Azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, [3aR-(3aalpha,4alpha,6aalpha,9alpha,9aalpha,9bbeta)]-
PubChem CID: 99967
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| Compound Synonyms | NSC295425, Grosheimine, SCHEMBL1711493, CHEMBL1968792, YGMIBVIKXJJQQJ-UHFFFAOYSA-N, NCI60_002463, 4-Hydroxy-9-methyl-3,6-dimethyleneoctahydroazuleno[4,5-b]furan-2,8(3H,4H)-dione #, 4-.beta.-H-Guaia-10(14),11(13)-dien-12-oic acid, 6-.alpha.,8-.alpha.-dihydroxy-3-oxo-,12,6-lactone, 4-hydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno [4,5-b]furan-2,8-dione, Azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, [3aR-(3a.alpha.,4.alpha.,6a.alpha.,9.alpha.,9a.alpha.,9b.beta.)]- |
|---|---|
| Topological Polar Surface Area | 63.6 |
| Hydrogen Bond Donor Count | 1.0 |
| Heavy Atom Count | 19.0 |
| Description | Grosheimin belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Grosheimin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Grosheimin is a bitter tasting compound found in globe artichoke, which makes grosheimin a potential biomarker for the consumption of this food product. |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 492.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Iupac Name | 4-hydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,9,9a,9b-octahydroazuleno[4,5-b]furan-2,8-dione |
| Prediction Hob | 1.0 |
| Class | Prenol lipids |
| Xlogp | 0.8 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Terpene lactones |
| Molecular Formula | C15H18O4 |
| Prediction Swissadme | 0.0 |
| Inchi Key | YGMIBVIKXJJQQJ-UHFFFAOYSA-N |
| Fcsp3 | 0.6 |
| Logs | -1.857 |
| Rotatable Bond Count | 0.0 |
| Logd | 0.873 |
| Synonyms | 8-Hydroxy-3-oxo-10(14),11(13)-guaiadien-12,6-olide, Grosheimin, Grossheimin, Grosshemin |
| Compound Name | Azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, [3aR-(3aalpha,4alpha,6aalpha,9alpha,9aalpha,9bbeta)]- |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 262.121 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 262.121 |
| Hydrogen Bond Acceptor Count | 4.0 |
| Molecular Weight | 262.3 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 6.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Esol | -1.9891909999999997 |
| Inchi | InChI=1S/C15H18O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7,9,11-14,17H,1,3-5H2,2H3 |
| Smiles | CC1C2C(CC1=O)C(=C)CC(C3C2OC(=O)C3=C)O |
| Nring | 3.0 |
| Defined Bond Stereocenter Count | 0.0 |
| Taxonomy Direct Parent | Guaianolides and derivatives |
- 1. Outgoing r'ship
FOUND_INto/from Carlina Acaulis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Cynara Scolymus (Plant) Rel Props:Source_db:fooddb_chem_all