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

Details

• Internal ID: 3ac82855-6e27-465a-a2d9-fe4e8da31f8c
• Taxonomy: Phenylpropanoids and polyketides > Tannins
• IUPAC Name: [(2S,3R,4S,5S,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-/m0/s1
• InChI Key: QJYNZEYHSMRWBK-CGKDMBANSA-N
• Popularity: 44 references in papers

Physical and Chemical Properties

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

Synonyms

• BETA-1,2,3,4,6-PENTA-O-GALLOYL-D-GLUCOPYRANOSE
• PD059955
• [(2S,3R,4S,5S,6S)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]tetrahydropyran-2-yl]methyl 3,4,5-trihydroxybenzoate

2D Structure

ADMET Properties (via admetSAR 2)

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

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4296326	P58335	Anthrax toxin receptor 2	58 nM; 100 nM; 300 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
CHEMBL1293237	P54132	Bloom syndrome protein	501.2 nM	Potency	via Super-PRED
CHEMBL244	P00742	Coagulation factor X	170 nM	IC50	via Super-PRED
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
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

• Ampelopsis japonica
• Angelica dahurica
• Paeonia suffruticosa
• Phyllanthus emblica
• Terminalia chebula

Cross-Links

• PubChem: 446509
• NPASS: NPC47272