Select a section from the left sidebar
2-hydroxy- 3,5-dimethyl-acetophenon-4-O-beta-D-glucopyranoside
- Family: Plantae - Apiaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Phenolic Glucoside
| Canonical Smiles | OCC1O[C@@H](Oc2c(C)cc(c(c2C)O)C(=O)C)C([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C16H22O8/c1-6-4-9(8(3)18)11(19)7(2)15(6)24-16-14(22)13(21)12(20)10(5-17)23-16/h4,10,12-14,16-17,19-22H,5H2,1-3H3/t10?,12-,13+,14?,16+/m1/s1 |
| InChIKey | PCJGXQXTGOTAQS-NNTUHADWSA-N |
| Formula | C16H22O8 |
| HBA | 8 |
| HBD | 5 |
| MW | 342.34 |
| Rotatable Bonds | 4 |
| TPSA | 136.68 |
| LogP | -0.61 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.56 |
| Exact Mass | 342.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Eryngium tricuspidatum | Apiaceae | Plantae | 488472 |
Showing of synonyms
2-hydroxy- 3,5-dimethyl-acetophenon-4-O-beta-D-glucopyranoside
- Benmerache A, Magid A.A, et al. (2016). Chemical composition, antibacterial, antioxidant and tyrosinase inhibitory activities of glycosides from aerial parts of Eryngium tricuspidatum. Phytochemistry Letters, 2016, 18, 23 - 28. [View]
No compound-protein relationship available.
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 342.34 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 342.34 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 342.34 g/mol
Antibacterial
Antioxidant
Absorption
- Caco-2 (logPapp)
- -5.49
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.19
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.11
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.58
- Plasma Protein Binding
- 60.92
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- 6.6
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.79
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.1
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.87
- 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
- -0.3
- Rat (Acute)
- 2.04
- Rat (Chronic Oral)
- 3.64
- Fathead Minnow
- 3.84
- 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
- 438.17
- Hydration Free Energy
- -16.07
- Log(D) at pH=7.4
- 0.31
- Log(P)
- 0.63
- Log S
- -1.86
- Log(Vapor Pressure)
- -10.17
- Melting Point
- 168.9
- pKa Acid
- 5.07
- pKa Basic
- 6.41
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9190 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8861 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8690 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8498 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8244 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8200 |
| Nicotinamide phosphoribosyltransferase | P43490 | NAMPT_HUMAN | Homo sapiens | 3 | 0.8189 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8095 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7914 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7889 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7745 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7710 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7702 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.7700 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7674 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7670 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7659 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7653 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7636 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7627 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7594 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7579 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7578 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7507 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7469 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7452 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7403 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7385 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7378 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7334 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7327 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7251 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7249 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7185 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7156 |
| UDP-glycosyltransferase 72B1 | Q9M156 | U72B1_ARATH | Arabidopsis thaliana | 4 | 0.7116 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7095 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7067 |
| Metallo-beta-lactamase type 2 | P26918 | BLAB_AERHY | Aeromonas hydrophila | 2 | 0.7067 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7060 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7015 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7014 |