pyrrolysine (CHEM045823)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 13:43:30 UTC
Update Date2016-11-09 01:23:25 UTC
Accession NumberCHEM045823
Identification
Common Namepyrrolysine
ClassSmall Molecule
DescriptionA N(6)-acyl-L-lysine having (2R,3R)-3-methyl-3,4-dihydro-2H-pyrrol-2-ylcarbonyl as the N(6)-acyl group.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2S)-2-Amino-6-[(2R,3R)-3-methyl-3,4-dihydro-2H-pyrrol-2-ylcarbonyl]aminohexanoic acidChEBI
Monomethylamine methyltransferase cofactor lysine adductChEBI
N6-((2R,3R)-3-Methyl-3,4-dihydro-2H-pyrrol-2-ylcarbonyl)-L-lysineChEBI
N6-(4-Methyl-1,2-didehydropyrrolidine-5-carboxyl)-L-lysineChEBI
N6-(4-Methyl-delta-1-pyrroline-5-carboxyl)-L-lysineChEBI
PyrrolysineChEBI
(2S)-2-Amino-6-[(2R,3R)-3-methyl-3,4-dihydro-2H-pyrrol-2-ylcarbonyl]aminohexanoateGenerator
N6-(4-Methyl-δ-1-pyrroline-5-carboxyl)-L-lysineGenerator
L-PyrrolysineMeSH
L-PyrrolysineMeSH
(2S)-2-Amino-6-({hydroxy[(2R,3R)-3-methyl-3,4-dihydro-2H-pyrrol-2-yl]methylidene}amino)hexanoateGenerator
Chemical FormulaC12H21N3O3
Average Molecular Mass255.313 g/mol
Monoisotopic Mass255.158 g/mol
CAS Registry Number448235-52-7
IUPAC Name(2S)-2-amino-6-({hydroxy[(2R,3R)-3-methyl-3,4-dihydro-2H-pyrrol-2-yl]methylidene}amino)hexanoic acid
Traditional Namepyrrolysine
SMILES[H][C@](N)(CCCCN=C(O)[C@]1([H])N=CC[C@@]1([H])C)C(O)=O
InChI IdentifierInChI=1S/C12H21N3O3/c1-8-5-7-14-10(8)11(16)15-6-3-2-4-9(13)12(17)18/h7-10H,2-6,13H2,1H3,(H,15,16)(H,17,18)/t8-,9+,10-/m1/s1
InChI KeyZFOMKMMPBOQKMC-KXUCPTDWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Pyrroline carboxylic acid or derivatives
  • Medium-chain fatty acid
  • Amino fatty acid
  • Heterocyclic fatty acid
  • Fatty acyl
  • Fatty acid
  • Pyrroline
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Imine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.37 g/LALOGPS
logP-2.4ALOGPS
logP-2.5ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area108.27 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity67 m³·mol⁻¹ChemAxon
Polarizability27.99 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08gs-3590000000-5a5b6bf2a8269d308d7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-9610000000-a22a9fede9bbbe4966f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9100000000-409db8753a6081aab3f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0190000000-255a0359c5c313d6babfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h11-3960000000-0399ae9e930b64052efdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9300000000-6e0685cc0fe000454ea2Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-3321
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPyrrolysine
Chemspider IDNot Available
ChEBI ID21860
PubChem Compound ID5460671
Kegg Compound IDC16138
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15329732
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16256420
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17360621
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17626042
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19063902
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19796638