(S)-3-hydroxy-3-methylglutaryl-CoA (YMDB00872)

Identification

YMDB ID

YMDB00872

Name

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

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

3-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

MOL SDF PDB SMILES InChI

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 number

1553-55-5

Weight

Average: 911.659
Monoisotopic: 911.157467109

InChI Key

CABVTRNMFUVUDM-VRHQGPGLSA-N

InChI

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

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 Name

HMG-CoA

Chemical Formula

C₂₇H₄₄N₇O₂₀P₃S

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

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

3-hydroxy fatty acyl-CoA (CHEBI:15467 )
3-hydroxy-3-methylglutaryl-CoA (CHEBI:15467 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	4.1 g/L	ALOGPS
logP	-0.53	ALOGPS
logP	-6.4	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	3.81	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	421.16 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	193.7 m³·mol⁻¹	ChemAxon
Polarizability	82.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Cholesterol biosynthesis and metabolism CE(10:0)	PW002545
Cholesterol biosynthesis and metabolism CE(12:0)	PW002548
Cholesterol biosynthesis and metabolism CE(14:0)	PW002544
Cholesterol biosynthesis and metabolism CE(16:0)	PW002550
Cholesterol biosynthesis and metabolism CE(18:0)	PW002551

KEGG Pathways

Butanoate metabolism	ec00650
Steroid biosynthesis	ec00100
Synthesis and degradation of ketone bodies	ec00072
Terpenoid backbone biosynthesis	ec00900
Valine, leucine and isoleucine degradation	ec00280

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0891000250-052d51ef28faa9ab5b73	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0971100000-dc16942c0a4531c8cb60	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1950000000-12dcb50a3caaf20a9aa5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00o4-4901031462-49fbf273ff8df18347bb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3900110010-0be1f0212b5d814ea24c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-fffa063c59d4fcd54e7a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dm-0000000094-b818de142848216a6af3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4u-9500001521-8d0d8c41c4c284cc696f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004m-9202503430-001456d7b42e54584702	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000169-47d0ed82d5acca38b9e0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002r-1500000391-9d63a322b718612b8587	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0011900000-766a56d8ca4793434590	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	15467
HMDB ID	HMDB01375
Pubchem Compound ID	50986137
Kegg ID	C00356
ChemSpider ID	392859
FOODB ID	FDB030158
Wikipedia	3-hydroxy-3-methylglutaryl-CoA
BioCyc ID	3-HYDROXY-3-METHYL-GLUTARYL-COA

Enzymes

Protein Details

1. Hydroxymethylglutaryl-CoA synthase

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.

(S)-3-hydroxy-3-methylglutaryl-CoA (YMDB00872)

Structure for #<Compound:0xaf0f364c>

Enzymes

Reactions