Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:21 UTC
Update Date2022-03-07 02:52:09 UTC
HMDB IDHMDB0029426
Secondary Accession Numbers
  • HMDB29426
Metabolite Identification
Common NameL-trans-5-Hydroxy-2-piperidinecarboxylic acid
DescriptionL-trans-5-Hydroxy-2-piperidinecarboxylic acid, also known as 5-hydroxypipecolate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). L-trans-5-Hydroxy-2-piperidinecarboxylic acid 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 a significant number of articles have been published on L-trans-5-Hydroxy-2-piperidinecarboxylic acid.
Structure
Data?1582753416
Synonyms
ValueSource
L-trans-5-Hydroxy-2-piperidinecarboxylateGenerator
L-trans-5-Hydroxypipecolic acidHMDB
5-Hydroxypipecolic acid, cis-isomerHMDB
5-Hydroxypipecolic acid, ion (1-)-cis-isomerHMDB
5-Hydroxypipecolic acid, trans-isomerHMDB
5-HydroxypipecolateHMDB
5-Hydroxypipecolic acidHMDB
Chemical FormulaC6H11NO3
Average Molecular Weight145.1564
Monoisotopic Molecular Weight145.073893223
IUPAC Name5-hydroxypiperidine-2-carboxylic acid
Traditional Name5-hydroxypiperidine-2-carboxylic acid
CAS Registry Number50439-45-7
SMILES
OC1CCC(NC1)C(O)=O
InChI Identifier
InChI=1S/C6H11NO3/c8-4-1-2-5(6(9)10)7-3-4/h4-5,7-8H,1-3H2,(H,9,10)
InChI KeyRKEYKDXXZCICFZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Piperidinecarboxylic acid
  • Piperidine
  • 1,2-aminoalcohol
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point235 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility258 g/LALOGPS
logP-3ALOGPS
logP-3.2ChemAxon
logS0.25ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.03 m³·mol⁻¹ChemAxon
Polarizability14.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+131.74131661259
DarkChem[M-H]-128.32231661259
DeepCCS[M+H]+128.34530932474
DeepCCS[M-H]-125.56730932474
DeepCCS[M-2H]-162.06930932474
DeepCCS[M+Na]+136.90730932474
AllCCS[M+H]+132.132859911
AllCCS[M+H-H2O]+127.532859911
AllCCS[M+NH4]+136.332859911
AllCCS[M+Na]+137.532859911
AllCCS[M-H]-127.832859911
AllCCS[M+Na-2H]-129.532859911
AllCCS[M+HCOO]-131.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-trans-5-Hydroxy-2-piperidinecarboxylic acidOC1CCC(NC1)C(O)=O2560.3Standard polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acidOC1CCC(NC1)C(O)=O1337.3Standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acidOC1CCC(NC1)C(O)=O1439.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,1TMS,isomer #1C[Si](C)(C)OC1CCC(C(=O)O)NC11544.4Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C1CCC(O)CN11501.7Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,1TMS,isomer #3C[Si](C)(C)N1CC(O)CCC1C(=O)O1509.8Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1CCC(O[Si](C)(C)C)CN11565.4Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,2TMS,isomer #2C[Si](C)(C)OC1CCC(C(=O)O)N([Si](C)(C)C)C11590.3Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C1CCC(O)CN1[Si](C)(C)C1544.7Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1CCC(O[Si](C)(C)C)CN1[Si](C)(C)C1608.4Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1CCC(O[Si](C)(C)C)CN1[Si](C)(C)C1649.9Standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCC(C(=O)O)NC11799.1Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1CCC(O)CN11746.8Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1CC(O)CCC1C(=O)O1765.1Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CCC(O[Si](C)(C)C(C)(C)C)CN12007.9Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)C12074.5Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1CCC(O)CN1[Si](C)(C)C(C)(C)C1998.0Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CCC(O[Si](C)(C)C(C)(C)C)CN1[Si](C)(C)C(C)(C)C2279.5Semi standard non polar33892256
L-trans-5-Hydroxy-2-piperidinecarboxylic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CCC(O[Si](C)(C)C(C)(C)C)CN1[Si](C)(C)C(C)(C)C2292.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9300000000-dfd5bcb87712ead45e0c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4920000000-c137749c969db4c3f9a72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 20V, Positive-QTOFNot Available2019-09-10HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid 10V, Positive-QTOFsplash10-004i-1900000000-cf03f58c0883bdc027582016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid 20V, Positive-QTOFsplash10-003r-7900000000-bff42ab0b681fb65d14f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid 40V, Positive-QTOFsplash10-001i-9100000000-ce01ad999976b4baf5c72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid 10V, Negative-QTOFsplash10-0006-1900000000-824c8cca1889293dffb02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid 20V, Negative-QTOFsplash10-0f9x-3900000000-4c68f6c4925bcb884a3b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid 40V, Negative-QTOFsplash10-0006-9100000000-dc8eb306c4c44ba41e9c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid 10V, Negative-QTOFsplash10-0006-0900000000-3d59768dce8a6fe46dfe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid 20V, Negative-QTOFsplash10-000f-9500000000-c386f694e3efac21f2de2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid 40V, Negative-QTOFsplash10-0006-9000000000-497d565ca64ed7fa6ff22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid 10V, Positive-QTOFsplash10-0f6t-1900000000-87958192ec7cd32323172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid 20V, Positive-QTOFsplash10-0ue9-9600000000-5ee3846e74d8ecfc59282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-5-Hydroxy-2-piperidinecarboxylic acid 40V, Positive-QTOFsplash10-053u-9000000000-0e1caa6dd5889d35fe482021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000527
KNApSAcK IDNot Available
Chemspider ID133730
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151730
PDB IDNot Available
ChEBI ID74048
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .