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Identification
YMDB IDYMDB00872
Name(S)-3-hydroxy-3-methylglutaryl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-Hydroxy-3-methylglutaryl-CoA, also known as hydroxymethylglutaroyl coenzyme A or HMG-CoA, 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. Thus, 3-hydroxy-3-methylglutaryl-CoA is considered to be a fatty ester lipid molecule. 3-Hydroxy-3-methylglutaryl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • (S)-3-Hydroxy-3-methylglutaryl-CoA
  • (S)-3-hydroxy-3-methylglutaryl-Coenzyme A
  • 3-hydroxy-3-methyl-Glutaryl-CoA
  • 3-hydroxy-3-methyl-Glutaryl-Coenzyme A
  • 3-hydroxy-3-methylglutaryl-coa
  • 3-Hydroxy-3-methylglutaryl-coenzyme A
  • hmg-coa
  • HMG-Coenzyme A
  • hydroxymethylglutaroyl coenzyme a
  • Hydroxymethylglutaryl-CoA
  • Hydroxymethylglutaryl-Coenzyme A
  • S-(Hydrogen 3-hydroxy-3-methylglutaryl)coenzyme A
  • S-(Hydrogen 3-hydroxy-3-methylpentanedioate
  • S-(Hydrogen 3-hydroxy-3-methylpentanedioate) coenzyme A
  • S-(Hydrogen 3-hydroxy-3-methylpentanedioic acid
  • (3S)-3-Hydroxy-3-methylglutaryl-coenzyme A
  • (3S)-3-Hydroxy-3-methylglutaryl-CoA
  • (S)-3-Hydroxy-3-methylglutaryl coenzyme A
  • 3-Hydroxy-3-methylglutaryl CoA
  • 3-Hydroxy-3-methylglutaryl coenzyme A
  • Hydroxymethylglutaryl CoA
  • Hydroxymethylglutaryl coenzyme A
  • beta-Hydroxy-beta-methylglutaryl CoA
  • beta-Hydroxy-beta-methylglutaryl-CoA
  • beta-Hydroxy-beta-methylglutaryl-coenzyme A
  • Β-hydroxy-β-methylglutaryl CoA
  • Β-hydroxy-β-methylglutaryl-CoA
  • Β-hydroxy-β-methylglutaryl-coenzyme A
CAS number1553-55-5
WeightAverage: 911.659
Monoisotopic: 911.157467109
InChI KeyCABVTRNMFUVUDM-VRHQGPGLSA-N
InChIInChI=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
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 IUPAC NameHMG-CoA
Chemical FormulaC27H44N7O20P3S
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
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Cholesterol biosynthesis and metabolism CE(10:0)PW002545 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(12:0)PW002548 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(14:0)PW002544 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(16:0)PW002550 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(18:0)PW002551 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Butanoate metabolismec00650 Map00650
Steroid biosynthesisec00100 Map00100
Synthesis and degradation of ketone bodiesec00072 Map00072
Terpenoid backbone biosynthesisec00900 Map00900
Valine, leucine and isoleucine degradationec00280 Map00280
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0891000250-052d51ef28faa9ab5b73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0971100000-dc16942c0a4531c8cb60JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1950000000-12dcb50a3caaf20a9aa5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00o4-4901031462-49fbf273ff8df18347bbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900110010-0be1f0212b5d814ea24cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-fffa063c59d4fcd54e7aJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Middleton, B. (1972). "The kinetic mechanism of 3-hydroxy-3-methylglutaryl-coenzyme A synthase from baker's yeast." Biochem J 126:35-47.4561618
  • Serafin, J., Kreczko, R. (1979). "[Use of transcondylar and metaphyseal osteotomies of the tibia in the treatment of degenerative changes of the knee joint]." Chir Narzadow Ruchu Ortop Pol 44:141-148.456161
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15467
HMDB IDHMDB01375
Pubchem Compound ID50986137
Kegg IDC00356
ChemSpider ID392859
FOODB IDFDB030158
Wikipedia3-hydroxy-3-methylglutaryl-CoA
BioCyc ID3-HYDROXY-3-METHYL-GLUTARYL-COA

Enzymes

General function:
Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase
Gene Name:
ERG13
Uniprot ID:
P54839
Molecular weight:
55013.10156
Reactions
Acetyl-CoA + H(2)O + acetoacetyl-CoA → (S)-3-hydroxy-3-methylglutaryl-CoA + CoA.