Midecamycin (CHEM018335)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:09:49 UTC
Update Date2016-11-09 01:15:47 UTC
Accession NumberCHEM018335
Identification
Common NameMidecamycin
ClassSmall Molecule
DescriptionMidecamycin is a naturally occurring 16-membered macrolide that fits under the category of acetoxy-substituted macrolide antibiotics. In this molecule, an acetoxy group is substituted on the position 9 of the 16-member ring and on position 4 of the terminal sugar. Until 2017, midecamycin was still under the list of approved antimicrobial active pharmaceutical ingredients by Health Canada.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
MDMKegg
MedemycinKegg
MosilMeSH
MyoxamMeSH
MidecaminMeSH
Midekamycin acetateMeSH
MydecamycinMeSH
NeoisomidecamycinMeSH
MidekamycinMeSH
MaidimeisuMeSH
Midecamycin diacetateMeSH
NormicinaMeSH
Midecamycin acetateMeSH
[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-[(2S,3R,4R,5S,6R)-4-(dimethylamino)-3-Hydroxy-5-[(2S,4R,5S,6S)-4-hydroxy-4,6-dimethyl-5-propanoyloxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl] propanoic acidGenerator
MidecamycinMeSH
Chemical FormulaC41H67NO15
Average Molecular Mass813.979 g/mol
Monoisotopic Mass813.451 g/mol
CAS Registry Number35457-80-8
IUPAC Name(2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-4-(dimethylamino)-5-hydroxy-6-{[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-4-(propanoyloxy)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl propanoate
Traditional Namemidecamycin
SMILES[H]\C1=C(\[H])/C(/[H])=C([H])/[C@]([H])(O)[C@]([H])(C)C[C@]([H])(CC=O)[C@]([H])(O[C@]2([H])O[C@]([H])(C)[C@@]([H])(O[C@@]3([H])C[C@@](C)(O)[C@@]([H])(OC(=O)CC)[C@]([H])(C)O3)[C@]([H])(N(C)C)[C@@]2([H])O)[C@@]([H])(OC)[C@@]([H])(CC(=O)O[C@]([H])(C)C1)OC(=O)CC
InChI IdentifierInChI=1S/C41H67NO15/c1-11-30(45)54-29-21-32(47)51-24(4)16-14-13-15-17-28(44)23(3)20-27(18-19-43)37(38(29)50-10)57-40-35(48)34(42(8)9)36(25(5)53-40)56-33-22-41(7,49)39(26(6)52-33)55-31(46)12-2/h13-15,17,19,23-29,33-40,44,48-49H,11-12,16,18,20-22H2,1-10H3/b14-13+,17-15+/t23-,24-,25-,26+,27+,28+,29-,33+,34-,35-,36-,37+,38+,39+,40+,41-/m1/s1
InChI KeyDMUAPQTXSSNEDD-QALJCMCCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Macrolide
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Oxane
  • Alpha-hydrogen aldehyde
  • Tertiary alcohol
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Lactone
  • Tertiary aliphatic amine
  • Secondary alcohol
  • Tertiary amine
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Aldehyde
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • 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 Solubility0.094 g/LALOGPS
logP3.09ALOGPS
logP3.19ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.71ChemAxon
pKa (Strongest Basic)7.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area206.05 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity206.51 m³·mol⁻¹ChemAxon
Polarizability87.12 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06xw-2001621910-6f444606b34cdb1515c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-4032952300-5e9a16aa17f9ca6075f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9214410100-1bd4f142e34bcc0c7017Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-07ii-4216300930-435b5bb70b66de54044eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-3111930400-becd5e0a9df1a67088acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-6113902200-69f639920c8583f5a3beSpectrum
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 IDDB13456
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 LinkMidecamycin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5282169
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available