General
Preferred name
UNDECYLENIC ACID
Synonyms
Cruex ()
10-Undecenoic acid ()
Undecenoic acid ()
Undecylenic acid derivative 1 ()
Undecylenate ()
FEMA NO. 3247 ()
NSC-2013 ()
P&D ID
PD000387
CAS
1333-28-4
112-38-9
Tags
natural product
drug
available
Approved by
FDA
Drug Status
investigational
approved
Drug indication
Antifungal
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
TOXICITY Acute oral LD50 in rat and mouse are 2500 mg/kg and 8150 mg/kg, respectively [MSDS]. Acute dermal LD50 in guinea pig and rat are 50 mg/kg and 2000 mg/kg, respectively [MSDS]. There are no data available on the carcinogenicity, mutagenicity, teratogenicity and developmental toxicity of undecylenate [MSDS]. ; ; Oral overdosage may lead to gastrointestinal disturbances, and may affect central nervous system (excitement, somnolence, muscle contraction or spasticity, headache, dizziness), and metabolism (loss of appetite). Prolonged or repeated exposure to undecylenate may cause anorexia or weight loss [MSDS].
ABSORPTION Undecylenic acid may be absorbed through the skin [MSDS].
METABOLISM No information regarding metabolism.
TOXICITY Acute oral LD50 in rat and mouse are 2500 mg/kg and 8150 mg/kg, respectively [MSDS]. Acute dermal LD50 in guinea pig and rat are 50 mg/kg and 2000 mg/kg, respectively [MSDS]. There are no data available on the carcinogenicity, mutagenicity, teratogenicity and developmental toxicity of undecylenate [MSDS]. Oral overdosage may lead to gastrointestinal disturbances, and may affect central nervous system (excitement, somnolence, muscle contraction or spasticity, headache, dizziness), and metabolism (loss of appetite). Prolonged or repeated exposure to undecylenate may cause anorexia or weight loss [MSDS].
INDICATION Indicated for the treatment of fungal infections as a salt form. No therapeutic indications on its own.
MOA Undecylenic acid demonstrated effectiveness against _Candida albicans_, which is an opportunistic pathogenic yeast with two cellular morphologies: the round yeast form and the filamentous form with elongated hyphae. Hyphae formation is associated with active infections and virulence [A32286]. A study proposed that undecylenic acid inhibits biofilm formation of _Candida albicans_ with optimal concentration above 3 mM and disrupts hyphal growth, which is the morphological transition from yeast to filamentous phase, at concentration above 4 mM [A32284]. Under the drug treatment, hyphal formation related genes, like HWP1, were significantly reduced in transcriptional level leading to poor biofilm formation [A32284]. Both biofilm and hyphae formation are critical virulence factors for the initiation of skin infection and late development of disseminated infection [A32284]. Undecylenic acid may also inhibit enzyme involved in lipid metabolism and abolish germ tube formation by carrying protons across the plasma membrane, thus altering cytoplasmic pH [A32286].
HALF-LIFE No information regarding half-life.
PHARMACODYNAMICS Zinc undecylendate acts as a fungistatic agent but fungicidal activity may be observed with chronic exposure in high concentrations [L1887]. It is effective against _Candida albicans_ [A32284, A32286]. It is proposed that undecylenic acid exerts antimicrobial actions via interacting with nonspecific components in the cell membrane [A32287].
ROE No information regarding route of elimination.
DESCRIPTION 10-Undecylenic Acid, a long-chain fatty acid substance, could be used as a monomer in the polymerization and also a raw material in the syntheses of Pheromone (11Z)-hexadecenal. (BOC Sciences Bioactive Compounds)
Cell lines
0
Organisms
1
Compound Sets
16
BOC Sciences Bioactive Compounds
10-undecenoic-acid-cas-112-38-9-294965
ChEMBL Drugs
CHEMBL1276010
Drug Repurposing Hub
DrugBank
DB11117
DrugBank Approved Drugs
DB11117
DrugCentral
3446
DrugCentral Approved Drugs
3446
DrugMAP
DMLJ2HE
Enamine BioReference Compounds
MedChem Express Bioactive Compound Library
HY-B0914
NCATS Inxight Approved Drugs
K3D86KJ24N
NPC Screening Collection
ReFrame library
Selleckchem Bioactive Compound Library
10-undecenoic-acid
TargetMol Bioactive Compound Library
T0306
The Spectrum Collection
External IDs
34
Properties
(calculated by RDKit )
Molecular Weight
184.15
Hydrogen Bond Acceptors
1
Hydrogen Bond Donors
1
Rotatable Bonds
9
Ring Count
0
Aromatic Ring Count
0
cLogP
3.38
TPSA
37.3
Fraction CSP3
0.73
Chiral centers
0.0
Largest ring
0.0
QED
0.44
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Microbiology/virology
Anti-infection
Metabolic Enzyme/Protease
Target
Antifungal
antibiotic
Endogenous Metabolite
Fungal
Indication
tinea pedis, tinea corporis
MOA
other antifungal
Solubility
10 mM in DMSO
Source data