Pentagalloylglucose

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	0146d12a-195c-4a5e-8c52-6bd936ec1386
Taxonomy	Phenylpropanoids and polyketides > Tannins
IUPAC Name	[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
SMILES (Canonical)	C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)OC(=O)C6=CC(=C(C(=C6)O)O)O
SMILES (Isomeric)	C1=C(C=C(C(=C1O)O)O)C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)OC(=O)C6=CC(=C(C(=C6)O)O)O
InChI	InChI=1S/C41H32O26/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16/h1-10,27,33-35,41-56H,11H2/t27-,33-,34+,35-,41+/m1/s1
InChI Key	QJYNZEYHSMRWBK-NIKIMHBISA-N
Popularity	374 references in papers

Physical and Chemical Properties

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Molecular Formula	C₄₁H₃₂O₂₆
Molecular Weight	940.70 g/mol
Exact Mass	940.11818112 g/mol
Topological Polar Surface Area (TPSA)	444.00 Å²
XlogP	3.60
Atomic LogP (AlogP)	1.69
H-Bond Acceptor	26
H-Bond Donor	15
Rotatable Bonds	11

Synonyms

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14937-32-7

1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose

Pentagalloyl glucose

1,2,3,4,6-Penta-O-galloyl-beta-D-glucose

1,2,3,4,6-Pentagalloylglucose

beta-Penta-O-galloyl-glucose

1,2,3,4,6-Pgg

GALLOTANNIN 15

1,2,3,4,6-Pentakis-O-galloyl-beta-D-glucose

beta-D-pentagalloylglucose

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5975	59.75%
Caco-2	-	0.8615	86.15%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7179	71.79%
OATP2B1 inhibitior	-	0.8524	85.24%
OATP1B1 inhibitior	-	0.6970	69.70%
OATP1B3 inhibitior	-	0.5698	56.98%
MATE1 inhibitior	+	0.7000	70.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.6662	66.62%
P-glycoprotein inhibitior	+	0.7578	75.78%
P-glycoprotein substrate	-	0.9615	96.15%
CYP3A4 substrate	+	0.5051	50.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8473	84.73%
CYP3A4 inhibition	-	0.8325	83.25%
CYP2C9 inhibition	-	0.7629	76.29%
CYP2C19 inhibition	-	0.8866	88.66%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.9107	91.07%
CYP2C8 inhibition	-	0.5719	57.19%
CYP inhibitory promiscuity	-	0.7781	77.81%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7506	75.06%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.8654	86.54%
Skin irritation	-	0.8336	83.36%
Skin corrosion	-	0.9589	95.89%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8006	80.06%
Micronuclear	+	0.6966	69.66%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8119	81.19%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9346	93.46%
Acute Oral Toxicity (c)	III	0.8042	80.42%
Estrogen receptor binding	+	0.7780	77.80%
Androgen receptor binding	+	0.7207	72.07%
Thyroid receptor binding	+	0.5343	53.43%
Glucocorticoid receptor binding	+	0.6237	62.37%
Aromatase binding	-	0.5453	54.53%
PPAR gamma	+	0.6902	69.02%
Honey bee toxicity	-	0.9138	91.38%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	+	0.9022	90.22%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4296326	P58335	Anthrax toxin receptor 2	300 nM 100 nM 58 nM	IC50 IC50 IC50	via Super-PRED via Super-PRED via Super-PRED
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	112.2 nM	Potency	via Super-PRED
CHEMBL4822	P56817	Beta-secretase 1	3760 nM	IC50	PMID: 24835197
CHEMBL1293237	P54132	Bloom syndrome protein	501.2 nM	Potency	via Super-PRED
CHEMBL244	P00742	Coagulation factor X	170 nM 170 nM	IC50 IC50	via Super-PRED PMID: 9834152
CHEMBL2392	P06746	DNA polymerase beta	158.5 nM	Potency	via Super-PRED
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	6.3 nM	Potency	via Super-PRED
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	177.8 nM	Potency	via Super-PRED
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	10 nM 3.1 nM 10 nM 10 nM 10 nM	IC50 Kd IC50 IC50 IC50	via Super-PRED via Super-PRED via Super-PRED via Super-PRED via Super-PRED
CHEMBL2478	P04745	Salivary alpha-amylase	2350 nM	IC50	PMID: 26395057
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	17.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.08%	95.64%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.84%	96.09%
CHEMBL3194	P02766	Transthyretin	90.47%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.80%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	88.85%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.16%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	86.82%	92.50%
CHEMBL4208	P20618	Proteasome component C5	84.98%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.56%	94.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.63%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.13%	89.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.05%	95.17%
CHEMBL2581	P07339	Cathepsin D	81.00%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.27%	99.15%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Acer truncatum

Aconitum burnatii

Actiniopteris radiata

Andrographis paniculata

Annona impressivenia

Aristolochia littoralis

Aristolochia zollingeriana

Artemisia carvifolia