EMBL-EBI | Chemical Biology | ChEBI
Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search
CHEBI:6574 - lupulone
| Formula | C26H38O4 |
| Net Charge | 0 |
| Average Mass | 414.586 |
| Monoisotopic Mass | 414.27701 |
| SMILES | CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(=O)CC(C)C)=C1O |
| InChI | InChI=1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19,28-29H,10,13-15H2,1-8H3 |
| InChIKey | LSDULPZJLTZEFD-UHFFFAOYSA-N |
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Humulus lupulus (ncbitaxon:3486) | - | PubMed (24948953) |
| Roles Classification |
|---|
| Biological Roles: | antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| Applications: | antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. angiogenesis inhibitor An agent and endogenous substances that antagonize or inhibit the development of new blood vessels. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| lupulone (CHEBI:6574) has role angiogenesis inhibitor (CHEBI:48422) |
| lupulone (CHEBI:6574) has role antimicrobial agent (CHEBI:33281) |
| lupulone (CHEBI:6574) has role antineoplastic agent (CHEBI:35610) |
| lupulone (CHEBI:6574) has role apoptosis inducer (CHEBI:68495) |
| lupulone (CHEBI:6574) is a β-bitter acid (CHEBI:136848) |
| lupulone (CHEBI:6574) is conjugate acid of lupulone(1−) (CHEBI:134343) |
| Incoming Relation(s) |
| lupulone(1−) (CHEBI:134343) is conjugate base of lupulone (CHEBI:6574) |
| IUPAC Name |
|---|
| 3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one |
| Synonyms | Source |
|---|---|
| Lupulon | ChemIDplus |
| beta-Lupulic acid | ChemIDplus |
| hop β-acid | ChEBI |
| Manual Xrefs | Databases |
|---|---|
| C10706 | KEGG COMPOUND |
| C00002701 | KNApSAcK |
| HMDB0030041 | HMDB |
| CPD-7110 | MetaCyc |
| Registry Numbers | Sources |
|---|---|
| Reaxys:6983327 | Reaxys |
| CAS:468-28-0 | KEGG COMPOUND |
| CAS:468-28-0 | ChemIDplus |
| Citations |
|---|