Oleandomycin
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Basic Info
| Common Name | Oleandomycin(F05844) |
| 2D Structure | |
| FRCD ID | F05844 |
| CAS Number | 3922-90-5 |
| PubChem CID | 72493 |
| Formula | C35H61NO12 |
| IUPAC Name | (3R,5S,6S,7R,8S,9R,12R,13R,14S,15R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione |
| InChI Key | RZPAKFUAFGMUPI-QESOVKLGSA-N |
| InChI | InChI=1S/C35H61NO12/c1-16-14-35(15-43-35)32(40)19(4)27(37)18(3)22(7)46-33(41)21(6)31(47-26-13-25(42-11)28(38)23(8)45-26)20(5)30(16)48-34-29(39)24(36(9)10)12-17(2)44-34/h16-31,34,37-39H,12-15H2,1-11H3/t16-,17+,18-,19+,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31-,34-,35+/m0/s1 |
| Canonical SMILES | CC1CC(C(C(O1)OC2C(CC3(CO3)C(=O)C(C(C(C(OC(=O)C(C(C2C)OC4CC(C(C(O4)C)O)OC)C)C)C)O)C)C)O)N(C)C |
| Isomeric SMILES | C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H](C[C@@]3(CO3)C(=O)[C@@H]([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]4C[C@@H]([C@H]([C@@H](O4)C)O)OC)C)C)C)O)C)C)O)N(C)C |
| Synonyms |
Oleandomycin A
oleandomycin
Landomycin
Matromycin
Amimycin
Romicil
3922-90-5
CHEBI:16869
UNII-P8ZQ646136
P8ZQ646136
|
| Classifies |
Veterinary Drug
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbohydrates and carbohydrate conjugates |
| Intermediate Tree Nodes | Aminosaccharides |
| Direct Parent | Aminoglycosides |
| Alternative Parents |
|
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Aminoglycoside core - Macrolide - Glycosyl compound - O-glycosyl compound - Monosaccharide - Oxane - 1,2-aminoalcohol - Amino acid or derivatives - Carboxylic acid ester - Ketone - Lactone - Secondary alcohol - Tertiary amine - Tertiary aliphatic amine - Acetal - Organoheterocyclic compound - Oxacycle - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Dialkyl ether - Oxirane - Ether - Organonitrogen compound - Alcohol - Carbonyl group - Hydrocarbon derivative - Organic nitrogen compound - Organopnictogen compound - Amine - Organic oxide - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 687.868 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 13 |
| Rotatable Bond Count | 6 |
| Complexity | 1090 |
| Monoisotopic Mass | 687.419 |
| Exact Mass | 687.419 |
| XLogP | 2.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 48 |
| Defined Atom Stereocenter Count | 18 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.9923 |
| Human Intestinal Absorption | HIA+ | 0.7173 |
| Caco-2 Permeability | Caco2- | 0.6499 |
| P-glycoprotein Substrate | Substrate | 0.7589 |
| P-glycoprotein Inhibitor | Inhibitor | 0.7890 |
| Non-inhibitor | 0.6658 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8605 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.4323 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8004 |
| CYP450 2D6 Substrate | Non-substrate | 0.9031 |
| CYP450 3A4 Substrate | Substrate | 0.6984 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9291 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9026 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.5537 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9629 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9931 |
| Non-inhibitor | 0.8978 | |
| AMES Toxicity | Non AMES toxic | 0.5307 |
| Carcinogens | Non-carcinogens | 0.9182 |
| Fish Toxicity | High FHMT | 0.7059 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7871 |
| Honey Bee Toxicity | Low HBT | 0.5000 |
| Biodegradation | Not ready biodegradable | 0.9968 |
| Acute Oral Toxicity | IV | 0.6828 |
| Carcinogenicity (Three-class) | Non-required | 0.5365 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.5809 | LogS |
| Caco-2 Permeability | 0.8888 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0423 | LD50, mol/kg |
| Fish Toxicity | 1.3050 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4980 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Chicken,Edible Offal | Japan | 0.2ppm | |||
| Other Poultry Animals,Kidney | Japan | 0.2ppm | |||
| Chicken,Kidney | Japan | 0.2ppm | |||
| Other Poultry Animals,Liver | Japan | 0.2ppm | |||
| Chicken,Liver | Japan | 0.2ppm | |||
| Other Poultry Animals,Fat | Japan | 0.2ppm | |||
| Chicken,Fat | Japan | 0.2ppm | |||
| Other Poultry Animals,Muscle | Japan | 0.2ppm | |||
| Chicken,Muscle | Japan | 0.2ppm | |||
| Milk | Japan | 0.05ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 0.1ppm | |||
| Other Poultry Animals,Edible Offal | Japan | 0.2ppm | |||
| Pig,Edible Offal | Japan | 0.1ppm | |||
| Edible Tissues Of Swine | United States | 0.15ppm | |||
| Edible Tissues Of Turkeys | United States | 0.15ppm | |||
| Edible Tissues Of Chickens | United States | 0.15ppm | |||
| Perciformes | Japan | 0.05ppm |