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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:58 UTC
HMDB IDHMDB0015418
Secondary Accession Numbers
  • HMDB15418
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
Data?1582753294
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
WilprafenHMDB
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 KeyXJSFLOJWULLJQS-NGVXBBESSA-N
Chemical Taxonomy
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
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Oxane
  • Alpha-hydrogen aldehyde
  • Tertiary alcohol
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Lactone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Aldehyde
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point131.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.054 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.054 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity211.03 m³·mol⁻¹ChemAxon
Polarizability87.91 ųChemAxon
Number of Rings3ChemAxon
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]+276.77130932474
DeepCCS[M-H]-275.11830932474
DeepCCS[M-2H]-309.15330932474
DeepCCS[M+Na]+282.92830932474
AllCCS[M+H]+283.832859911
AllCCS[M+H-H2O]+283.632859911
AllCCS[M+NH4]+284.032859911
AllCCS[M+Na]+284.032859911
AllCCS[M-H]-262.432859911
AllCCS[M+Na-2H]-269.032859911
AllCCS[M+HCOO]-276.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
JosamycinCO[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]1O4307.2Standard polar33892256
JosamycinCO[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]1O4774.9Standard non polar33892256
JosamycinCO[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]1O4830.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Josamycin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Josamycin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Josamycin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Josamycin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Josamycin 10V, Positive-QTOFsplash10-06vi-3002921760-f1a621e9c87868e86a702017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Josamycin 20V, Positive-QTOFsplash10-0573-7022931100-55728374a750214dcfd22017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Josamycin 40V, Positive-QTOFsplash10-002f-9112300000-6fad22ed83270743a8072017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Josamycin 10V, Negative-QTOFsplash10-0a7i-7427620970-15829300f9319bfce32a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Josamycin 20V, Negative-QTOFsplash10-0a6r-3312930210-7346fec1317f39fec6da2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Josamycin 40V, Negative-QTOFsplash10-004i-6302901100-988bf63a81925c47fc8d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Josamycin 10V, Positive-QTOFsplash10-01u0-0000000950-d1915db52ffd3fe328232021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Josamycin 20V, Positive-QTOFsplash10-002f-1001000920-ab7b990bff987b9f90062021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Josamycin 40V, Positive-QTOFsplash10-05mo-8906110300-66f764c251505c96cd852021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Josamycin 10V, Negative-QTOFsplash10-05r0-2000011960-b7b5d06cbb899d1f68532021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Josamycin 20V, Negative-QTOFsplash10-0a59-9100011400-fd587738c70572c9acaa2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Josamycin 40V, Negative-QTOFsplash10-052f-9103100120-a381a9435caad097f5612021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01321 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01321 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01321
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00018736
Chemspider ID4445361
KEGG Compound IDC12662
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkJosamycin
METLIN IDNot Available
PubChem Compound5282165
PDB IDNot Available
ChEBI ID31739
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. 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. [PubMed: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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]