1,3-o-Di-p-coumaroylglycerol

Details

• Internal ID: b20c0379-2c37-4ce4-9d81-b5d5860f3551
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [2-hydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxypropyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OCC(COC(=O)C=CC2=CC=C(C=C2)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=O)OCC(O)COC(=O)/C=C/C2=CC=C(C=C2)O)O
• InChI: InChI=1S/C21H20O7/c22-17-7-1-15(2-8-17)5-11-20(25)27-13-19(24)14-28-21(26)12-6-16-3-9-18(23)10-4-16/h1-12,19,22-24H,13-14H2/b11-5+,12-6+
• InChI Key: KBVRKOFXCCIDFX-YDWXAUTNSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₇
• Molecular Weight: 384.40 g/mol
• Exact Mass: 384.12090297 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.27
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9608	96.08%
Caco-2	-	0.7471	74.71%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.8433	84.33%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9252	92.52%
OATP1B3 inhibitior	+	0.9085	90.85%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.5517	55.17%
P-glycoprotein inhibitior	-	0.6261	62.61%
P-glycoprotein substrate	-	0.9454	94.54%
CYP3A4 substrate	-	0.6202	62.02%
CYP2C9 substrate	+	0.6000	60.00%
CYP2D6 substrate	-	0.8470	84.70%
CYP3A4 inhibition	-	0.9090	90.90%
CYP2C9 inhibition	-	0.8141	81.41%
CYP2C19 inhibition	-	0.8321	83.21%
CYP2D6 inhibition	-	0.9058	90.58%
CYP1A2 inhibition	-	0.8657	86.57%
CYP2C8 inhibition	-	0.6315	63.15%
CYP inhibitory promiscuity	-	0.7982	79.82%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7959	79.59%
Carcinogenicity (trinary)	Non-required	0.5930	59.30%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.7281	72.81%
Skin irritation	-	0.8648	86.48%
Skin corrosion	-	0.9706	97.06%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5144	51.44%
Micronuclear	+	0.5608	56.08%
Hepatotoxicity	-	0.7217	72.17%
skin sensitisation	-	0.5740	57.40%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	-	0.6333	63.33%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.7067	70.67%
Acute Oral Toxicity (c)	III	0.8129	81.29%
Estrogen receptor binding	+	0.6819	68.19%
Androgen receptor binding	+	0.7993	79.93%
Thyroid receptor binding	-	0.5891	58.91%
Glucocorticoid receptor binding	+	0.5991	59.91%
Aromatase binding	-	0.5367	53.67%
PPAR gamma	+	0.5204	52.04%
Honey bee toxicity	-	0.8744	87.44%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.9651	96.51%

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	92.04%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.01%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.96%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.23%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.53%	99.17%
CHEMBL3194	P02766	Transthyretin	88.35%	90.71%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.84%	89.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.88%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.74%	94.45%
CHEMBL2581	P07339	Cathepsin D	82.59%	98.95%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.42%	91.71%

Plants that contains it

• Asparagus officinalis
• Greigia sphacelata

Cross-Links

• PubChem: 14034127
• LOTUS: LTS0212095
• wikiData: Q105138553