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1,2,6-tri-O-galloylglucose

Family: Plantae - Myrtaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Phenolic Glycoside

Canonical Smiles	O[C@@H]1[C@@H](COC(=O)c2cc(O)c(c(c2)O)O)O[C@H]([C@@H]([C@H]1O)OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O
InChI	InChI=1S/C27H24O18/c28-11-1-8(2-12(29)18(11)34)24(39)42-7-17-21(37)22(38)23(44-25(40)9-3-13(30)19(35)14(31)4-9)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
InChIKey	LLENXGNWVNSBQG-VFTFQOQOSA-N
Formula	C₂₇H₂₄O₁₈
HBA	18
HBD	11
MW	636.47
Rotatable Bonds	7
TPSA	310.66
LogP	-0.28
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	45
Formal Charge	0
Fraction CSP3	0.22
Exact Mass	636.1
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Epilobium hirsutum	Onagraceae	Plantae	210355
2	Syzygium cumini	Myrtaceae	Plantae	—

Showing of synonyms

Eldin Elhawary S.S, Elmotyam A.K.E, et al. (2022). Cytotoxic and anti-diabetic potential, metabolic profiling and insilico studies of Syzygium cumini (L.) Skeels belonging to family Myrtaceae. Natural product research,2022, 36(4), 1026-1030. [View] [PubMed]
Barakat HH, Hussein SAM, et al. (1997). Polyphenolic metabolites of Epilobium hirsutum. Phytochemistry,1997,46(5),935-941. [View]

Pubchem: 440308

Gnps: CCMSLIB00000848078

Zinc: ZINC000004096393

Kegg Ligand: C04360

Chebi: 27395

Nmrshiftdb2: 60026770

Chembl: CHEMBL447974

Bindingdb: 50250504

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC2CCC(OC(=O)c3ccccc3)C(O2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 636.47 g/mol

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 636.47 g/mol

SMILES: c1ccccc1C(=O)OCC2CCC(CO2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 636.47 g/mol

SMILES: c1ccccc1C(=O)OC2C(OCCC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 636.47 g/mol

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 636.47 g/mol

SMILES: c1ccccc1C(=O)OC2CCCOC2

Level: 1

Mol. Weight: 636.47 g/mol

SMILES: c1ccccc1C(=O)OC2CCCCO2

Level: 1

Mol. Weight: 636.47 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 636.47 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 636.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.81
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.45
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 12.41

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.45
Plasma Protein Binding: 40.67
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 12.81
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.6
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.9
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.83
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -22720.41
Rat (Acute): 2.26
Rat (Chronic Oral): 4.41
Fathead Minnow: 47.88
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 449.31
Hydration Free Energy: -3.04
Log(D) at pH=7.4: -0.04
Log(P): 0.24
Log S: -5.41
Log(Vapor Pressure): -17.15
Melting Point: 251.54
pKa Acid: 5.6
pKa Basic: 5.73

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9232
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9232
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9211
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9211
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9015
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9015
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8923
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8923
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8770
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8770
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8732
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8732
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8703
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8703
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8674
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8674
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8659
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8659
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8627
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8627
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8557
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8557
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8507
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8507
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8503
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8503
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8478
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8478
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8435
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8435
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8391
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8391
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8335
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8335
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8325
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8325
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8248
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8248
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8200
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8200
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8187
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8187
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8179
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8179
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8077
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8077
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8048
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8048
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7995
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7995
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7936
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7936
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7883
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7883
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7846
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7846
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7821
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7821
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7779
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7779
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7713
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7713
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7670
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7670
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7661
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7661
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7658
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7658
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7649
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7649
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7576
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7576
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7547
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7547
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7540
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7540
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7472
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7472
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7470
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7470
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7446
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7446
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7415
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7415
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7387
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7387
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7325
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7325
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7320
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7320
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7279
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7279
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7266
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7266
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7265
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7265
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7256
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7256
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7245
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7245
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7243
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7243
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7242
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7242
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7220
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7220
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7218
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7218
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7216
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7216
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7175
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7175
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7148
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7148
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7124
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7124
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7123
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7123
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7100
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7100
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7070
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7070
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7064
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7064
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7063
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7063
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7035
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7035
Purine nucleoside phosphorylase	B9JYS2	B9JYS2_AGRVS	Agrobacterium vitis	4	0.7034
Purine nucleoside phosphorylase	B9JYS2	B9JYS2_AGRVS	Agrobacterium vitis	4	0.7034
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7016
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7016
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7016
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7016
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7006
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7006

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