You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:30:27 UTC
Update Date2020-06-25 18:50:32 UTC
HMDB IDHMDB0029444
Secondary Accession Numbers
  • HMDB29444
Metabolite Identification
Common Name2-Pyrrolidineacetic acid
Description2-Pyrrolidineacetic acid (CAS: 56879-46-0), also known as homoproline, belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. 2-Pyrrolidineacetic acid has been identified in the urine of pregnant women (PMID: 32101413 ). 2-Pyrrolidineacetic acid is found in tea. 2-Pyrrolidineacetic acid occurs in Tussilago farfara (coltsfoot).
Structure
Data?1593110735
Synonyms
ValueSource
(2S)-2-Pyrrolidineacetic acidHMDB
(S)-2-(2-Pyrrolidinyl)acetic acidHMDB
(S)-2-Pyrrolidineacetic acidHMDB
(S)-HomoprolineHMDB
2-(Pyrrolidin-2-yl)acetic acidHMDB
2-[(2S)-Pyrrolidin-1-ium-2-yl]acetateHMDB
2-[(2S)-Pyrrolidin-2-yl]acetic acidHMDB
2-Pyrrolidineacetic acidHMDB
HomoprolineHMDB
L-(+)-HomoprolineHMDB
L-beta-HomoprolineHMDB
L-β-HomoprolineHMDB
beta-HomoprolineHMDB
β-HomoprolineHMDB
Chemical FormulaC6H11NO2
Average Molecular Weight129.159
Monoisotopic Molecular Weight129.078978598
IUPAC Name2-[(2S)-pyrrolidin-2-yl]acetic acid
Traditional Name(2S)-pyrrolidin-2-ylacetic acid
CAS Registry Number56633-75-1
SMILES
OC(=O)C[C@@H]1CCCN1
InChI Identifier
InChI=1S/C6H11NO2/c8-6(9)4-5-2-1-3-7-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1
InChI KeyADSALMJPJUKESW-YFKPBYRVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassNot Available
Direct ParentPyrrolidines
Alternative Parents
Substituents
  • Pyrrolidine
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Secondary amine
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility120 g/LALOGPS
logP-2.4ALOGPS
logP-2.5ChemAxon
logS-0.03ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)11.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.69 m³·mol⁻¹ChemAxon
Polarizability13.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemalePregnancy details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000554
KNApSAcK IDNot Available
Chemspider ID2042269
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2761541
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhao H, Zheng Y, Zhu L, Xiang L, Zhou Y, Li J, Fang J, Xu S, Xia W, Cai Z: Paraben Exposure Related To Purine Metabolism and Other Pathways Revealed by Mass Spectrometry-Based Metabolomics. Environ Sci Technol. 2020 Mar 17;54(6):3447-3454. doi: 10.1021/acs.est.9b07634. Epub 2020 Mar 6. [PubMed:32101413 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .