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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2023-02-21 17:16:08 UTC
HMDB IDHMDB0002087
Secondary Accession Numbers
  • HMDB02087
Metabolite Identification
Common NameIsovalerylsarcosine
DescriptionIsovalerylsarcosine, also known as isopentanoylsarcosine, 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. Isovalerylsarcosine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make isovalerylsarcosine a potential biomarker for the consumption of these foods. Isovalerylsarcosine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Isovalerylsarcosine.
Structure
Data?1676999768
Synonyms
ValueSource
(3-Methylbutanoyl)sarcosineChEBI
IsopentanoylsarcosineChEBI
N-(3-Methylbutanoyl)sarcosineChEBI
N-IsopentanoylsarcosineChEBI
N-IsovalerylsarcosineHMDB
IsovalerylsarcosineChEBI
Chemical FormulaC8H15NO3
Average Molecular Weight173.2096
Monoisotopic Molecular Weight173.105193351
IUPAC Name2-(N,3-dimethylbutanamido)acetic acid
Traditional Nameisovalerylsarcosine
CAS Registry Number88127-29-1
SMILES
CC(C)CC(=O)N(C)CC(O)=O
InChI Identifier
InChI=1S/C8H15NO3/c1-6(2)4-7(10)9(3)5-8(11)12/h6H,4-5H2,1-3H3,(H,11,12)
InChI KeyGPFSWCRCPHKNBU-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
  • N-acyl-amine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility27.3 g/LALOGPS
logP0.44ALOGPS
logP0.33ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)4.25ChemAxon
pKa (Strongest Basic)-0.86ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity44.12 m³·mol⁻¹ChemAxon
Polarizability17.99 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]+141.11831661259
DarkChem[M-H]-137.08931661259
DeepCCS[M+H]+141.93830932474
DeepCCS[M-H]-138.10630932474
DeepCCS[M-2H]-175.48430932474
DeepCCS[M+Na]+151.14930932474
AllCCS[M+H]+140.032859911
AllCCS[M+H-H2O]+136.332859911
AllCCS[M+NH4]+143.532859911
AllCCS[M+Na]+144.532859911
AllCCS[M-H]-139.532859911
AllCCS[M+Na-2H]-141.332859911
AllCCS[M+HCOO]-143.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsovalerylsarcosineCC(C)CC(=O)N(C)CC(O)=O2194.8Standard polar33892256
IsovalerylsarcosineCC(C)CC(=O)N(C)CC(O)=O1348.5Standard non polar33892256
IsovalerylsarcosineCC(C)CC(=O)N(C)CC(O)=O1478.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isovalerylsarcosine,1TMS,isomer #1CC(C)CC(=O)N(C)CC(=O)O[Si](C)(C)C1507.0Semi standard non polar33892256
Isovalerylsarcosine,1TBDMS,isomer #1CC(C)CC(=O)N(C)CC(=O)O[Si](C)(C)C(C)(C)C1731.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isovalerylsarcosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ko-9300000000-2abc21fb95df3a641d0e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isovalerylsarcosine GC-MS (1 TMS) - 70eV, Positivesplash10-009x-9400000000-b98179bb7f0f3cb48e4d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isovalerylsarcosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isovalerylsarcosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylsarcosine 10V, Positive-QTOFsplash10-00di-3900000000-85c8cc39698d110da0e62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylsarcosine 20V, Positive-QTOFsplash10-0abc-9200000000-40284d92db56052815df2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylsarcosine 40V, Positive-QTOFsplash10-0abc-9000000000-159245318505250d21d42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylsarcosine 10V, Negative-QTOFsplash10-00di-0900000000-fad5216b8aa9f3c43d112017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylsarcosine 20V, Negative-QTOFsplash10-00fr-3900000000-e6139a170ba4f23573432017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylsarcosine 40V, Negative-QTOFsplash10-0ab9-9100000000-3d231daac696c7d359e42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylsarcosine 10V, Positive-QTOFsplash10-0076-9300000000-8964b1f70135ed68fdc62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylsarcosine 20V, Positive-QTOFsplash10-000f-9000000000-00a8e4564652edf79ac02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylsarcosine 40V, Positive-QTOFsplash10-0006-9000000000-edab2fb03e52cd059c832021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylsarcosine 10V, Negative-QTOFsplash10-000i-9800000000-d34b4159870ef87bbb9a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylsarcosine 20V, Negative-QTOFsplash10-000i-9200000000-6a3d39369964ccb1cabc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isovalerylsarcosine 40V, Negative-QTOFsplash10-00xu-9000000000-dfeb4f4e642a861556ce2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022838
KNApSAcK IDNot Available
Chemspider ID121068
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6480
PubChem Compound137394
PDB IDNot Available
ChEBI ID136917
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lehnert W: N-Isovalerylalanine and N-isovalerylsarcosine: two new minor metabolites in isovaleric acidemia. Clin Chim Acta. 1983 Oct 31;134(1-2):207-12. [PubMed:6197208 ]

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
References
  1. Lehnert W: N-Isovalerylalanine and N-isovalerylsarcosine: two new minor metabolites in isovaleric acidemia. Clin Chim Acta. 1983 Oct 31;134(1-2):207-12. [PubMed:6197208 ]