General
Preferred name
CERULENIN
Synonyms
P&D ID
PD028502
CAS
17397-89-6
Tags
available
drug
covalent binder
Drug indication
Weight loss
Drug Status
experimental
approved
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS
Cerulenin is an antifungal antibiotic isolated from Cephalosporium caerulens. It interrupts fungal growth by inhibiting the biosynthesis of sterols and fatty acids (inhibits bacterial fatty acid synthesis). It also inhibits HMG-CoA synthetase activity. Cerulenin produces metabolic effects similar to effects of leptin, but through mechanisms that are independent of, or down-stream from, both leptin and melanocortin receptors.
MOA
Irreversibly binds to fatty acid synthase, specifically b-ketoacyl-acyl carrier protein synthase (FabH, FabB and FabF condensation enzymes). A number of tumor cells and cell lines have been observed to have highly upregulated expression and activity of fatty acid synthase (FAS). Inhibition of FAS by cerulenin leads to cytotoxicity and apoptosis in human cancer cell lines, an effect believed to be mediated by the accumulation of malonyl-coenzyme A in cells with an upregulated FAS pathway.
INDICATION
For use as a biochemical tool, Cerulenin is shown to cause dramatic weight loss in animals
TOXICITY
Oral, mouse LD50: 547 mg/kg. Symptoms of overexposure include moderate to severe erythema (redness) and moderate edema (raised skin), nausea, vomiting, and headache.
DESCRIPTION
inhibitor of fatty acid synthase; inhibitor of HMG-CoA synthase
(Informer Set)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
1
Organisms
2
Compound Sets
13
Cayman Chemical Bioactives
CovalentInDB
CovBinderInPDB
Drug Repurposing Hub
DrugBank
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Informer Set
MedChem Express Bioactive Compound Library
Other bioactive compounds
ReFrame library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
43
Molecular Weight
223.12
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
1
Rotatable Bonds
7
Ring Count
1
Aromatic Ring Count
0
cLogP
1.11
TPSA
72.69
Fraction CSP3
0.5
Chiral centers
2.0
Largest ring
3.0
QED
0.52
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
FASN
HMGCS1
Fatty Acid Synthase (FAS)
antibiotic
Fatty Acid Synthase (FASN)
Fungal
Compound status
probe
Indication
fungal infection
MOA
Fatty Acid Synthase inhibitor
Therapeutic Class
Antiinfective Agents
Pathway
Anti-infection
Apoptosis
Metabolic Enzyme/Protease
Source data
