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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:32:50 UTC
HMDB IDHMDB15418
Secondary Accession NumbersNone
Metabolite Identification
Common NameJosamycin
DescriptionJosamycin is only found in individuals that have used or taken this drug. It is a macrolide antibiotic from Streptomyces narbonensis. The drug has antimicrobial activity against a wide spectrum of pathogens. [PubChem]The mechanism of action of macrolides such as Josamycin is via inhibition of bacterial protein biosynthesis by binding reversibly to the subunit 50S of the bacterial ribosome, thereby inhibiting translocation of peptidyl tRNA. This action is mainly bacteriostatic, but can also be bactericidal in high concentrations. Macrolides tend to accumulate within leukocytes, and are therefore actually transported into the site of infection.
Structure
Thumb
Synonyms
ValueSource
Antibiotic yl-704 a3ChEBI
EN-141ChEBI
JMChEBI
JosamicinaChEBI
JosamycineChEBI
JosamycinumChEBI
Kitasamycin a3ChEBI
Leucomycin a3ChEBI
Leucomycin V 3-acetate 4b-(3-methylbutanoate)ChEBI
Leucomycin V 3-acetate 4(b)-(3-methylbutanoate)ChEBI
Leucomycin V 3-acetate 4(beta)-(3-methylbutanoate)ChEBI
Turimycin a5ChEBI
yl-704 a3ChEBI
Leucomycin V 3-acetic acid 4b-(3-methylbutanoic acid)Generator
Leucomycin V 3-acetic acid 4(b)-(3-methylbutanoic acid)Generator
Leucomycin V 3-acetate 4(β)-(3-methylbutanoate)Generator
Leucomycin V 3-acetic acid 4(beta)-(3-methylbutanoic acid)Generator
Leucomycin V 3-acetic acid 4(β)-(3-methylbutanoic acid)Generator
Leucomycin V, 3-acetate 4b-(3-methylbutanoate)HMDB
Chemical FormulaC42H69NO15
Average Molecular Weight827.995
Monoisotopic Molecular Weight827.466720543
IUPAC Name(2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-(acetyloxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate
Traditional Namejosamycin
CAS Registry Number16846-24-5
SMILES
CO[C@H]1[C@H](OC(=O)C)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]1O[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@H](N(C)C)[C@H]1O
InChI Identifier
InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
InChI KeyInChIKey=XJSFLOJWULLJQS-NGVXBBESSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Glucosamine
  • Amino sugar
  • Desosamine
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Amino saccharide
  • Fatty acid ester
  • Fatty acyl
  • Oxane
  • Dicarboxylic acid or derivatives
  • Saccharide
  • Acetate salt
  • Tertiary alcohol
  • Alpha-hydrogen aldehyde
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aldehyde
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Bacterial Agents
  • Antibacterial Agents
  • Macrolides
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point131.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.35e-02 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.053 mg/mLALOGPS
logP3.47ALOGPS
logP3.22ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)12.67ChemAxon
pKa (Strongest Basic)7.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area206.05 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity211.03 m3·mol-1ChemAxon
Polarizability87.91 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Josamycin Action PathwaySMP00731Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01321
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01321
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01321
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4445361
KEGG Compound IDC12662
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkJosamycin
NuGOwiki LinkHMDB15418
Metagene LinkHMDB15418
METLIN IDNot Available
PubChem Compound5282165
PDB IDNot Available
ChEBI ID474015
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Przybylski P, Pyta K, Stefanska J, Brzezinski B, Bartl F: Structure elucidation, complete NMR assignment and PM5 theoretical studies of new hydroxy-aminoalkyl-alpha,beta-unsaturated derivatives of the macrolide antibiotic josamycin. Magn Reson Chem. 2010 Apr;48(4):286-96. doi: 10.1002/mrc.2574. [20186698 ]

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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. [19934256 ]