Oxyresveratrol 2-O-beta-D-glucopyranoside - Compound Card

Oxyresveratrol 2-O-beta-D-glucopyranoside

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Oxyresveratrol 2-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Juncaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glycoside
Canonical Smiles OC[C@H]1O[C@@H](Oc2cc(O)ccc2/C=C\c2cc(O)cc(c2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-15-8-12(22)4-3-11(15)2-1-10-5-13(23)7-14(24)6-10/h1-8,16-27H,9H2/b2-1-/t16-,17-,18+,19-,20-/m1/s1
InChIKey UPUMEBJDZQEUFC-BUFXCDORSA-N
Formula C20H22O9
HBA 9
HBD 7
MW 406.39
Rotatable Bonds 5
TPSA 160.07
LogP 0.15
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 406.13
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Juncus acutus Juncaceae Plantae 308385

Showing of synonyms

  • Awaad AS (2006). Phenolic glycosides of Juncus acutus and its anti-eczematic activity. Chemistry of Natural Compounds,2006,42(2),152-155. [View]
Pubchem: 11842780
Nmrshiftdb2: 70090542

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=Cc2c(cccc2)OC3CCCCO3

Level: 2

Mol. Weight: 406.39 g/mol

Structure

SMILES: c1ccccc1C=Cc2ccccc2

Level: 1

Mol. Weight: 406.39 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 406.39 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 406.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 406.39 g/mol

Anti-eczematic

Absorption

Caco-2 (logPapp)
-6.88
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.390
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.900
Plasma Protein Binding
75.8
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
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
13.910
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.350
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.970
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.290
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
-14.160
Rat (Acute)
2.240
Rat (Chronic Oral)
4.030
Fathead Minnow
3.950
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
553.400
Hydration Free Energy
-10.510
Log(D) at pH=7.4
0.740
Log(P)
0.12
Log S
-3.41
Log(Vapor Pressure)
-11.93
Melting Point
185.78
pKa Acid
5.96
pKa Basic
5.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9362
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9362
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9183
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9183
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9175
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9175
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9117
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9117
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9109
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9109
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.8921
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.8921
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8729
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8729
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8693
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8693
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8681
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8681
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.8613
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.8613
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8524
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8524
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8510
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8510
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8398
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8398
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.8392
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.8392
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8375
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8375
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8359
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8359
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8328
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8328
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8310
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8310
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8201
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8201
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8193
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8193
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.8164
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.8164
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8034
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8034
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7889
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7889
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7879
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7879
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7871
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7871
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7845
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7845
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7842
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7842
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7775
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7775
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7772
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7772
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7738
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7738
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7715
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7715
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7669
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7669
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7603
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7603
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7591
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7591
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8ZMF7 ISPF_SALTY Salmonella typhimurium 4 0.7589
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8ZMF7 ISPF_SALTY Salmonella typhimurium 4 0.7589
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7584
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7584
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7571
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7571
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7544
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7544
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7522
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7522
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7506
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7506
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7436
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7436
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7429
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7429
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7333
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7333
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7321
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7321
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7257
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7257
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7257
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7257
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7252
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7252
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7250
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7250
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7233
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7233
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7224
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7224
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7220
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7220
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7219
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7219
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7192
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7192
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7183
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7183
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7175
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7175
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7152
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7152
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7148
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7148
Epothilone C/D epoxidase Q9KIZ4 C167_SORCE Sorangium cellulosum 3 0.7140
Epothilone C/D epoxidase Q9KIZ4 C167_SORCE Sorangium cellulosum 3 0.7140
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7123
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7123
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7116
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7116
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7115
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7115
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7110
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7110
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7096
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7096
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7076
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7076
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7060
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7060
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7059
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7059
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7052
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7052
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7044
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7044
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7032
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7032
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7025
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7025
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7015
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7015

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