Reaction participants Show >> << Hide
- Name help_outline ML-236A carboxylate Identifier CHEBI:142048 Charge -1 Formula C18H27O5 InChIKeyhelp_outline CKSMAJWSIYUHLV-DZSDEGEFSA-M SMILEShelp_outline [C@@]12([C@H](CCC=C1C=C[C@@H]([C@@H]2CC[C@H](C[C@H](CC(=O)[O-])O)O)C)O)[H] 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
-
Namehelp_outline
(S)-2-methylbutanoyl-[2-methylbutanoate polyketide synthase]
Identifier
RHEA-COMP:10261
Reactive part
help_outline
- Name help_outline O-[S-2-methylbutenoylpantetheine-4'-phosphoryl]serine residue Identifier CHEBI:82764 Charge -1 Formula C19H33N3O9PS SMILEShelp_outline CC[C@H](C)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP([O-])(=O)OC[C@H](N-*)C(-*)=O 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline mevinic carboxylate Identifier CHEBI:142050 Charge -1 Formula C23H35O6 InChIKeyhelp_outline BOZILQFLQYBIIY-INTXDZFKSA-M SMILEShelp_outline [C@@]12([C@H](CCC=C1C=C[C@@H]([C@@H]2CC[C@H](C[C@H](CC(=O)[O-])O)O)C)OC([C@H](CC)C)=O)[H] 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
-
Namehelp_outline
holo-[2-methylbutanoate polyketide synthase]
Identifier
RHEA-COMP:10260
Reactive part
help_outline
- Name help_outline O-(pantetheine-4ʼ-phosphoryl)-L-serine residue Identifier CHEBI:64479 Charge -1 Formula C14H25N3O8PS SMILEShelp_outline C(NC(CCNC(=O)[C@@H](C(COP(OC[C@@H](C(*)=O)N*)(=O)[O-])(C)C)O)=O)CS 2D coordinates Mol file for the small molecule Search links Involved in 207 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:57636 | RHEA:57637 | RHEA:57638 | RHEA:57639 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
|
Publications
-
Compactin-a review.
Chakravarti R., Sahai V.
Compactin, a hypocholesterolemic molecule, is a competitive inhibitor of 3-hydroxy-3-methyl-glutaryl (HMG)-CoA reductase, which is a regulatory enzyme for cholesterol biosynthesis. The structural similarity and high affinity of the acid form of compactin and HMG, the natural substrate of enzyme, r ... >> More
Compactin, a hypocholesterolemic molecule, is a competitive inhibitor of 3-hydroxy-3-methyl-glutaryl (HMG)-CoA reductase, which is a regulatory enzyme for cholesterol biosynthesis. The structural similarity and high affinity of the acid form of compactin and HMG, the natural substrate of enzyme, results in specific and effective inhibition of this enzyme. Inhibition results in reduced levels of mevalonic acid in the body, leading to pleiotropic effects. Various fungi have been used for the commercial production of compactin. Using different strategies for improving production levels, yields have been increased to around 900 times of the amount originally produced. Recently, the gene sequence responsible for compactin production has been cloned and sequenced. This review deals with the chemistry, mode of action, pharmacology, biosynthesis, and production of compactin. A comparative study of various reports dealing with the production of compactin is also included. << Less
Appl Microbiol Biotechnol 64:618-624(2004) [PubMed] [EuropePMC]
This publication is cited by 6 other entries.
-
Molecular cloning and characterization of an ML-236B (compactin) biosynthetic gene cluster in Penicillium citrinum.
Abe Y., Suzuki T., Ono C., Iwamoto K., Hosobuchi M., Yoshikawa H.
Cloning of genes encoding polyketide synthases (PKSs) has allowed us to identify a gene cluster for ML-236B biosynthesis in Penicillium citrinum. Like lovastatin, which is produced by Aspergillus terreus, ML-236B (compactin) inhibits the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reduc ... >> More
Cloning of genes encoding polyketide synthases (PKSs) has allowed us to identify a gene cluster for ML-236B biosynthesis in Penicillium citrinum. Like lovastatin, which is produced by Aspergillus terreus, ML-236B (compactin) inhibits the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase. Genomic sequencing and Northern analysis showed that nine predicted genes for ML-236B biosynthesis were located within a 38-kb region and were transcribed when ML-236B was produced. The predicted amino acid sequences encoded by these nine genes, designated mlcA-mlcH and mlcR, were similar to those encoded by the genes for lovastatin synthesis, and were therefore assumed to be involved either directly or indirectly in ML-236B biosynthesis. Targeted disruption experiments provided evidence that two PKS genes in the cluster, mlcA and mlcB, are required for the biosynthesis of the nonaketide and the diketide moieties, respectively, of ML-236B, suggesting that the gene cluster as a whole is responsible for ML-236B biosynthesis in P. citrinum. Bioconversion of some of the predicted intermediates by an mlcA-disrupted mutant was also investigated in order to analyze the ML-236B biosynthetic pathway. The molecular organization of the gene cluster and proposed functions for the ML-236B biosynthetic genes in P. citrinum are described. << Less
Mol. Genet. Genomics 267:636-646(2002) [PubMed] [EuropePMC]
This publication is cited by 6 other entries.