Lincomycin (CHEM021213)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 03:15:08 UTC
Update Date2026-04-13 20:59:57 UTC
Accession NumberCHEM021213
Identification
Common NameLincomycin
ClassSmall Molecule
DescriptionA carbohydrate-containing antibiotic produced by the actinomyces Streptomyces lincolnensis.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • Suspected Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CillimycinChEBI
LincomicinaChEBI
LincomycineChEBI
LincomycinumChEBI
Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-alpha-D-galacto-octopyranosideChEBI
LCMKegg
Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-a-D-galacto-octopyranosideGenerator
Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-α-D-galacto-octopyranosideGenerator
(2S,4R)-N-[(1R,2R)-2-Hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulphanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamideGenerator
LincomycinMeSH
Lincomycin hydrochlorideMeSH
LincocinMeSH
LincolnensinMeSH
Lincomycin monohydrochlorideMeSH
Lincomycin monohydrochloride, (2S-cis)-isomerMeSH
Lincomycin, (L-threo)-isomerMeSH
EpilincomycinMeSH
Lincomycin, (2S-cis)-isomerMeSH
Lincomycin aMeSH
Hemihydrate lincomycin monohydrochlorideMeSH
Lincomycin monohydrochloride, (L-threo)-isomerMeSH
Lincomycin monohydrochloride, hemihydrateMeSH
Chemical FormulaC18H34N2O6S
Average Molecular Mass406.540 g/mol
Monoisotopic Mass406.214 g/mol
CAS Registry Number154-21-2
IUPAC Name(2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboximidic acid
Traditional Namelincomycin
SMILES[H][C@](C)(O)[C@@]([H])(N=C(O)[C@]1([H])C[C@@]([H])(CCC)CN1C)[C@@]1([H])O[C@]([H])(SC)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O
InChI IdentifierInChI=1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1
InChI KeyOJMMVQQUTAEWLP-KIDUDLJLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline and derivatives
Alternative Parents
Substituents
  • Proline or derivatives
  • Alpha-amino acid amide
  • Glycosyl compound
  • S-glycosyl compound
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Monosaccharide
  • Oxane
  • N-alkylpyrrolidine
  • Monothioacetal
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Sulfenyl compound
  • Polyol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.02 g/LALOGPS
logP0.34ALOGPS
logP-2.2ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)8.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area125.98 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity103.19 m³·mol⁻¹ChemAxon
Polarizability43.91 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000j-0900000000-1f46f29c3d5dbc6c25f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0901000000-3fc103447a71fd95ceddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-016r-0895000000-4b0507fffd39d9fc075fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00mk-0952000000-ca2f735ea2244e1cb32eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0901200000-cc68fda14967bfcd7357Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-70466cfb7e0692d073a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-b712dc39bbf605193fb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0109000000-cdbfa33f16a571dd85eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0209000000-8ec5c595eb6720c93c13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0139200000-0ae0c9c5bf2307881534Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2951000000-37be68b79f7837d036a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0059-6910000000-30c39a7746457725f6a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052s-6292200000-d9cdc7cb1a9a5e733e30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052s-9222000000-11e6c0710cf9c0991d42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kg-9420000000-f890def7678249613c20Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01627
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLincomycin
Chemspider IDNot Available
ChEBI ID6472
PubChem Compound ID3000540
Kegg Compound IDC06812
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24324587