Select a section from the left sidebar
4-(beta-D-glucopyranosyloxy)benzyl alcohol
- Family: Plantae - Cucurbitaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Benzyl Alcohol
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2ccc(cc2)CO)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C13H18O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1 |
| InChIKey | PUQSUZTXKPLAPR-UJPOAAIJSA-N |
| Formula | C13H18O7 |
| HBA | 7 |
| HBD | 5 |
| MW | 286.28 |
| Rotatable Bonds | 4 |
| TPSA | 119.61 |
| LogP | -1.64 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.54 |
| Exact Mass | 286.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Citrullus colocynthis | Cucurbitaceae | Plantae | 252529 |
Showing of synonyms
4-(beta-D-glucopyranosyloxy)benzyl alcohol
Gastrodin
62499-27-8
Gastrodine
UNII-5YS9U2W3RQ
5YS9U2W3RQ
Beta-D-Glucopyranoside, 4-(hydroxymethyl)phenyl
(-)-GASTRODIN
4-(Hydroxymethyl)phenyl-beta-D-glucopyranoside
4-(beta-D-GLUCOPYRANOSYL)-BENZYLALCOHOL
Beta-D-GLUCOPYRANOSIDE, 4-(HYDROXYMETHYL)PHENYL-
4-HYDROXYBENZYL ALCOHOL 4-O-beta-D-GLUCOPYRANOSIDE
Gastrodin Hemihydrate
B-D-Glucopyranoside, 4-(hydroxymethyl)phenyl
4-(Hydroxymethyl)phenyl beta-D-Glucopyranoside
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triol
CHEMBL274739
CHEBI:80828
Ss-D-Glucopyranoside, 4-(hydroxymethyl)phenyl
4-(Hydroxymethyl)phenyl ss-D-glucopyranoside
4-(ss-D-Glucopyranosyl)-benzylalcohol
4-(ss-D-Glucopyranosyloxy)benzyl alcohol
4-Hydroxybenzyl alcohol 4-O-ss-D-glucopyranoside
Gastrodin (Standard)
Gastrodin (Gastrodine)
GASTRODIN [MI]
GASTRODIN [WHO-DD]
SCHEMBL1076037
Gastrodin, >=98% (HPLC)
HY-N0115R
DTXSID30978086
GLXC-03177
HMS3884L15
HY-N0115
MSK40094
BDBM50177403
MFCD00272169
S2383
AKOS015951256
AC-8028
BCP9000710
CCG-267336
CS-7969
MG11579
NCGC00346601-02
1ST40094
4Hydroxybenzyl alcohol 4-O-b-D-glucoside
AS-17473
DA-53519
Gastrodin, from Gastrodia alata, >=98%
4-[beta-d-glucopyranosyloxy] benzyl alcohol
NS00124520
4-(Hydroxymethyl)phenylbeta-D-Glucopyranoside
C16964
4-(.BETA.-D-GLUCOPYRANOSYL)-BENZYLALCOHOL
A833810
Q5526833
4-(.BETA.-D-GLUCOPYRANOSYLOXY)BENZYL ALCOHOL
.BETA.-D-GLUCOPYRANOSIDE, 4-(HYDROXYMETHYL)PHENYL
.BETA.-D-GLUCOPYRANOSIDE, 4-(HYDROXYMETHYL)PHENYL-
4-HYDROXYBENZYL ALCOHOL 4-O-.BETA.-D-GLUCOPYRANOSIDE
NCGC00346601-02_C13H18O7_beta-D-Glucopyranoside, 4-(hydroxymethyl)phenyl
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-(hydroxymethyl)phenoxy)-tetrahydro-2H-pyran-3,4,5-triol
Pubchem:
115067
Cas:
62499-27-8
Gnps:
CCMSLIB00006438887
Zinc:
ZINC000003881790
Kegg Ligand:
C16964
Chebi:
80828
Nmrshiftdb2:
60029428
Chembl:
CHEMBL274739
Bindingdb:
50177403
Selleck:
Gastrodin(Gastrodine)
CPRiL:
65291
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 286.28 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 286.28 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 286.28 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.27
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.120
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.89
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.680
- Plasma Protein Binding
- 57.16
- 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
- 3.900
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.940
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.350
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 3.800
- 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
- -2.350
- Rat (Acute)
- 1.880
- Rat (Chronic Oral)
- 3.260
- Fathead Minnow
- 3.060
- 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
- 407.510
- Hydration Free Energy
- -19.460
- Log(D) at pH=7.4
- -0.680
- Log(P)
- -1.63
- Log S
- -1.05
- Log(Vapor Pressure)
- -11.25
- Melting Point
- 167.86
- pKa Acid
- 7.25
- pKa Basic
- 3.53
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.9206 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8908 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.8851 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8759 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8636 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8589 |
| Isoleucine--tRNA ligase | P56690 | SYI_THET8 | Thermus thermophilus | 3 | 0.8448 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.8444 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8428 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8382 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8104 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8099 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8098 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8037 |
| Galactoside O-acetyltransferase | P07464 | THGA_ECOLI | Escherichia coli | 4 | 0.7979 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7943 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7876 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7789 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7789 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7781 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7715 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7672 |
| Adenylate cyclase 2 | A0A2U2H3Y1 | A0A384LKY8_YERPE | Yersinia pestis | 3 | 0.7647 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7577 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.7522 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 3 | 0.7476 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7412 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7401 |
| Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 3 | 0.7386 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7372 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 3 | 0.7367 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7367 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7315 |
| Chorismate mutase AroH | P19080 | AROH_BACSU | Bacillus subtilis | 2 | 0.7308 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7305 |
| Serine/threonine-protein kinase RAD53 | P22216 | RAD53_YEAST | Saccharomyces cerevisiae | 4 | 0.7299 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7287 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7272 |
| Repressor protein | Q7X0D9 | Q7X0D9_ACIAD | Acinetobacter baylyi | 3 | 0.7259 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7255 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7251 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7240 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7240 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7219 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7204 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7197 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7194 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7184 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7179 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7174 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7153 |
| 6-phosphogluconate dehydrogenase, decarboxylating | P96789 | 6PGD_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7135 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7129 |
| Pyridoxal kinase | O00764 | PDXK_HUMAN | Homo sapiens | 2 | 0.7121 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7100 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7090 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 2 | 0.7083 |
| 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 | O50008 | METE1_ARATH | Arabidopsis thaliana | 2 | 0.7073 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 3 | 0.7058 |
| D-alanyl-D-alanine carboxypeptidase | P15555 | DAC_STRSR | Streptomyces sp | 2 | 0.7049 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7039 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7033 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7032 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 4 | 0.7028 |
| 16S rRNA (guanine(1405)-N(7))-methyltransferase | Q763K9 | Q763K9_ECOLX | Escherichia coli | 3 | 0.7026 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7026 |
| 4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic | P49235 | HGGL1_MAIZE | Zea mays | 2 | 0.7019 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 3 | 0.7009 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7009 |