ChemFOnt: Showing chemical card for 3-Hydroxy-3-methylglutaryl-CoA (CFc000001063)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:37 UTC

Chemfont ID

CFc000001063

Molecule Identification

Common Name

3-Hydroxy-3-methylglutaryl-CoA

Definition

3-Hydroxy-3-methylglutaryl-CoA (HMG-CoA) (CAS: 1553-55-5) is formed when acetyl-CoA condenses with acetoacetyl-CoA in a reaction that is catalyzed by the enzyme HMG-CoA synthase in the mevalonate pathway or mevalonate-dependent (MAD) route, an important cellular metabolic pathway present in virtually all organisms. HMG-CoA reductase (EC 1.1.1.34) inhibitors, more commonly known as statins, are cholesterol-lowering drugs that have been widely used for many years to reduce the incidence of adverse cardiovascular events. HMG-CoA reductase catalyzes the rate-limiting step in the mevalonate pathway and these agents lower cholesterol by inhibiting its synthesis in the liver and in peripheral tissues. Androgen also stimulates lipogenesis in human prostate cancer cells directly by increasing transcription of the fatty acid synthase and HMG-CoA-reductase genes (PMID: 14689582 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-3-Hydroxy-3-methylglutaryl-CoA	HMDB
(S)-3-Hydroxy-3-methylglutaryl-coenzyme A	HMDB
3-Hydroxy-3-methyl-glutaryl-CoA	HMDB
3-Hydroxy-3-methyl-glutaryl-coenzyme A	HMDB
3-Hydroxy-3-methylglutaryl-coenzyme A	HMDB
HMG-CoA	HMDB
HMG-coenzyme A	HMDB
Hydroxymethylglutaroyl coenzyme A	HMDB
Hydroxymethylglutaryl-CoA	HMDB
Hydroxymethylglutaryl-coenzyme A	HMDB
S-(Hydrogen 3-hydroxy-3-methylglutaryl)coenzyme A	HMDB
S-(Hydrogen 3-hydroxy-3-methylpentanedioate	HMDB
S-(Hydrogen 3-hydroxy-3-methylpentanedioate) coenzyme A	HMDB
S-(Hydrogen 3-hydroxy-3-methylpentanedioic acid	HMDB
3-Hydroxy-3-methylglutaryl-coenzyme A, (S)-isomer	HMDB
3-Hydroxy-3-methylglutaryl-coenzyme A, mono(3-oxobutanoate)	HMDB

Chemical Formula

C₂₇H₄₄N₇O₂₀P₃S

Average Molecular Weight

911.659

Monoisotopic Molecular Weight

911.157467109

IUPAC Name

(3S)-5-{[2-(3-{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

(3S)-5-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-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

CAS Registry Number

26926-09-0

SMILES

C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)C(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-MIGRVSMKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-hydroxy-3-alkylglutaryl coas. These are alpha, omega dicarboxyacyl-CoA that result from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-alkylglutaric acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

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

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0001375)
Mitochondrion (HMDB: HMDB0001375)
Peroxisome (HMDB: HMDB0001375)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0001375)

Fibroblasts (HMDB: HMDB0001375)

Organ

Gland

Adrenal Gland (HMDB: HMDB0001375)
Adrenal Gland (HMDB: HMDB0001375)

Intestine (HMDB: HMDB0001375)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0001375)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001375)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001375)

Source

Endogenous

Endogenous (HMDB: HMDB0001375)

Animal

Animal (HMDB: HMDB0001375)

Exogenous

Food

Food (HMDB: HMDB0001375)

Exogenous (HMDB: HMDB0001375)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Valine, Leucine, and Isoleucine Degradation (HMDB: HMDB0001375)
Butyrate Metabolism (HMDB: HMDB0001375)
Ketone Body Metabolism (HMDB: HMDB0001375)
Steroid Biosynthesis (HMDB: HMDB0001375)
Fatty Acid Metabolism (HMDB: HMDB0001375)
Leucine Degradation (PathBank: SMP0002433)
Mevalonate Pathway (PathBank: SMP0121209)
Steroid Biosynthesis (PathBank: SMP0002381)
Ketone Body Metabolism (PathBank: SMP0002383)
Terpenoid Backbone Biosynthesis (PathBank: SMP0002384)
Cholesterol Biosynthesis and Metabolism CE(14:0) (PathBank: SMP0002435)
Cholesterol Biosynthesis and Metabolism CE(10:0) (PathBank: SMP0002436)
Cholesterol Biosynthesis and Metabolism CE(12:0) (PathBank: SMP0002438)
Cholesterol Biosynthesis and Metabolism CE(16:0) (PathBank: SMP0002440)
Cholesterol Biosynthesis and Metabolism CE(18:0) (PathBank: SMP0002441)
Butanoate metabolism (PathBank: SMP0012467)
Cholesterol Biosynthesis and Metabolism (PathBank: SMP0070041)

Disease pathway

3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency (HMDB: HMDB0001375)
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120439)
Smith-Lemli-Opitz Syndrome (SLOS) (PathBank: SMP0120515)
Methylmalonate Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120523)
Isovaleric Acidemia (PathBank: SMP0120589)
3-Methylglutaconic Aciduria Type I (PathBank: SMP0120663)
Beta-Ketothiolase Deficiency (PathBank: SMP0120679)
Desmosterolosis (PathBank: SMP0120692)
Mevalonic Aciduria (PathBank: SMP0120794)
3-Hydroxyisobutyric Aciduria (PathBank: SMP0120806)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (HMDB: HMDB0001375)
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I (PathBank: SMP0120441)
3-Methylglutaconic Aciduria Type IV (PathBank: SMP0120444)
Lysosomal Acid Lipase Deficiency (Wolman Disease) (PathBank: SMP0120512)
Methylmalonic Aciduria (PathBank: SMP0120525)
Cholesteryl Ester Storage Disease (PathBank: SMP0120573)
3-Methylglutaconic Aciduria Type III (PathBank: SMP0120664)
CHILD Syndrome (PathBank: SMP0120464)
Maple Syrup Urine Disease (PathBank: SMP0120516)
Propionic Acidemia (PathBank: SMP0120537)
Wolman Disease (PathBank: SMP0120576)
Isobutyryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120588)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (PathBank: SMP0120685)
Isovaleric Aciduria (PathBank: SMP0120723)
Hypercholesterolemia (PathBank: SMP0120769)
Hyper-IgD Syndrome (PathBank: SMP0120574)
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency (PathBank: SMP0120586)
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0000137)

Drug action pathway

Alendronate Action Pathway (HMDB: HMDB0001375)
Ibandronate Action Pathway (PathBank: SMP0000079)
Simvastatin Action Pathway (PathBank: SMP0000082)
Pravastatin Action Pathway (PathBank: SMP0000089)
Rosuvastatin Action Pathway (PathBank: SMP0000092)
Alendronate Action Pathway (PathBank: SMP0000095)
Lovastatin Action Pathway (PathBank: SMP0000099)
Zoledronate Action Pathway (PathBank: SMP0000107)
Cerivastatin Action Pathway (PathBank: SMP0000111)
Risedronate Action Pathway (PathBank: SMP0000112)
Pamidronate Action Pathway (PathBank: SMP0000117)
Fluvastatin Action Pathway (PathBank: SMP0000119)
Atorvastatin Action Pathway (PathBank: SMP0000131)

Succinyl CoA: 3-ketoacid CoA transferase deficiency (PathBank: SMP0120633)
Lipid metabolism pathway (HMDB: HMDB0001375)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0001375)

Cellular process

Cell signaling (HMDB: HMDB0001375)

Biochemical process

Lipid transport (HMDB: HMDB0001375)

Role

Biological role

Human metabolite (HMDB: HMDB0001375)
Energy source (HMDB: HMDB0001375)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001375)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.1 g/L	ALOGPS
logP	-0.53	ALOGPS
logP	-7.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	5	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	81.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0001375

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022587

KNApSAcK ID

Not Available

Chemspider ID

388357

KEGG Compound ID

C00356

BioCyc ID

Not Available

BiGG ID

34727

Wikipedia Link

Not Available

METLIN ID

6201

PubChem Compound

439218

PDB ID

Not Available

ChEBI ID

15467

Food Biomarker Ontology

Not Available

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.

Showing chemical card for 3-Hydroxy-3-methylglutaryl-CoA (CFc000001063)

MOL for CFc000001063 (3-Hydroxy-3-methylglutaryl-CoA)

3D MOL for CFc000001063 (3-Hydroxy-3-methylglutaryl-CoA)

3D SDF for CFc000001063 (3-Hydroxy-3-methylglutaryl-CoA)

3D-SDF for CFc000001063 (3-Hydroxy-3-methylglutaryl-CoA)

PDB for CFc000001063 (3-Hydroxy-3-methylglutaryl-CoA)

3D PDB for CFc000001063 (3-Hydroxy-3-methylglutaryl-CoA)

SMILES for CFc000001063 (3-Hydroxy-3-methylglutaryl-CoA)

INCHI for CFc000001063 (3-Hydroxy-3-methylglutaryl-CoA)

Structure for CFc000001063 (3-Hydroxy-3-methylglutaryl-CoA)

3D Structure for CFc000001063 (3-Hydroxy-3-methylglutaryl-CoA)