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Di-O-galloyl-2,4-chebuloyl glucose

Family: Plantae - Combretaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Chebulic Ellagitannin

Canonical Smiles	OC(=O)C[C@@H]1C(=O)OC2[C@@H](COC(=O)c3cc(O)c(c(c3)O)O)O[C@H]([C@@H]([C@H]2OC(=O)c2cc(O)c(c(c2)O)O)OC(=O)c2c3[C@H]1[C@H](O)C(=O)Oc3c(c(c2)O)O)OC(=O)c1cc(O)c(c(c1)O)O
InChI	InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22+,24-,30-,31?,33-,34+,41-/m0/s1
InChIKey	YGVHOSGNOYKRIH-FBOASRQDSA-N
Formula	C₄₁H₃₂O₂₇
HBA	26
HBD	13
MW	956.68
Rotatable Bonds	9
TPSA	447.09
LogP	0.02
Number Rings	7
Number Aromatic Rings	4
Heavy Atom Count	68
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	956.11
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Terminalia species	Combretaceae	Plantae	39992

Showing of synonyms

Pfundstein B, El Desouky SK, et al. (2010). Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica, Terminalia chebula and Terminalia horrida): Characterization, quantitation and determination of antioxidant capacities. Phytochemistry,2010,71(10),1132-1148. [View] [PubMed]

Pubchem: 162890427

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC2C(OC3=O)C(OC(=O)c4ccccc4)OC(COC(=O)c5ccccc5)C2OC(=O)CC6CC(=O)Oc7cccc3c67

Level: 3

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1C(=O)OC2C(OC3=O)COC(COC(=O)c4ccccc4)C2OC(=O)CC5CC(=O)Oc6cccc3c56

Level: 2

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1C(=O)OC(C(C2)OC3=O)OC(COC(=O)c4ccccc4)C2OC(=O)CC5CC(=O)Oc6cccc3c56

Level: 2

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1C(=O)OC(OC2)C(OC3=O)C(OC(=O)c4ccccc4)C2OC(=O)CC5CC(=O)Oc6cccc3c56

Level: 2

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1C(=O)OCC(OCC(C2)OC3=O)C2OC(=O)CC4CC(=O)Oc5cccc3c45

Level: 1

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1C(=O)OC(OC2)C(OC3=O)CC2OC(=O)CC4CC(=O)Oc5cccc3c45

Level: 1

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1C(=O)OC(C(OC2=O)COC3)C3OC(=O)CC4CC(=O)Oc5cccc2c45

Level: 1

Mol. Weight: 956.68 g/mol

SMILES: c12c3cccc1OC(=O)CC2CC(=O)OC4CC(OC3=O)COC4

Level: 0

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 956.68 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -6.52
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 6859.61
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 897338.7

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.43
Plasma Protein Binding: 17.42
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: Non-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: Inhibitor

Excretion

Clearance: 10.55
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -20863.2
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.16
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.05
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: -1628625209.81
Rat (Acute): 2.5
Rat (Chronic Oral): 6.92
Fathead Minnow: 2055803.53
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: 183163767.6
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -92.62
Log(P): -0.24
Log S: -5.86
Log(Vapor Pressure): -6031507.86
Melting Point: 358.76
pKa Acid: -43902.85
pKa Basic: -324.79

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8900
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8900
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	4	0.8792
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	4	0.8792
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8791
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8791
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8626
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8626
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8531
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8531
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8416
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8416
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8391
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8391
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8283
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8283
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8260
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8260
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8247
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8247
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8223
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8223
Avidin	P02701	AVID_CHICK	Gallus gallus	4	0.8155
Avidin	P02701	AVID_CHICK	Gallus gallus	4	0.8155
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8137
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8137
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8116
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8116
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8031
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8031
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7961
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7961
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7757
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7757
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7466
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7466
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7443
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7443
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7434
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7434
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7426
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7426
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7407
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7407
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7270
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7270
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7253
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7253
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7200
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7200
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7195
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7195
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7184
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7184
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7183
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7183
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7145
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7145
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7107
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7107
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7075
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7075
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7075
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7075
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7043
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7043
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7029
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7029
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7015
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7015
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7005
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7005

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