Caffeoylglucose

Details

• Internal ID: fde7f072-b0ab-4c02-8c7b-c93733ab563d
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives
• IUPAC Name: (E,5R,6S,7R,8R)-1-(3,4-dihydroxyphenyl)-5,6,7,8,9-pentahydroxynon-1-ene-3,4-dione
• SMILES (Canonical): C1=CC(=C(C=C1C=CC(=O)C(=O)C(C(C(C(CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/C(=O)C(=O)[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)O)O
• InChI: InChI=1S/C15H18O9/c16-6-11(20)13(22)15(24)14(23)12(21)9(18)4-2-7-1-3-8(17)10(19)5-7/h1-5,11,13-17,19-20,22-24H,6H2/b4-2+/t11-,13-,14+,15+/m1/s1
• InChI Key: HUXWBFFRUHXOBU-CPRQJHDUSA-N
• Popularity: 51 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): 176.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.31
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8342	83.42%
Caco-2	-	0.8764	87.64%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5230	52.30%
OATP2B1 inhibitior	-	0.5702	57.02%
OATP1B1 inhibitior	+	0.9425	94.25%
OATP1B3 inhibitior	+	0.9735	97.35%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8838	88.38%
BSEP inhibitior	-	0.9190	91.90%
P-glycoprotein inhibitior	-	0.9381	93.81%
P-glycoprotein substrate	-	0.8960	89.60%
CYP3A4 substrate	-	0.6133	61.33%
CYP2C9 substrate	-	0.8080	80.80%
CYP2D6 substrate	-	0.8271	82.71%
CYP3A4 inhibition	-	0.7061	70.61%
CYP2C9 inhibition	-	0.9221	92.21%
CYP2C19 inhibition	-	0.9583	95.83%
CYP2D6 inhibition	-	0.9117	91.17%
CYP1A2 inhibition	-	0.7195	71.95%
CYP2C8 inhibition	-	0.7585	75.85%
CYP inhibitory promiscuity	-	0.9558	95.58%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8632	86.32%
Carcinogenicity (trinary)	Non-required	0.7586	75.86%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.8495	84.95%
Skin irritation	-	0.6424	64.24%
Skin corrosion	-	0.9156	91.56%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5638	56.38%
Micronuclear	+	0.5041	50.41%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	+	0.7086	70.86%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.8107	81.07%
Acute Oral Toxicity (c)	III	0.7102	71.02%
Estrogen receptor binding	-	0.5401	54.01%
Androgen receptor binding	+	0.6481	64.81%
Thyroid receptor binding	-	0.5491	54.91%
Glucocorticoid receptor binding	-	0.4860	48.60%
Aromatase binding	-	0.6796	67.96%
PPAR gamma	-	0.5292	52.92%
Honey bee toxicity	-	0.9375	93.75%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.8133	81.33%

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	98.89%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.87%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.59%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.58%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.57%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.41%	86.33%
CHEMBL3194	P02766	Transthyretin	88.75%	90.71%
CHEMBL2581	P07339	Cathepsin D	88.37%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.34%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.91%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.19%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.15%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.63%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	81.02%	94.73%

Plants that contains it

• Ribes nigrum

Cross-Links

• PubChem: 129629071
• LOTUS: LTS0028362
• wikiData: Q105110541