Showing Compound Card for L-Glutamic γ-semialdehyde (CDB005107)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:10:01 UTC
Updated at2020-11-18 16:39:22 UTC
CannabisDB IDCDB005107
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameL-Glutamic γ-semialdehyde
DescriptionL-Glutamic gamma-semialdehyde, also known as L-glutamate 5-semialdehyde or 5-oxo-L-norvaline, 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. L-Glutamic gamma-semialdehyde is a very strong basic compound (based on its pKa). L-Glutamic gamma-semialdehyde exists in all living species, ranging from bacteria to humans. A glutamic semialdehyde arising from formal reduction of the side-chain carboxy group of L-glutamic acid. Outside of the human body, L-Glutamic gamma-semialdehyde has been detected, but not quantified in, several different foods, such as oil palms, pak choy, oregon yampahs, chicory leaves, and broad beans. This could make L-glutamic gamma-semialdehyde a potential biomarker for the consumption of these foods. L-Glutamic γ-semialdehyde is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-oxo-L-NorvalineChEBI
L-Glutamate 5-semialdehydeChEBI
L-Glutamate gamma-semialdehydeChEBI
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
L-Glutamic g-semialdehydeGenerator
L-Glutamic γ-semialdehydeGenerator
Glutamate-semialdehydeHMDB
Glutamic gamma-semialdehydeHMDB
L-Glutamate-5-semialdehydeHMDB
L-Glutamate-gamma-semialdehydeHMDB
L-Glutamic-gamma-semialdehydeHMDB
gamma-Glutamyl semialdehydeHMDB
Glutamate gamma-semialdehydeHMDB
Glutamic acid gamma-semialdehydeHMDB
Glutamic acid gamma-semialdehyde, (L)-isomerHMDB
Chemical FormulaC5H9NO3
Average Molecular Weight131.13
Monoisotopic Molecular Weight131.0582
IUPAC Name(2S)-2-amino-5-oxopentanoic acid
Traditional Name4-carboxy-4-aminobutanal
CAS Registry Number496-92-4
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 KeyKABXUUFDPUOJMW-BYPYZUCNSA-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
  • 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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.36 m³·mol⁻¹ChemAxon
Polarizability12.56 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSL-Glutamic γ-semialdehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-059l-9000000000-c907c5e28c6d3b047532Spectrum
Predicted GC-MSL-Glutamic γ-semialdehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-9200000000-b09702360bf061bd64dbSpectrum
Predicted GC-MSL-Glutamic γ-semialdehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02a9-9700000000-ffc8c81a881bac7a0ca72015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9100000000-7061d8b19402303b61af2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-fa50d608bfaec666722d2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-485c1c464e6d065cb4ac2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-7900000000-cd2ef70374a324d28ee02015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-8685f6b3a1d6936c24c32015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-30a10f2c9d729eb39f1f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-6900000000-22f02534479a7a01c5bf2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-cb0e34b8ef2d18870f9b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-69607aaecb41dd2d014a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014u-9000000000-d6928830fd6c484b658f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-915ef2dc6a2dda8f2ee62021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrialALDH4A11p36P30038 details
Ornithine aminotransferase, mitochondrialOAT10q26P04181 details
Delta-1-pyrroline-5-carboxylate synthaseALDH18A110q24.3P54886 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002104
DrugBank IDDB04388
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030963
KNApSAcK IDC00007475
Chemspider ID167744
KEGG Compound IDC01165
BioCyc IDL-GLUTAMATE_GAMMA-SEMIALDEHYDE
BiGG ID36962
Wikipedia LinkNot Available
METLIN ID6488
PubChem Compound193305
PDB IDNot Available
ChEBI ID17232
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial
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
Enzyme Details
2. Ornithine aminotransferase, mitochondrial
General function:
Involved in transaminase activity
Specific function:
Not Available
Gene Name:
OAT
Uniprot ID:
P04181
Molecular weight:
48534.39
Enzyme Details
3. Delta-1-pyrroline-5-carboxylate synthase
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