Feruloyl-caffeoylglycerol

Details

• Internal ID: b2d71ee7-eca3-4182-8ac4-a9be7600d1f6
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (1E,6E)-4-(1,2-dihydroxyethyl)-1-(3,4-dihydroxyphenyl)-4-hydroxy-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)C(C(CO)O)(C(=O)C=CC2=CC(=C(C=C2)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)C(C(CO)O)(C(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
• InChI: InChI=1S/C22H22O9/c1-31-18-11-14(3-7-16(18)25)5-9-20(28)22(30,21(29)12-23)19(27)8-4-13-2-6-15(24)17(26)10-13/h2-11,21,23-26,29-30H,12H2,1H3/b8-4+,9-5+
• InChI Key: IBLAUOUKBQBTPV-KBXRYBNXSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₉
• Molecular Weight: 430.40 g/mol
• Exact Mass: 430.12638228 g/mol
• Topological Polar Surface Area (TPSA): 165.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.76
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9364	93.64%
Caco-2	-	0.8633	86.33%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6869	68.69%
OATP2B1 inhibitior	-	0.5710	57.10%
OATP1B1 inhibitior	+	0.9048	90.48%
OATP1B3 inhibitior	+	0.9578	95.78%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6838	68.38%
BSEP inhibitior	+	0.8965	89.65%
P-glycoprotein inhibitior	-	0.6090	60.90%
P-glycoprotein substrate	-	0.8658	86.58%
CYP3A4 substrate	-	0.5098	50.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8226	82.26%
CYP3A4 inhibition	-	0.6910	69.10%
CYP2C9 inhibition	-	0.7687	76.87%
CYP2C19 inhibition	-	0.8298	82.98%
CYP2D6 inhibition	-	0.9141	91.41%
CYP1A2 inhibition	+	0.5425	54.25%
CYP2C8 inhibition	+	0.6449	64.49%
CYP inhibitory promiscuity	-	0.8937	89.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9032	90.32%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.7913	79.13%
Skin irritation	-	0.8114	81.14%
Skin corrosion	-	0.9190	91.90%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4447	44.47%
Micronuclear	-	0.5182	51.82%
Hepatotoxicity	-	0.8196	81.96%
skin sensitisation	-	0.6572	65.72%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8539	85.39%
Acute Oral Toxicity (c)	III	0.7668	76.68%
Estrogen receptor binding	+	0.7141	71.41%
Androgen receptor binding	+	0.7924	79.24%
Thyroid receptor binding	+	0.6689	66.89%
Glucocorticoid receptor binding	+	0.7802	78.02%
Aromatase binding	+	0.6939	69.39%
PPAR gamma	+	0.7271	72.71%
Honey bee toxicity	-	0.8402	84.02%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9083	90.83%

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	99.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.73%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.72%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.90%	96.00%
CHEMBL2581	P07339	Cathepsin D	92.50%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.11%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.86%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.96%	89.62%
CHEMBL1951	P21397	Monoamine oxidase A	90.92%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.76%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.24%	89.00%
CHEMBL3194	P02766	Transthyretin	89.02%	90.71%
CHEMBL4208	P20618	Proteasome component C5	84.90%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	84.62%	94.73%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.58%	80.78%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.34%	95.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.23%	99.15%
CHEMBL2535	P11166	Glucose transporter	81.02%	98.75%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.51%	86.92%

Plants that contains it

• Ananas comosus

Cross-Links

• PubChem: 129892683
• LOTUS: LTS0197150
• wikiData: Q105036564