1,3,6-tri-O-galloyl-beta-D-glucose

Details

• Internal ID: 75589778-e9d7-4eb4-817a-c8fcf8325efb
• Taxonomy: Phenylpropanoids and polyketides > Tannins
• IUPAC Name: [(2R,3R,4S,5R,6S)-3,5-dihydroxy-4,6-bis[(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)O)OC(=O)C4=CC(=C(C(=C4)O)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)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)O
• InChI: InChI=1S/C27H24O18/c28-11-1-8(2-12(29)18(11)34)24(39)42-7-17-21(37)23(44-25(40)9-3-13(30)19(35)14(31)4-9)22(38)27(43-17)45-26(41)10-5-15(32)20(36)16(33)6-10/h1-6,17,21-23,27-38H,7H2/t17-,21-,22-,23+,27+/m1/s1
• InChI Key: RNKMOGIPOMVCHO-SJMVAQJGSA-N
• Popularity: 35 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₄O₁₈
• Molecular Weight: 636.50 g/mol
• Exact Mass: 636.09626391 g/mol
• Topological Polar Surface Area (TPSA): 311.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.28
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 7

Synonyms

• 1,3,6-tri-O-galloyl-beta-D-glucose
• 1,3,6-Tri-O-galloyl-b-D-glucose
• 1,3,6-tri-o-galloylglucose
• 1,3,6-Tri-O-galloyl-b-D-glucopyranose
• UNII-O8718334XJ
• O8718334XJ
• beta-D-Glucopyranose 1,3,6-trigallate
• 1,3,6-tri-o-galloyl-beta-d-glucopyranose
• Glucopyranose, 1,3,6-trigallate, beta-D-
• beta-D-Glucopyranose, 1,3,6-tris(3,4,5-trihydroxybenzoate)
• CHEBI:24182
• NSC 69861
• Gallotannins
• .beta.-D-Glucopyranose, 1,3,6-tris(3,4,5-trihydroxybenzoate)
• NSC-69861
• 1,3,6-Tri-O-galloyl glucose
• .Tannin
• 1,3,6-Tri-O-galloyl-D-glucose
• Tannic acid (Corilagin)
• 1,3,6-Trigalloyl glucose
• CHEMBL389895
• MEGxp0_001387
• SCHEMBL1004538
• DTXSID3041667
• ACon1_002062
• 1,3,6-Tri-O-galloyl--D-glucose
• HY-N6006
• NCGC00179867-01
• NCGC00179867-02
• 1,3,6-Tri-O-galloyl- beta -D-glucose
• AC-20241
• MS-30889
• .beta.-D-Glucopyranose 1,3,6-trigallate
• J303.464J
• CS-0032136
• Glucopyranose, 1,3,6-trigallate, .beta.-D-
• C17458
• E87143
• 1,3,6-Trigalloylglucose, >=95% (LC/MS-ELSD)
• W-201661
• 1,3,6-TRI-O-GALLOYL-.BETA.-D-GLUCOPYRANOSE
• Q13423012
• ?-d-glucopiranosa, 1,3,6-tris(3,4,5-trihidroxibenzoate)
• 1,3,6-Tri-O-galloyl-beta-D-glucose, analytical standard
• 1,3,6-tris(3,4,5-trihydroxybenzoate)beta-D-glucopyranose
• beta-D-Glucopyranose-1,3,6-tris(3,4,5-trihydroxybenzoate
• (2S,3R,4S,5R,6R)-3,5-Dihydroxy-6-(((3,4,5-trihydroxybenzoyl)oxy)methyl)tetrahydro-2H-pyran-2,4-diyl bis(3,4,5-trihydroxybenzoate)
• [(2R,3R,4S,5R,6S)-3,5-dihydroxy-4,6-bis[(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	-	0.6029	60.29%
Caco-2	-	0.8742	87.42%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6859	68.59%
OATP2B1 inhibitior	-	0.5642	56.42%
OATP1B1 inhibitior	-	0.4714	47.14%
OATP1B3 inhibitior	-	0.4608	46.08%
MATE1 inhibitior	-	0.5000	50.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.7278	72.78%
P-glycoprotein inhibitior	+	0.6522	65.22%
P-glycoprotein substrate	-	0.9314	93.14%
CYP3A4 substrate	+	0.5284	52.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8372	83.72%
CYP3A4 inhibition	-	0.8919	89.19%
CYP2C9 inhibition	-	0.8621	86.21%
CYP2C19 inhibition	-	0.9098	90.98%
CYP2D6 inhibition	-	0.9612	96.12%
CYP1A2 inhibition	-	0.9265	92.65%
CYP2C8 inhibition	-	0.5900	59.00%
CYP inhibitory promiscuity	-	0.8660	86.60%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7448	74.48%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.8392	83.92%
Skin irritation	-	0.8346	83.46%
Skin corrosion	-	0.9620	96.20%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7211	72.11%
Micronuclear	+	0.6866	68.66%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8296	82.96%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.9462	94.62%
Acute Oral Toxicity (c)	III	0.7660	76.60%
Estrogen receptor binding	+	0.7518	75.18%
Androgen receptor binding	+	0.6531	65.31%
Thyroid receptor binding	-	0.5264	52.64%
Glucocorticoid receptor binding	+	0.6152	61.52%
Aromatase binding	-	0.5743	57.43%
PPAR gamma	+	0.6656	66.56%
Honey bee toxicity	-	0.8910	89.10%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.9091	90.91%

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	99.01%	91.11%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	94.97%	95.64%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	94.75%	83.00%
CHEMBL1951	P21397	Monoamine oxidase A	93.40%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.25%	96.09%
CHEMBL3194	P02766	Transthyretin	90.70%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.50%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.20%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	86.25%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.07%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.76%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.69%	94.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.63%	95.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.64%	89.34%
CHEMBL2581	P07339	Cathepsin D	81.86%	98.95%

Plants that contains it

• Bupleurum chinense
• Carphephorus odoratissimus
• Carya tonkinensis
• Dryopteris aitoniana
• Hedyosmum arborescens
• Heliotropium arboreum
• Holocarpha obconica
• Lagerstroemia speciosa
• Leonurus sibiricus
• Plantago indica
• Plectranthus fruticosus
• Psorospermum adamauense
• Zanthoxylum americanum

Cross-Links

• PubChem: 452707
• NPASS: NPC61152
• ChEMBL: CHEMBL389895