Record Information
Version1.0
Creation date2011-09-21 00:18:47 UTC
Update date2015-10-09 22:31:19 UTC
Primary IDFDB022735
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAzythromycin
DescriptionAzithromycin is an azalide, a subclass of macrolide antibiotics. Azithromycin is derived from erythromycin; however, it differs chemically from erythromycin in that a methyl-substituted nitrogen atom is incorporated into the lactone ring, thus making the lactone ring 15-membered. Azithromycin is sold under the brand names Zithromax ("Zmax") and Sumamed, and is one of the world's best-selling antibiotics. Azithromycin is used to treat certain bacterial infections, most often bacteria causing middle ear infections, tonsillitis, throat infections, laryngitis, bronchitis, pneumonia and sinusitis. It is also effective against certain sexually transmitted infectious diseases, such as non-gonococcal urethritis and cervicitis. [HMDB]
CAS Number83905-01-5
Structure
Thumb
Synonyms
SynonymSource
AzithramycineHMDB
AzithromycinHMDB
Azithromycin (aids initiative)HMDB
Azithromycin dihydrateHMDB
Azithromycin plus tumor necrosis factorHMDB
Azithromycin sterileHMDB
AzithromycineHMDB
N,N-Dimethyl-4-amino-benzaldehydeHMDB
ZITHMDB
ZithromaxHMDB
Azithromycin monohydrateMeSH
GoxalMeSH
Azithromycin pfizer brandMeSH
Dihydrate, azithromycinMeSH
Pfizer brand OF azithromycin dihydrateMeSH
SumamedMeSH
ToraseptolMeSH
ZentavionMeSH
Monohydrate, azithromycinMeSH
AzadoseMeSH
Bayer brand OF azithromycin dihydrateMeSH
Funk brand OF azithromycin dihydrateMeSH
Pharmacia brand OF azithromycin dihydrateMeSH
Mack brand OF azithromycin dihydrateMeSH
Pfizer brand OF azithromycinMeSH
AzitrocinMeSH
UltreonMeSH
Lesvi brand OF azithromycin dihydrateMeSH
VinzamMeSH
Vita brand OF azithromycin dihydrateMeSH
ZitromaxMeSH
Azithromycin (AIDS Initiative)hmdb
Azithromycin plus Tumor Necrosis Factorhmdb
Azithromycin Sterilehmdb
N,N-dimethyl-4-amino-benzaldehydehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.51 g/LALOGPS
logP3.03ALOGPS
logP2.44ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.43ChemAxon
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area180.08 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity194.11 m³·mol⁻¹ChemAxon
Polarizability82.63 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC38H72N2O12
IUPAC name(2S,3S,4R,5S,8S,10S,11S,12R,13S,14R)-11-{[(2R,3S,4R,6S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2S,4S,5R,6R)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
InChI IdentifierInChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23+,24-,25+,26+,27-,28+,29-,30-,31+,32+,33-,35+,36-,37-,38+/m0/s1
InChI KeyMQTOSJVFKKJCRP-HHZDEWPHSA-N
Isomeric SMILESCC[C@@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2C[C@](C)(OC)[C@H](O)[C@@H](C)O2)[C@@H](C)[C@H](O[C@H]2O[C@@H](C)C[C@H]([C@@H]2O)N(C)C)[C@@](C)(O)C[C@H](C)CN(C)[C@@H](C)[C@@H](O)[C@]1(C)O
Average Molecular Weight748.9845
Monoisotopic Molecular Weight748.508525778
Classification
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
  • Glycosyl compound
  • O-glycosyl compound
  • Monosaccharide
  • Oxane
  • Tertiary alcohol
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Oxacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Polyol
  • Azacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAzythromycin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9400002500-41dea9c95a10a1b1de40Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01qa-2044934000-670a2beaa7b4316167f8Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052f-1900060200-80884ad6c0b54df8b85bSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-069r-4900010000-b34e6c942611229a8609Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-007p-0100290400-f97f9446792b49c1a832Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0300890000-aa49938acff2f1c214f1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ur-8400960000-49810538b6bcf8ea2e03Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006t-0600080900-fee1f0abdfbfb82970b2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0096-0200291100-29db3b9984786e09583fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7400930000-91a6d08218a89b846c68Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID30776548
ChEMBL IDNot Available
KEGG Compound IDC06838
Pubchem Compound ID53477736
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01916
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference