A0A2P1DP94 · MACC_PENTR
- ProteinCytochrome P450 monooxygenase macC
- GenemacC
- StatusUniProtKB reviewed (Swiss-Prot)
- Organism
- Amino acids536 (go to sequence)
- Protein existenceInferred from homology
- Annotation score3/5
Function
function
Cytochrome P450 monooxygenase; part of the gene cluster that mediates the biosynthesis of macrophorins, isoprenoid epoxycyclohexenones containing cyclized drimane moieties (PubMed:28926261).
The first step of the pathway is the synthesis of 6-methylsalicylic acid (6-MSA) by the polyketide synthase macA (PubMed:28926261).
6-MSA is then converted to m-cresol by the decarboxylase macB (By similarity).
The cytochrome P450 monooxygenase macC then catalyzes the oxidation of m-cresol to toluquinol (By similarity).
Epoxidation of toluquinol is then performed by the short chain dehydrogenase macD, with the help of macE, and a further prenylation by macG leads to 7-deacetoxyyanuthone A (By similarity).
The next step is the hydroxylation of C-22 of 7-deacetoxyyanuthone A by the cytochrome P450 monooxygenase macH to yield 22-deacetylyanuthone A (By similarity).
O-Mevalon transferase macI then attaches mevalon to the hydroxyl group of 22-deacetylyanuthone A to produce yanuthone E (By similarity).
The terpene cyclase macJ catalyzes the cyclization of 22-deacetylyanuthone A to macrophorin A (PubMed:28926261).
MacJ is also able to catalyze cyclization of yanuthone E and 7-deacetoxyyanuthone A to their corresponding macrophorins (PubMed:28926261).
The macJ products can be further modified by macH and macJ, as well as by the FAD-dependent monooxygenase macF, to produce additional macrophorins, including 4'-oxomacrophorin A, 4'-oxomacrophorin D and 4'-oxomacrophorin E (PubMed:28926261).
The first step of the pathway is the synthesis of 6-methylsalicylic acid (6-MSA) by the polyketide synthase macA (PubMed:28926261).
6-MSA is then converted to m-cresol by the decarboxylase macB (By similarity).
The cytochrome P450 monooxygenase macC then catalyzes the oxidation of m-cresol to toluquinol (By similarity).
Epoxidation of toluquinol is then performed by the short chain dehydrogenase macD, with the help of macE, and a further prenylation by macG leads to 7-deacetoxyyanuthone A (By similarity).
The next step is the hydroxylation of C-22 of 7-deacetoxyyanuthone A by the cytochrome P450 monooxygenase macH to yield 22-deacetylyanuthone A (By similarity).
O-Mevalon transferase macI then attaches mevalon to the hydroxyl group of 22-deacetylyanuthone A to produce yanuthone E (By similarity).
The terpene cyclase macJ catalyzes the cyclization of 22-deacetylyanuthone A to macrophorin A (PubMed:28926261).
MacJ is also able to catalyze cyclization of yanuthone E and 7-deacetoxyyanuthone A to their corresponding macrophorins (PubMed:28926261).
The macJ products can be further modified by macH and macJ, as well as by the FAD-dependent monooxygenase macF, to produce additional macrophorins, including 4'-oxomacrophorin A, 4'-oxomacrophorin D and 4'-oxomacrophorin E (PubMed:28926261).
Miscellaneous
The macrophorins cluster contains a single gene insertion (encoding for the terpene cyclase macJ) compared with the yanuthone cluster that produces the linear compound yanuthone.
Cofactor
Pathway
Secondary metabolite biosynthesis; terpenoid biosynthesis.
Features
Showing features for binding site.
GO annotations
Aspect | Term | |
---|---|---|
Cellular Component | membrane | |
Molecular Function | heme binding | |
Molecular Function | iron ion binding | |
Molecular Function | monooxygenase activity | |
Molecular Function | oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen | |
Biological Process | mycotoxin biosynthetic process | |
Biological Process | terpenoid biosynthetic process |
Keywords
- Molecular function
- Ligand
Enzyme and pathway databases
Names & Taxonomy
Protein names
- Recommended nameCytochrome P450 monooxygenase macC
- EC number
- Alternative names
Gene names
Organism names
- Organism
- Strain
- Taxonomic lineageEukaryota > Fungi > Dikarya > Ascomycota > Pezizomycotina > Eurotiomycetes > Eurotiomycetidae > Eurotiales > Aspergillaceae > Penicillium
Accessions
- Primary accessionA0A2P1DP94
Subcellular Location
UniProt Annotation
GO Annotation
Membrane ; Single-pass membrane protein
Features
Showing features for transmembrane.
Type | ID | Position(s) | Description | |||
---|---|---|---|---|---|---|
Transmembrane | 2-22 | Helical | ||||
Sequence: ALLYITTAALALLLLFLRAVF |
Keywords
- Cellular component
PTM/Processing
Features
Showing features for chain.
Type | ID | Position(s) | Description | |||
---|---|---|---|---|---|---|
Chain | PRO_0000454086 | 1-536 | Cytochrome P450 monooxygenase macC | |||
Sequence: MALLYITTAALALLLLFLRAVFKSWRIQRKLPPGPPGLPLIGNIHQIPAVRAHQKFTEWAKVYGGLYTFRIGPATAAVITDRGLVKELLDKRSALYSSRPVSYVGQNLITGGDHLLLMDNNEMWRLFRKTVHQHFKASMCEKEHVKLLEAEHTQMMRDFLLYPEKHMLHTKRTTNSIIMSLLYGIRTPSWDTPHMRELYEIMEQWSKVMETGATPPVDIFPWLRWIPQRWLGNWVDRSVEVGSGMKALYGSFRRRAIEARREAEQSSQSRARTFIDHVLDLQEKANLTDNQVDFLGGVMMEGGSDTGSTMLLVMIQALVRYPEVQERARAELDAVCGEGRSPTWADFSRLPYINMIVKETMRWRPVTPLSFPHALNQDDWVNGYLLPKGTTVFLNVWGLHHDESIFPNPERFDPSHYEGRHNLASDYAASPDYMQRDHFIYGAGRRLCPGIHLSERSMFIGAAKLLWCFQFEPEMDESGRPVAIDTDPITGYTEGFLVCPQAYKCKVSPRSTARAETIMREFAQAESEVLCQYATP |
Structure
Sequence
- Sequence statusComplete
- Length536
- Mass (Da)61,412
- Last updated2018-05-23 v1
- ChecksumC980E6537D1E4DA4