Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-27 01:41:32 UTC |
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Update Date | 2016-11-09 01:22:32 UTC |
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Accession Number | CHEM041769 |
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Identification |
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Common Name | (S)-3-hydroxy-3-methylglutaryl-CoA |
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Class | Small Molecule |
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Description | |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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(3S)-3-Hydroxy-3-methylglutaryl-coenzyme A | ChEBI | (S)-3-Hydroxy-3-methylglutaryl-CoA | ChEBI | (S)-3-Hydroxy-3-methylglutaryl-coenzyme A | ChEBI | HMG-CoA | ChEBI | HMG-coenzyme A | ChEBI | Hydroxymethylglutaroyl coenzyme A | ChEBI | Hydroxymethylglutaryl-CoA | ChEBI | (3S)-3-Hydroxy-3-methylglutaryl-CoA | HMDB | (S)-3-Hydroxy-3-methylglutaryl coenzyme A | HMDB | 3-Hydroxy-3-methylglutaryl CoA | HMDB | 3-Hydroxy-3-methylglutaryl coenzyme A | HMDB | Hydroxymethylglutaryl CoA | HMDB | Hydroxymethylglutaryl coenzyme A | HMDB | beta-Hydroxy-beta-methylglutaryl CoA | HMDB | beta-Hydroxy-beta-methylglutaryl-CoA | HMDB | beta-Hydroxy-beta-methylglutaryl-coenzyme A | HMDB | Β-hydroxy-β-methylglutaryl CoA | HMDB | Β-hydroxy-β-methylglutaryl-CoA | HMDB | Β-hydroxy-β-methylglutaryl-coenzyme A | HMDB | 3-Hydroxy-3-methylglutaryl-CoA | ChEBI, KEGG |
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Chemical Formula | C27H44N7O20P3S |
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Average Molecular Mass | 911.659 g/mol |
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Monoisotopic Mass | 911.157 g/mol |
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CAS Registry Number | Not Available |
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IUPAC Name | (3S)-5-[(2-{3-[(2R)-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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Traditional Name | HMG-CoA |
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SMILES | C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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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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-VRHQGPGLSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as (s)-3-hydroxy-3-alkylglutaryl coas. These are 3-hydroxy-3-alkylglutaryl-CoAs where the 3-hydroxy-3-alkylglutaryl component has (S)-configuration. |
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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 | (S)-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 | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000l-0891000250-052d51ef28faa9ab5b73 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0971100000-dc16942c0a4531c8cb60 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1950000000-12dcb50a3caaf20a9aa5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00o4-4901031462-49fbf273ff8df18347bb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-3900110010-0be1f0212b5d814ea24c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-057i-6900100000-fffa063c59d4fcd54e7a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03dm-0000000094-b818de142848216a6af3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4u-9500001521-8d0d8c41c4c284cc696f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004m-9202503430-001456d7b42e54584702 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0000000169-47d0ed82d5acca38b9e0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002r-1500000391-9d63a322b718612b8587 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-0011900000-766a56d8ca4793434590 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0001375 |
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FooDB ID | FDB030158 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | C00007270 |
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BiGG ID | Not Available |
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BioCyc ID | 3-HYDROXY-3-METHYL-GLUTARYL-COA |
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METLIN ID | Not Available |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | 392859 |
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ChEBI ID | 15467 |
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PubChem Compound ID | 445127 |
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Kegg Compound ID | C00356 |
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YMDB ID | YMDB00872 |
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ECMDB ID | M2MDB004267 |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. Williamson I P; Rodwell V W Isolation and purification of 3-hydroxy-3-methylglutaryl-coenzyme A by ion-exchange chromatography. Journal of lipid research (1981), 22(1), 184-7. | 2. Li X, Liu L, Tupper JC, Bannerman DD, Winn RK, Sebti SM, Hamilton AD, Harlan JM: Inhibition of protein geranylgeranylation and RhoA/RhoA kinase pathway induces apoptosis in human endothelial cells. J Biol Chem. 2002 May 3;277(18):15309-16. Epub 2002 Feb 11. | 3. Mital BK, Garg SK: Anticarcinogenic, hypocholesterolemic, and antagonistic activities of Lactobacillus acidophilus. Crit Rev Microbiol. 1995;21(3):175-214. | 4. Nozaki S, Nakagawa T, Nakata A, Yamashita S, Kameda-Takemura K, Nakamura T, Keno Y, Tokunaga K, Matsuzawa Y: Effects of pravastatin on plasma and urinary mevalonate concentrations in subjects with familial hypercholesterolaemia: a comparison of morning and evening administration. Eur J Clin Pharmacol. 1996;49(5):361-4. | 5. Ubels FL, Muntinga JH, van Doormaal JJ, Reitsma WD, Smit AJ: Effects of initial and long-term lipid-lowering therapy on vascular wall characteristics. Atherosclerosis. 2001 Jan;154(1):155-61. | 6. Huang L, Wang Y, Grimm S: ATP-dependent transport of rosuvastatin in membrane vesicles expressing breast cancer resistance protein. Drug Metab Dispos. 2006 May;34(5):738-42. Epub 2006 Jan 13. | 7. Sato T, Oouchi M, Nagakubo H, Chiba T, Ogawa S, Sato C, Sugimura K, Fukuda M: Effect of pravastatin on plasma ketone bodies in diabetics with hypercholesterolemia. Tohoku J Exp Med. 1998 May;185(1):25-9. | 8. Son BK, Kozaki K, Iijima K, Eto M, Kojima T, Ota H, Senda Y, Maemura K, Nakano T, Akishita M, Ouchi Y: Statins protect human aortic smooth muscle cells from inorganic phosphate-induced calcification by restoring Gas6-Axl survival pathway. Circ Res. 2006 Apr 28;98(8):1024-31. Epub 2006 Mar 23. | 9. Gianni L, Di Padova F, Zuin M, Podda M: Bile acid-induced inhibition of the lymphoproliferative response to phytohemagglutinin and pokeweed mitogen: an in vitro study. Gastroenterology. 1980 Feb;78(2):231-5. | 10. Jenke HS, Lowel M, Berndt J: Effect of alterations in vitro and in vivo of the cholesterol content in rat liver microsomes on the activity of 3-hydroxy-3-methylglutaryl-CoA reductase. Hoppe Seylers Z Physiol Chem. 1983 Feb;364(2):135-40. | 11. Naseem SM, Heald FP: Sex mediated lipid metabolism in human aortic smooth muscle cells. Biochem Biophys Res Commun. 1987 Apr 14;144(1):284-91. | 12. Wysocki SJ, Wilkinson SP, Hahnel R, Wong CY, Panegyres PK: 3-Hydroxy-3-methylglutaric aciduria, combined with 3-methylglutaconic aciduria. Clin Chim Acta. 1976 Aug 2;70(3):399-406. | 13. Knight BL, Patel DD, Soutar AK: The regulation of 3-hydroxy-3-methylglutaryl-CoA reductase activity, cholesterol esterification and the expression of low-density lipoprotein receptors in cultured monocyte-derived macrophages. Biochem J. 1983 Feb 15;210(2):523-32. | 14. Lange Y, Ye J, Steck TL: Activation of membrane cholesterol by displacement from phospholipids. J Biol Chem. 2005 Oct 28;280(43):36126-31. Epub 2005 Aug 29. | 15. Martin J, Denver R, Bailey M, Krum H: In vitro inhibitory effects of atorvastatin on cardiac fibroblasts: implications for ventricular remodelling. Clin Exp Pharmacol Physiol. 2005 Sep;32(9):697-701. | 16. Plotkin D, Miller S, Nakajima S, Peskin E, Burkman R, Richardson D, Mitchel Y, Waldstreicher J, Liu M, Shapiro D, Santoro N: Lowering low density lipoprotein cholesterol with simvastatin, a hydroxy-3-methylglutaryl-coenzyme a reductase inhibitor, does not affect luteal function in premenopausal women. J Clin Endocrinol Metab. 2002 Jul;87(7):3155-61. | 17. Gil G, Smith JR, Goldstein JL, Brown MS: Optional exon in the 5'-untranslated region of 3-hydroxy-3-methylglutaryl coenzyme A synthase gene: conserved sequence and splicing pattern in humans and hamsters. Proc Natl Acad Sci U S A. 1987 Apr;84(7):1863-6. | 18. Freeman MR, Solomon KR: Cholesterol and prostate cancer. J Cell Biochem. 2004 Jan 1;91(1):54-69. | 19. https://www.ncbi.nlm.nih.gov/pubmed/?term=20640529 | 20. https://www.ncbi.nlm.nih.gov/pubmed/?term=4052443 | 21. https://www.ncbi.nlm.nih.gov/pubmed/?term=6135457 | 22. https://www.ncbi.nlm.nih.gov/pubmed/?term=9160173 |
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