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Identification
YMDB IDYMDB00720
NameL-4-hydroxyglutamic semialdehyde
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-4-Hydroxyglutamate semialdehyde, also known as (4R)-4-hydroxy-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-4-Hydroxyglutamate semialdehyde is a very strong basic compound (based on its pKa). L-4-Hydroxyglutamate semialdehyde exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • (4R)-4-hydroxy-5-oxo-L-norvaline
  • 4-amino-3,4-dideoxy-D-erythro-penturonic acid
  • L-4-Hydroxyglutamate semialdehyde
  • 4-Amino-3,4-dideoxy-D-erythro-penturonate
  • L-4-Hydroxyglutamic acid semialdehyde
CAS numberNot Available
WeightAverage: 147.1293
Monoisotopic: 147.053157781
InChI KeyXCXUZPXOFFRGGP-DMTCNVIQSA-N
InChIInChI=1S/C5H9NO4/c6-4(5(9)10)1-3(8)2-7/h2-4,8H,1,6H2,(H,9,10)/t3-,4+/m1/s1
IUPAC Name(2S,4R)-2-amino-4-hydroxy-5-oxopentanoic acid
Traditional IUPAC Name(2S,4R)-2-amino-4-hydroxy-5-oxopentanoic acid
Chemical FormulaC5H9NO4
SMILESN[C@@H](C[C@@H](O)C=O)C(O)=O
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
  • Short-chain hydroxy acid
  • Fatty acid
  • 1,3-aminoalcohol
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility128 g/LALOGPS
logP-3ALOGPS
logP-4.3ChemAxon
logS-0.06ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)8.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.81 m³·mol⁻¹ChemAxon
Polarizability13.13 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
SMPDB ReactionsNot Available
KEGG Reactions
water + hydron + 1-pyrroline-3-hydroxy-5-carboxylic acidL-4-hydroxyglutamic semialdehyde
NAD + water + L-4-hydroxyglutamic semialdehydeNADH + hydron + erythro-4-hydroxy-L-glutamic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID27809
HMDB IDHMDB06556
Pubchem Compound ID440851
Kegg IDC05938
ChemSpider ID389693
FOODB IDFDB023970
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 H(2)O = L-glutamate + NAD(P)H
Gene Name:
PUT2
Uniprot ID:
P07275
Molecular weight:
64434.60156
Reactions
(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 H(2)O → L-glutamate + NAD(P)H.