Showing Metabocard for L-glutamate 5-semialdehyde (BASm0003174)

Common NameL-glutamate 5-semialdehyde
DescriptionGlutamic gamma-semialdehyde is the metabolic precursor for proline biosynthesis. The conversion from L-Glutamate, an ATP- and NADPH-dependent reaction, is catalyzed by the enzyme Delta-1-pyrroline-5-carboxylate synthetase (P5CS) (OMIM 138250 ). L-Glutamic-gamma-semialdehyde can also be converted to or be formed from the amino acids L-ornithine (EC 2.6.1.13) and L-proline (EC 1.5.99.8 and EC 1.5.1.2). It is also one of the few metabolites that can be a precursor to other metabolites of both the urea cycle and the citric acid cycle (BioCyc).
Structure
Molecular FormulaC5H9NO3
Average Mass131.12990
Monoisotopic Mass131.05824
IUPAC Name(2S)-2-amino-5-oxopentanoic acid
Traditional Name4-carboxy-4-aminobutanal
CAS Registry Number496-92-4
SMILES[NH3+][C@@H](CCC=O)C(=O)[O-]
InChI IdentifierInChI=1S/C5H9NO3/c6-4(5(8)9)2-1-3-7/h3-4H,1-2,6H2,(H,8,9)/t4-/m0/s1
InChI KeyKABXUUFDPUOJMW-BYPYZUCNSA-N
CHEBI IDCHEBI:58066
HMDB IDHMDB0002104
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 Solubility1.44e+02 g/l
logP-2.57
logS0.04
pKa (Strongest Acidic)2.12
pKa (Strongest Basic)9.11
Hydrogen Acceptor Count4
Hydrogen Donor Count2
Polar Surface Area80.39 Ų
Rotatable Bond Count4
Physiological Charge0
Formal Charge0
Refractivity30.36 m³·mol⁻¹
Polarizability12.43

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