Bovine Metabolome Database: Showing metabocard for 3-Hydroxy-3-methylglutaryl-CoA (BMDB0001375)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:44:58 UTC

Update Date

2020-05-21 16:28:46 UTC

BMDB ID

BMDB0001375

Secondary Accession Numbers

BMDB01375

Metabolite Identification

Common Name

3-Hydroxy-3-methylglutaryl-CoA

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

Value	Source
(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

Chemical Formula

C₂₇H₄₄N₇O₂₀P₃S

Average Molecular Weight

911.659

Monoisotopic Molecular Weight

911.157467109

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 Name

HMG-CoA

CAS Registry Number

1553-55-5

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

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

InChI Key

CABVTRNMFUVUDM-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.

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 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane
Mitochondria
Peroxisome

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0891000250-052d51ef28faa9ab5b73	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0971100000-dc16942c0a4531c8cb60	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1950000000-12dcb50a3caaf20a9aa5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00o4-4901031462-49fbf273ff8df18347bb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3900110010-0be1f0212b5d814ea24c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-fffa063c59d4fcd54e7a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dm-0000000094-b818de142848216a6af3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4u-9500001521-8d0d8c41c4c284cc696f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004m-9202503430-001456d7b42e54584702	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000169-47d0ed82d5acca38b9e0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002r-1500000391-9d63a322b718612b8587	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0011900000-766a56d8ca4793434590	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane
Mitochondria
Peroxisome

Biospecimen Locations

Adrenal Gland
Fibroblasts
Intestine

Pathways

Name	SMPDB/Pathwhiz	KEGG
Butyrate Metabolism		Not Available
Ketone Body Metabolism		Not Available
Steroid Biosynthesis		Not Available
Valine, Leucine, and Isoleucine Degradation		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adrenal Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001375

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

3-HYDROXY-3-METHYL-GLUTARYL-COA

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

445127

PDB ID

Not Available

ChEBI ID

15467

References

Synthesis Reference

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Hydroxymethylglutaryl-CoA synthase, mitochondrial

General function:: Lipid transport and metabolism
Specific function:: This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:: HMGCS2
Uniprot ID:: Q2KIE6
Molecular weight:: 56895.0

Reactions

Acetyl-CoA + Acetoacetyl-CoA + Water → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A	details

Enzyme Details

2. Hydroxymethylglutaryl-CoA lyase, mitochondrial

General function:: Amino acid transport and metabolism
Specific function:: Mitochondrial 3-hydroxymethyl-3-methylglutaryl-CoA lyase that catalyzes a cation-dependent cleavage of (S)-3-hydroxy-3-methylglutaryl-CoA into acetyl-CoA and acetoacetate, a key step in ketogenesis. Terminal step in leucine catabolism. Ketone bodies (beta-hydroxybutyrate, acetoacetate and acetone) are essential as an alternative source of energy to glucose, as lipid precursors and as regulators of metabolism.
Gene Name:: HMGCL
Uniprot ID:: Q29448
Molecular weight:: 34168.0

Reactions

3-Hydroxy-3-methylglutaryl-CoA → Acetoacetic acid + Acetyl-CoA	details
3-Hydroxy-3-methylglutaryl-CoA → Acetyl-CoA	details
3-Hydroxy-3-methylglutaryl-CoA → Acetoacetic acid	details

Enzyme Details

3. 3-hydroxy-3-methylglutaryl-coenzyme A reductase

General function:: Lipid transport and metabolism
Specific function:: Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.
Gene Name:: HMGCR
Uniprot ID:: A7Z064
Molecular weight:: 97727.0

Reactions

3-Hydroxy-3-methylglutaryl-CoA + NADPH → Mevalonic acid + NADP + Coenzyme A	details

Enzyme Details

4. Enoyl-CoA hydratase domain-containing protein 2, mitochondrial

General function:: Not Available
Specific function:: Not Available
Gene Name:: ECHDC2
Uniprot ID:: Q2TBT3
Molecular weight:: 31604.0

Reactions

3-Methylglutaconyl-CoA + Water → 3-Hydroxy-3-methylglutaryl-CoA	details

Showing metabocard for 3-Hydroxy-3-methylglutaryl-CoA (BMDB0001375)

Structure for BMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)

Enzymes

Reactions

Reactions

Reactions

Reactions