Quinupristin (CHEM022298)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:27:13 UTC
Update Date2016-11-09 01:17:28 UTC
Accession NumberCHEM022298
Identification
Common NameQuinupristin
ClassSmall Molecule
DescriptionQuinupristin/dalfopristin is a combination of two antibiotics used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium. Dalfopristin inhibits the early phase of protein synthesis in the bacterial ribosome and quinupristin inhibits the late phase of protein synthesis. The combination of the two components acts synergistically and is more effective in vitro than each component alone.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5DElta-(3-quinuclidinyl)thiomethylpristinamycin iaHMDB
Chemical FormulaC53H67N9O10S
Average Molecular Mass1022.218 g/mol
Monoisotopic Mass1021.473 g/mol
CAS Registry Number120138-50-3
IUPAC NameN-[(3S,6S,12R,15S,16R,19S)-25-{[(3S)-1-azabicyclo[2.2.2]octan-3-ylsulfanyl]methyl}-3-{[4-(dimethylamino)phenyl]methyl}-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
Traditional Namequinupristin
SMILESCC[C@H]1NC(=O)[C@@H](NC(=O)C2=NC=CC=C2O)[C@@H](C)OC(=O)[C@@H](NC(=O)C2CC(=O)C(CS[C@@H]3CN4CCC3CC4)CN2C(=O)[C@H](CC2=CC=C(C=C2)N(C)C)N(C)C(=O)[C@@H]2CCCN2C1=O)C1=CC=CC=C1
InChI IdentifierInChI=1S/C53H67N9O10S/c1-6-37-50(68)61-23-11-14-38(61)51(69)59(5)40(26-32-16-18-36(19-17-32)58(3)4)52(70)62-28-35(30-73-43-29-60-24-20-33(43)21-25-60)42(64)27-39(62)47(65)57-45(34-12-8-7-9-13-34)53(71)72-31(2)44(48(66)55-37)56-49(67)46-41(63)15-10-22-54-46/h7-10,12-13,15-19,22,31,33,35,37-40,43-45,63H,6,11,14,20-21,23-30H2,1-5H3,(H,55,66)(H,56,67)(H,57,65)/t31-,35?,37-,38+,39?,40+,43-,44+,45+/m1/s1
InChI KeyWTHRRGMBUAHGNI-MJWHERSYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassDepsipeptides
Direct ParentCyclic depsipeptides
Alternative Parents
Substituents
  • Cyclic depsipeptide
  • Macrolide lactam
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid ester
  • Macrolactam
  • Alpha-amino acid or derivatives
  • Pyridine carboxylic acid or derivatives
  • Pyridinecarboxamide
  • 2-heteroaryl carboxamide
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Quinuclidine
  • Tertiary aliphatic/aromatic amine
  • Piperidinone
  • Hydroxypyridine
  • Monocyclic benzene moiety
  • Piperidine
  • Benzenoid
  • Pyridine
  • Vinylogous acid
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid ester
  • Ketone
  • Lactam
  • Lactone
  • Cyclic ketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Organoheterocyclic compound
  • Amine
  • Organic oxide
  • Organooxygen compound
  • Organosulfur compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.044 g/LALOGPS
logP2.99ALOGPS
logP2.18ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)7.45ChemAxon
pKa (Strongest Basic)8.28ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area231.2 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity272.84 m³·mol⁻¹ChemAxon
Polarizability107.02 ųChemAxon
Number of Rings8ChemAxon
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, Positivesplash10-0c00-6970000181-0021de1f1b30de2483f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h4o-2920000022-e4668837cc5c1097a5c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-3892312000-c8bc1d8139f72acffabaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-1952020010-0842fbe50825cbb08da5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-1910000011-7462578de298c38c44e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900100000-b123fe4501640b802cd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9100000001-eaa02d5f171652e68468Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9500000012-190a4b6a9e83296377d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01t9-9300000125-1464978e45207a6789afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000001-7f4cef8f5acead1cb1a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9400000014-979b65d16b1acb016f95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7900000000-e4ef6350037b608e09adSpectrum
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 IDNot Available
HMDB IDHMDB0015455
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkQuinupristin
Chemspider ID26329518
ChEBI ID8732
PubChem Compound ID23724509
Kegg Compound IDC08032
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Lamb HM, Figgitt DP, Faulds D: Quinupristin/dalfopristin: a review of its use in the management of serious gram-positive infections. Drugs. 1999 Dec;58(6):1061-97.
2. Paradisi F, Corti G, Messeri D: Antistaphylococcal (MSSA, MRSA, MSSE, MRSE) antibiotics. Med Clin North Am. 2001 Jan;85(1):1-17.
3. Allington DR, Rivey MP: Quinupristin/dalfopristin: a therapeutic review. Clin Ther. 2001 Jan;23(1):24-44.
4. Manzella JP: Quinupristin-dalfopristin: a new antibiotic for severe gram-positive infections. Am Fam Physician. 2001 Dec 1;64(11):1863-6.