| Common Name |
L-Glutamic gamma-semialdehyde
| Description |
Glutamic 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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
5-oxo-L-NorvalineChEBI
L-Glutamate 5-semialdehydeChEBI
L-Glutamate gamma-semialdehydeChEBI
L-Glutamic g-semialdehydeGenerator
L-Glutamic γ-semialdehydeGenerator
L-Glutamic acid 5-semialdehydeGenerator
L-Glutamate g-semialdehydeGenerator
L-Glutamate γ-semialdehydeGenerator
L-Glutamic acid g-semialdehydeGenerator
L-Glutamic acid gamma-semialdehydeGenerator
L-Glutamic acid γ-semialdehydeGenerator
Glutamate-semialdehydeHMDB
Glutamic gamma-semialdehydeHMDB
L-Glutamate-5-semialdehydeHMDB
L-Glutamate-gamma-semialdehydeHMDB
L-Glutamic-gamma-semialdehydeHMDB
gamma-Glutamyl semialdehydeMeSH
Glutamate gamma-semialdehydeMeSH
Glutamic acid gamma-semialdehydeMeSH
Glutamic acid gamma-semialdehyde, (L)-isomerMeSH
| Chemical Formlia |
C5H9NO3
| Average Molecliar Weight |
131.1299
| Monoisotopic Molecliar Weight |
131.058243159
| IUPAC Name |
(2S)-2-amino-5-oxopentanoic acid
| Traditional Name |
4-carboxy-4-aminobutanal
| CAS Registry Number |
496-92-4
| SMILES |
N[C@@H](CCC=O)C(O)=O
| InChI Identifier |
InChI=1S/C5H9NO3/c6-4(5(8)9)2-1-3-7/h3-4H,1-2,6H2,(H,8,9)/t4-/m0/s1
| InChI Key |
KABXUUFDPUOJMW-BYPYZUCNSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Carboxylic acids and derivatives
| Direct Parent |
L-alpha-amino acids
| Alternative Parents |
Fatty acids and conjugates
Alpha-hydrogen aldehydes
Amino acids
Monocarboxylic acids and derivatives
Carboxylic acids
Organopnictogen compounds
Organic oxides
Monoalkylamines
Hydrocarbon derivatives
| Substituents |
L-alpha-amino acid
Fatty acid
Alpha-hydrogen aldehyde
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Aldehyde
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Aliphatic acyclic compound
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
glutamic semialdehyde (CHEBI:17232 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Protein synthesis, amino acid biosynthesis
| Application |
Not Available
| Cellliar locations |
Cytoplasm
Mitochondria
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility144.0 mg/mLALOGPS
logP-2.6ALOGPS
logP-3.4ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)2.12ChemAxon
pKa (Strongest Basic)9.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.36 m3·mol-1ChemAxon
Polarizability12.56 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted GC-MS |
Predicted GC-MS Spectrum – GC-MSNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-02a9-9700000000-ffc8c81a881bac7a0ca7View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-00kr-9100000000-7061d8b19402303b61afView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0a4l-9000000000-fa50d608bfaec666722dView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-001i-1900000000-485c1c464e6d065cb4acView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-01q9-7900000000-cd2ef70374a324d28ee0View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0006-9000000000-8685f6b3a1d6936c24c3View in MoNA
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Mitochondria
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
Arginine and Proline MetabolismSMP00020map00330
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)SMP00362Not Available
Creatine deficiency, guanidinoacetate methyltransferase deficiencySMP00504Not Available
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)SMP00188Not Available
Hyperornithinemia with gyrate atrophy (HOGA)SMP00505Not Available
Hyperornithinemia-hyperammonemia-homocitrlilinuria [HHH-syndrome]SMP00506Not Available
Hyperprolinemia Type ISMP00361Not Available
Hyperprolinemia Type IISMP00360Not Available
L-arginine:glycine amidinotransferase deficiencySMP00507Not Available
Ornithine Aminotransferase Deficiency (OAT Deficiency)SMP00363Not Available
Prolidase Deficiency (PD)SMP00207Not Available
Prolinemia Type IISMP00208Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022847
| KNApSAcK ID |
Not Available
| Chemspider ID |
167744
| KEGG Compound ID |
C01165
| BioCyc ID |
L-GLUTAMATE_GAMMA-SEMIALDEHYDE
| BiGG ID |
36962
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02104
| Metagene Link |
HMDB02104
| METLIN ID |
6488
| PubChem Compound |
193305
| PDB ID |
Not Available
| ChEBI ID |
17232
Product: BRD7116
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
Not Available |
Enzymes
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Irreversible conversion of delta-1-pyrroline-5-carboxylate (P5C), derived either from proline or ornithine, to glutamate. This is a necessary step in the pathway interconnecting the urea and tricarboxylic acid cycles. The preferred substrate is glutamic gamma-semialdehyde, other substrates include succinic, glutaric and adipic semialdehydes.
- Gene Name:
- ALDH4A1
- Uniprot ID:
- P30038
- Molecular weight:
- 55117.24
Reactions
| L-Glutamic gamma-semialdehyde + NAD + Water → L-Glutamic acid + NADH + Hydrogen Ion |
details |
- General function:
- Involved in transaminase activity
- Specific function:
- Not Available
- Gene Name:
- OAT
- Uniprot ID:
- P04181
- Molecular weight:
- 48534.39
Reactions
| Ornithine + a 2-oxo acid → L-Glutamic gamma-semialdehyde + an L-amino acid |
details |
| Ornithine + Oxoglutaric acid → L-Glutamic gamma-semialdehyde + L-Glutamic acid |
details |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Bifunctional enzyme that converts glutamate to glutamate 5-semialdehyde, an intermediate in the biosynthesis of proline, ornithine and arginine.
- Gene Name:
- ALDH18A1
- Uniprot ID:
- P54886
- Molecular weight:
- 87088.29
Reactions
| L-Glutamic gamma-semialdehyde + Phosphoric acid + NADP → L-Glutamic acid 5-phosphate + NADPH |
details |
| L-Glutamic gamma-semialdehyde + Phosphoric acid + NADP → L-Glutamic acid 5-phosphate + NADPH + Hydrogen Ion |
details |
PMID: 19133994