Cannabis Compound Database: Showing Compound Card for 3-Hydroxy-3-methylglutaryl-CoA (CDB004909)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (6) Show 7 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:49:25 UTC

Updated at

2020-12-07 19:11:15 UTC

CannabisDB ID

CDB004909

Secondary Accession Numbers

Not Available

Cannabis Compound 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. 3-Hydroxy-3-methylglutaryl-CoA is expected to be in Cannabis as all living plants are known to produce and metabolize it.

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

911.66

Monoisotopic Molecular Weight

911.1575

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

26926-09-0

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Organ and components:

Intestine

Endocrine gland:

Adrenal gland

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Cell:

Fibroblast

Role

Industrial application:

Biological role:

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

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0891000250-052d51ef28faa9ab5b73	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0971100000-dc16942c0a4531c8cb60	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1950000000-12dcb50a3caaf20a9aa5	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00o4-4901031462-49fbf273ff8df18347bb	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3900110010-0be1f0212b5d814ea24c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-fffa063c59d4fcd54e7a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dm-0000000094-b818de142848216a6af3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4u-9500001521-8d0d8c41c4c284cc696f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004m-9202503430-001456d7b42e54584702	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000169-47d0ed82d5acca38b9e0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002r-1500000391-9d63a322b718612b8587	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0011900000-766a56d8ca4793434590	2021-09-22	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Butyrate Metabolism
Valine, Leucine and Isoleucine Degradation
Steroid Biosynthesis
Ketone Body Metabolism
Succinyl CoA: 3-ketoacid CoA transferase deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Hydroxymethylglutaryl-CoA lyase, mitochondrial	HMGCL	1p36.1-p35	P35914	details
Hydroxymethylglutaryl-CoA synthase, mitochondrial	HMGCS2	1p13-p12	P54868	details
Hydroxymethylglutaryl-CoA synthase, cytoplasmic	HMGCS1	5p14-p13	Q01581	details
3-hydroxy-3-methylglutaryl-coenzyme A reductase	HMGCR	5q13.3-q14	P04035	details
Methylglutaconyl-CoA hydratase, mitochondrial	AUH	9q22.31	Q13825	details
3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmic	HMGCLL1	6p12.1	Q8TB92	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmic	HMGCLL1	6p12.1	Q8TB92	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001375

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

General References

Not Available

Enzymes

Enzyme Details

1. Hydroxymethylglutaryl-CoA lyase, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Key enzyme in ketogenesis (ketone body formation). Terminal step in leucine catabolism.
Gene Name:: HMGCL
Uniprot ID:: P35914
Molecular weight:: 34359.84

Enzyme Details

2. Hydroxymethylglutaryl-CoA synthase, mitochondrial

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:: HMGCS2
Uniprot ID:: P54868
Molecular weight:: 52481.065

Enzyme Details

3. Hydroxymethylglutaryl-CoA synthase, cytoplasmic

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:: HMGCS1
Uniprot ID:: Q01581
Molecular weight:: 57293.105

Enzyme Details

4. 3-hydroxy-3-methylglutaryl-coenzyme A reductase

General function:: Involved in hydroxymethylglutaryl-CoA reductase (NADPH) activity
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:: P04035
Molecular weight:: 97475.155

Enzyme Details

5. Methylglutaconyl-CoA hydratase, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of 3-methylglutaconyl-CoA to 3-hydroxy-3-methylglutaryl-CoA. Has very low enoyl-CoA hydratase activity. Was originally identified as RNA-binding protein that binds in vitro to clustered 5'-AUUUA-3' motifs.
Gene Name:: AUH
Uniprot ID:: Q13825
Molecular weight:: 35608.18

Enzyme Details

6. 3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmic

General function:: Involved in catalytic activity
Specific function:: Non-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, the products of which support energy production in nonhepatic animal tissues.
Gene Name:: HMGCLL1
Uniprot ID:: Q8TB92
Molecular weight:: 36327.465

Showing Compound Card for 3-Hydroxy-3-methylglutaryl-CoA (CDB004909)

Structure for CDB004909 (3-Hydroxy-3-methylglutaryl-CoA)

Enzymes