Pinoresinol-4-beta-D-glucopyranoside - Compound Card

Pinoresinol-4-beta-D-glucopyranoside

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Pinoresinol-4-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Scrophulariaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles OC[C@@H]1O[C@H](Oc2ccc(cc2OC)[C@H]2OC[C@H]3[C@@H]2CO[C@@H]3c2ccc(c(c2)OC)O)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C26H32O11/c1-32-18-7-12(3-5-16(18)28)24-14-10-35-25(15(14)11-34-24)13-4-6-17(19(8-13)33-2)36-26-23(31)22(30)21(29)20(9-27)37-26/h3-8,14-15,20-31H,9-11H2,1-2H3/t14-,15-,20-,21-,22+,23-,24+,25+,26-/m0/s1
InChIKey QLJNETOQFQXTLI-XBIPQKSQSA-N
Formula C26H32O11
HBA 11
HBD 5
MW 520.53
Rotatable Bonds 7
TPSA 156.53
LogP 0.66
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.54
Exact Mass 520.19
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Eremophila maculata Scrophulariaceae Plantae 1214565

Showing of synonyms

  • Youssef F.S, Ashour M.L, et al. (2016). Eremophila maculata —Isolation of a rare naturally-occurring lignan glycoside and the hepatoprotective activity of the leaf extract. Phytomedicine : international journal of phytotherapy and phytopharmacology, 2016, 23(12), 1484-1493. [View] [PubMed]
Pubchem: 154827849

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccc(cc4)OC5CCCCO5

Level: 3

Mol. Weight: 520.53 g/mol

Structure

SMILES: C1OCC(C12)COC2c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 520.53 g/mol

Structure

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 520.53 g/mol

Structure

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 520.53 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 520.53 g/mol

Structure

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 520.53 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 520.53 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 520.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.37
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.920
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.06

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.960
Plasma Protein Binding
88.04
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.130
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.690
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.370
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.660
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
-1782.730
Rat (Acute)
2.510
Rat (Chronic Oral)
3.830
Fathead Minnow
6.300
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
493.630
Hydration Free Energy
-2.840
Log(D) at pH=7.4
1.410
Log(P)
-0.05
Log S
-3.83
Log(Vapor Pressure)
-11.16
Melting Point
216.32
pKa Acid
6.23
pKa Basic
3.0
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 0.9467
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9410
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9259
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.9239
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.9233
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9201
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9178
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9102
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9077
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.9060
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9007
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8886
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8865
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8833
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8809
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8737
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8711
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8689
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8651
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.8591
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8568
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8476
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8430
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8429
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8422
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8418
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8366
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8333
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8285
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8265
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8146
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8135
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8104
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8099
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8092
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8089
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8057
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8045
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7994
UDP-3-O-acyl-N-acetylglucosamine deacetylase O67648 LPXC_AQUAE Aquifex aeolicus 3 0.7863
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7825
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7811
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 4 0.7802
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7757
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7752
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7737
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7704
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7695
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7671
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7662
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7651
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7607
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7597
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7591
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7589
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7585
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7568
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7543
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7542
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7518
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7510
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7507
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7474
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7457
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7450
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7443
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7442
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7421
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7408
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7403
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7402
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7390
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7382
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7378
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7367
clade A/E 93TH057 HIV-1 gp120 core A0A0M3KKW9 A0A0M3KKW9_9HIV1 Human immunodeficiency virus 1 2 0.7344
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7339
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7333
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7332
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7328
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7320
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7318
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7311
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7304
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7302
Aminopeptidase N P04825 AMPN_ECOLI Escherichia coli 3 0.7299
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7297
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7286
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7277
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7258
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7258
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7255
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7252
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7252
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7250
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7236
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7236
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7235
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7235
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7232
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7231
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7231
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7231
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7227
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7227
Beta-lactamase Q79MP6 Q79MP6_PSEAI Pseudomonas aeruginosa 2 0.7225
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7220
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7217
Adenosine receptor A2a P29274 AA2AR_HUMAN Homo sapiens 4 0.7200
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7199
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7196
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7194
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7190
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7176
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7173
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7171
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7157
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7146
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7138
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7130
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7130
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7130
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 2 0.7122
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7118
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7118
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7117
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7112
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7110
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7104
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7097
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7088
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7087
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7085
Pol polyprotein Q90K99 Q90K99_9HIV1 Human immunodeficiency virus 1 4 0.7083
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7074
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7071
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7068
Transitional endoplasmic reticulum ATPase P55072 TERA_HUMAN Homo sapiens 3 0.7067
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7067
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7060
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7058
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7050
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7046
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7035
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7031
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7031
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7029
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7028
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7026
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7024
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7019
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7015
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7012
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7004

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