Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:16:21 UTC |
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Update date | 2015-07-21 06:57:16 UTC |
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Primary ID | FDB022587 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 3-Hydroxy-3-methylglutaryl-CoA |
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Description | 3-hydroxy-3-methylglutaryl CoA (HMG-CoA) is formed when Acetyl-CoA condenses with acetoacetyl-CoA in a reaction that is catalyzed by the enzyme HMG-CoA synthase in the mevalonate pathway or mevalonate-dependent (MAD) route, an important cellular metabolic pathway present in virtually all organisms. HMG-CoA reductase (EC 1.1.1.34) inhibitors, more commonly known as statins, are cholesterol-lowering drugs that have been widely used for many years to reduce the incidence of adverse cardiovascular events. HMG-CoA reductase catalyzes the rate-limiting step in the mevalonate pathway and these agents lower cholesterol by inhibiting its synthesis in the liver and in peripheral tissues. Androgen also stimulates lipogenesis in human prostate cancer cells directly by increasing transcription of the fatty acid synthase and HMG-CoA-reductase genes. (PMID: 14689582) [HMDB] |
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CAS Number | 1553-55-5 |
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Structure | |
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Synonyms | Synonym | Source |
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(S)-3-Hydroxy-3-methylglutaryl-CoA | HMDB | (S)-3-Hydroxy-3-methylglutaryl-coenzyme A | HMDB | 3-Hydroxy-3-methyl-glutaryl-CoA | HMDB | 3-Hydroxy-3-methyl-glutaryl-coenzyme A | HMDB | 3-Hydroxy-3-methylglutaryl-coenzyme A | HMDB | HMG-CoA | HMDB | HMG-coenzyme A | HMDB | Hydroxymethylglutaroyl coenzyme A | HMDB | Hydroxymethylglutaryl-CoA | HMDB | Hydroxymethylglutaryl-coenzyme A | HMDB | S-(Hydrogen 3-hydroxy-3-methylglutaryl)coenzyme A | HMDB | S-(Hydrogen 3-hydroxy-3-methylpentanedioate | HMDB | S-(Hydrogen 3-hydroxy-3-methylpentanedioate) coenzyme A | HMDB | S-(Hydrogen 3-hydroxy-3-methylpentanedioic acid | HMDB | 3-Hydroxy-3-methylglutaryl-coenzyme A, (S)-isomer | HMDB | 3-Hydroxy-3-methylglutaryl-coenzyme A, mono(3-oxobutanoate) | HMDB | (S)-3-hydroxy-3-methylglutaryl-CoA | hmdb | (S)-3-hydroxy-3-methylglutaryl-Coenzyme A | hmdb | 3-hydroxy-3-methyl-Glutaryl-CoA | hmdb | 3-hydroxy-3-methyl-Glutaryl-Coenzyme A | hmdb | 3-hydroxy-3-methylglutaryl-CoA | hmdb | HMG-Coenzyme A | hmdb | Hydroxymethylglutaryl-Coenzyme A | hmdb |
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Predicted Properties | |
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Chemical Formula | C27H44N7O20P3S |
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IUPAC name | (3S)-5-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-3-hydroxy-3-methyl-5-oxopentanoic acid |
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InChI Identifier | InChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21?,25-,27+/m1/s1 |
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InChI Key | CABVTRNMFUVUDM-MIGRVSMKSA-N |
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Isomeric SMILES | C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N |
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Average Molecular Weight | 911.659 |
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Monoisotopic Molecular Weight | 911.157467109 |
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Classification |
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Description | Belongs to the class of organic compounds known as 3-hydroxy-3-alkylglutaryl coas. These are alpha, omega dicarboxyacyl-CoA that result from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-alkylglutaric acid. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acyl thioesters |
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Direct Parent | 3-hydroxy-3-alkylglutaryl CoAs |
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Alternative Parents | |
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Substituents | - Coenzyme a or derivatives
- Purine ribonucleoside 3',5'-bisphosphate
- Purine ribonucleoside bisphosphate
- Purine ribonucleoside diphosphate
- Ribonucleoside 3'-phosphate
- Pentose phosphate
- Pentose-5-phosphate
- Beta amino acid or derivatives
- Glycosyl compound
- N-glycosyl compound
- 6-aminopurine
- Monosaccharide phosphate
- Organic pyrophosphate
- Pentose monosaccharide
- Imidazopyrimidine
- Purine
- Monoalkyl phosphate
- Aminopyrimidine
- Alkyl phosphate
- Imidolactam
- N-acyl-amine
- N-substituted imidazole
- Organic phosphoric acid derivative
- Monosaccharide
- Fatty amide
- Pyrimidine
- Phosphoric acid ester
- Tetrahydrofuran
- Tertiary alcohol
- Imidazole
- Heteroaromatic compound
- Azole
- Secondary alcohol
- Thiocarboxylic acid ester
- Amino acid
- Carboxamide group
- Amino acid or derivatives
- Carbothioic s-ester
- Secondary carboxylic acid amide
- Organoheterocyclic compound
- Sulfenyl compound
- Thiocarboxylic acid or derivatives
- Azacycle
- Oxacycle
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Primary amine
- Hydrocarbon derivative
- Carbonyl group
- Organosulfur compound
- Organopnictogen compound
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Alcohol
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Not Available |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000l-0891000250-052d51ef28faa9ab5b73 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0971100000-dc16942c0a4531c8cb60 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1950000000-12dcb50a3caaf20a9aa5 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00o4-4901031462-49fbf273ff8df18347bb | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-3900110010-0be1f0212b5d814ea24c | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-057i-6900100000-fffa063c59d4fcd54e7a | 2016-08-03 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 388357 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C00356 |
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Pubchem Compound ID | 439218 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15467 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB01375 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 34727 |
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KNApSAcK ID | Not Available |
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HET ID | 1DQ9 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | 3-hydroxy-3-methylglutaryl-CoA |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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3-hydroxy-3-methylglutaryl-coenzyme A reductase | HMGCR | P04035 | Hydroxymethylglutaryl-CoA lyase, mitochondrial | HMGCL | P35914 | Hydroxymethylglutaryl-CoA synthase, mitochondrial | HMGCS2 | P54868 | Hydroxymethylglutaryl-CoA synthase, cytoplasmic | HMGCS1 | Q01581 | Methylglutaconyl-CoA hydratase, mitochondrial | AUH | Q13825 | 3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmic | HMGCLL1 | Q8TB92 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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