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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-07-25 00:11:35 UTC
Update Date2023-02-21 17:17:53 UTC
HMDB IDHMDB0013010
Secondary Accession Numbers
  • HMDB13010
Metabolite Identification
Common NameN-Heptanoylglycine
DescriptionN-Heptanoylglycine is an acylglycine with C-7 fatty acid group as the acyl moiety. Acylglycines 1 possess a common amidoacetic acid moiety and are normally minor metabolites of fatty acids. Elevated levels of certain acylglycines appear in the urine and blood of patients with various fatty acid oxidation disorders. They are normally produced through the action of glycine N-acyltransferase which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine ↔ CoA + N-acylglycine.
Structure
Data?1676999873
Synonyms
ValueSource
(Heptanoylamino)acetic acidChEBI
2-(Heptanoylamino)acetic acidChEBI
N-(1-Oxoheptyl)glycineChEBI
N-(Carboxymethyl)heptanamideChEBI
(Heptanoylamino)acetateGenerator
2-(Heptanoylamino)acetateGenerator
Chemical FormulaC9H17NO3
Average Molecular Weight187.2362
Monoisotopic Molecular Weight187.120843415
IUPAC Name2-[(1-hydroxyheptylidene)amino]acetic acid
Traditional Name[(1-hydroxyheptylidene)amino]acetic acid
CAS Registry Number23783-23-5
SMILES
CCCCCCC(O)=NCC(O)=O
InChI Identifier
InChI=1S/C9H17NO3/c1-2-3-4-5-6-8(11)10-7-9(12)13/h2-7H2,1H3,(H,10,11)(H,12,13)
InChI KeyRNFCYFVPNIXAHP-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
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 Solubility1.75 g/LALOGPS
logP1.64ALOGPS
logP1.87ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)2.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.89 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity49 m³·mol⁻¹ChemAxon
Polarizability21.03 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]+144.99231661259
DarkChem[M-H]-141.99131661259
DeepCCS[M+H]+143.80130932474
DeepCCS[M-H]-139.82730932474
DeepCCS[M-2H]-177.23430932474
DeepCCS[M+Na]+152.60930932474
AllCCS[M+H]+144.232859911
AllCCS[M+H-H2O]+140.532859911
AllCCS[M+NH4]+147.632859911
AllCCS[M+Na]+148.632859911
AllCCS[M-H]-144.632859911
AllCCS[M+Na-2H]-145.932859911
AllCCS[M+HCOO]-147.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-HeptanoylglycineCCCCCCC(O)=NCC(O)=O2537.1Standard polar33892256
N-HeptanoylglycineCCCCCCC(O)=NCC(O)=O1493.5Standard non polar33892256
N-HeptanoylglycineCCCCCCC(O)=NCC(O)=O1612.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Heptanoylglycine,1TMS,isomer #1CCCCCCC(=NCC(=O)O)O[Si](C)(C)C1716.1Semi standard non polar33892256
N-Heptanoylglycine,1TMS,isomer #2CCCCCCC(O)=NCC(=O)O[Si](C)(C)C1689.8Semi standard non polar33892256
N-Heptanoylglycine,2TMS,isomer #1CCCCCCC(=NCC(=O)O[Si](C)(C)C)O[Si](C)(C)C1744.6Semi standard non polar33892256
N-Heptanoylglycine,1TBDMS,isomer #1CCCCCCC(=NCC(=O)O)O[Si](C)(C)C(C)(C)C1917.7Semi standard non polar33892256
N-Heptanoylglycine,1TBDMS,isomer #2CCCCCCC(O)=NCC(=O)O[Si](C)(C)C(C)(C)C1898.0Semi standard non polar33892256
N-Heptanoylglycine,2TBDMS,isomer #1CCCCCCC(=NCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2137.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Heptanoylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fdo-9300000000-e18346fb9a57d5ba8ca12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Heptanoylglycine GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9110000000-8a2c330ade02ece4552c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Heptanoylglycine 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 - N-Heptanoylglycine 10V, Positive-QTOFsplash10-000i-3900000000-09f5edaa6809a2a9aa822017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Heptanoylglycine 20V, Positive-QTOFsplash10-0a70-9300000000-e0f3666f006c52c2ab072017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Heptanoylglycine 40V, Positive-QTOFsplash10-0a6u-9000000000-11580cb92a875b798c872017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Heptanoylglycine 10V, Negative-QTOFsplash10-000i-0900000000-20e9e287e60709f6d22f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Heptanoylglycine 20V, Negative-QTOFsplash10-0079-4900000000-bf970b193cebaea851ce2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Heptanoylglycine 40V, Negative-QTOFsplash10-05fu-9100000000-8025af9d71c2ed8962662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Heptanoylglycine 10V, Positive-QTOFsplash10-000i-8900000000-f5e1c5f11584bef852c62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Heptanoylglycine 20V, Positive-QTOFsplash10-0a4i-9000000000-bb1ed780a4bbbfb04b892021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Heptanoylglycine 40V, Positive-QTOFsplash10-0a4i-9000000000-cde75003abd22c50c66e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Heptanoylglycine 10V, Negative-QTOFsplash10-0229-9500000000-eb47ead2c780ae0cd0372021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Heptanoylglycine 20V, Negative-QTOFsplash10-00di-9500000000-e4fa6025a0ca341290002021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Heptanoylglycine 40V, Negative-QTOFsplash10-0ab9-9000000000-19b379e6e08be0168d152021-09-23Wishart 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
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029243
KNApSAcK IDNot Available
Chemspider ID9107408
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10932172
PDB IDNot Available
ChEBI ID74433
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 ReferencesNot Available

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