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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2018-05-20 20:20:28 UTC
HMDB IDHMDB0015564
Secondary Accession Numbers
  • HMDB15564
Metabolite Identification
Common NameLincomycin
DescriptionLincomycin is only found in individuals that have used or taken this drug. It is an antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections. [PubChem]Lincomycin inhibits protein synthesis in susceptible bacteria by binding to the 50 S subunits of bacterial ribosomes and preventing peptide bond formation upon transcription. It is usually considered bacteriostatic, but may be bactericidal in high concentrations or when used against highly susceptible organisms.
Structure
Thumb
Synonyms
ValueSource
LCMHMDB
LincomycineHMDB
LincomyocinHMDB
EpilincomycinMeSH
Hemihydrate lincomycin monohydrochlorideMeSH
LincocinMeSH
LincolnensinMeSH
Lincomycin aMeSH
Lincomycin hydrochlorideMeSH
Lincomycin monohydrochlorideMeSH
Lincomycin monohydrochloride, (2S-cis)-isomerMeSH
Lincomycin monohydrochloride, (L-threo)-isomerMeSH
Lincomycin monohydrochloride, hemihydrateMeSH
Lincomycin, (2S-cis)-isomerMeSH
Lincomycin, (L-threo)-isomerMeSH
Chemical FormulaC18H34N2O6S
Average Molecular Weight406.537
Monoisotopic Molecular Weight406.21375752
IUPAC Name(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-carboxamide
Traditional Namelincomycin
CAS Registry Number154-21-2
SMILES
[H][C@@]1(O[C@]([H])([C@H](NC(=O)C2C[C@@H](CCC)CN2C)[C@@H](C)O)[C@H](O)[C@H](O)[C@H]1O)SC
InChI Identifier
InChI=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-ISVUEQNNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as proline and derivatives. These 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 DescriptorsNot Available
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility29.3 g/LNot Available
LogP0.56HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility29.3 g/LALOGPS
logP0.5ALOGPS
logP-0.32ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)12.37ChemAxon
pKa (Strongest Basic)7.97ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area122.49 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity102.67 m³·mol⁻¹ChemAxon
Polarizability43.72 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2913000000-d125ca442f4c601e9a39View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00c0-9602106000-31350d9eb8fe0368bfa6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0319200000-139ddcba34e19650ea5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2931000000-bed26638dffce4e95302View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-7910000000-7d724ec0afa72d0b45a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4s-6292200000-03967da3887e930924aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap1-9213000000-00ec697880a56054289fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kg-9531000000-92262505990e7631d58aView in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01627 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01627 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01627
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID570892
KEGG Compound IDC06812
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLincomycin
METLIN IDNot Available
PubChem Compound656509
PDB IDNot Available
ChEBI ID6472
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available