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Thymol beta-D-glucopyranoside
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Glycoside
- Subclass: Monoterpene Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2cc(C)ccc2C(C)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C16H24O6/c1-8(2)10-5-4-9(3)6-11(10)21-16-15(20)14(19)13(18)12(7-17)22-16/h4-6,8,12-20H,7H2,1-3H3/t12-,13-,14+,15-,16-/m1/s1 |
| InChIKey | GKQGIQVSMCHAFX-IBEHDNSVSA-N |
| Formula | C16H24O6 |
| HBA | 6 |
| HBD | 4 |
| MW | 312.36 |
| Rotatable Bonds | 4 |
| TPSA | 99.38 |
| LogP | 0.3 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.62 |
| Exact Mass | 312.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Chiliadenus montanus | Asteraceae | Plantae | 1458965 |
| 2 | Jasonia montana | Asteraceae | Plantae | 441235 |
| 3 | Sphaeranthus bullatus | Asteraceae | Plantae | 1548657 |
Showing of synonyms
Thymol beta-D-glucopyranoside
20772-23-0
Thymol-beta-D-glucoside
Beta-D-Glucopyranoside, 5-methyl-2-(1-methylethyl)phenyl
THYMOL-BETA-D-GLUCOPYRANOSIDE
THYMOL-B-D-GLUCOPYRANOSIDE
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(5-methyl-2-propan-2-ylphenoxy)oxane-3,4,5-triol
(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(2-isopropyl-5-methylphenoxy)tetrahydro-2H-pyran-3,4,5-triol
1-O-Thymyl-beta-D-glucopyranoside
Glucopyranoside, 1-O-thymyl-, beta-D-
Thymolglucoside
CHEBI:182146
AKOS027327245
MT06890
NCGC00380175-01
2-isopropyl-5-methylphenol-O-beta-d-glucopyranoside
|A-D-Glucopyranoside, 5-methyl-2-(1-methylethyl)phenyl
5-Methyl-2-(1-methylethyl)phenyl-beta-D-glucopyranoside
(2R,3S,4S,5R,6S)-2-(HYDROXYMETHYL)-6-(2-ISOPROPYL-5-METHYLPHENOXY)OXANE-3,4,5-TRIOL
- Machumi F, Yenesew A, et al. (2012). Antiparasitic and anticancer carvotacetone derivatives of Sphaeranthus bullatus. Natural Product Communications,2012,7(9),1123-1126. [View] [PubMed]
- Hegazy MEF, Matsuda H, et al. (2014). Chemical constituents and their antibacterial and antifungal activity from the Egyptian herbal medicine Chiliadenus montanus. Phytochemistry,2014,103,154-161. [View] [PubMed]
- Ahmed AA, Jakupovic J (1990). Sesqui- and monoterpenes from Jasonia montana. Phytochemistry,1990,29(11),3658-3661. [View]
Pubchem:
88687
Cas:
20772-23-0
Gnps:
CCMSLIB00004694620
Zinc:
ZINC000005765311
Chebi:
182146
Nmrshiftdb2:
70004114
No compound-protein relationship available.
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 312.36 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 312.36 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 312.36 g/mol
Antimicrobial
Absorption
- Caco-2 (logPapp)
- -4.97
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.450
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.85
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.870
- Plasma Protein Binding
- 73.7
- 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
- 6.690
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.340
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.090
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.310
- 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
- -1.420
- Rat (Acute)
- 2.460
- Rat (Chronic Oral)
- 3.200
- Fathead Minnow
- 3.590
- 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
- 384.900
- Hydration Free Energy
- -17.330
- Log(D) at pH=7.4
- 1.400
- Log(P)
- 1.22
- Log S
- -1.96
- Log(Vapor Pressure)
- -10.0
- Melting Point
- 153.28
- pKa Acid
- 7.49
- pKa Basic
- 4.24
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 3 | 0.8305 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 3 | 0.8305 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 3 | 0.8193 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 3 | 0.8193 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8080 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8080 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.8027 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.8027 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7893 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7893 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7571 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7571 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7554 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7554 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7438 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7438 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7380 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7380 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7298 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7298 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7298 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7298 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7123 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7123 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7119 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7119 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7050 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7050 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7049 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7049 |
| Nitroreductase domain-containing protein | Q8DW21 | Q8DW21_STRMU | Streptococcus mutans serotype c | 3 | 0.7020 |
| Nitroreductase domain-containing protein | Q8DW21 | Q8DW21_STRMU | Streptococcus mutans serotype c | 3 | 0.7020 |