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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-16 18:04:18 UTC
NP-MRD IDNP0000206
Secondary Accession NumbersNone
Natural Product Identification
Common NameCapryloylglycine
DescriptionCapryloylglycine is an acylglycine consisting of caprylic acid (an 8-carbon medium chain fatty acid) conjugated to glycine. Acylglycines have an aliphatic acyl chain attached to the amino group of glycine through a peptide bond. Capryloylglycine is a solid with moderate solubility in water. Acylglycines are produced through the action of the enzyme glycine N-acyltransferase (EC 2.3.1.13). Acylglycines are normally minor metabolites of fatty acids. However, the excretion of certain acylglycines 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, including medium-chain acyl-coenzyme A (CoA) dehydrogenase (MCAD) deficiency and multiple acyl-CoA dehydrogenation defect (MAD) (PMID: 10708405 ). Capryloylglycine is frequently used as a cosmetic ingredient where it functions as a conditioning agent or a surfactant. It helps protect the skin’s surface from water loss and can enhance the effectiveness of cosmetic preservatives. Capryloylglycine-containing creams have been shown to inhibit hair growth in individuals suffering from hypertrichosis (PMID: 33934471 ), Due to it inhibiting ornithine decarboxylase 1, which is present in hair follicles.
Structure
Thumb
Synonyms
ValueSource
2-Octanamidoacetic acidChEBI
CaprylylglycineChEBI
N-(1-Oxooctyl)glycineChEBI
2-OctanamidoacetateGenerator
Capryloyl glycineHMDB
Lipacide C 8gHMDB
N-(1-Oxooctyl)-glycineHMDB
N-Octanoyl-glycineHMDB
N-OctanoylglycineHMDB
Chemical FormulaC10H19NO3
Average Mass201.2628 Da
Monoisotopic Mass201.13649 Da
IUPAC Name2-octanamidoacetic acid
Traditional NameN-octanoylglycine
CAS Registry Number14246-53-8
SMILES
CCCCCCCC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C10H19NO3/c1-2-3-4-5-6-7-9(12)11-8-10(13)14/h2-8H2,1H3,(H,11,12)(H,13,14)
InChI KeySAVLIIGUQOSOEP-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchos
Anatidae
Anser anser
Bison bison
Bos taurus
Bos taurus X Bison bison
Bubalus bubalis
Capra aegagrus hircus
Cervidae
Cervus canadensis
Columba
Columbidae
Dromaius novaehollandiae
Equus caballus
Gallus gallus
Lagopus muta
Leporidae
Lepus timidus
Melanitta fusca
Meleagris gallopavo
Numida meleagris
Odocoileus
Oryctolagus
Ovis aries
Phasianidae
Phasianus colchicus
Struthio camelus
Sus scrofa
Sus scrofa domestica
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1 g/LALOGPS
logP2.07ALOGPS
logP1.59ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity53.08 m³·mol⁻¹ChemAxon
Polarizability22.92 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000832
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022273
KNApSAcK IDNot Available
Chemspider ID76040
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5795
PubChem Compound84290
PDB IDNot Available
ChEBI ID74099
Good Scents IDrw1358991
References
General References
  1. Costa CG, Guerand WS, Struys EA, Holwerda U, ten Brink HJ, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of urinary acylglycines for the diagnosis of beta-oxidation defects using GC-NCI-MS. J Pharm Biomed Anal. 2000 Jan;21(6):1215-24. doi: 10.1016/s0731-7085(99)00235-6. [PubMed:10708405 ]
  2. Barbareschi M, Benetti F, Gaio E, Angileri L, Veraldi S: Capryloyl glycine and soy isoflavonoids in hypertrichosis: An experimental and placebo-controlled clinical study. J Cosmet Dermatol. 2021 Apr;20 Suppl 1:18-22. doi: 10.1111/jocd.14096. [PubMed:33934471 ]