Showing Metabocard for D-proline (BASm0002915)

Common NameD-proline
DescriptionD-proline is an isomer of the naturally occurring amino acid, L-Proline. D-amino acids have been found in relatively high abundance in human plasma and saliva (PMID: 16480744 ). These amino acids may be of bacterial origin, but there is also evidence that they are endogenously produced through amino acid racemase activity (PMID: 1426150 ).
Structure
Molecular FormulaC5H9NO2
Average Mass115.13050
Monoisotopic Mass115.06333
IUPAC Name(2R)-pyrrolidine-2-carboxylic acid
Traditional NameD-proline
CAS Registry Number344-25-2
SMILESO=C([O-])[C@H]1CCC[NH2+]1
InChI IdentifierInChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1
InChI KeyONIBWKKTOPOVIA-SCSAIBSYSA-N
CHEBI IDCHEBI:57726
HMDB IDHMDB0003411
Pathways
NameSMPDB/PathBank
Arginine and proline metabolism
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)
Prolidase Deficiency (PD)
Prolinemia Type II
Hyperprolinemia Type II
Hyperprolinemia Type I
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)
Ornithine Aminotransferase Deficiency (OAT Deficiency)
Creatine deficiency, guanidinoacetate methyltransferase deficiency
Hyperornithinemia with gyrate atrophy (HOGA)
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]
L-arginine:glycine amidinotransferase deficiency
StateSolid
Water Solubility3.65e+02 g/l
logP-2.71
logS0.50
pKa (Strongest Acidic)1.94
pKa (Strongest Basic)11.33
Hydrogen Acceptor Count3
Hydrogen Donor Count2
Polar Surface Area49.33 Ų
Rotatable Bond Count1
Physiological Charge0
Formal Charge0
Refractivity28.06 m³·mol⁻¹
Polarizability11.39

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