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Literature summary for 1.14.14.154 extracted from
- Design, synthesis, and antifungal activities in vitro of novel tetrahydroisoquinoline compounds based on the structure of lanosterol 14alpha-demethylase (CYP51) of fungi (2006), Bioorg. Med. Chem. Lett., 16, 5285-5289.
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| (2R,4S)-ketoconazole | - |
Aspergillus fumigatus |  |
| (2R,4S)-ketoconazole | - |
Candida albicans | |
| (2R,4S)-ketoconazole | - |
Candida parapsilosis | |
| (2R,4S)-ketoconazole | - |
Cryptococcus neoformans | |
| (2R,4S)-ketoconazole | - |
Microsporum canis | |
| (2R,4S)-ketoconazole | - |
Trichophyton rubrum | |
| 2-decyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Aspergillus fumigatus | |
| 2-decyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Candida albicans | |
| 2-decyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Candida parapsilosis | |
| 2-decyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Cryptococcus neoformans | |
| 2-decyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Microsporum canis | |
| 2-decyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Trichophyton rubrum | |
| 2-dodecyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Aspergillus fumigatus | |
| 2-dodecyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Candida albicans | |
| 2-dodecyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Candida parapsilosis | |
| 2-dodecyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Cryptococcus neoformans | |
| 2-dodecyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Microsporum canis | |
| 2-dodecyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Trichophyton rubrum | |
| 2-octyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Aspergillus fumigatus | |
| 2-octyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Candida albicans | |
| 2-octyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Candida parapsilosis | |
| 2-octyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Cryptococcus neoformans | |
| 2-octyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Microsporum canis | |
| 2-octyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol | - |
Trichophyton rubrum | |
| fluconazole | - |
Aspergillus fumigatus | |
| fluconazole | - |
Candida albicans | |
| fluconazole | - |
Candida parapsilosis | |
| fluconazole | - |
Cryptococcus neoformans | |
| fluconazole | - |
Microsporum canis | |
| fluconazole | - |
Trichophyton rubrum | |
| itraconzole | - |
Aspergillus fumigatus | |
| itraconzole | - |
Candida albicans | |
| itraconzole | - |
Candida parapsilosis | |
| itraconzole | - |
Cryptococcus neoformans | |
| itraconzole | - |
Microsporum canis | |
| itraconzole | - |
Trichophyton rubrum | |
| additional information | design of non-azole antifungal lead compounds based on the constructed three-dimensional model of CYP51by coupling structure-based de novo design, overview | Aspergillus fumigatus | |
| additional information | design of non-azole antifungal lead compounds based on the constructed three-dimensional model of CYP51by coupling structure-based de novo design, overview | Candida albicans | |
| additional information | design of non-azole antifungal lead compounds based on the constructed three-dimensional model of CYP51by coupling structure-based de novo design, overview | Candida parapsilosis | |
| additional information | design of non-azole antifungal lead compounds based on the constructed three-dimensional model of CYP51by coupling structure-based de novo design, overview | Cryptococcus neoformans | |
| additional information | design of non-azole antifungal lead compounds based on the constructed three-dimensional model of CYP51by coupling structure-based de novo design, overview | Microsporum canis | |
| additional information | design of non-azole antifungal lead compounds based on the constructed three-dimensional model of CYP51by coupling structure-based de novo design, overview | Trichophyton rubrum | |
| voriconazole | - |
Aspergillus fumigatus | |
| voriconazole | - |
Candida albicans | |
| voriconazole | - |
Candida parapsilosis | |
| voriconazole | - |
Cryptococcus neoformans | |
| voriconazole | - |
Microsporum canis | |
| voriconazole | - |
Trichophyton rubrum | |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | Candida albicans | low activity | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | Cryptococcus neoformans | low activity | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | Candida parapsilosis | low activity | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | Aspergillus fumigatus | low activity | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | Trichophyton rubrum | low activity | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | Microsporum canis | low activity | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Aspergillus fumigatus | - |
- |
- |
| Candida albicans | - |
- |
- |
| Candida parapsilosis | - |
- |
- |
| Cryptococcus neoformans | - |
- |
- |
| Microsporum canis | - |
- |
- |
| Trichophyton rubrum | - |
- |
- |
Reaction
| Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|
| a 14alpha-methylsteroid + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 = a DELTA14-steroid + formate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O | active site structure, structure-function relationship | Candida albicans | |
| a 14alpha-methylsteroid + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 = a DELTA14-steroid + formate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O | active site structure, structure-function relationship | Cryptococcus neoformans | |
| a 14alpha-methylsteroid + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 = a DELTA14-steroid + formate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O | active site structure, structure-function relationship | Candida parapsilosis | |
| a 14alpha-methylsteroid + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 = a DELTA14-steroid + formate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O | active site structure, structure-function relationship | Aspergillus fumigatus | |
| a 14alpha-methylsteroid + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 = a DELTA14-steroid + formate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O | active site structure, structure-function relationship | Trichophyton rubrum | |
| a 14alpha-methylsteroid + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 = a DELTA14-steroid + formate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O | active site structure, structure-function relationship | Microsporum canis |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | - |
Candida albicans | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | - |
Cryptococcus neoformans | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | - |
Candida parapsilosis | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | - |
Aspergillus fumigatus | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | - |
Trichophyton rubrum | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | - |
Microsporum canis | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | low activity | Candida albicans | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | low activity | Cryptococcus neoformans | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | low activity | Candida parapsilosis | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | low activity | Aspergillus fumigatus | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | low activity | Trichophyton rubrum | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| obtusifoliol + [reduced NADPH-hemoprotein reductase] + O2 | low activity | Microsporum canis | 4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
Subunits
| Subunits | Comment | Organism |
|---|---|---|
| More | three-dimensional structure analysis: the S1 subsite is the hydrophilic hydrogen-bonding region, the S2 subsite is the hydrophobic region, the S3 subsite is the narrow hydrophobic cleft formed by the residues in the helix B'-meander1 loop and the N-terminus of helix I, the S4 subsite adjacent to the beta6-1/beta1-4 sheet is another important hydrogen-bonding region in the active site, overview | Candida albicans |
| More | three-dimensional structure analysis: the S1 subsite is the hydrophilic hydrogen-bonding region, the S2 subsite is the hydrophobic region, the S3 subsite is the narrow hydrophobic cleft formed by the residues in the helix B'-meander1 loop and the N-terminus of helix I, the S4 subsite adjacent to the beta6-1/beta1-4 sheet is another important hydrogen-bonding region in the active site, overview | Cryptococcus neoformans |
| More | three-dimensional structure analysis: the S1 subsite is the hydrophilic hydrogen-bonding region, the S2 subsite is the hydrophobic region, the S3 subsite is the narrow hydrophobic cleft formed by the residues in the helix B'-meander1 loop and the N-terminus of helix I, the S4 subsite adjacent to the beta6-1/beta1-4 sheet is another important hydrogen-bonding region in the active site, overview | Candida parapsilosis |
| More | three-dimensional structure analysis: the S1 subsite is the hydrophilic hydrogen-bonding region, the S2 subsite is the hydrophobic region, the S3 subsite is the narrow hydrophobic cleft formed by the residues in the helix B'-meander1 loop and the N-terminus of helix I, the S4 subsite adjacent to the beta6-1/beta1-4 sheet is another important hydrogen-bonding region in the active site, overview | Aspergillus fumigatus |
| More | three-dimensional structure analysis: the S1 subsite is the hydrophilic hydrogen-bonding region, the S2 subsite is the hydrophobic region, the S3 subsite is the narrow hydrophobic cleft formed by the residues in the helix B'-meander1 loop and the N-terminus of helix I, the S4 subsite adjacent to the beta6-1/beta1-4 sheet is another important hydrogen-bonding region in the active site, overview | Trichophyton rubrum |
| More | three-dimensional structure analysis: the S1 subsite is the hydrophilic hydrogen-bonding region, the S2 subsite is the hydrophobic region, the S3 subsite is the narrow hydrophobic cleft formed by the residues in the helix B'-meander1 loop and the N-terminus of helix I, the S4 subsite adjacent to the beta6-1/beta1-4 sheet is another important hydrogen-bonding region in the active site, overview | Microsporum canis |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| CYP51 | - |
Candida albicans |
| CYP51 | - |
Cryptococcus neoformans |
| CYP51 | - |
Candida parapsilosis |
| CYP51 | - |
Aspergillus fumigatus |
| CYP51 | - |
Trichophyton rubrum |
| CYP51 | - |
Microsporum canis |
| lanosterol 14alpha-demethylase | - |
Candida albicans |
| lanosterol 14alpha-demethylase | - |
Cryptococcus neoformans |
| lanosterol 14alpha-demethylase | - |
Candida parapsilosis |
| lanosterol 14alpha-demethylase | - |
Aspergillus fumigatus |
| lanosterol 14alpha-demethylase | - |
Trichophyton rubrum |
| lanosterol 14alpha-demethylase | - |
Microsporum canis |
| More | CYP51 is a member of the cytochrome P450 superfamily | Candida albicans |
| More | CYP51 is a member of the cytochrome P450 superfamily | Cryptococcus neoformans |
| More | CYP51 is a member of the cytochrome P450 superfamily | Candida parapsilosis |
| More | CYP51 is a member of the cytochrome P450 superfamily | Aspergillus fumigatus |
| More | CYP51 is a member of the cytochrome P450 superfamily | Trichophyton rubrum |
| More | CYP51 is a member of the cytochrome P450 superfamily | Microsporum canis |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 35 | - |
assay at | Candida albicans |
| 35 | - |
assay at | Cryptococcus neoformans |
| 35 | - |
assay at | Candida parapsilosis |
| 35 | - |
assay at | Aspergillus fumigatus |
| 35 | - |
assay at | Trichophyton rubrum |
| 35 | - |
assay at | Microsporum canis |
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