Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:51 UTC |
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Update Date | 2022-03-07 02:51:51 UTC |
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HMDB ID | HMDB0015089 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Dirithromycin |
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Description | Dirithromycin is only found in individuals that have used or taken this drug. It is a macrolide glycopeptide antibiotic. It is used to treat many different types of bacterial infections, such as bronchitis, pneumonia, tonsillitis, and even skin infections.Dirithromycin prevents bacteria from growing, by interfering with their protein synthesis. Dirithromycin binds to the 50S subunit of the 70S bacterial ribosome, and thus inhibits the translocation of peptides. Dirithromycin has over 10 times higher affinity to the subunit 50S than erythromycin. In addition, dirithromycin binds simultaneously in to two domains of 23S RNA of the ribosomal subunit 50S, where older macrolides bind only in one. Dirithromycin can also inhibit the formation of ribosomal subunits 50S and 30S. |
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Structure | CC[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)[C@@H]2N[C@@H](COCCOC)O[C@@H]([C@@H]2C)[C@]1(C)O InChI=1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24-,25-,26-,27+,28+,29-,30-,31+,32+,33-,34-,35+,36-,37+,39+,40-,41-,42-/m1/s1 |
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Synonyms | Value | Source |
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Lilly brand OF dirithromycin | HMDB | Pharmafarm brand OF dirithromycin | HMDB | Dista brand OF dirithromycin | HMDB | Muro brand OF dirithromycin | HMDB | Dynabac | HMDB | Nortron | HMDB | (9S)-9-Deoxo-11-deoxy-9,11-(imino((1R)-2-(2-methoxyethoxy)ethylidene)oxy)erythromycin | HMDB | Dirithromycin | MeSH |
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Chemical Formula | C42H78N2O14 |
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Average Molecular Weight | 835.0737 |
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Monoisotopic Molecular Weight | 834.545305214 |
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IUPAC Name | (1S,2R,3R,6R,7R,8R,9R,10R,12R,13S,15R,17R)-9-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-3-ethyl-2,10-dihydroxy-7-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-15-[(2-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one |
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Traditional Name | dynabac |
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CAS Registry Number | 62013-04-1 |
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SMILES | CC[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)[C@@H]2N[C@@H](COCCOC)O[C@@H]([C@@H]2C)[C@]1(C)O |
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InChI Identifier | InChI=1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24-,25-,26-,27+,28+,29-,30-,31+,32+,33-,34-,35+,36-,37+,39+,40-,41-,42-/m1/s1 |
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InChI Key | WLOHNSSYAXHWNR-PBIGORBISA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Aminoglycosides |
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Alternative Parents | |
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Substituents | - Aminoglycoside core
- Macrolide
- O-glycosyl compound
- Glycosyl compound
- Monosaccharide
- 1,3-oxazinane
- Oxane
- Oxazinane
- Tertiary alcohol
- Tertiary amine
- Lactone
- Secondary alcohol
- Tertiary aliphatic amine
- Hemiaminal
- Carboxylic acid ester
- Amino acid or derivatives
- 1,2-aminoalcohol
- Acetal
- Carboxylic acid derivative
- Oxacycle
- Dialkyl ether
- Secondary aliphatic amine
- Ether
- Azacycle
- Organoheterocyclic compound
- Secondary amine
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Alcohol
- Amine
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Organonitrogen compound
- Organopnictogen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.23 g/L | Not Available | LogP | 1.6 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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