4-Galloylchlorogenic acid

Details

• Internal ID: 379b4edb-f332-487d-bf53-7578208923fc
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
• IUPAC Name: (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyl)oxycyclohexane-1-carboxylic acid
• SMILES (Canonical): C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C3=CC(=C(C(=C3)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)C3=CC(=C(C(=C3)O)O)O)O
• InChI: InChI=1S/C23H22O13/c24-12-3-1-10(5-13(12)25)2-4-18(29)35-17-9-23(34,22(32)33)8-16(28)20(17)36-21(31)11-6-14(26)19(30)15(27)7-11/h1-7,16-17,20,24-28,30,34H,8-9H2,(H,32,33)/b4-2+/t16-,17-,20-,23+/m1/s1
• InChI Key: JODSXMBDAMZIDL-HXYPBPKPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₁₃
• Molecular Weight: 506.40 g/mol
• Exact Mass: 506.10604075 g/mol
• Topological Polar Surface Area (TPSA): 232.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.34
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

• 4-Galloylchlorogenic acid
• 48W86P70I0
• UNII-48W86P70I0
• 574747-59-4
• Benzoic acid, 3,4,5-trihydroxy-, (1R,2R,4S,6R)-4-carboxy-2-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-4,6-dihydroxycyclohexyl ester
• Benzoic acid, 3,4,5-trihydroxy-, (1R,2R,4S,6R)-4-carboxy-2-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,6-dihydroxycyclohexyl ester
• CHEMBL458307
• Q27259187

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8460	84.60%
Caco-2	-	0.9236	92.36%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6770	67.70%
OATP2B1 inhibitior	-	0.5670	56.70%
OATP1B1 inhibitior	+	0.8747	87.47%
OATP1B3 inhibitior	+	0.9424	94.24%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8338	83.38%
BSEP inhibitior	+	0.7047	70.47%
P-glycoprotein inhibitior	-	0.4703	47.03%
P-glycoprotein substrate	-	0.6671	66.71%
CYP3A4 substrate	+	0.6105	61.05%
CYP2C9 substrate	-	0.5941	59.41%
CYP2D6 substrate	-	0.8566	85.66%
CYP3A4 inhibition	-	0.8744	87.44%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9069	90.69%
CYP2D6 inhibition	-	0.9388	93.88%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.5977	59.77%
CYP inhibitory promiscuity	-	0.9686	96.86%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8864	88.64%
Carcinogenicity (trinary)	Non-required	0.6128	61.28%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.8935	89.35%
Skin irritation	-	0.6985	69.85%
Skin corrosion	-	0.9034	90.34%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8867	88.67%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.6266	62.66%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9456	94.56%
Acute Oral Toxicity (c)	III	0.7775	77.75%
Estrogen receptor binding	+	0.8131	81.31%
Androgen receptor binding	+	0.8267	82.67%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5874	58.74%
Aromatase binding	-	0.5265	52.65%
PPAR gamma	+	0.6461	64.61%
Honey bee toxicity	-	0.8442	84.42%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9928	99.28%

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	99.80%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.06%	91.49%
CHEMBL3194	P02766	Transthyretin	96.21%	90.71%
CHEMBL221	P23219	Cyclooxygenase-1	94.82%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.81%	86.33%
CHEMBL4208	P20618	Proteasome component C5	92.24%	90.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.67%	83.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	91.66%	85.31%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.55%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.41%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.25%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.29%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.07%	96.09%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	86.95%	97.53%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.14%	97.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.46%	94.08%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.24%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.17%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.10%	91.19%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.99%	94.62%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.12%	96.95%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	80.04%	94.97%

Plants that contains it

• Alangium grisolleoides
• Cryptocarya alba
• Goniothalamus amuyon
• Manilkara zapota
• Uvaria griffithii
• Zephyranthes citrina

Cross-Links

• PubChem: 10929258
• NPASS: NPC42464
• ChEMBL: CHEMBL458307
• LOTUS: LTS0256499
• wikiData: Q27259187