| Compound Information | SONAR Target prediction |
| Name: | AMPHOTERICIN B |
| Unique Identifier: | SPE01500122 |
| MolClass: | Checkout models in ver1.5 and ver1.0 |
| Molecular Formula: | |
| Molecular Weight: | 850.499 g/mol |
| X log p: | 23.067 (online calculus) |
| Lipinksi Failures | 2 |
| TPSA | 71.06 |
| Hydrogen Bond Donor Count: | 0 |
| Hydrogen Bond Acceptors Count: | 18 |
| Rotatable Bond Count: | 3 |
| Canonical Smiles: | CC1OC(OC2CC3OC(O)(CC(O)CC(O)C(O)CCC(O)CC(O)CC(=O)OC(C)C(C)C(O)C(C)C=CC =CC=CC=CC=CC=CC=C2)CC(O)C3C(O)=O)C(O)C(N)C1O |
| Class: | macrolide |
| Source: | Streptomycetes nodosus |
| Reference: | New Engl J Med 296: 784 (1977) |
| Therapeutics: | antifungal |
| Generic_name: | Amphotericin B |
| Chemical_iupac_name: | 3-(4-amino-3,5-dihydroxy-6-methyl-oxan-2-yl)oxy-19,25,27,30,31,33,35,37-octahydroxy- 18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16- heptaene-38-carboxylic acid |
| Drug_type: | Approved Drug |
| Pharmgkb_id: | PA448415 |
| Kegg_compound_id: | C06573 |
| Drugbank_id: | APRD00797 |
| Melting_point: | 170.0 oC |
| H2o_solubility: | 750 mg/L |
| Logp: | 0.947 |
| Cas_registry_number: | 1397-89-3 |
| Drug_category: | Amebicides; Anti-Bacterial Agents; Antifungal Agents; Antiprotozoal Agents; ATC:A01AB04; ATC:A07AA07; ATC:G01AA03; ATC:J02AA01 |
| Indication: | Used to treat potentially life threatening fungal infections. |
| Pharmacology: | Amphotericin B shows a high order of in vitro activity against many species of fungi. Histoplasma capsulatum, Coccidioides immitis, Candida species, Blastomyces dermatitidis, Rhodotorula, Cryptococcus neoformans, Sporothrix schenckii, Mucor mucedo, and Aspergillus fumigatus are all inhibited by concentrations of amphotericin B ranging from 0.03 to 1.0 mcg/mL in vitro. While Candida albicans is generally quite susceptible to amphotericin B, non-albicans species may be less susceptible. Pseudallescheria boydii and Fusarium sp. are often resistant to amphotericin B. The antibiotic is without effect on bacteria, rickettsiae, and viruses. |
| Mechanism_of_action: | Amphotericin B is fungistatic or fungicidal depending on the concentration obtained in body fluids and the susceptibility of the fungus. The drug acts by binding to sterols in the cell membrane of susceptible fungi with a resultant change in membrane permeability allowing leakage of intracellular components. Ergosterol, the principal sterol in the fungal cytoplasmic membrane, is the target site of action of amphotericin B and the azoles. Amphotericin B, a polyene, binds irreversibly to ergosterol, resulting in disruption of membrane integrity and ultimately cell death. |
| Organisms_affected: | Various Fungus Species |
| Found: 80 active | as graph: single | with analogs | 1 2 3 4 5 6 7 8 9 10 Next >> [80] |
| Species: | 4932 |
| Condition: | AAT2 |
| Replicates: | 2 |
| Raw OD Value: r im | 0.0536±0.000777817 |
| Normalized OD Score: sc h | 0.0727±0.00130397 |
| Z-Score: | -49.2603±1.15269 |
| p-Value: | 0 |
| Z-Factor: | 0.921139 |
| Fitness Defect: | INF |
| Bioactivity Statement: | Toxic |
| ps |
| DBLink | Rows returned: 28 | 1 2 3 4 5 Next >> |
| 1972 | 33-(4-amino-3,5-dihydroxy-6-methyl-oxan-2-yl)oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-ox o-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid |
| 14956 | (1R,3S,5R,6R,9R,11R,15S,16S,17R,18S,33R,35S,36S,37S)-33-[(2S,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyl -oxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatr iaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid |
| 352546 | (1R,3S,5R,6R,9R,11R,15S,16S,17R,18S,33R,35S,36S,37S)-33-(4-amino-3,5-dihydroxy-6-methyl-oxan-2-yl)oxy-1, 3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23, 25,27,29,31-heptaene-36-carboxylic acid |
| 354192 | (1S,3R,19R,25R,27R,30R,31R,33S,35R,38S)-3-(4-amino-3,5-dihydroxy-6-methyl-oxan-2-yl)oxy-19,25,27,30,31,3 3,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16- heptaene-38-carboxylic acid |
| 429301 | methyl 33-(4-amino-3,5-dihydroxy-6-methyl-oxan-2-yl)oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-ox o-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate |
| 451404 | (1R,3S,5S,8S,9S,11R,15S,16R,17R,18S,33R,35S,36S,37S)-33-[(2S,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyl -oxan-2-yl]oxy-1,3,5,8,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatr iaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid |
| internal high similarity DBLink | Rows returned: 1 |
| SPE01500446 | 0.9854 |
| active | Cluster 7118 | Additional Members: 11 | Rows returned: 5 |
| SPE01503432 | 0.401639344262295 |
| SPE01505560 | 0.392857142857143 |
| SPE01500446 | 0.229357798165138 |
| LAT005H11 | 0.229357798165138 |
| LAT006F08 | 0 |
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