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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:31:18 UTC
HMDB IDHMDB0000832
Secondary Accession Numbers
  • HMDB00832
Metabolite 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
Data?1582752159
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 Molecular Weight201.2628
Monoisotopic Molecular Weight201.136493479
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
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
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point403.00 to 404.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility980.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.065 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.31831661259
DarkChem[M-H]-145.531661259
AllCCS[M+H]+148.17532859911
AllCCS[M-H]-149.26132859911
DeepCCS[M+H]+148.78330932474
DeepCCS[M-H]-144.75730932474
DeepCCS[M-2H]-182.25530932474
DeepCCS[M+Na]+157.88130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CapryloylglycineCCCCCCCC(=O)NCC(O)=O2723.6Standard polar33892256
CapryloylglycineCCCCCCCC(=O)NCC(O)=O1628.3Standard non polar33892256
CapryloylglycineCCCCCCCC(=O)NCC(O)=O1809.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Capryloylglycine,1TMS,isomer #1CCCCCCCC(=O)NCC(=O)O[Si](C)(C)C1807.0Semi standard non polar33892256
Capryloylglycine,1TMS,isomer #2CCCCCCCC(=O)N(CC(=O)O)[Si](C)(C)C1794.8Semi standard non polar33892256
Capryloylglycine,2TMS,isomer #1CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1840.0Semi standard non polar33892256
Capryloylglycine,2TMS,isomer #1CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1869.9Standard non polar33892256
Capryloylglycine,2TMS,isomer #1CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1986.4Standard polar33892256
Capryloylglycine,1TBDMS,isomer #1CCCCCCCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C2035.3Semi standard non polar33892256
Capryloylglycine,1TBDMS,isomer #2CCCCCCCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C2028.7Semi standard non polar33892256
Capryloylglycine,2TBDMS,isomer #1CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2305.3Semi standard non polar33892256
Capryloylglycine,2TBDMS,isomer #1CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2257.6Standard non polar33892256
Capryloylglycine,2TBDMS,isomer #1CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2250.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Capryloylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kfx-9300000000-65a0f0b1f51f64e885b72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Capryloylglycine GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9110000000-c57e7cf876a1e77e8ae02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Capryloylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Capryloylglycine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Capryloylglycine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Capryloylglycine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Capryloylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-03ca05ec686d1dda5b8a2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capryloylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-62dc4fa9a9a964274ce92012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capryloylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0le9-9410000000-2ee2571efa7db061b49d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capryloylglycine 40V, Negative-QTOFsplash10-00di-9000000000-fc6cc7311141fc5fe7172021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capryloylglycine 10V, Negative-QTOFsplash10-00di-9020000000-d03999d949be77b4d8a62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capryloylglycine 20V, Negative-QTOFsplash10-00di-9000000000-70b04aa8b2675c21fa162021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capryloylglycine 20V, Positive-QTOFsplash10-0a4i-9000000000-874f5c3a11de4ee900312021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capryloylglycine 40V, Positive-QTOFsplash10-052f-9000000000-e2229641a6019ff1a56d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capryloylglycine 20V, Positive-QTOFsplash10-0a4i-9000000000-bca784da02e2fac6d0ba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capryloylglycine 10V, Positive-QTOFsplash10-056r-9100000000-8d0322475c5030f907a32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capryloylglycine 10V, Positive-QTOFsplash10-056r-9100000000-0d09d6d23bc8462fa3e42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capryloylglycine 40V, Positive-QTOFsplash10-0a4l-9000000000-2daf8062135b4c7bbfd82021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capryloylglycine 10V, Positive-QTOFsplash10-0zi0-7890000000-57a37a082260c6fadf122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capryloylglycine 20V, Positive-QTOFsplash10-0a6r-9300000000-ed7dd37f13803abae61c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capryloylglycine 40V, Positive-QTOFsplash10-0a6u-9000000000-5b71e57265e05e05caf02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capryloylglycine 10V, Negative-QTOFsplash10-0udi-0390000000-1a1e6edc2e6566ff36b02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capryloylglycine 20V, Negative-QTOFsplash10-0zmi-7960000000-dbf3a16fa0aa2d14fa422017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capryloylglycine 40V, Negative-QTOFsplash10-05fu-9000000000-f6cc9608b6c803996d2b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capryloylglycine 10V, Positive-QTOFsplash10-0fb9-9030000000-7f1b4ff2c9242662a6a92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capryloylglycine 20V, Positive-QTOFsplash10-0a6r-9000000000-4b500c86935ecdb797c42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capryloylglycine 40V, Positive-QTOFsplash10-0a4i-9000000000-45956863a016267b72c22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capryloylglycine 10V, Negative-QTOFsplash10-0udi-2090000000-24660e2b635d6ddb6dfd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capryloylglycine 20V, Negative-QTOFsplash10-00di-9000000000-67d5d2d94d2b5bccd9dd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capryloylglycine 40V, Negative-QTOFsplash10-00di-9000000000-d0d8d779699b764c9cb02021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified<0.0015–0.0347 umol/mmol creatinineAdult (25-30 years old)Both
Not Available
details
UrineDetected and Quantified<0.0015–0.0414 umol/mmol creatinineAdult (25-30 years old)Both
Not Available
details
UrineDetected and Quantified<0.0015–0.0489 umol/mmol creatinineAdult (25-30 years old)Both
Not Available
details
UrineDetected and Quantified<0.2 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.2-1.7 umol/mmol creatinineChildren (1 - 13 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency details
Associated Disorders and Diseases
Disease References
Medium Chain Acyl-CoA Dehydrogenase Deficiency
  1. Gregersen N, Kolvraa S, Rasmussen K, Mortensen PB, Divry P, David M, Hobolth N: General (medium-chain) acyl-CoA dehydrogenase deficiency (non-ketotic dicarboxylic aciduria): quantitative urinary excretion pattern of 23 biologically significant organic acids in three cases. Clin Chim Acta. 1983 Aug 15;132(2):181-91. [PubMed:6616873 ]
Associated OMIM IDs
  • 201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029861
Good Scents IDrw1358991
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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 ]

Enzymes

General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:
GLYATL1
Uniprot ID:
Q969I3
Molecular weight:
35100.895
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:
GLYATL2
Uniprot ID:
Q8WU03
Molecular weight:
34277.055
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:
GLYATL3
Uniprot ID:
Q5SZD4
Molecular weight:
32703.3