%
Thyroid receptor binding	+	0.6426	64.26%
Glucocorticoid receptor binding	+	0.6914	69.14%
Aromatase binding	+	0.7362	73.62%
PPAR gamma	+	0.7374	73.74%
Honey bee toxicity	-	0.8726	87.26%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	-	0.5421	54.21%

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	99.81%	91.11%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	97.17%	89.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.89%	96.09%
CHEMBL1914	P06276	Butyrylcholinesterase	96.01%	95.00%
CHEMBL2535	P11166	Glucose transporter	93.82%	98.75%
CHEMBL2581	P07339	Cathepsin D	93.04%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	92.97%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.52%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.15%	96.00%
CHEMBL1255126	O15151	Protein Mdm4	92.11%	90.20%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.59%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.46%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.20%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.14%	94.45%
CHEMBL255	P29275	Adenosine A2b receptor	88.24%	98.59%
CHEMBL3194	P02766	Transthyretin	87.76%	90.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.59%	91.71%
CHEMBL4208	P20618	Proteasome component C5	84.46%	90.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.98%	85.31%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	80.86%	97.03%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.74%	94.33%
CHEMBL213	P08588	Beta-1 adrenergic receptor	80.67%	95.56%

Plants that contains it

• Amberboa moschata
• Carthamus tinctorius
• Centaurea arenaria
• Centaurea cyanus
• Centaurea nigra
• Centella asiatica
• Phyllostachys reticulata

Cross-Links

• PubChem: 5969616
• NPASS: NPC266931
• ChEMBL: CHEMBL564482
• LOTUS: LTS0064948
• wikiData: Q25099720