(S)-3-hydroxy-3-methylglutaryl-CoA (CED0020841)

Record Information
Version1.0
Creation Date2016-05-27 01:41:32 UTC
Update Date2026-08-22 07:51:19 UTC
Accession NumberCHEM041769
Identification
Common Name(S)-3-hydroxy-3-methylglutaryl-CoA
ClassSmall Molecule
Description
(S)-3-hydroxy-3-methylglutaryl-CoA belongs to the fatty acyl thioesters, a subclass of fatty acyls within the organic compounds. This compound has the chemical formula C27H44N7O20P3S. With an average molecular weight of 911.66 g/mol, (S)-3-hydroxy-3-methylglutaryl-CoA is a heavy molecule. The substance has been identified in or released from three recorded sources. These include food, food processing, and cookware, specifically in the processing of fish and the preparation of vinegar. Additionally, it is associated with electrical and electronic equipment, specifically antennas.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3S)-3-Hydroxy-3-methylglutaryl-coenzyme AChEBI
(S)-3-Hydroxy-3-methylglutaryl-CoAChEBI
(S)-3-Hydroxy-3-methylglutaryl-coenzyme AChEBI
HMG-CoAChEBI
HMG-coenzyme AChEBI
Hydroxymethylglutaroyl coenzyme AChEBI
Hydroxymethylglutaryl-CoAChEBI
(3S)-3-Hydroxy-3-methylglutaryl-CoAHMDB
(S)-3-Hydroxy-3-methylglutaryl coenzyme AHMDB
3-Hydroxy-3-methylglutaryl CoAHMDB
3-Hydroxy-3-methylglutaryl coenzyme AHMDB
Hydroxymethylglutaryl CoAHMDB
Hydroxymethylglutaryl coenzyme AHMDB
beta-Hydroxy-beta-methylglutaryl CoAHMDB
beta-Hydroxy-beta-methylglutaryl-CoAHMDB
beta-Hydroxy-beta-methylglutaryl-coenzyme AHMDB
Β-hydroxy-β-methylglutaryl CoAHMDB
Β-hydroxy-β-methylglutaryl-CoAHMDB
Β-hydroxy-β-methylglutaryl-coenzyme AHMDB
3-Hydroxy-3-methylglutaryl-CoAChEBI, KEGG
Chemical FormulaC27H44N7O20P3S
Average Molecular Mass911.659 g/mol
Monoisotopic Mass911.157 g/mol
CAS Registry Number1553-55-5
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
Traditional NameHMG-CoA
SMILESC[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
InChI IdentifierInChI=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
InChI KeyCABVTRNMFUVUDM-VRHQGPGLSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent(S)-3-hydroxy-3-alkylglutaryl CoAs
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.1 g/LALOGPS
logP-0.53ALOGPS
logP-6.4ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)3.81ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area421.16 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity193.7 m³·mol⁻¹ChemAxon
Polarizability82.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000l-0891000250-052d51ef28faa9ab5b73Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0971100000-dc16942c0a4531c8cb60Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-1950000000-12dcb50a3caaf20a9aa5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00o4-4901031462-49fbf273ff8df18347bbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-3900110010-0be1f0212b5d814ea24cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-057i-6900100000-fffa063c59d4fcd54e7aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dm-0000000094-b818de142848216a6af3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4u-9500001521-8d0d8c41c4c284cc696fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004m-9202503430-001456d7b42e54584702Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0000000169-47d0ed82d5acca38b9e0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002r-1500000391-9d63a322b718612b8587Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0011900000-766a56d8ca4793434590Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity ValuesNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
506AntennasElectrical & Electronic EquipmentNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
1,4-dihydroxy-2-naphthoyl-CoA synthase structureClick to view 3D structure1,4-dihydroxy-2-naphthoyl-CoA synthaseP9WNP5Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)0.0778492
Click to view 3D structureAminoglycoside acetyltransferaseQ70E71Enterococcus duransPredicted (SEA)0.0778492
N-alpha-acetyltransferase 40 structureClick to view 3D structureN-alpha-acetyltransferase 40Q86UY6HumansPredicted (SEA)0.233548
Click to view 3D structureHistone acetyltransferase GCN5Q245K9Tetrahymena thermophila (strain SB210)Predicted (SEA)0.544945
P2Y purinoceptor 1 structureClick to view 3D structureP2Y purinoceptor 1P47900HumansPredicted (SEA)10.5875
Click to view 3D structureHeat shock cognate 71 kDa proteinP19120Bos taurusPredicted (SEA)5.13805
Click to view 3D structureSensor protein kinase WalKQ9RDT3Staphylococcus aureusPredicted (SEA)5.13805
P2X purinoceptor 1 structureClick to view 3D structureP2X purinoceptor 1P51575HumansPredicted (SEA)5.52729
Click to view 3D structureP2Y purinoceptor 2P41231HumansPredicted (SEA)9.34191
P2X purinoceptor 3 structureClick to view 3D structureP2X purinoceptor 3P56373HumansPredicted (SEA)5.99439
Click to view 3D structureS-adenosylmethionine synthase isoform type-2P18298Rattus norvegicusPredicted (SEA)3.81461
ADP-ribose glycohydrolase MACROD1 structureClick to view 3D structureADP-ribose glycohydrolase MACROD1Q9BQ69HumansPredicted (SEA)4.7488
ADP-ribose glycohydrolase MACROD2 structureClick to view 3D structureADP-ribose glycohydrolase MACROD2A1Z1Q3HumansPredicted (SEA)4.7488
Click to view 3D structureP2Y purinoceptor 1P49652Meleagris gallopavoPredicted (SEA)7.39568
Click to view 3D structureGTP:AMP phosphotransferase AK3, mitochondrialP29411Rattus norvegicusPredicted (SEA)4.43741
Click to view 3D structureGlycylpeptide N-tetradecanoyltransferaseP14743Saccharomyces cerevisiae S288cPredicted (SEA)0.0778492
Click to view 3D structureP2Y purinoceptor 12Q9EPX4Rattus norvegicusPredicted (SEA)5.13805
Click to view 3D structureP2Y purinoceptor 11Q96G91HumansPredicted (SEA)5.44945
P2X purinoceptor 4 structureClick to view 3D structureP2X purinoceptor 4Q99571HumansPredicted (SEA)3.89246
Click to view 3D structureP2Y purinoceptor 1P49651Rattus norvegicusPredicted (SEA)5.3716
Click to view 3D structure6-phosphogluconate dehydrogenase, decarboxylatingP85968Rattus norvegicusPredicted (SEA)1.24559
Click to view 3D structureGlutamine--tRNA ligaseP00962Escherichia coli (strain K12)Predicted (SEA)4.28171
Click to view 3D structureAdenylate kinase 2, mitochondrialP29410Rattus norvegicusPredicted (SEA)4.35956
Click to view 3D structureGlutamate dehydrogenase 1, mitochondrialP00366Bos taurusPredicted (SEA)3.50322
Ribonuclease pancreatic structureClick to view 3D structureRibonuclease pancreaticP07998HumansPredicted (SEA)2.49118
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0001375
FooDB IDFDB030158
Phenol Explorer IDNot Available
KNApSAcK IDC00007270
BiGG IDNot Available
BioCyc ID3-HYDROXY-3-METHYL-GLUTARYL-COA
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID392859
ChEBI ID15467
PubChem Compound ID445127
Kegg Compound IDC00356
YMDB IDYMDB00872
ECMDB IDM2MDB004267
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
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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