ContaminantDB: 3-Hydroxy-3-methylglutaryl-CoA

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (25)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:10:46 UTC

Update Date

2026-04-05 14:25:29 UTC

Accession Number

CHEM003227

Identification

Common Name

3-Hydroxy-3-methylglutaryl-CoA

Class

Small Molecule

Description

3-Hydroxy-3-methylglutaryl-CoA (C27H44N7O20P3S) is an endogenous compound that exists as a solid at room temperature. 3-Hydroxy-3-methylglutaryl-CoA belongs to the fatty acyl thioesters, a subclass of fatty acyls within the organic compounds. With an average molecular weight of 911.66 g/mol, 3-Hydroxy-3-methylglutaryl-CoA is a heavy molecule. Biologically, the compound serves as a human metabolite and has been detected in the intestine, fibroblasts, and the adrenal gland. It is formed when acetoacetyl-CoA condenses with Acetyl-CoA via a reaction catalyzed by the enzyme HMG-CoA synthase in the mevalonate pathway, also known as the mevalonate-dependent (MAD) route. HMG-CoA reductase catalyzes the rate-limiting step in this pathway. Statins are cholesterol-lowering drugs that inhibit HMG-CoA reductase to reduce cholesterol synthesis in peripheral tissues and the liver. Additionally, androgen increases the transcription of the HMG-CoA-reductase gene to stimulate lipogenesis in human prostate cancer cells. This compound is also found in electrical and electronic equipment antennas.

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Amine
Animal Toxin
Ester
Ether
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical 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 Mass

911.659 g/mol

Monoisotopic Mass

911.157 g/mol

CAS Registry Number

1553-55-5

IUPAC Name

Not Available

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

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

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane
Mitochondria
Peroxisome

Biofluid Locations

Not Available

Tissue Locations

Adrenal Gland
Fibroblasts
Intestine

Pathways

Name	SMPDB Link	KEGG Link
Butyrate Metabolism	SMP00073	map00650
Ketone Body Metabolism	SMP00071	map00072
Steroid Biosynthesis	SMP00023	map00100
Valine, Leucine and Isoleucine Degradation	SMP00032	map00280
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency	SMP00138	Not Available
Butyrate Metabolism	SMP0000073	Not Available
Ketone Body Metabolism	SMP0000071	Not Available
Steroid Biosynthesis	SMP0000023	Not Available
Valine, Leucine, and Isoleucine Degradation	SMP0000032	Not Available
beta-Ketothiolase Deficiency	SMP0000173	Not Available
2-Methyl-3-hydroxybutyryl-CoA Dehydrogenase Deficiency	SMP0000137	Not Available
Propionic Acidemia	SMP0000236	Not Available
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency	SMP0000138	Not Available
Maple Syrup Urine Disease	SMP0000199	Not Available
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I	SMP0000237	Not Available
3-Methylglutaconic Aciduria Type I	SMP0000139	Not Available
3-Methylglutaconic Aciduria Type III	SMP0000140	Not Available
Methylmalonate Semialdehyde Dehydrogenase Deficiency	SMP0000384	Not Available
Methylmalonic Aciduria	SMP0000200	Not Available
Isovaleric Aciduria	SMP0000238	Not Available
Smith-Lemli-Opitz Syndrome (SLOS)	SMP0000389	Not Available
CHILD Syndrome	SMP0000387	Not Available
Desmosterolosis	SMP0000386	Not Available
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2)	SMP0000388	Not Available
Lysosomal Acid Lipase Deficiency (Wolman Disease)	SMP0000319	Not Available
Ibandronate Action Pathway	SMP0000079	Not Available
Simvastatin Action Pathway	SMP0000082	Not Available
Pravastatin Action Pathway	SMP0000089	Not Available
Rosuvastatin Action Pathway	SMP0000092	Not Available
Alendronate Action Pathway	SMP0000095	Not Available
3-Methylglutaconic Aciduria Type IV	SMP0000141	Not Available
Hypercholesterolemia	SMP0000209	Not Available
Lovastatin Action Pathway	SMP0000099	Not Available
Zoledronate Action Pathway	SMP0000107	Not Available
Cerivastatin Action Pathway	SMP0000111	Not Available
Risedronate Action Pathway	SMP0000112	Not Available
Pamidronate Action Pathway	SMP0000117	Not Available
Fluvastatin Action Pathway	SMP0000119	Not Available
Cholesteryl Ester Storage Disease	SMP0000508	Not Available
Hyper-IgD Syndrome	SMP0000509	Not Available
Mevalonic Aciduria	SMP0000510	Not Available
Wolman Disease	SMP0000511	Not Available
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency	SMP0000521	Not Available
3-Hydroxyisobutyric Aciduria	SMP0000522	Not Available
Isobutyryl-CoA Dehydrogenase Deficiency	SMP0000523	Not Available
Isovaleric Acidemia	SMP0000524	Not Available
Succinyl CoA: 3-Ketoacid CoA Transferase Deficiency	SMP0000569	Not Available
Mevalonate Pathway	SMP0121055	Not Available
Atorvastatin Action Pathway	SMP0000131	Not Available
Alendronate Action Pathway (New)	SMP0122691	Not Available
Atorvastatin Action Pathway (New)	SMP0124555	Not Available
Fluvastatin Action Pathway (New)	SMP0124569	Not Available
Lovastatin Action Pathway (New)	SMP0124570	Not Available
Pravastatin Action Pathway (New)	SMP0124576	Not Available
Rosuvastatin	SMP0124577	Not Available
Simvastatin Action Pathway (New)	SMP0124578	Not Available
Smith-Lemli-Opitz Syndrome (SLOS)	SMP0125635	Not Available
CHILD Syndrome	SMP0125637	Not Available
Desmosterolosis	SMP0125638	Not Available
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2)	SMP0125639	Not Available
Lysosomal Acid Lipase Deficiency (Wolman Disease)	SMP0125640	Not Available
Hypercholesterolemia	SMP0125641	Not Available
Hyper-IgD Syndrome	SMP0125642	Not Available
Mevalonic Aciduria	SMP0125643	Not Available
beta-Ketothiolase Deficiency	SMP0125657	Not Available
2-Methyl-3-hydroxybutyryl-CoA Dehydrogenase Deficiency	SMP0125658	Not Available
Propionic Acidemia	SMP0125659	Not Available
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency	SMP0125660	Not Available
Maple Syrup Urine Disease	SMP0125661	Not Available
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I	SMP0125662	Not Available
3-Methylglutaconic Aciduria Type I	SMP0125664	Not Available
3-Methylglutaconic Aciduria Type III	SMP0125667	Not Available
Methylmalonate Semialdehyde Dehydrogenase Deficiency	SMP0125669	Not Available
Methylmalonic Aciduria	SMP0125670	Not Available
Isovaleric Aciduria	SMP0125671	Not Available
3-Methylglutaconic Aciduria Type IV	SMP0125672	Not Available
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency	SMP0125673	Not Available
3-Hydroxyisobutyric Aciduria	SMP0125674	Not Available
Isobutyryl-CoA Dehydrogenase Deficiency	SMP0125675	Not Available
Isovaleric Acidemia	SMP0125676	Not Available
Glutaric Aciduria Type I (Lysine Degradation)	SMP0125698	Not Available
Glutaric Aciduria Type I (Fatty Acid Metabolism)	SMP0125737	Not Available
Succinyl CoA: 3-Ketoacid CoA Transferase Deficiency	SMP0125783	Not Available
Clodronic Acid Action Pathway	SMP0126307	Not Available
Alendronate Action Pathway (New Revised)	SMP0126316	Not Available
Ibandronate Action Pathway	SMP0126317	Not Available
Pamidronate Action Pathway (new)	SMP0126321	Not Available
Risedronate Action Pathway (new)	SMP0126323	Not Available
Zoledronate Action Pathway	SMP0126324	Not Available
Etidronic Acid Action Pathway	SMP0126349	Not Available
Tiludronic Acid Action Pathway	SMP0126351	Not Available
Pitavastatin Action Pathway	SMP0126665	Not Available
Glutaric Acidemia Type I (GA-I)	SMP0658920	Not Available

Applications

Not Available

Biological Roles

human metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0891000250-052d51ef28faa9ab5b73	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0971100000-dc16942c0a4531c8cb60	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1950000000-12dcb50a3caaf20a9aa5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00o4-4901031462-49fbf273ff8df18347bb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3900110010-0be1f0212b5d814ea24c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-fffa063c59d4fcd54e7a	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC.

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0001375

FooDB ID

FDB022587

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

34727

BioCyc ID

Not Available

METLIN ID

6201

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

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.

MSDS

Not Available

General References

1. 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.

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.