1-benzyl-[6-p-hydroxybenzoyl]-beta-D-glucopyranosyl-(1→3)-beta-D-glucopyranoside - Compound Card

1-benzyl-[6-p-hydroxybenzoyl]-beta-D-glucopyranosyl-(1→3)-beta-D-glucopyranoside

Select a section from the left sidebar

1-benzyl-[6-p-hydroxybenzoyl]-beta-D-glucopyranosyl-(1→3)-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Bignoniaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glycoside
Canonical Smiles OCC1O[C@@H](OCc2ccccc2)[C@H](C([C@@H]1O)O[C@@H]1OC(COC(=O)c2ccc(cc2)O)[C@H](C([C@@H]1O)O)O)O
InChI InChI=1S/C26H32O13/c27-10-16-19(30)23(22(33)25(37-16)36-11-13-4-2-1-3-5-13)39-26-21(32)20(31)18(29)17(38-26)12-35-24(34)14-6-8-15(28)9-7-14/h1-9,16-23,25-33H,10-12H2/t16?,17?,18-,19-,20?,21+,22+,23?,25-,26+/m1/s1
InChIKey CHRSDYCVKRENEB-BIQSSIORSA-N
Formula C26H32O13
HBA 13
HBD 7
MW 552.53
Rotatable Bonds 9
TPSA 204.83
LogP -1.6
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 552.18
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Tabebuia argentea Bignoniaceae Plantae 3350745

Showing of synonyms

  • De Abreu B, Temraz A, et al. (2014). Phenolic glycosides from Tabebuia argentea and Catalpa bignonioides. Phytochemistry Letters,2014,7,85-88. [View]
Pubchem: 162853797
Nmrshiftdb2: 70002391

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)OC3CC(OCC3)OCc4ccccc4

Level: 3

Mol. Weight: 552.53 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)OC3CCOCC3

Level: 2

Mol. Weight: 552.53 g/mol

Structure

SMILES: c1ccccc1COC(OCC2)CC2OC3CCCCO3

Level: 2

Mol. Weight: 552.53 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 552.53 g/mol

Structure

SMILES: c1ccccc1COC2CCCCO2

Level: 1

Mol. Weight: 552.53 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 552.53 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 552.53 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 552.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.49
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.06
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
54.54
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
6.47
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.91
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.78
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.64
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
-2526.16
Rat (Acute)
2.39
Rat (Chronic Oral)
3.89
Fathead Minnow
6.66
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
505.07
Hydration Free Energy
-2.93
Log(D) at pH=7.4
0.98
Log(P)
0.39
Log S
-2.86
Log(Vapor Pressure)
-11.52
Melting Point
168.23
pKa Acid
3.3
pKa Basic
3.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9567
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9567
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9409
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9409
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8986
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8986
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8698
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8698
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8637
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8637
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8611
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8611
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8516
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8516
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8373
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8373
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8221
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8221
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8174
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8174
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8169
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8169
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8083
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8083
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8035
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8035
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8035
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8035
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7981
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7981
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7951
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7951
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7925
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7925
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7845
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7845
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7839
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7839
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7782
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7782
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7778
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7778
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7734
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7734
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7732
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7732
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7698
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7698
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7696
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7696
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7652
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7652
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7462
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7462
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7457
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7457
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7450
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7450
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7448
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7448
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7425
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7425
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7404
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7404
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7390
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7390
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7363
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7363
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7343
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7343
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7325
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7325
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7316
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7316
Genome polyprotein C0LMU0 C0LMU0_9FLAV dengue virus type 3 3 0.7303
Genome polyprotein C0LMU0 C0LMU0_9FLAV dengue virus type 3 3 0.7303
CCR4-NOT transcription complex subunit 6-like Q96LI5 CNO6L_HUMAN Homo sapiens 4 0.7292
CCR4-NOT transcription complex subunit 6-like Q96LI5 CNO6L_HUMAN Homo sapiens 4 0.7292
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7267
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7267
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7247
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7247
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7224
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7224
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7215
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7215
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7213
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7213
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7179
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7179
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7179
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7179
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7165
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7165
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7156
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7156
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7155
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7155
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7141
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7141
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7132
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7132
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7106
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7106
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7095
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7095
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7081
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7081
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7066
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7066
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7061
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7061
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.7059
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.7059
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7055
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7055
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7042
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7042
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7036
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7036
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7034
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7034
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7034
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7034
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7032
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7032
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7024
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7024
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7012
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7012
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7010
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7010
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7004
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7004
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7004
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7004

Download SDF