Syringaresinol-beta-D-glucoside - Compound Card

Syringaresinol-beta-D-glucoside

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Syringaresinol-beta-D-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Convolvulaceae
  • Kingdom: Plantae
  • Class: Glycoside
Canonical Smiles OC[C@H]1O[C@@H](Oc2c(OC)cc(cc2OC)[C@H]2OC[C@H]3[C@@H]2CO[C@@H]3c2cc(OC)c(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C28H36O13/c1-34-16-5-12(6-17(35-2)21(16)30)25-14-10-39-26(15(14)11-38-25)13-7-18(36-3)27(19(8-13)37-4)41-28-24(33)23(32)22(31)20(9-29)40-28/h5-8,14-15,20,22-26,28-33H,9-11H2,1-4H3/t14-,15-,20+,22+,23-,24+,25+,26+,28-/m0/s1
InChIKey WEKCEGQSIIQPAQ-IRBNZIFYSA-N
Formula C28H36O13
HBA 13
HBD 5
MW 580.58
Rotatable Bonds 9
TPSA 174.99
LogP 0.68
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 580.22
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Cressa cretica Convolvulaceae Plantae 1465651

Showing of synonyms

  • Shaha A.A, Abdel-Azim N.S, et al. (2004). Isolation and NMR spectra of syringaresinol-beta-D-glucoside from Cressa cretica. Fitoterapia, 2004,75(1),771– 773. [View] [PubMed]
Pubchem: 443024
Kegg Ligand: C10890
Chebi: 28603
Nmrshiftdb2: 60027894
Metabolights: MTBLC28603
CPRiL: 91565
Structure

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

Level: 3

Mol. Weight: 580.58 g/mol

Structure

SMILES: C1OCC(C12)COC2c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 580.58 g/mol

Structure

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 580.58 g/mol

Structure

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 580.58 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 580.58 g/mol

Structure

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 580.58 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 580.58 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 580.58 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.24
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.960
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
5.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.870
Plasma Protein Binding
86.11
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
8.170
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.550
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.330
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.280
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
-10915.010
Rat (Acute)
2.480
Rat (Chronic Oral)
4.140
Fathead Minnow
26.250
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
384.820
Hydration Free Energy
-2.920
Log(D) at pH=7.4
0.890
Log(P)
-0.63
Log S
-4.01
Log(Vapor Pressure)
-13.31
Melting Point
204.31
pKa Acid
6.36
pKa Basic
1.28
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9686
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9505
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9453
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9314
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9291
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9290
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9281
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.9213
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.9091
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9082
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9064
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8721
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8709
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8693
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8636
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.8632
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8601
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8546
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8514
Uracil-DNA glycosylase P20536 UNG_VACCC Vaccinia virus 4 0.8467
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8337
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8301
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8300
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8244
Uracil-DNA glycosylase P9WFQ9 UNG_MYCTU Mycobacterium tuberculosis 4 0.8243
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8205
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.8204
Uracil-DNA glycosylase P13051 UNG_HUMAN Homo sapiens 4 0.8194
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8190
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.8090
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.8077
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8003
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7994
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 4 0.7929
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7896
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7883
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7867
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7856
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 4 0.7752
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7747
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7739
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.7709
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7708
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7702
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7673
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7672
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7663
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7632
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7618
Nucleoside phosphorylase, putative Q57VZ2 Q57VZ2_TRYB2 Trypanosoma brucei brucei 4 0.7611
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7601
Uridine phosphorylase 2 O95045 UPP2_HUMAN Homo sapiens 4 0.7590
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7572
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7571
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7544
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7519
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7498
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7497
UDP-3-O-acyl-N-acetylglucosamine deacetylase O67648 LPXC_AQUAE Aquifex aeolicus 3 0.7494
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7487
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7476
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7469
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7456
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7392
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7387
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7374
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 4 0.7372
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7368
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7364
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7361
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7356
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7343
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7334
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7326
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7324
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7322
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7320
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7320
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 4 0.7272
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7244
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7237
Aminopeptidase N P04825 AMPN_ECOLI Escherichia coli 3 0.7228
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7221
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7220
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7218
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7181
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7181
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7175
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7163
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7154
Acetylglutamate kinase Q0ASS9 Q0ASS9_MARMM Maricaulis maris 3 0.7146
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7143
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7141
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7136
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7125
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7097
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7092
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7092
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7086
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7085
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7084
Putative snRNP Sm-like protein Q8ZYG5 Q8ZYG5_PYRAE Pyrobaculum aerophilum 3 0.7083
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7080
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7069
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7069
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7069
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7062
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7060
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7052
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7051
Cell division control protein 42 homolog P60953 CDC42_HUMAN Homo sapiens 2 0.7037
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7032
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7024
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7017
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7016
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7013
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7010
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7009
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7006

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