1-Caffeoyl-beta-D-glucose

Details

• Internal ID: a2f47dce-e5ee-4817-a303-b37515af4184
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Hydroxycinnamic acid glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=C(C=C1C=CC(=O)OC2C(C(C(C(O2)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O
• InChI: InChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(23-10)24-11(19)4-2-7-1-3-8(17)9(18)5-7/h1-5,10,12-18,20-22H,6H2/b4-2+/t10-,12-,13+,14-,15+/m1/s1
• InChI Key: WQSDYZZEIBAPIN-VBQORRLJSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₉
• Molecular Weight: 342.30 g/mol
• Exact Mass: 342.09508215 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: -0.60

Synonyms

• 14364-08-0
• 1-O-caffeoyl-beta-D-glucose
• CHEBI:614
• [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• b-D-Glucopyranose, 1-[3-(3,4-dihydroxyphenyl)-2-propenoate]
• Caffeoyl glucoside
• caffeic acid glucoside
• CHEMBL482242
• ACon1_001812
• DTXSID30415188
• 1-O-[(E)-caffeoyl]-beta-D-glucose
• AKOS040735825
• NCGC00180114-01
• Q27105318
• 1-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranose

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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.74%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.61%	96.00%
CHEMBL3194	P02766	Transthyretin	92.62%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.39%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	92.20%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.54%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.59%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.20%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	88.95%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.78%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.32%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.36%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.15%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.96%	94.45%
CHEMBL4208	P20618	Proteasome component C5	80.79%	90.00%

Plants that contains it

• Aruncus dioicus
• Balanophora fungosa
• Balanophora harlandii
• Balanophora japonica
• Balanophora laxiflora
• Capsicum annuum
• Centella asiatica
• Clematis tashiroi
• Coussarea hydrangeifolia
• Hypericum perforatum
• Ligustrum obtusifolium
• Moricandia arvensis
• Ribes nigrum

Cross-Links

• PubChem: 5281761
• NPASS: NPC232880
• ChEMBL: CHEMBL482242
• LOTUS: LTS0223743
• wikiData: Q27105318