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2-O-dehydrodigallic acid monocarboxyloyl-3-O-galloyl-(alpha/beta)-glucose

Family: Plantae - Tamaricaceae
Kingdom: Plantae
Class: Tannin
- Subclass: Ellagitannin

Canonical Smiles	OCC1O[C@@H](O)C([C@H]([C@@H]1O)OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)Oc1c(cc(c(c1O)O)O)C(=O)O)O
InChI	InChI=1S/C27H24O19/c28-6-15-19(36)22(45-25(40)7-1-10(29)16(33)11(30)2-7)23(27(42)44-15)46-26(41)8-3-12(31)17(34)14(4-8)43-21-9(24(38)39)5-13(32)18(35)20(21)37/h1-5,15,19,22-23,27-37,42H,6H2,(H,38,39)/t15?,19-,22+,23?,27-/m1/s1
InChIKey	RYMZYVZCMNCUDN-KWCBYRDUSA-N
Formula	C₂₇H₂₄O₁₉
HBA	18
HBD	12
MW	652.47
Rotatable Bonds	8
TPSA	330.89
LogP	-0.36
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	46
Formal Charge	0
Fraction CSP3	0.22
Exact Mass	652.09
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Reaumuria vermiculata	Tamaricaceae	Plantae	1518163

Showing of synonyms

Nawwar MA, Ayoub NA, et al. (2012). Cytotoxic ellagitannins from Reaumuria vermiculata. Fitoterapia,2012,83(7),1256-1266. [View] [PubMed]

Pubchem: 162857704

Nmrshiftdb2: 60033264

No compound-protein relationship available.

SMILES: c1ccccc1Oc(ccc2)cc2C(=O)OC(COCC3)C3OC(=O)c4ccccc4

Level: 3

Mol. Weight: 652.47 g/mol

SMILES: c1ccccc1C(=O)OC2C(COCC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 652.47 g/mol

SMILES: C1OCCCC1OC(=O)c2cc(ccc2)Oc3ccccc3

Level: 2

Mol. Weight: 652.47 g/mol

SMILES: c1ccccc1C(=O)OC2CCOCC2

Level: 1

Mol. Weight: 652.47 g/mol

SMILES: c1ccccc1C(=O)OC2CCCOC2

Level: 1

Mol. Weight: 652.47 g/mol

SMILES: c1ccccc1Oc2ccccc2

Level: 1

Mol. Weight: 652.47 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 652.47 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 652.47 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -6.56
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.85
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 18.83

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.82
Plasma Protein Binding: 39.59
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: Non-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: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.77
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -3.98
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.79
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.21
Micronucleos: Toxic
NR-AhR: Safe
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: -34715.27
Rat (Acute): 2.39
Rat (Chronic Oral): 3.79
Fathead Minnow: 61.33
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 461.98
Hydration Free Energy: -3.17
Log(D) at pH=7.4: -2.93
Log(P): 0.15
Log S: -4.19
Log(Vapor Pressure): -22.91
Melting Point: 220.87
pKa Acid: 6.53
pKa Basic: 4.93

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.9440
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.9440
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.9382
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.9382
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9307
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9307
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.9106
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.9106
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8791
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8791
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8790
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8790
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8642
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8642
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8612
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8612
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8493
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8493
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8471
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8471
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8433
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8433
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8394
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8394
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8322
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8322
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8241
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8241
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	5	0.8210
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	5	0.8210
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8154
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8154
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.8126
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.8126
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8092
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8092
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8086
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8086
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8080
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8080
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8065
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8065
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8061
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8061
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8021
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8021
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8019
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8019
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7965
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7965
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7936
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7936
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.7882
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.7882
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7805
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7805
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7794
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7794
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7768
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7768
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7754
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7754
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7735
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7735
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7707
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7707
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7702
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7702
Shikimate dehydrogenase (NADP(+))	P56119	AROE_HELPY	Helicobacter pylori	3	0.7667
Shikimate dehydrogenase (NADP(+))	P56119	AROE_HELPY	Helicobacter pylori	3	0.7667
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.7607
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.7607
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7599
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7599
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7519
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7519
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7516
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7516
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	3	0.7439
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	3	0.7439
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7361
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7361
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7350
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7350
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7256
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7256
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7227
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7227
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7221
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7221
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7196
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7196
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7190
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7190
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7188
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7188
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7170
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7170
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7167
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7167
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	3	0.7148
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	3	0.7148
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7143
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7143
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7102
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7102
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7095
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7095
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7071
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7071
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7060
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7060
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7053
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7053
Glucose-1-phosphate thymidylyltransferase 1	P37744	RMLA1_ECOLI	Escherichia coli	5	0.7049
Glucose-1-phosphate thymidylyltransferase 1	P37744	RMLA1_ECOLI	Escherichia coli	5	0.7049
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7038
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7038
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7023
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7023

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