[(6E,10E)-9-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate
PubChem CID: 54600668
Connections displayed (default: 10).
Loading graph...
| Compound Synonyms | Eucannabinolide, 38458-58-1, NSC311052, NSC-311052, 2-Butenoic acid, 9-(acetyloxy)-2,3,3a,4,5,8,9,11a-octahydro-6,10-dimethyl-3-methylene-2-oxocyclodeca[b]furan-4-yl ester, [3aR-[3aR*,4R*(Z),6E,9S*,10Z,11aR*]]- |
|---|---|
| Topological Polar Surface Area | 119.0 |
| Hydrogen Bond Donor Count | 2.0 |
| Heavy Atom Count | 30.0 |
| Description | Eucannabinolide belongs to germacranolides and derivatives class of compounds. Those are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Eucannabinolide is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Eucannabinolide can be found in roman camomile, which makes eucannabinolide a potential biomarker for the consumption of this food product. |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 804.0 |
| Database Name | fooddb_chem_all;hmdb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Iupac Name | [(6E,10E)-9-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate |
| Nih Violation | True |
| Class | Prenol lipids |
| Xlogp | 0.6 |
| Superclass | Lipids and lipid-like molecules |
| Is Pains | False |
| Subclass | Terpene lactones |
| Molecular Formula | C22H28O8 |
| Inchi Key | XYPJAWWDSQFSQA-VISQRNLASA-N |
| Rotatable Bond Count | 7.0 |
| Synonyms | Eucannabinolide, Eupaformosanin, Hiyodorilactone A, Hydroxychromolaenide, Schkuhrin I, 9-(Acetyloxy)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoic acid |
| Compound Name | [(6E,10E)-9-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate |
| Kingdom | Organic compounds |
| Exact Mass | 420.178 |
| Formal Charge | 0.0 |
| Brenk Violation | True |
| Monoisotopic Mass | 420.178 |
| Hydrogen Bond Acceptor Count | 8.0 |
| Molecular Weight | 420.5 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 4.0 |
| Total Bond Stereocenter Count | 3.0 |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Inchi | InChI=1S/C22H28O8/c1-12-5-6-17(28-15(4)25)13(2)10-19-20(14(3)21(26)29-19)18(9-12)30-22(27)16(11-24)7-8-23/h5,7,10,17-20,23-24H,3,6,8-9,11H2,1-2,4H3/b12-5+,13-10+,16-7+ |
| Smiles | C/C/1=C\CC(/C(=C/C2C(C(C1)OC(=O)/C(=C/CO)/CO)C(=C)C(=O)O2)/C)OC(=O)C |
| Defined Bond Stereocenter Count | 3.0 |
| Taxonomy Direct Parent | Germacranolides and derivatives |
- 1. Outgoing r'ship
FOUND_INto/from Chamaemelum Nobile (Plant) Rel Props:Source_db:fooddb_chem_all