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5-Aminolevulinic acid (YMDB00083)

Identification
YMDB IDYMDB00083
Name5-Aminolevulinic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Aminolevulinic acid is an intermediate in tetrapyrrole biosynthesis pathway. 5-Aminolevulinic acid is produced by the enzyme ALA synthase from glycine and succinyl CoA. Uroporphyrinogen-III, the final product in this pathway, is a major branch point that leads to biosynthesis of different tetrapyrrole compounds (e.g. porphyrins). Tetrapyrroles usually function as a metal-binding cofactor in many important enzymes, proteins and pigments, such as heme, chlorophyll, cobalamine, siroheme, and cofator F430. [Biocyc PWY-5189]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 5-amino-4-oxo-Pentanoate
  • 5-amino-4-oxo-Pentanoic acid
  • 5-Amino-4-oxopentanoate
  • 5-Amino-4-oxopentanoic acid
  • 5-Amino-4-oxovalerate
  • 5-Amino-4-oxovaleric acid
  • 5-amino-Levulinate
  • 5-amino-Levulinic acid
  • 5-aminolaevulinate
  • 5-Aminolaevulinic acid
  • 5-Aminolevulinate
  • ALA
  • Aladerm
  • Amino-levulinic acid
  • Aminolevulinate
  • Aminolevulinic acid
  • delta-aminolevulinate
  • delta-Aminolevulinic acid
  • Kerastick
  • 5-ALA
  • DALA
  • delta-ALA
  • Δ-ala
  • Δ-aminolevulinate
  • Δ-aminolevulinic acid
  • 5 Aminolevulinate
  • Acid, Delta-aminolevulinic
  • Levulan
  • 5 Aminolaevulinate
  • Acid hydrochloride, aminolevulinic
  • Bertek brand OF aminolevulinic acid hydrochloride
  • Hydrochloride, aminolevulinic acid
  • Acid, aminolevulinic
  • Aminolevulinic acid hydrochloride
  • Delta Aminolevulinic acid
CAS number106-60-5
WeightAverage: 131.1299
Monoisotopic: 131.058243159
InChI KeyZGXJTSGNIOSYLO-UHFFFAOYSA-N
InChIInChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
IUPAC Name5-amino-4-oxopentanoic acid
Traditional IUPAC Nameaminolevulinic acid
Chemical FormulaC5H9NO3
SMILES[H]OC(=O)C([H])([H])C([H])([H])C(=O)C([H])([H])N([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDelta amino acids and derivatives
Alternative Parents
Substituents
  • Delta amino acid or derivatives
  • Gamma-keto acid
  • Short-chain keto acid
  • Keto acid
  • Alpha-aminoketone
  • Amino acid
  • Ketone
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organooxygen compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point156-158 °C
Experimental Properties
PropertyValueReference
Water Solubility1000 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility173 g/LALOGPS
logP-2.8ALOGPS
logP-3.3ChemAxon
logS0.12ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
pKa (Strongest Basic)7.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.45 m³·mol⁻¹ChemAxon
Polarizability12.55 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
Porphyrin MetabolismPW002462 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycine, serine and threonine metabolismec00260 Map00260
Porphyrin and chlorophyll metabolismec00860 Map00860
SMPDB Reactions
Glycine + Succinyl-CoA → 5-Aminolevulinic acid + Carbon dioxide
5-Aminolevulinic acid → Porphobilinogen + water
KEGG Reactions
Glycine + hydron + Succinyl-CoA → 5-Aminolevulinic acid + Carbon dioxide + Coenzyme A
5-Aminolevulinic acid → water + Porphobilinogen + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fki-2910000000-12bd38ce6e25c61b8e60JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dr-4900000000-c11a861a1638dd2c20d8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00dr-2911000000-d5b5567862328f5a46cdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00dr-3900000000-538e027ec9932b3f56a5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS; 1 MEOX)splash10-00di-9500000000-c0d571fa1aa74cf69ea6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS; 1 MEOX)splash10-00di-9600000000-d0a9f31de64870117dfeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-00di-1911000000-117a44ade2fd70812e5cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-00dr-2900000000-635a7d4012b9ef5150f9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fki-2910000000-12bd38ce6e25c61b8e60JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-4900000000-c11a861a1638dd2c20d8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-2911000000-d5b5567862328f5a46cdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-3900000000-538e027ec9932b3f56a5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9500000000-c0d571fa1aa74cf69ea6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9600000000-d0a9f31de64870117dfeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1911000000-117a44ade2fd70812e5cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00dr-2900000000-635a7d4012b9ef5150f9JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-b1941f10190ebb6e1343JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05ai-9200000000-6a559cb30668be35a1edJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-5900000000-cf9a0266243b1a1d0f73JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-995eb11961b16f254be2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-64b1ef51cceb8d346f52JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-01q9-1900000000-a5686c059e357bc14e96JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9300000000-8e219c18bb0fd0837d82JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0avr-9000000000-b0d0d9b25a36e5c49f2aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-96cc61ad07db2c38c952JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9000000000-7b8165e702ac7e6d5f34JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-01p9-8900000000-0b739a89ed524e47e3a2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-1ffb96adb6268888f722JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-1ffb96adb6268888f722JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01q9-1900000000-a5686c059e357bc14e96JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9300000000-8e219c18bb0fd0837d82JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4900000000-1669ed2d77c2a1921a2dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0292-9300000000-c07de16859b85d8fb54cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-9000000000-316eb66f80f8b40f4ae2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4900000000-1669ed2d77c2a1921a2dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0292-9300000000-c07de16859b85d8fb54cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-9000000000-316eb66f80f8b40f4ae2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-e2f3aecb5b3f533e4905JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu0-9600000000-fc4f9eaeca47b90745aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-304beef010b4b4fdbb53JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-e2f3aecb5b3f533e4905JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu0-9600000000-fc4f9eaeca47b90745aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-304beef010b4b4fdbb53JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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
  • Volland, C., Felix, F. (1984). "Isolation and properties of 5-aminolevulinate synthase from the yeast Saccharomyces cerevisiae." Eur J Biochem 142:551-557.6381051
  • Chelstowska, A., Rytka, J. (1993). "[Biosynthesis of heme in yeast Saccharomyces cerevisiae]." Postepy Biochem 39:173-185.8234090
Synthesis Reference:Goli?ski J., D?browski Z., Obukowicz B., Kami?ski J., Be?dowicz M., Kwa?ny M.: "Synthesis of 5-aminolevulinic acid (5-ALA)", ICRI Annual Report '99, 2000, 119-122.
External Links:
ResourceLink
CHEBI ID17549
HMDB IDHMDB01149
Pubchem Compound ID137
Kegg IDC00430
ChemSpider ID134
FOODB IDFDB022452
WikipediaAminolevulinic_acid
BioCyc ID5-AMINO-LEVULINATE

Enzymes

Protein Details
1. 5-aminolevulinate synthase, mitochondrial
General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Succinyl-CoA + glycine = 5-aminolevulinate + CoA + CO(2)
Gene Name:
HEM1
Uniprot ID:
P09950
Molecular weight:
59361.69922
Reactions
Succinyl-CoA + glycine → 5-aminolevulinate + CoA + CO(2).
Protein Details
2. Delta-aminolevulinic acid dehydratase
General function:
Involved in porphobilinogen synthase activity
Specific function:
Catalyzes an early step in the biosynthesis of tetrapyrroles. Binds two molecules of 5-aminolevulinate per subunit, each at a distinct site, and catalyzes their condensation to form porphobilinogen
Gene Name:
HEM2
Uniprot ID:
P05373
Molecular weight:
37739.69922
Reactions
2 5-aminolevulinate → porphobilinogen + 2 H(2)O.

Transporters

Protein Details
1. GABA-specific permease
General function:
Involved in transport
Specific function:
Required for high-affinity, high-specificity GABA transport. Also transports putrescine
Gene Name:
UGA4
Uniprot ID:
P32837
Molecular weight:
61872.30078