Services
Research
Training
Industry
About us
ChEBI
Examples:
iron*
,
InChI=1S/CH4O/c1-2/h2H,1H3
,
caffeine
Advanced
Home
Advanced Search
Browse
Documentation
Download
Tools
About ChEBI
Submit
Contact us
DiNA
Statistics
Entity of the Month
Periodic Table
Ontology
Train online
User Manual
Annotation Manual
Developer Manual
FAQ's
BiNChE
libChEBI
Web Services
ChEBI
> Main
CHEBI:6574 - lupulone
Main
ChEBI Ontology
Automatic Xrefs
Reactions
Pathways
Models
ChEBI Name
lupulone
ChEBI ID
CHEBI:6574
Definition
A β-bitter acid in which the acyl group is specified as 3-methylbutanoyl.
Stars
This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download
Molfile
XML
SDF
Find compounds which contain this structure
Find compounds which resemble this structure
Take structure to the Advanced Search
more structures >>
Molfile
Formula
C26H38O4
Net Charge
0
Average Mass
414.579
Monoisotopic Mass
414.27701
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
SMILES
C=1(C(C(C(C(CC(C)C)=O)=C(C1CC=C(C)C)O)=O)(CC=C(C)C)CC=C(C)C)O
Metabolite of Species
Details
Humulus lupulus
(NCBI:txid3486)
See:
PubMed
Roles Classification
Biological Role
(s):
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.
(via
beta-bitter acid
)
Application
(s):
angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
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
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
Sources
beta-Lupulic acid
ChemIDplus
hop β-acid
ChEBI
Lupulon
ChemIDplus
Manual Xrefs
Databases
C00002701
KNApSAcK
C10706
KEGG COMPOUND
CPD-7110
MetaCyc
HMDB0030041
HMDB
View more database links
Registry Numbers
Types
Sources
468-28-0
CAS Registry Number
ChemIDplus
6983327
Reaxys Registry Number
Reaxys
Citations
Types
Sources
14827882
PubMed citation
Europe PMC
14920156
PubMed citation
Europe PMC
17434926
PubMed citation
Europe PMC
18276602
PubMed citation
Europe PMC
18383859
PubMed citation
Europe PMC
18726190
PubMed citation
Europe PMC
20885891
PubMed citation
Europe PMC
21517917
PubMed citation
Europe PMC
21519792
PubMed citation
Europe PMC
24168111
PubMed citation
Europe PMC
24948953
PubMed citation
Europe PMC
24954859
PubMed citation
Europe PMC
Last Modified
18 April 2017