Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:59 UTC
HMDB IDHMDB0015455
Secondary Accession Numbers
  • HMDB15455
Metabolite Identification
Common NameQuinupristin
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.
Structure
Data?1582753299
Synonyms
ValueSource
5DElta-(3-quinuclidinyl)thiomethylpristinamycin iaHMDB
Chemical FormulaC53H67N9O10S
Average Molecular Weight1022.218
Monoisotopic Molecular Weight1021.473160099
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
CAS Registry Number120138-50-3
SMILES
CC[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 Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.044 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+300.330932474
DeepCCS[M-H]-298.51530932474
DeepCCS[M-2H]-332.54730932474
DeepCCS[M+Na]+306.56830932474
AllCCS[M+H]+313.332859911
AllCCS[M+H-H2O]+313.732859911
AllCCS[M+NH4]+312.832859911
AllCCS[M+Na]+312.732859911
AllCCS[M-H]-214.432859911
AllCCS[M+Na-2H]-219.732859911
AllCCS[M+HCOO]-225.432859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinupristin 10V, Positive-QTOFsplash10-0c00-6970000181-0021de1f1b30de2483f92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinupristin 20V, Positive-QTOFsplash10-0h4o-2920000022-e4668837cc5c1097a5c62016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinupristin 40V, Positive-QTOFsplash10-0fb9-3892312000-c8bc1d8139f72acffaba2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinupristin 10V, Negative-QTOFsplash10-03dl-1952020010-0842fbe50825cbb08da52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinupristin 20V, Negative-QTOFsplash10-052f-1910000011-7462578de298c38c44e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinupristin 40V, Negative-QTOFsplash10-0006-0900100000-b123fe4501640b802cd12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinupristin 10V, Positive-QTOFsplash10-00di-9100000001-eaa02d5f171652e684682021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinupristin 20V, Positive-QTOFsplash10-00di-9500000012-190a4b6a9e83296377d62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinupristin 40V, Positive-QTOFsplash10-01t9-9300000125-1464978e45207a6789af2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinupristin 10V, Negative-QTOFsplash10-00di-9000000001-7f4cef8f5acead1cb1a32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinupristin 20V, Negative-QTOFsplash10-0006-9400000014-979b65d16b1acb016f952021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinupristin 40V, Negative-QTOFsplash10-0006-7900000000-e4ef6350037b608e09ad2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01369 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01369 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID26329518
KEGG Compound IDC08032
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuinupristin
METLIN IDNot Available
PubChem Compound23724509
PDB IDNot Available
ChEBI ID8732
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:10651391 ]
  2. Paradisi F, Corti G, Messeri D: Antistaphylococcal (MSSA, MRSA, MSSE, MRSE) antibiotics. Med Clin North Am. 2001 Jan;85(1):1-17. [PubMed:11190346 ]
  3. Allington DR, Rivey MP: Quinupristin/dalfopristin: a therapeutic review. Clin Ther. 2001 Jan;23(1):24-44. [PubMed:11219478 ]
  4. Manzella JP: Quinupristin-dalfopristin: a new antibiotic for severe gram-positive infections. Am Fam Physician. 2001 Dec 1;64(11):1863-6. [PubMed:11764864 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Rubinstein E, Prokocimer P, Talbot GH: Safety and tolerability of quinupristin/dalfopristin: administration guidelines. J Antimicrob Chemother. 1999 Sep;44 Suppl A:37-46. [PubMed:10511396 ]
  2. Bearden DT: Clinical pharmacokinetics of quinupristin/dalfopristin. Clin Pharmacokinet. 2004;43(4):239-52. [PubMed:15005638 ]
  3. Delgado G Jr, Neuhauser MM, Bearden DT, Danziger LH: Quinupristin-dalfopristin: an overview. Pharmacotherapy. 2000 Dec;20(12):1469-85. [PubMed:11130220 ]