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2,3-dimethyl-4-hydroxymethyl-phenyl-1-hydroxymethyl-O-beta-D-glucopyranoside
- Family: Plantae - Apiaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Phenolic Glucoside
| Canonical Smiles | OCC1O[C@@H](OCc2ccc(c(c2C)C)CO)C([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C16H24O7/c1-8-9(2)11(4-3-10(8)5-17)7-22-16-15(21)14(20)13(19)12(6-18)23-16/h3-4,12-21H,5-7H2,1-2H3/t12?,13-,14+,15?,16-/m1/s1 |
| InChIKey | SHTZHHIANOXZBV-KVDYFSNESA-N |
| Formula | C16H24O7 |
| HBA | 7 |
| HBD | 5 |
| MW | 328.36 |
| Rotatable Bonds | 5 |
| TPSA | 119.61 |
| LogP | -0.89 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.62 |
| Exact Mass | 328.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Eryngium tricuspidatum | Apiaceae | Plantae | 488472 |
Showing of synonyms
2,3-dimethyl-4-hydroxymethyl-phenyl-1-hydroxymethyl-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: c1ccccc1COC2CCCCO2
Level: 1
Mol. Weight: 328.36 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 328.36 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 328.36 g/mol
Antibacterial
Antioxidant
Absorption
- Caco-2 (logPapp)
- -5.21
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.69
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.29
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.63
- Plasma Protein Binding
- 47.3
- 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
- 5.18
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.55
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.97
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.03
- 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
- -1.87
- Rat (Acute)
- 2.05
- Rat (Chronic Oral)
- 3.33
- Fathead Minnow
- 3.19
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 422.12
- Hydration Free Energy
- -16.89
- Log(D) at pH=7.4
- 0.12
- Log(P)
- -0.71
- Log S
- -1.52
- Log(Vapor Pressure)
- -10.59
- Melting Point
- 154.51
- pKa Acid
- 7.55
- pKa Basic
- 4.58
| 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 | 0.9476 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9126 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.8535 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8185 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8122 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8053 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8037 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7964 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7915 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7887 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7849 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 3 | 0.7840 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7838 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 4 | 0.7817 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7662 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7618 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7592 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7484 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7483 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7475 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7350 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7340 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7327 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 2 | 0.7321 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7318 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7287 |
| Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 3 | 0.7279 |
| Probable bifunctional SAT/APS kinase | O67174 | SATC_AQUAE | Aquifex aeolicus | 3 | 0.7202 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7197 |
| Dihydroorotate dehydrogenase (quinone), mitochondrial | Q02127 | PYRD_HUMAN | Homo sapiens | 3 | 0.7178 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7174 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7164 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7134 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7091 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7091 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 3 | 0.7090 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7077 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7075 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 2 | 0.7062 |
| 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 | O50008 | METE1_ARATH | Arabidopsis thaliana | 2 | 0.7053 |
| glutaryl-CoA dehydrogenase (ETF) | Q3JP94 | Q3JP94_BURP1 | Burkholderia pseudomallei | 3 | 0.7028 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7022 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7009 |