Lincomycin hydrochloride (CHEM019622)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:20:44 UTC
Update Date2016-11-09 01:16:02 UTC
Accession NumberCHEM019622
Identification
Common NameLincomycin hydrochloride
ClassSmall Molecule
DescriptionLincomycin is a lincosamide antibiotic that comes from the actinomycete Streptomyces lincolnensis. A related compound, clindamycin, is derived from lincomycin by using thionyl chloride to replace the 7-hydroxy group with a chlorine atom with inversion of chirality. It was released for medical use in September 1964.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Lincomycin, (2S-cis)-isomerMeSH
Lincomycin monohydrochlorideMeSH
Lincomycin, (L-threo)-isomerMeSH
Lincomycin monohydrochloride, (2S-cis)-isomerMeSH
Lincomycin monohydrochloride, hemihydrateMeSH
Lincomycin aMeSH
Hemihydrate lincomycin monohydrochlorideMeSH
LincomycinMeSH
EpilincomycinMeSH
LincocinMeSH
LincolnensinMeSH
Lincomycin monohydrochloride, (L-threo)-isomerMeSH
Lincomycin HCLChEMBL
(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-carboxamide;hydrochlorideGenerator
Lincomycin hydrochlorideMeSH
(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-carboximidate hydrochlorideGenerator
(2S,4R)-N-[(1R,2R)-2-Hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulphanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboximidate hydrochlorideGenerator
(2S,4R)-N-[(1R,2R)-2-Hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulphanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboximidic acid hydrochlorideGenerator
Chemical FormulaC18H35ClN2O6S
Average Molecular Mass443.000 g/mol
Monoisotopic Mass442.190 g/mol
CAS Registry Number859-18-7
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 hydrochloride
Traditional Namelincomycin hydrochloride
SMILESCl.[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.ClH/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);1H/t9-,10-,11+,12-,13+,14-,15-,16-,18-;/m1./s1
InChI KeyPOUMFISTNHIPTI-BOMBIWCESA-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
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Sulfenyl compound
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Polyol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Hydrochloride
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000900000-bfa5cd62958f87704028Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000900000-bfa5cd62958f87704028Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0000900000-bfa5cd62958f87704028Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-38e1867b15014bed1e8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000900000-38e1867b15014bed1e8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0000900000-38e1867b15014bed1e8cSpectrum
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 IDDBSALT000109
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 IDNot Available
PubChem Compound ID64710
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available