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Literature summary extracted from
- Structural insights into human heme oxygenase-1 inhibition by potent and selective azole-based compounds (2013), J. R. Soc. Interface, 10, 20120697.
Application
| EC Number | Application | Comment | Organism |
|---|---|---|---|
| 1.14.14.18 | drug development | heme oxygenase has cytoprotective properties and may play a role in several disease states, making it an interesting therapeutic target | Homo sapiens |
Crystallization (Commentary)
| EC Number | Crystallization (Comment) | Organism |
|---|---|---|
| 1.14.14.18 | crystal structure determination and analysis of HO-1 in complex with different inhibitors, i.e. 2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl) methyl]-1,3-dioxolane, (2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[((5-trifluoromethylpyridin-2-yl)thio)methyl]-1,3-dioxolane, 1-(adamantan-1-yl)-2-(1H-imidazol-1-yl)ethanone, 4-phenyl-1-(1,2,4-1H-triazol-1-yl)butan-2-one, and 1-(1H-imidazol-1-yl)-4,4-diphenyl-2-butanone, overview | Homo sapiens |
Inhibitors
| EC Number | Inhibitors | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.14.14.18 | (2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[((5-trifluoromethylpyridin-2-yl)thio)methyl]-1,3-dioxolane | - |
Homo sapiens |  |
| 1.14.14.18 | (2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(phenylsulphanyl)methyl]-1,3-dioxolane | - |
Homo sapiens | |
| 1.14.14.18 | 1-(1H-imidazol-1-yl)-4,4-diphenyl-2-butanone | - |
Homo sapiens | |
| 1.14.14.18 | 1-(adamantan-1-yl)-2-(1H-imidazol-1-yl)ethanone | - |
Homo sapiens | |
| 1.14.14.18 | 2-[2-(4-bromophenyl)ethyl]-2-[(1H-imidazol-1-yl) methyl]-1,3-dioxolane | - |
Homo sapiens | |
| 1.14.14.18 | 2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl) methyl]-1,3-dioxolane | - |
Homo sapiens | |
| 1.14.14.18 | 2-[2-(4-fluorophenyl)ethyl]-2-[(1H-imidazol-1-yl) methyl]-1,3-dioxolane | - |
Homo sapiens | |
| 1.14.14.18 | 2-[2-phenylethyl]-2-[(1H-imidazol-1-yl) methyl]-1,3-dioxolane | - |
Homo sapiens | |
| 1.14.14.18 | 2-[2-phenylethyl]-2-[(1H-imidazol-1-yl)methyl]1,3-dioxolane | - |
Homo sapiens | |
| 1.14.14.18 | 4-phenyl-1-(1,2,4-1H-triazol-1-yl)butan-2-one | - |
Homo sapiens | |
| 1.14.14.18 | 4-phenyl-1-(1H-imidazol-1-yl)-2-butanone | - |
Homo sapiens | |
| 1.14.14.18 | azalanstat | - |
Homo sapiens | |
| 1.14.14.18 | chromium protoporphyrin | - |
Homo sapiens | |
| 1.14.14.18 | additional information | metalloporphyrins are used as competitive enzyme inhibitors. Development of isozyme-selective heme oxygenase inhibitors. Development and evaluation of non-competitive inhibitors with selectivity for isozyme HO-1, and synthesis and analysis of a series of 2-oxy-substituted 1-(1H-imidazol-1-yl)-4-phenylbutanes, overview. Synthesis of a series of alpha-(1H-imidazol-1-yl)-omega-phenylalkanes to examine the effect of introducing heteroatoms into the central alkyl linker. Imidazole-dioxolane-based HO inhibitors are all selective for HO-1, and exhibit substantially lower activity towards HO-2. HO-1-inhibitor, binding mechanism, detailed overview. HO-1 inducible binding mode, overview | Homo sapiens | |
| 1.14.14.18 | pegylated zinc protoporphyrin | inhibition of isozyme HO-1 | Homo sapiens | |
| 1.14.14.18 | tin protoporphyrin | - |
Homo sapiens | |
| 1.14.14.18 | zinc protoporphyrin | low inhibition | Homo sapiens | |
Molecular Weight [Da]
| EC Number | Molecular Weight [Da] | Molecular Weight Maximum [Da] | Comment | Organism |
|---|---|---|---|---|
| 1.14.14.18 | 32000 | - |
x * 32000, isozyme HO-1 | Homo sapiens |
| 1.14.14.18 | 36500 | - |
x * 36500, isozyme HO-2 | Homo sapiens |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.14.18 | heme + 3 AH2 + 3 O2 | Homo sapiens | - |
biliverdin + Fe2+ + CO + 3 A + 3 H2O | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.14.14.18 | Homo sapiens | P09601 | inducible isozyme HO-1 | - |
| 1.14.14.18 | Homo sapiens | P30519 | constitutive isozyme HO-2 | - |
Source Tissue
| EC Number | Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|---|
| 1.14.14.18 | brain | isozyme HO-2 | Homo sapiens | - |
| 1.14.14.18 | breast cancer cell | - |
Homo sapiens | - |
| 1.14.14.18 | lymph node cancer cell | - |
Homo sapiens | - |
| 1.14.14.18 | additional information | isozyme HO-2 has a wider tissue distribution than isozyme HO-1 | Homo sapiens | - |
| 1.14.14.18 | pancreatic cancer cell | - |
Homo sapiens | - |
| 1.14.14.18 | prostate cancer cell | - |
Homo sapiens | - |
| 1.14.14.18 | spleen | - |
Homo sapiens | - |
| 1.14.14.18 | spleen | predominant expression of isozyme HO-1 | Homo sapiens | - |
| 1.14.14.18 | testis | isozyme HO-2 | Homo sapiens | - |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.14.18 | heme + 3 AH2 + 3 O2 | - |
Homo sapiens | biliverdin + Fe2+ + CO + 3 A + 3 H2O | - |
? | |
Subunits
| EC Number | Subunits | Comment | Organism |
|---|---|---|---|
| 1.14.14.18 | ? | x * 32000, isozyme HO-1 | Homo sapiens |
| 1.14.14.18 | ? | x * 36500, isozyme HO-2 | Homo sapiens |
| 1.14.14.18 | More | structure comparison of isozymes HO-1 and HO-2, overview. Both apo- and holoenzymes contain a hydrogen-bond network involving Asn210, Arg136, as well as a second level of residues, which includes Tyr58 and Tyr114 to stabilize the position of the catalytically critical Asp140 residue for HO-1 and Asp160 for HO-2. Structure-activity relationship analysis | Homo sapiens |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.14.14.18 | heme oxygenase-1 | - |
Homo sapiens |
| 1.14.14.18 | HO-1 | - |
Homo sapiens |
| 1.14.14.18 | HO-2 | - |
Homo sapiens |
IC50 Value
| EC Number | IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|---|
| 1.14.14.18 | 0.00014 | - |
pH and temperature not specified in the publication | Homo sapiens | 2-[2-(4-bromophenyl)ethyl]-2-[(1H-imidazol-1-yl) methyl]-1,3-dioxolane | |
| 1.14.14.18 | 0.00027 | - |
pH and temperature not specified in the publication | Homo sapiens | 1-(1H-imidazol-1-yl)-4,4-diphenyl-2-butanone | |
| 1.14.14.18 | 0.0005 | - |
pH and temperature not specified in the publication | Homo sapiens | 2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl) methyl]-1,3-dioxolane | |
| 1.14.14.18 | 0.00076 | - |
pH and temperature not specified in the publication | Homo sapiens | 2-[2-phenylethyl]-2-[(1H-imidazol-1-yl)methyl]1,3-dioxolane | |
| 1.14.14.18 | 0.0014 | - |
pH and temperature not specified in the publication | Homo sapiens | 2-[2-(4-fluorophenyl)ethyl]-2-[(1H-imidazol-1-yl) methyl]-1,3-dioxolane | |
| 1.14.14.18 | 0.0021 | - |
pH and temperature not specified in the publication | Homo sapiens | (2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[((5-trifluoromethylpyridin-2-yl)thio)methyl]-1,3-dioxolane | |
| 1.14.14.18 | 0.0025 | - |
pH and temperature not specified in the publication | Homo sapiens | 4-phenyl-1-(1,2,4-1H-triazol-1-yl)butan-2-one | |
| 1.14.14.18 | 0.00406 | - |
pH and temperature not specified in the publication | Homo sapiens | 4-phenyl-1-(1H-imidazol-1-yl)-2-butanone | |
| 1.14.14.18 | 0.0062 | - |
pH and temperature not specified in the publication | Homo sapiens | 2-[2-phenylethyl]-2-[(1H-imidazol-1-yl) methyl]-1,3-dioxolane | |
Expression
| EC Number | Organism | Comment | Expression |
|---|---|---|---|
| 1.14.14.18 | Homo sapiens | HO-1 activity is upregulated in response to several therapeutic treatments and is implicated in promoting tumour growth | up |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 1.14.14.18 | additional information | structure-activity relationship analysis | Homo sapiens |
| 1.14.14.18 | physiological function | heme oxygenase has cytoprotective properties and may play a role in several disease states. HO-1 activity is upregulated in response to several therapeutic treatments and is implicated in promoting tumour growth. HO-1-derived CO is associated with angiogenesis, inducing vascular endothelial growth factor synthesis, and stimulating the proliferation of endothelial cells. Role of the HO/CO system in neuronal complications, particularly of HO-1 | Homo sapiens |
| 1.14.14.18 | physiological function | heme oxygenase has cytoprotective properties and may play a role in several disease states. Role of the HO/CO system in neuronal complications, particularly of HO-1 | Homo sapiens |
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