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Showing metabocard for Pyroglutamine (HMDB0062558)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2017-03-23 04:24:35 UTC
Update Date2020-06-15 17:04:53 UTC
HMDB IDHMDB0062558
Secondary Accession Numbers
  • HMDB62558
Metabolite Identification
Common NamePyroglutamine
DescriptionPyroglutamine (CAS: 2353-44-8), also known as alpha-aminoglutarimide or 3-amino-1,6-dioxopiperidine, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Pyroglutamine is considered to be soluble (in water) and acidic. Pyroglutamine has been identified in the human placenta (PMID: 32033212 ).
Structure
Data?1571244723
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3S)-3-Amino-2,6-piperidinedioneHMDB
(3S)-3-Aminohexahydro-2,6-pyridinedioneHMDB
(3S)-3-Aminopiperidine-2,6-dioneHMDB
3-Amino-2,6-dioxopiperidineHMDB
3-Amino-2,6-piperidinedioneHMDB
3-AminoglutarimideHMDB
3-Aminopiperidine-2,6-dioneHMDB
Glutamic acid imideHMDB
GlutamimideHMDB
alpha-AminoglutarimideHMDB
α-AminoglutarimideHMDB
Chemical FormulaC5H8N2O2
Average Molecular Weight128.131
Monoisotopic Molecular Weight128.058577506
IUPAC Name(3S)-3-aminopiperidine-2,6-dione
Traditional Name(3S)-3-aminopiperidine-2,6-dione
CAS Registry Number29883-25-8
SMILES
N[C@H]1CCC(=O)NC1=O
InChI Identifier
InChI=1S/C5H8N2O2/c6-3-1-2-4(8)7-5(3)9/h3H,1-2,6H2,(H,7,8,9)/t3-/m0/s1
InChI KeyNPWMTBZSRRLQNJ-VKHMYHEASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Piperidinedione
  • 3-aminopiperidine
  • Delta-lactam
  • Piperidinone
  • Piperidine
  • Carboxylic acid imide
  • Dicarboximide
  • Carboxylic acid imide, n-unsubstituted
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility259 g/lALOGPS
LogP-1.59ALOGPS
Predicted Properties
PropertyValueSource
logP-1.6ALOGPS
logP-1.5ChemAxon
logS0.3ALOGPS
pKa (Strongest Acidic)11.62ChemAxon
pKa (Strongest Basic)6.71ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.19 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.03 m³·mol⁻¹ChemAxon
Polarizability12.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
Associated Disorders and Diseases
Disease References
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11984188
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]