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1-O-galloyl-2,3-HHDP-alpha-D-glucose

Family: Plantae - Euphorbiaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Polyphenol

Canonical Smiles	OCC1O[C@H](OC(=O)c2cc(O)c(c(c2)O)O)[C@@H]2C([C@@H]1O)OC(=O)c1cc(O)c(c(c1c1c(C(=O)O2)cc(O)c(c1O)O)O)O
InChI	InChI=1S/C27H22O18/c28-5-13-19(36)22-23(27(42-13)45-24(39)6-1-9(29)16(33)10(30)2-6)44-26(41)8-4-12(32)18(35)21(38)15(8)14-7(25(40)43-22)3-11(31)17(34)20(14)37/h1-4,13,19,22-23,27-38H,5H2/t13?,19-,22?,23+,27-/m1/s1
InChIKey	MBPYHNAWMKVREM-AXHZIQKYSA-N
Formula	C₂₇H₂₂O₁₈
HBA	18
HBD	11
MW	634.46
Rotatable Bonds	3
TPSA	310.66
LogP	-0.3
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	45
Formal Charge	0
Fraction CSP3	0.22
Exact Mass	634.08
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Euphorbia helioscopia	Euphorbiaceae	Plantae	154990

Showing of synonyms

Mohamed AH, Hegazy MF, et al. (2012). Euphorbia helioscopia: Chemical constituents and biological activities. International Journal of Phytopharmacology,2012,3(1),78-90. [View]

Pubchem: 162917609

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC(OCC2)C(OC(=O)c3cccc4)C2OC(=O)c(c5c34)cccc5

Level: 1

Mol. Weight: 634.46 g/mol

SMILES: c1cccc(c1c23)C(=O)OC4C(CCOC4)OC(=O)c2cccc3

Level: 0

Mol. Weight: 634.46 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 634.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.5
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.33
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 19.22

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.5
Plasma Protein Binding: 24.07
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: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 12.09
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.41
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.2
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.91
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: -29465.84
Rat (Acute): 2.5
Rat (Chronic Oral): 4.2
Fathead Minnow: 57.27
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: 406.82
Hydration Free Energy: -2.93
Log(D) at pH=7.4: -1.13
Log(P): 0.25
Log S: -4.87
Log(Vapor Pressure): -19.24
Melting Point: 256.46
pKa Acid: 6.15
pKa Basic: 6.48

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	0.9306
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9306
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9094
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9094
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8981
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8981
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8814
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8814
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8736
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8736
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8603
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8603
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8564
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8564
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8496
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8496
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8465
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8465
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8426
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8426
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8354
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8354
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8333
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8333
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8318
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8318
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8298
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8298
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8239
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8239
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8236
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8236
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8221
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8221
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8207
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8207
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8201
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8201
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8127
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8127
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7903
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7903
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7897
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7897
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7806
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7806
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7801
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7801
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7785
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7785
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7750
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7750
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7736
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7736
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7726
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7726
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7726
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7726
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7673
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7673
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7668
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7668
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7556
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7556
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7534
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7534
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7480
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7480
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7455
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7455
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.7439
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.7439
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7424
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7424
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7399
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7399
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7340
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7340
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7276
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7276
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7264
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7264
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7250
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7250
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7202
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7202
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7198
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7198
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7189
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7189
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7182
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7182
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7171
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7171
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7168
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7168
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7163
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7163
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7138
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7138
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7125
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7125
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7118
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7118
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7064
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7064
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7048
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7048
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7030
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7030

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