1-O-p-hydroxybenzoyl-beta-D-glucopyranoside - Compound Card

1-O-p-hydroxybenzoyl-beta-D-glucopyranoside

Select a section from the left sidebar

1-O-p-hydroxybenzoyl-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Bignoniaceae, Cruciferae-Brassicaceea
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glycoside
Canonical Smiles OC[C@H]1O[C@@H](OC(=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C13H16O8/c14-5-8-9(16)10(17)11(18)13(20-8)21-12(19)6-1-3-7(15)4-2-6/h1-4,8-11,13-18H,5H2/t8-,9-,10+,11-,13+/m1/s1
InChIKey XWTGDGASXRARSP-HMUNZLOLSA-N
Formula C13H16O8
HBA 8
HBD 5
MW 300.26
Rotatable Bonds 3
TPSA 136.68
LogP -1.65
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.46
Exact Mass 300.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tabebuia argentea Bignoniaceae Plantae 3350745
2 Moricandia arvensis Cruciferae-Brassicaceea Plantae 180540

Showing of synonyms

  • Braham H, Mighri Z, et al. (2005). Antioxidant phenolic glycosides from Moricandia arvensis. Journal of Natural Products,2005,68(4),517-522. [View]
  • De Abreu B, Temraz A, et al. (2014). Phenolic glycosides from Tabebuia argentea and Catalpa bignonioides. Phytochemistry Letters,2014,7,85-88. [View]
Pubchem: 14132342
Chebi: 145301
Nmrshiftdb2: 60024843
Metabolights: MTBLC145301

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2CCCCO2

Level: 1

Mol. Weight: 206.24 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-5.41
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.91
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
55.18
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
7.9
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.08
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.91
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.65
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
-1.46
Rat (Acute)
1.88
Rat (Chronic Oral)
3.35
Fathead Minnow
3.81
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
421.28
Hydration Free Energy
-15.28
Log(D) at pH=7.4
-0.73
Log(P)
-0.78
Log S
-1.5
Log(Vapor Pressure)
-10.18
Melting Point
166.2
pKa Acid
5.12
pKa Basic
4.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8917
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8917
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8753
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8753
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8675
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8675
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8657
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8657
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8368
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8368
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8315
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8315
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8251
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8251
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8231
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8231
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8170
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8170
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8111
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8111
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7988
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7988
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7967
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7967
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7964
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7964
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7892
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7892
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7875
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7875
Ribosome-inactivating protein alpha-trichosanthin P09989 RIPT_TRIKI Trichosanthes kirilowii 4 0.7871
Ribosome-inactivating protein alpha-trichosanthin P09989 RIPT_TRIKI Trichosanthes kirilowii 4 0.7871
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7840
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7840
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7779
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7779
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7669
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7669
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7645
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7645
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7625
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7625
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7545
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7545
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7516
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7516
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7515
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7515
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7504
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7504
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7477
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7477
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7475
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7475
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7460
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7460
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7460
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7460
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7456
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7456
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7376
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7376
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7358
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7358
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7355
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7355
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7354
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7354
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7341
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7341
CCR4-NOT transcription complex subunit 6-like Q96LI5 CNO6L_HUMAN Homo sapiens 4 0.7335
CCR4-NOT transcription complex subunit 6-like Q96LI5 CNO6L_HUMAN Homo sapiens 4 0.7335
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7284
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7284
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7281
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7281
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7254
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7254
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7254
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7254
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7223
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7223
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7194
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7194
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7181
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7181
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7179
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7179
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7173
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7173
Adenosine 5'-monophosphoramidase HINT1 P49773 HINT1_HUMAN Homo sapiens 3 0.7169
Adenosine 5'-monophosphoramidase HINT1 P49773 HINT1_HUMAN Homo sapiens 3 0.7169
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7166
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7166
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7162
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7162
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7150
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7150
Glucose-1-phosphate thymidylyltransferase P26393 RMLA_SALTY Salmonella typhimurium 3 0.7133
Glucose-1-phosphate thymidylyltransferase P26393 RMLA_SALTY Salmonella typhimurium 3 0.7133
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 3 0.7118
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 3 0.7118
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7111
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7111
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7111
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7111
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7100
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7100
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7094
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7094
7-methylguanosine phosphate-specific 5'-nucleotidase Q9W197 5NT3B_DROME Drosophila melanogaster 3 0.7080
7-methylguanosine phosphate-specific 5'-nucleotidase Q9W197 5NT3B_DROME Drosophila melanogaster 3 0.7080
Phosphoglycerate kinase Q83AU6 PGK_COXBU Coxiella burnetii 3 0.7070
Phosphoglycerate kinase Q83AU6 PGK_COXBU Coxiella burnetii 3 0.7070
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7066
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7066
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7046
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7046
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7042
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7042
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7041
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7041
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7034
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7034
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7029
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7029
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7018
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7018
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7014
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7014

Download SDF