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Benzyl beta-D-glucopyranoside
- Family: Plantae - Rhamnaceae
- Kingdom: Plantae
- Class: Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](OCc2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C13H18O6/c14-6-9-10(15)11(16)12(17)13(19-9)18-7-8-4-2-1-3-5-8/h1-5,9-17H,6-7H2/t9-,10-,11+,12-,13-/m1/s1 |
| InChIKey | GKHCBYYBLTXYEV-UJPOAAIJSA-N |
| Formula | C13H18O6 |
| HBA | 6 |
| HBD | 4 |
| MW | 270.28 |
| Rotatable Bonds | 4 |
| TPSA | 99.38 |
| LogP | -1.0 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.54 |
| Exact Mass | 270.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tabebuia argentea | Bignoniaceae | Plantae | 3350745 |
| 2 | Rhamnus disperma | Rhamnaceae | Plantae | 1813078 |
Showing of synonyms
Benzyl beta-D-glucopyranoside
4304-12-5
(2R,3R,4S,5S,6R)-2-(Benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
B-D-Glucopyranoside, phenylmethyl
7ILL1IJM8R
Benzyl .beta.-D-glucopyranoside
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-phenylmethoxyoxane-3,4,5-triol
124492-59-7
BENZYL ?-D-GLUCOPYRANOSIDE
Benzyl glucoside
Benzyl hexopyranoside
Benzyl ?-D-glucoside
Benzyl alcohol glucoside
Benzyl beta-d-glucoside
Benzyl-beta-D-glucoside
UNII-7ILL1IJM8R
TimTec1_005150
Benzyl beta -D-Glucopyranoside
Benzyl-o-beta-d-glucopyranoside
SCHEMBL5026363
CHEMBL2336738
1-O-benzyl-beta-D-glucopyranose
ACon1_002322
DTXSID30962864
(2R,3R,4S,5S,6R)-2-(BENZYLOXY)-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL
CHEBI:141411
GKHCBYYBLTXYEV-UJPOAAIJSA-N
Benzyl beta-D-gluco-hexopyranoside
HMS1548K02
Phenylmethyl beta-D-glucopyranoside
Benzyl alcohol-7-O-beta-D-glucoside
AKOS016012289
HY-W153847
(-)-BENZYL .BETA.-D-GLUCOSIDE
NCGC00169955-01
NCGC00169955-02
BENZYL-O-.BETA.-D-GLUCOPYRANOSIDE
WS-01270
Benzyl alcohol-7-O-beta-D-glucopyranoside
CS-0210263
.BETA.-D-GLUCOPYRANOSIDE, PHENYLMETHYL
Benzyl glucopyranoside, >=95% (LC/MS-ELSD)
D86091
BRD-K55170554-001-02-6
Q27268359
C2542227-8A44-4AA0-ACE1-5CB5555F52EE
NCGC00169955-02_C13H18O6_Benzyl beta-D-glucopyranoside
(2R,3R,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
- Mohammed H.A, Abd El-Wahab M.F, et al. (2021). Isolation, Characterization, Complete Structural Assignment,and Anticancer Activities of the Methoxylated Flavonoids from Rhamnus disperma Roots. Molecules, 2021, 26(19), 5827. [View] [PubMed]
- De Abreu B, Temraz A, et al. (2014). Phenolic glycosides from Tabebuia argentea and Catalpa bignonioides. Phytochemistry Letters,2014,7,85-88. [View]
Pubchem:
188977
Cas:
4304-12-5
Gnps:
CCMSLIB00000855173
Zinc:
ZINC000005736909
Chebi:
141411
Nmrshiftdb2:
60021241
Metabolights:
MTBLC141411
Chembl:
CHEMBL2336738
No compound-protein relationship available.
SMILES: c1ccccc1COC2CCCCO2
Level: 1
Mol. Weight: 270.28 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 270.28 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 270.28 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.15
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.570
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.75
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.840
- Plasma Protein Binding
- 60.14
- 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
- 6.350
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.130
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.570
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.880
- 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
- -1.940
- Rat (Acute)
- 1.860
- Rat (Chronic Oral)
- 3.020
- Fathead Minnow
- 3.400
- 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
- 373.390
- Hydration Free Energy
- -19.960
- Log(D) at pH=7.4
- -0.030
- Log(P)
- -0.88
- Log S
- -1.25
- Log(Vapor Pressure)
- -10.43
- Melting Point
- 158.72
- pKa Acid
- 8.51
- pKa Basic
- 3.0
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.9158 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.9158 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8811 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8811 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8726 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8726 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.8611 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.8611 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8575 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8575 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8537 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8537 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8492 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8492 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8377 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8377 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8277 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8277 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.8212 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.8212 |
| Adenosine 5'-monophosphoramidase HINT1 | P80912 | HINT1_RABIT | Oryctolagus cuniculus | 3 | 0.8097 |
| Adenosine 5'-monophosphoramidase HINT1 | P80912 | HINT1_RABIT | Oryctolagus cuniculus | 3 | 0.8097 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8078 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8078 |
| Beta-glucosidase | Q8T0W7 | Q8T0W7_9NEOP | Neotermes koshunensis | 4 | 0.7877 |
| Beta-glucosidase | Q8T0W7 | Q8T0W7_9NEOP | Neotermes koshunensis | 4 | 0.7877 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7842 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7842 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7821 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7821 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7759 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7759 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7751 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7751 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 3 | 0.7682 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 3 | 0.7682 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7664 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7664 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7578 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7578 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 4 | 0.7529 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 4 | 0.7529 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7524 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7524 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7417 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7417 |
| Phosphoribosylformylglycinamidine synthase subunit PurL | Q9X0X3 | PURL_THEMA | Thermotoga maritima | 3 | 0.7411 |
| Phosphoribosylformylglycinamidine synthase subunit PurL | Q9X0X3 | PURL_THEMA | Thermotoga maritima | 3 | 0.7411 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7372 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7372 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7357 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7357 |
| Nicotinamide phosphoribosyltransferase | P43490 | NAMPT_HUMAN | Homo sapiens | 3 | 0.7352 |
| Nicotinamide phosphoribosyltransferase | P43490 | NAMPT_HUMAN | Homo sapiens | 3 | 0.7352 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7350 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7350 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7319 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7319 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7291 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7291 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7286 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7286 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7234 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7234 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 2 | 0.7230 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 2 | 0.7230 |
| Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 3 | 0.7229 |
| Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 3 | 0.7229 |
| Cytosol aminopeptidase | O86436 | AMPA_PSEPU | Pseudomonas putida | 3 | 0.7228 |
| Cytosol aminopeptidase | O86436 | AMPA_PSEPU | Pseudomonas putida | 3 | 0.7228 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7211 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7211 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7199 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7199 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7190 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7190 |
| Oxygen-insensitive NAD(P)H nitroreductase | P38489 | NFSB_ECOLI | Escherichia coli | 4 | 0.7178 |
| Oxygen-insensitive NAD(P)H nitroreductase | P38489 | NFSB_ECOLI | Escherichia coli | 4 | 0.7178 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 2 | 0.7175 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 2 | 0.7175 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7163 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7163 |
| Ribosome-inactivating protein alpha-trichosanthin | P09989 | RIPT_TRIKI | Trichosanthes kirilowii | 3 | 0.7155 |
| Ribosome-inactivating protein alpha-trichosanthin | P09989 | RIPT_TRIKI | Trichosanthes kirilowii | 3 | 0.7155 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7144 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7144 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7144 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7144 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7141 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7141 |
| Multidrug efflux pump subunit AcrB | P31224 | ACRB_ECOLI | Escherichia coli | 3 | 0.7133 |
| Multidrug efflux pump subunit AcrB | P31224 | ACRB_ECOLI | Escherichia coli | 3 | 0.7133 |
| 6-phosphogluconate dehydrogenase, decarboxylating | P96789 | 6PGD_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7122 |
| 6-phosphogluconate dehydrogenase, decarboxylating | P96789 | 6PGD_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7122 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7119 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7119 |
| Nucleoside 2-deoxyribosyltransferase | Q8RLY5 | Q8RLY5_LACHE | Lactobacillus helveticus | 3 | 0.7096 |
| Nucleoside 2-deoxyribosyltransferase | Q8RLY5 | Q8RLY5_LACHE | Lactobacillus helveticus | 3 | 0.7096 |
| Adenosine 5'-monophosphoramidase HINT1 | P49773 | HINT1_HUMAN | Homo sapiens | 3 | 0.7095 |
| Adenosine 5'-monophosphoramidase HINT1 | P49773 | HINT1_HUMAN | Homo sapiens | 3 | 0.7095 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 2 | 0.7089 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 2 | 0.7089 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7085 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7085 |
| Fructose-1,6-bisphosphatase 1 | P09467 | F16P1_HUMAN | Homo sapiens | 2 | 0.7083 |
| Fructose-1,6-bisphosphatase 1 | P09467 | F16P1_HUMAN | Homo sapiens | 2 | 0.7083 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7073 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7073 |
| Epothilone C/D epoxidase | Q9KIZ4 | C167_SORCE | Sorangium cellulosum | 2 | 0.7061 |
| Epothilone C/D epoxidase | Q9KIZ4 | C167_SORCE | Sorangium cellulosum | 2 | 0.7061 |
| Diamine acetyltransferase 1 | P21673 | SAT1_HUMAN | Homo sapiens | 2 | 0.7057 |
| Diamine acetyltransferase 1 | P21673 | SAT1_HUMAN | Homo sapiens | 2 | 0.7057 |
| Protein claret segregational | P20480 | NCD_DROME | Drosophila melanogaster | 2 | 0.7042 |
| Protein claret segregational | P20480 | NCD_DROME | Drosophila melanogaster | 2 | 0.7042 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 2 | 0.7041 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 2 | 0.7041 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7032 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7032 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7013 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7013 |