Showing Metabocard for L-pipecolate (BASm0004063)

Common NameL-pipecolate
DescriptionL-pipecolic acid is a normal human metabolite present in human blood, where is present as the primary enantiomer of pipecolic acid. L-pipecolic acid is a cyclic imino acid (contains both imino (>C=NH) and carboxyl (-C(=O)-OH) functional groups) produced during the degradation of lysine, accumulates in body fluids of infants with generalized genetic peroxisomal disorders, including Zellweger syndrome (OMIM 214100 ), neonatal adrenoleukodystrophy (OMIM 202370 ), and infantile Refsum disease (OMIM 266510 ). L-pipecolic acid levels are also elevated in patients with chronic liver diseases. L-pipecolic acid is the substrate of delta1-piperideine-2-carboxylate reductase (EC 1.5.1.21) in the pathway of lysine degradation (PMID: 2717271 , 8305590 , 1050990 ).
Structure
Molecular FormulaC6H11NO2
Average Mass129.15700
Monoisotopic Mass129.07898
IUPAC Name(2S)-piperidine-2-carboxylic acid
Traditional NameL-pipecolic acid
CAS Registry Number3105-95-1
SMILESO=C([O-])[C@@H]1CCCC[NH2+]1
InChI IdentifierInChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1
InChI KeyHXEACLLIILLPRG-YFKPBYRVSA-N
CHEBI IDCHEBI:61185
HMDB IDHMDB0000716
Pathways
NameSMPDB/PathBank
Lysine degradation
Glutaric Aciduria Type I
Saccharopinuria/Hyperlysinemia II
Hyperlysinemia I, Familial
Hyperlysinemia II or Saccharopinuria
Pyridoxine dependency with seizures
2-aminoadipic 2-oxoadipic aciduria
StateSolid
Water Solubility1.58e+02 g/l
logP-2.17
logS0.09
pKa (Strongest Acidic)2.06
pKa (Strongest Basic)10.39
Hydrogen Acceptor Count3
Hydrogen Donor Count2
Polar Surface Area49.33 Ų
Rotatable Bond Count1
Physiological Charge0
Formal Charge0
Refractivity32.67 m³·mol⁻¹
Polarizability13.49

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