Virginiamycin (CHEM024521)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:45:37 UTC
Update Date2016-11-09 01:17:54 UTC
Accession NumberCHEM024521
Identification
Common NameVirginiamycin
ClassSmall Molecule
DescriptionAntibacterial food additive. Discontinued Virginiamycin is a streptogramin antibiotic similar to pristinamycin and quinupristin/dalfopristin. It is a combination of pristinamycin IIA (virginiamycin M1) and virginiamycin S1. Virginiamycin is used in the fuel ethanol industry to prevent microbial contamination
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Virginiamycin factor SKegg
Antibiotic 1754Z3bHMDB
Cebin VHMDB
Eskalin VHMDB
EskamicinHMDB
MikamycinHMDB
OstreogrycinHMDB
PatricinHMDB
PristinamycinHMDB
StafacHMDB
Staphylomycin SHMDB
Staphylomycin S1HMDB
StephylomycinHMDB
StreptograminHMDB
VernamycinHMDB
Virginiamycin factor S1HMDB
Virginiamycin S1HMDB
Virginiamycin, ban, inn, usanHMDB
VirginiamycinVirginiamycin S1HMDB
Dihydrovirginiamycin S1HMDB
Chemical FormulaC43H49N7O10
Average Molecular Mass823.890 g/mol
Monoisotopic Mass823.354 g/mol
CAS Registry Number11006-76-1
IUPAC NameN-{3-benzyl-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 Namevirginiamycin factor S1
SMILESCCC1NC(=O)C(NC(=O)C2=NC=CC=C2O)C(C)OC(=O)C(NC(=O)C2CC(=O)CCN2C(=O)C(CC2=CC=CC=C2)N(C)C(=O)C2CCCN2C1=O)C1=CC=CC=C1
InChI IdentifierInChI=1S/C43H49N7O10/c1-4-29-40(56)49-21-12-17-30(49)41(57)48(3)32(23-26-13-7-5-8-14-26)42(58)50-22-19-28(51)24-31(50)37(53)47-35(27-15-9-6-10-16-27)43(59)60-25(2)34(38(54)45-29)46-39(55)36-33(52)18-11-20-44-36/h5-11,13-16,18,20,25,29-32,34-35,52H,4,12,17,19,21-24H2,1-3H3,(H,45,54)(H,46,55)(H,47,53)
InChI KeyFEPMHVLSLDOMQC-UHFFFAOYSA-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
  • Alpha-amino acid ester
  • Macrolactam
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Pyridine carboxylic acid or derivatives
  • Pyridinecarboxamide
  • 2-heteroaryl carboxamide
  • Hydroxypyridine
  • Piperidinone
  • Benzenoid
  • Pyridine
  • Monocyclic benzene moiety
  • Piperidine
  • Vinylogous acid
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Heteroaromatic compound
  • Carboxamide group
  • Carboxylic acid ester
  • Ketone
  • Lactam
  • Lactone
  • Cyclic ketone
  • Secondary carboxylic acid amide
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.14 g/LALOGPS
logP2.25ALOGPS
logP1.85ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.53ChemAxon
pKa (Strongest Basic)1.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area224.72 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity213.24 m³·mol⁻¹ChemAxon
Polarizability82.27 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-2491106050-93de58c83883a820420eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ai-7921000310-b3dbe42a9b0a7d161ba5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056s-6931000000-b83f8bea2e7202206d6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-2794042000-228fdff1ed817529fbc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-7941143600-2fb816345cceb90bfd5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-2963230100-18b6ad489184b42dfdd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1000000290-a996fb04fb507fda738cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000001840-fc34e7a46980c6034e72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000100-ac3c127095b860829f0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0100000290-a615f7321a3bda6f5f0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-5400000490-d7eb31a64f7bc5ada5bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00p1-6000000910-3ae72f4dd6f1d934b611Spectrum
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 IDHMDB0030520
FooDB IDFDB002392
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkVirginiamycin
Chemspider ID109411
ChEBI IDNot Available
PubChem Compound ID122731
Kegg Compound IDC11269
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Zvenigorodskii VI, Tiaglov BV, Voeikova TA: [Isolation of peptide antibiotic virginiamycin components and selection of their producer Streptomyces virginiae]. Prikl Biokhim Mikrobiol. 2001 May-Jun;37(3):301-8.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.