| Common Name |
Josamycin
| Description |
Josamycin 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 accumliate within leukocytes, and are therefore actually transported into the site of infection.
| Structure |
| Synonyms |
| Value |
Source |
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
WilprafenMeSH
| Chemical Formlia |
C42H69NO15
| Average Molecliar Weight |
827.995
| Monoisotopic Molecliar Weight |
827.466720543
| 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 Name |
josamycin
| CAS Registry Number |
16846-24-5
| SMILES |
CO[C@H]1[C@H](OC(=O)C)CC(=O)O[C@H](C)CC=CC=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 Key |
XJSFLOJWULLJQS-NGVXBBESSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as aminoglycosides. These are moleclies or a portion of a moleclie composed of amino-modified sugars.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic oxygen compounds
| Sub Class |
Organooxygen compounds
| Direct Parent |
Aminoglycosides
| Alternative Parents |
Macrolides and analogues
Disaccharides
O-glycosyl compounds
Tricarboxylic acids and derivatives
Fatty acid esters
Oxanes
Tertiary alcohols
Alpha-hydrogen aldehydes
1,2-aminoalcohols
Secondary alcohols
Lactones
Trialkylamines
Carboxylic acid esters
Amino acids and derivatives
Dialkyl ethers
Acetals
Oxacyclic compounds
Organopnictogen compounds
Organic oxides
Hydrocarbon derivatives
| 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
| Molecliar Framework |
Aliphatic heteromonocyclic compounds
| External Descriptors |
tertiary alcohol (CHEBI:31739 )
tertiary amino compound (CHEBI:31739 )
macrolide antibiotic (CHEBI:31739 )
acetate ester (CHEBI:31739 )
disaccharide derivative (CHEBI:31739 )
glycoside (CHEBI:31739 )
aldehyde (CHEBI:31739 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Anti-Bacterial Agents
Antibacterial Agents
Macrolides
| Application |
Pharmaceutical
| Cellliar locations |
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point131.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.35e-02 g/LNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
Josamycin Action PathwaySMP00731Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01321
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01321
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB01321
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
4445361
| KEGG Compound ID |
C12662
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Josamycin
| NuGOwiki Link |
HMDB15418
| Metagene Link |
HMDB15418
| METLIN ID |
Not Available
| PubChem Compound |
5282165
| PDB ID |
Not Available
| ChEBI ID |
474015
Product: Zofenopril (calcium)
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- 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
- 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 ]
PMID: 23382074
