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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:53:58 UTC
Update Date2022-09-22 18:34:24 UTC
HMDB IDHMDB0033143
Secondary Accession Numbers
  • HMDB33143
Metabolite Identification
Common NamePyrraline
DescriptionPyrraline, also known as 2-FHMPN, 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). Based on a literature review very few articles have been published on Pyrraline.
Structure
Data?1563862358
Synonyms
ValueSource
2-Amino-6-(2-formyl-5-hydroxymethylpyrrol-1-yl)hexanoic acidMeSH
2-Formyl-5-(hydroxymethyl)pyrrole-1-norleucineMeSH
2-FHMPNMeSH
2-Amino-6-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]hexanoateGenerator
PyrralineMeSH
Chemical FormulaC12H18N2O4
Average Molecular Weight254.2823
Monoisotopic Molecular Weight254.126657074
IUPAC Name2-amino-6-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]hexanoic acid
Traditional Name2-amino-6-[2-formyl-5-(hydroxymethyl)pyrrol-1-yl]hexanoic acid
CAS Registry Number74509-14-1
SMILES
NC(CCCCN1C(CO)=CC=C1C=O)C(O)=O
InChI Identifier
InChI=1S/C12H18N2O4/c13-11(12(17)18)3-1-2-6-14-9(7-15)4-5-10(14)8-16/h4-5,7,11,16H,1-3,6,8,13H2,(H,17,18)
InChI KeyVTYFITADLSVOAS-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
  • Medium-chain fatty acid
  • Amino fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Aryl-aldehyde
  • Substituted pyrrole
  • Fatty acid
  • Fatty acyl
  • Pyrrole
  • Heteroaromatic compound
  • Amino acid
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Aldehyde
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Aromatic alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
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 Solubility2.16 g/LALOGPS
logP-1.6ALOGPS
logP-2.3ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.03ChemAxon
pKa (Strongest Basic)9.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.55 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity66.76 m³·mol⁻¹ChemAxon
Polarizability26.66 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]+160.54231661259
DarkChem[M-H]-158.74731661259
DeepCCS[M+H]+158.12630932474
DeepCCS[M-H]-155.76830932474
DeepCCS[M-2H]-191.14830932474
DeepCCS[M+Na]+166.78630932474
AllCCS[M+H]+157.032859911
AllCCS[M+H-H2O]+153.632859911
AllCCS[M+NH4]+160.032859911
AllCCS[M+Na]+160.932859911
AllCCS[M-H]-159.032859911
AllCCS[M+Na-2H]-159.332859911
AllCCS[M+HCOO]-159.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PyrralineNC(CCCCN1C(CO)=CC=C1C=O)C(O)=O2975.0Standard polar33892256
PyrralineNC(CCCCN1C(CO)=CC=C1C=O)C(O)=O2209.8Standard non polar33892256
PyrralineNC(CCCCN1C(CO)=CC=C1C=O)C(O)=O2398.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pyrraline,1TMS,isomer #1C[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(N)C(=O)O2441.6Semi standard non polar33892256
Pyrraline,1TMS,isomer #2C[Si](C)(C)OC(=O)C(N)CCCCN1C(C=O)=CC=C1CO2349.6Semi standard non polar33892256
Pyrraline,1TMS,isomer #3C[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO)C(=O)O2464.0Semi standard non polar33892256
Pyrraline,2TMS,isomer #1C[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(N)C(=O)O[Si](C)(C)C2383.4Semi standard non polar33892256
Pyrraline,2TMS,isomer #2C[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO[Si](C)(C)C)C(=O)O2495.2Semi standard non polar33892256
Pyrraline,2TMS,isomer #3C[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO)C(=O)O[Si](C)(C)C2395.0Semi standard non polar33892256
Pyrraline,2TMS,isomer #4C[Si](C)(C)N(C(CCCCN1C(C=O)=CC=C1CO)C(=O)O)[Si](C)(C)C2617.8Semi standard non polar33892256
Pyrraline,3TMS,isomer #1C[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO[Si](C)(C)C)C(=O)O[Si](C)(C)C2445.5Semi standard non polar33892256
Pyrraline,3TMS,isomer #1C[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO[Si](C)(C)C)C(=O)O[Si](C)(C)C2536.1Standard non polar33892256
Pyrraline,3TMS,isomer #2C[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2657.2Semi standard non polar33892256
Pyrraline,3TMS,isomer #2C[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2639.7Standard non polar33892256
Pyrraline,3TMS,isomer #3C[Si](C)(C)OC(=O)C(CCCCN1C(C=O)=CC=C1CO)N([Si](C)(C)C)[Si](C)(C)C2592.1Semi standard non polar33892256
Pyrraline,3TMS,isomer #3C[Si](C)(C)OC(=O)C(CCCCN1C(C=O)=CC=C1CO)N([Si](C)(C)C)[Si](C)(C)C2624.4Standard non polar33892256
Pyrraline,4TMS,isomer #1C[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2646.8Semi standard non polar33892256
Pyrraline,4TMS,isomer #1C[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2652.9Standard non polar33892256
Pyrraline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(N)C(=O)O2672.5Semi standard non polar33892256
Pyrraline,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(N)CCCCN1C(C=O)=CC=C1CO2608.5Semi standard non polar33892256
Pyrraline,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO)C(=O)O2710.7Semi standard non polar33892256
Pyrraline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(N)C(=O)O[Si](C)(C)C(C)(C)C2846.8Semi standard non polar33892256
Pyrraline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO[Si](C)(C)C(C)(C)C)C(=O)O2933.3Semi standard non polar33892256
Pyrraline,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO)C(=O)O[Si](C)(C)C(C)(C)C2881.4Semi standard non polar33892256
Pyrraline,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(C(CCCCN1C(C=O)=CC=C1CO)C(=O)O)[Si](C)(C)C(C)(C)C3066.4Semi standard non polar33892256
Pyrraline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3073.8Semi standard non polar33892256
Pyrraline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3162.1Standard non polar33892256
Pyrraline,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3287.7Semi standard non polar33892256
Pyrraline,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3213.6Standard non polar33892256
Pyrraline,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CCCCN1C(C=O)=CC=C1CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3254.3Semi standard non polar33892256
Pyrraline,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(CCCCN1C(C=O)=CC=C1CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3226.5Standard non polar33892256
Pyrraline,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3502.9Semi standard non polar33892256
Pyrraline,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3401.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pyrraline GC-MS (Non-derivatized) - 70eV, Positivesplash10-01dl-9520000000-0b433cd9cded35aa23ef2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrraline GC-MS (2 TMS) - 70eV, Positivesplash10-008l-8954000000-7e420e3240531df4ca372017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrraline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrraline 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 - Pyrraline 10V, Positive-QTOFsplash10-0a4i-0190000000-10655c1012b66e94ba402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrraline 20V, Positive-QTOFsplash10-0a5c-3980000000-eea702f0360e6881ff9a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrraline 40V, Positive-QTOFsplash10-0560-9800000000-cb66f0e04f4bd6b989452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrraline 10V, Negative-QTOFsplash10-0udi-0090000000-5fe59c9e31f9d1b82c6d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrraline 20V, Negative-QTOFsplash10-0fk9-2590000000-7fd7c78887e5c6a4c28a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrraline 40V, Negative-QTOFsplash10-00di-9400000000-db3eeb1ed3f6503bf2e72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrraline 10V, Positive-QTOFsplash10-0540-8590000000-d040968f2b23fff76e532021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrraline 20V, Positive-QTOFsplash10-0a59-7960000000-10b916022566e97e56992021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrraline 40V, Positive-QTOFsplash10-001i-9200000000-e40604bb69ce47768a7a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrraline 10V, Negative-QTOFsplash10-0uk9-3190000000-ccdcd07268989aa6afcc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrraline 20V, Negative-QTOFsplash10-0596-3950000000-3fc3da416f4839b6e60a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrraline 40V, Negative-QTOFsplash10-006x-9710000000-40f1c72a3cac98237ca92021-09-25Wishart 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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
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
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Cardiosvacular risk
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011144
KNApSAcK IDNot Available
Chemspider ID19980286
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14274616
PDB IDNot Available
ChEBI IDNot Available
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.. .