ChemFOnt: Showing chemical card for Hexanoylglycine (CFc000000553)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:58 UTC

Chemfont ID

CFc000000553

Molecule Identification

Common Name

Hexanoylglycine

Definition

Hexanoylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycineHexanoylglycine is a fatty acid metabolite, it appears in the urine of patients with hereditary medium-chain acyl-CoA dehydrogenase (MCAD) deficiency (PMID 2775902 ), which is a genetic disorder.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Caproylglycine	ChEBI
N-(1-Oxohexyl)glycine	ChEBI
N-Caproylglycine	ChEBI
N-Hexanoyl-glycine	HMDB
N-Hexanoylglycine	HMDB
Hexanoylglycine	ChEBI

Chemical Formula

C₈H₁₅NO₃

Average Molecular Weight

173.2096

Monoisotopic Molecular Weight

173.105193351

IUPAC Name

2-hexanamidoacetic acid

Traditional Name

hexanoylglycine

CAS Registry Number

24003-67-6

SMILES

CCCCCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C8H15NO3/c1-2-3-4-5-7(10)9-6-8(11)12/h2-6H2,1H3,(H,9,10)(H,11,12)

InChI Key

UPCKIPHSXMXJOX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acylglycine (CHEBI:64390 )

Functional Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 2026685)
Feces (PMID: 27543620)

Source

Endogenous

Endogenous (HMDB: HMDB0000701)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Short-Chain Acyl-CoA Dehydrogenase Deficiency (SCAD Deficiency) (HMDB: HMDB0000701)

Role

Biological role

Metabolite (HMDB: HMDB0000701)
Metabolite (HMDB: HMDB0000701)

Industrial application

Pharmaceutical industry

Biomarker

Medium Chain Acyl Co A Dehydrogenase Deficiency (MarkerDB: MDB00000227)
Ethylmalonic encephalopathy (MarkerDB: MDB00000227)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.61 g/L	ALOGPS
logP	0.9	ALOGPS
logP	0.71	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	43.88 m³·mol⁻¹	ChemAxon
Polarizability	18.75 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000701

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022190

KNApSAcK ID

Not Available

Chemspider ID

89859

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5669

PubChem Compound

99463

PDB ID

Not Available

ChEBI ID

64390

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Toth, Eugene; Weiss, Benjamine; Banay-Schwartz, Miriam; Lajtha, Abel. Effect of glycine derivatives on behavioral changes induced by 3-mercaptopropionic acid or phencyclidine in mice. Research Communications in Psychology, Psychiatry and Behavior (1986), 11(1), 1-9.

Showing chemical card for Hexanoylglycine (CFc000000553)

MOL for CFc000000553 (Hexanoylglycine)

3D MOL for CFc000000553 (Hexanoylglycine)

3D SDF for CFc000000553 (Hexanoylglycine)

3D-SDF for CFc000000553 (Hexanoylglycine)

PDB for CFc000000553 (Hexanoylglycine)

3D PDB for CFc000000553 (Hexanoylglycine)

SMILES for CFc000000553 (Hexanoylglycine)

INCHI for CFc000000553 (Hexanoylglycine)

Structure for CFc000000553 (Hexanoylglycine)

3D Structure for CFc000000553 (Hexanoylglycine)