Pleuromutilin (CED0005711)

Record Information
Version1.0
Creation Date2016-05-22 06:39:02 UTC
Update Date2026-04-15 17:00:56 UTC
Accession NumberCHEM019946
Identification
Common NamePleuromutilin
ClassSmall Molecule
Description
Pleuromutilin is an organic compound with the formula C22H34O5 and an average molecular weight of 378.51 g/mol. Pleuromutilin belongs to the diterpenoids, a subclass of prenol lipids within the organic compounds. This substance is found in or released from two recorded sources: drinking water and water supply, as well as healthcare, pharmaceuticals and veterinary products in the form of antibiotics. Recorded exposure routes for the compound include inhalation and oral administration.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0,]tetradecan-6-yl 2-hydroxyacetic acidGenerator
octahydro-5,8-Dihydroxy-4,6,9,10- tetramethyl-6-vinyl-3a,9-propano-3ah-cyclopenta- cycloocten-1(4H)-one 8-glycolateMeSH, HMDB
Drosophilin bMeSH, HMDB
4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl 2-hydroxyacetic acidGenerator, HMDB
[(1S,2R,3S,4S,6R,7R,14R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-hydroxyacetic acidGenerator
Chemical FormulaC22H34O5
Average Molecular Mass378.509 g/mol
Monoisotopic Mass378.241 g/mol
CAS Registry Number125-65-5
IUPAC Name4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl 2-hydroxyacetate
Traditional Namepleuromutilin
SMILESCC1CCC23CCC(=O)C2C1(C)C(CC(C)(C=C)C(O)C3C)OC(=O)CO
InChI IdentifierInChI=1S/C22H34O5/c1-6-20(4)11-16(27-17(25)12-23)21(5)13(2)7-9-22(14(3)19(20)26)10-8-15(24)18(21)22/h6,13-14,16,18-19,23,26H,1,7-12H2,2-5H3
InChI KeyZRZNJUXESFHSIO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pleuromutilin and derivatives. These are mutilins with a hydroxyacetate derivative attached to the C8 carbon atom of the cyclopenta[8]annulene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentPleuromutilin and derivatives
Alternative Parents
Substituents
  • Pleuromutilin
  • Secondary alcohol
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.037 g/LALOGPS
logP2.6ALOGPS
logP2.6ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)13.11ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity102.24 m³·mol⁻¹ChemAxon
Polarizability41.46 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0o7i-9417000000-60fc87336927d2fab46aNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0imi-1009000000-abb163b925c98cf97eecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-114r-3029000000-98982c4ab03ec89a838cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gbc-9676000000-048138a61b1de5ee5e92Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-1009000000-f7a431c392fa3ebae120Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kxr-2009000000-ccaf421cd3843bbc0e67Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-102j-9144000000-91cc16a9034c3e4f30acNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ufr-0129000000-3ea8434da5c8f67d0a7fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0h50-0369000000-62287d385b08d4c585eeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f8c-4219000000-dea7249ab7e626fd9bdeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016r-2009000000-1da5c0493a2478094804Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9002000000-793640d510d8f5e2919aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0v00-9028000000-b28614dc499646081bcbNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
651.0Log mg/kg[370:1200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
605Pest RepellantsAgriculture & land managementNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)191.743
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)427.237
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)32.6188
Click to view 3D structureAdenylate cyclase type 1P19754Bos taurusPredicted (SEA)1.08989
Click to view 3D structureNuclear receptor subfamily 1 group I member 2Q9R1A7Rattus norvegicusPredicted (SEA)5.60514
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)47.2545
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)1187.82
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)1050.03
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)39.781
Proto-oncogene vav structureClick to view 3D structureProto-oncogene vavP15498HumansPredicted (SEA)1.94623
Click to view 3D structureTyrosine aminotransferaseP04694Rattus norvegicusPredicted (SEA)4.20386
Phospholipase A2, membrane associated structureClick to view 3D structurePhospholipase A2, membrane associatedP14555HumansPredicted (SEA)781.295
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)76.2144
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)417.428
Click to view 3D structureGlucocorticoid receptorP06537Mus musculusPredicted (SEA)24.0554
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)4112.15
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)2538.2
Click to view 3D structureTransient receptor potential cation channel subfamily M member 2E9PTA2Rattus norvegicusPredicted (SEA)10.4318
Solute carrier family 2, facilitated glucose transporter member 1 structureClick to view 3D structureSolute carrier family 2, facilitated glucose transporter member 1P11166HumansPredicted (SEA)3096.45
Protein kinase C gamma type structureClick to view 3D structureProtein kinase C gamma typeP05129HumansPredicted (SEA)6503.6
Click to view 3D structureAcidic phospholipase A2 2P15445Naja najaPredicted (SEA)1.94623
Protein kinase C delta type structureClick to view 3D structureProtein kinase C delta typeQ05655HumansPredicted (SEA)6778.02
Click to view 3D structureGlycogen [starch] synthase, liverP54840HumansPredicted (SEA)23.744
Click to view 3D structureGlucose-6-phosphatase catalytic subunit 1P43428Rattus norvegicusPredicted (SEA)23.744
Click to view 3D structure11-beta-hydroxysteroid dehydrogenase type 2P80365HumansPredicted (SEA)325.565
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0256641
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID29062
ChEBI IDNot Available
PubChem Compound ID31326
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References