ContaminantDB: Lincomycin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 03:15:08 UTC

Update Date

2016-11-09 01:17:18 UTC

Accession Number

CHEM021213

Identification

Common Name

Lincomycin

Class

Small Molecule

Description

A carbohydrate-containing antibiotic produced by the actinomyces Streptomyces lincolnensis.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
Suspected Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cillimycin	ChEBI
Lincomicina	ChEBI
Lincomycine	ChEBI
Lincomycinum	ChEBI
Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-alpha-D-galacto-octopyranoside	ChEBI
LCM	Kegg
Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-a-D-galacto-octopyranoside	Generator
Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-α-D-galacto-octopyranoside	Generator
(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	Generator
Lincomycin	MeSH
Lincomycin hydrochloride	MeSH
Lincocin	MeSH
Lincolnensin	MeSH
Lincomycin monohydrochloride	MeSH
Lincomycin monohydrochloride, (2S-cis)-isomer	MeSH
Lincomycin, (L-threo)-isomer	MeSH
Epilincomycin	MeSH
Lincomycin, (2S-cis)-isomer	MeSH
Lincomycin a	MeSH
Hemihydrate lincomycin monohydrochloride	MeSH
Lincomycin monohydrochloride, (L-threo)-isomer	MeSH
Lincomycin monohydrochloride, hemihydrate	MeSH

Chemical Formula

C₁₈H₃₄N₂O₆S

Average Molecular Mass

406.540 g/mol

Monoisotopic Mass

406.214 g/mol

CAS Registry Number

Not Available

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 Name

lincomycin

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 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 Key

OJMMVQQUTAEWLP-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:6472 )
pyrrolidinecarboxamide (CHEBI:6472 )
L-proline derivative (CHEBI:6472 )
carbohydrate-containing antibiotic (CHEBI:6472 )
S-glycosyl compound (CHEBI:6472 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.02 g/L	ALOGPS
logP	0.34	ALOGPS
logP	-2.2	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	8.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	125.98 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.19 m³·mol⁻¹	ChemAxon
Polarizability	43.91 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000j-0900000000-1f46f29c3d5dbc6c25f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0901000000-3fc103447a71fd95cedd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-016r-0895000000-4b0507fffd39d9fc075f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00mk-0952000000-ca2f735ea2244e1cb32e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0901200000-cc68fda14967bfcd7357	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0900000000-70466cfb7e0692d073a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0900000000-b712dc39bbf605193fb4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0109000000-cdbfa33f16a571dd85ee	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0209000000-8ec5c595eb6720c93c13	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0139200000-0ae0c9c5bf2307881534	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-2951000000-37be68b79f7837d036a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0059-6910000000-30c39a7746457725f6a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052s-6292200000-d9cdc7cb1a9a5e733e30	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052s-9222000000-11e6c0710cf9c0991d42	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kg-9420000000-f890def7678249613c20	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01627

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Lincomycin

Chemspider ID

Not Available

ChEBI ID

6472

PubChem Compound ID

3000540

Kegg Compound ID

C06812

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24324587

Lincomycin (CHEM021213)

Structure for CHEM021213: Lincomycin