1-O-Vanilloyl-beta-D-glucose
PubChem CID: 14132344
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| Compound Synonyms | 1-O-vanilloyl-beta-D-glucose, CHEBI:71512, 1-O-(4-hydroxy-3-methoxybenzoyl)-beta-D-glucopyranose, [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 4-hydroxy-3-methoxybenzoate, Vanilloyl glucose, ((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl) 4-hydroxy-3-methoxybenzoate, 68985-14-8, C20470, 1-O-(4-hydroxy-3-methoxybenzoyl)-beta-D-glucose, Q27139670 |
|---|---|
| Ghose Rule | False |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 146.0 |
| Hydrogen Bond Donor Count | 5.0 |
| Pfizer 3 75 Rule | True |
| Scaffold Graph Level | CC(CC1CCCCC1)C1CCCCC1 |
| Np Classifier Class | Simple phenolic acids |
| Deep Smiles | OC[C@H]O[C@@H]OC=O)cccccc6)OC)))O)))))))[C@@H][C@H][C@@H]6O))O))O |
| Heavy Atom Count | 23.0 |
| Classyfire Class | Tannins |
| Description | Vanilloyl glucose is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Vanilloyl glucose is soluble (in water) and a very weakly acidic compound (based on its pKa). Vanilloyl glucose can be found in a number of food items such as orange bell pepper, yellow bell pepper, pepper (c. annuum), and red bell pepper, which makes vanilloyl glucose a potential biomarker for the consumption of these food products. |
| Scaffold Graph Node Level | OC(OC1CCCCO1)C1CCCCC1 |
| Classyfire Subclass | Hydrolyzable tannins |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 404.0 |
| Database Name | fooddb_chem_all;imppat_phytochem;pubchem |
| Defined Atom Stereocenter Count | 5.0 |
| Iupac Name | [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 4-hydroxy-3-methoxybenzoate |
| Veber Rule | False |
| Classyfire Superclass | Phenylpropanoids and polyketides |
| Xlogp | -0.7 |
| Gsk 4 400 Rule | True |
| Molecular Formula | C14H18O9 |
| Scaffold Graph Node Bond Level | O=C(OC1CCCCO1)c1ccccc1 |
| Inchi Key | YROOZUQRTLHXIO-DIACKHNESA-N |
| Silicos It Class | Soluble |
| Rotatable Bond Count | 5.0 |
| Synonyms | glucovanillic acid |
| Esol Class | Very soluble |
| Functional Groups | CO, cC(=O)O[C@@H](C)OC, cO, cOC |
| Compound Name | 1-O-Vanilloyl-beta-D-glucose |
| Exact Mass | 330.095 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 330.095 |
| Hydrogen Bond Acceptor Count | 9.0 |
| Molecular Weight | 330.29 |
| Gi Absorption | False |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 5.0 |
| Total Bond Stereocenter Count | 0.0 |
| Lipinski Rule Of 5 | True |
| Inchi | InChI=1S/C14H18O9/c1-21-8-4-6(2-3-7(8)16)13(20)23-14-12(19)11(18)10(17)9(5-15)22-14/h2-4,9-12,14-19H,5H2,1H3/t9-,10-,11+,12-,14+/m1/s1 |
| Smiles | COC1=C(C=CC(=C1)C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O |
| Np Classifier Biosynthetic Pathway | Shikimates and Phenylpropanoids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | False |
| Np Classifier Superclass | Phenolic acids (C6-C1) |
- 1. Outgoing r'ship
FOUND_INto/from Capsicum Annuum (Plant) Rel Props:Source_db:fooddb_chem_all - 2. Outgoing r'ship
FOUND_INto/from Catharanthus Roseus (Plant) Rel Props:Reference:https://doi.org/10.1093/database/bav075