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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] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Animalia
  • 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
    External Links
    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 IDNot Available
    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 ]