Sinapine

Details

• Internal ID: e98a1904-e4e2-45cd-a3ce-619b49627b77
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: 2-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxyethyl-trimethylazanium
• SMILES (Canonical): C[N+](C)(C)CCOC(=O)C=CC1=CC(=C(C(=C1)OC)O)OC
• SMILES (Isomeric): C[N+](C)(C)CCOC(=O)/C=C/C1=CC(=C(C(=C1)OC)O)OC
• InChI: InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1
• InChI Key: HUJXHFRXWWGYQH-UHFFFAOYSA-O
• Popularity: 84 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄NO₅+
• Molecular Weight: 310.36 g/mol
• Exact Mass: 310.16544787 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 1.80

Synonyms

• 18696-26-9
• Sinapoylcholine
• O-sinapoylcholine
• sinapin
• Sinapine cation
• trans-Sinapine
• Sinapine ion
• Sinapine bisulphate
• 4-Hydroxy-3,5-dimethoxycinnamate choline
• 09211A0HHL
• Ethanaminium, 2-((3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl)oxy)-N,N,N-trimethyl-
• CHEBI:16353
• DTXSID10171957
• Choline, 4-hydroxy-3,5-dimethoxycinnamate (ester)
• 2-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxyethyl-trimethylazanium
• Cinnamic acid, 4-hydroxy-3,5-dimethoxy-, choline ester
• 2-((3-(4-Hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propen-1-yl)oxy)-N,N,N-trimethylethanaminium
• 84123-22-8
• Ethanaminium, 2-(((2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propen-1-yl)oxy)-N,N,N-trimethyl-
• Ethanaminium, 2-((3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propen-1-yl)oxy)-N,N,N-trimethyl-
• 2-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyloxy]-N,N,N-trimethylethanaminium
• 2-(3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyloxy)ethyl-trimethylazanium
• 2-[3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyloxy]ethyl-trimethylazanium
• 2-((2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyloxy)-N,N,N-trimethylethanaminium
• 2-((E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl)oxyethyl-trimethylazanium
• RefChem:183144
• DTXCID5094448
• Sinapine [MI]
• trans-Sinapoylcholine
• 2-((3-(4-Hydroxy-3,5-dimethoxyphenyl)acryloyl)oxy)-N,N,N-trimethylethan-1-aminium
• 2-(4-hydroxy-3,5-dimethoxycinnamoyloxy)-N,N,N-trimethylethanaminium
• SCHEMBL424527
• UNII-09211A0HHL
• SCHEMBL424529
• MEGxp0_001763
• ACon1_000255
• HY-N5077
• s3235
• AKOS030626997
• 2-((3-(4-Hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl)oxy)-N,N,N-trimethylethanaminium
• AC-34366
• DA-77851
• CS-0032305
• NS00097137
• C00933
• Choline 4-hydroxy-3,5-dimethoxycinnamate, 8CI
• Q891772
• BRD-K21295184-064-01-0
• 2-[[3-(4-Hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl]oxy]-N,N,N- trimethylethanaminium, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.46%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.04%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.82%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.99%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.07%	99.17%
CHEMBL3194	P02766	Transthyretin	88.92%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.11%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.35%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	82.10%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.73%	94.45%

Plants that contains it

• Alliaria petiolata
• Allium cepa
• Arabidopsis thaliana
• Brassica juncea
• Brassica napus
• Brassica nigra
• Brassica oleracea
• Capparis spinosa
• Citrus limon
• Foeniculum vulgare
• Pterocarpus santalinus
• Raphanus raphanistrum subsp. sativus
• Sinapis alba
• Urtica dioica

Cross-Links

• PubChem: 5280385
• NPASS: NPC136281
• LOTUS: LTS0049545
• wikiData: Q891772