1-Caffeoylglycerol

Details

• Internal ID: 6ddfb5b2-a7a6-4e50-b4e5-a43bf88bbde5
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: 2,3-dihydroxypropyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=C(C=C1C=CC(=O)OCC(CO)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/C(=O)OCC(CO)O)O)O
• InChI: InChI=1S/C12H14O6/c13-6-9(14)7-18-12(17)4-2-8-1-3-10(15)11(16)5-8/h1-5,9,13-16H,6-7H2/b4-2+
• InChI Key: NOHROAYVCRHDHO-DUXPYHPUSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₄O₆
• Molecular Weight: 254.24 g/mol
• Exact Mass: 254.07903816 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.01
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 1-Caffeoylglycerol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9594	95.94%
Caco-2	-	0.7939	79.39%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7882	78.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9567	95.67%
OATP1B3 inhibitior	+	0.9640	96.40%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6318	63.18%
P-glycoprotein inhibitior	-	0.9833	98.33%
P-glycoprotein substrate	-	0.9499	94.99%
CYP3A4 substrate	-	0.6028	60.28%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8542	85.42%
CYP3A4 inhibition	-	0.9246	92.46%
CYP2C9 inhibition	-	0.9672	96.72%
CYP2C19 inhibition	-	0.9386	93.86%
CYP2D6 inhibition	-	0.9374	93.74%
CYP1A2 inhibition	-	0.5754	57.54%
CYP2C8 inhibition	-	0.7498	74.98%
CYP inhibitory promiscuity	-	0.9483	94.83%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.7066	70.66%
Eye corrosion	-	0.9893	98.93%
Eye irritation	+	0.6753	67.53%
Skin irritation	-	0.6436	64.36%
Skin corrosion	-	0.9564	95.64%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7470	74.70%
Micronuclear	-	0.5444	54.44%
Hepatotoxicity	-	0.6446	64.46%
skin sensitisation	+	0.7374	73.74%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9051	90.51%
Acute Oral Toxicity (c)	III	0.6507	65.07%
Estrogen receptor binding	+	0.7482	74.82%
Androgen receptor binding	+	0.6952	69.52%
Thyroid receptor binding	-	0.5999	59.99%
Glucocorticoid receptor binding	+	0.5520	55.20%
Aromatase binding	+	0.5766	57.66%
PPAR gamma	+	0.6999	69.99%
Honey bee toxicity	-	0.8643	86.43%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.8535	85.35%

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	98.42%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.06%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.80%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.69%	96.00%
CHEMBL3194	P02766	Transthyretin	92.17%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.83%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.05%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.69%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.55%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.85%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.01%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.56%	86.92%
CHEMBL2581	P07339	Cathepsin D	82.41%	98.95%
CHEMBL4208	P20618	Proteasome component C5	81.63%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	80.23%	94.73%

Plants that contains it

• Ananas comosus
• Populus euphratica

Cross-Links

• PubChem: 5315606
• NPASS: NPC154146
• LOTUS: LTS0044902
• wikiData: Q105182585