Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB000275
Identification
Name: 5-Aminolevulinic acid
Description:5-Aminolevulinic acid is an intermediate in heme synthesis. This is the first compound in the porphyrin synthesis pathway. It is produced by the enzyme ALA synthase, from glycine and succinyl CoA. This reaction is known as the Shemin pathway.
Structure
Thumb
Synonyms:
  • δ-aminolevulinate
  • δ-aminolevulinic acid
  • γ-aminolevulinate
  • γ-aminolevulinic acid
  • 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
  • 5-aminolevulinic acid
  • ALA
  • Aladerm
  • Amino-levulinate
  • Amino-levulinic acid
  • Aminolevulinate
  • Aminolevulinic acid
  • Delta-Aminolevulinate
  • Delta-Aminolevulinic acid
  • g-Aminolevulinate
  • g-Aminolevulinic acid
  • Gamma-Aminolevulinate
  • Gamma-Aminolevulinic acid
  • Kerastick
  • γ-Aminolevulinate
  • γ-Aminolevulinic acid
  • δ-Aminolevulinate
  • δ-Aminolevulinic acid
Chemical Formula: C5H9NO3
Average Molecular Weight: 131.1299
Monoisotopic Molecular Weight: 131.058243159
InChI Key: ZGXJTSGNIOSYLO-UHFFFAOYSA-N
InChI:InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
CAS number: 106-60-5
IUPAC Name:5-amino-4-oxopentanoic acid
Traditional IUPAC Name: aminolevulinic acid
SMILES:NCC(=O)CCC(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as delta amino acids and derivatives. These are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Delta amino acids and derivatives
Alternative Parents
Substituents
  • Delta amino acid or derivatives
  • Gamma-keto acid
  • Short-chain keto acid
  • Keto acid
  • Alpha-aminoketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 156-158 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility173.0 mg/mLALOGPS
logP-2.9ALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.45 m3·mol-1ChemAxon
Polarizability12.55 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fki-2910000000-12bd38ce6e25c61b8e60View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dr-4900000000-c11a861a1638dd2c20d8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00dr-2911000000-d5b5567862328f5a46cdView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00dr-3900000000-538e027ec9932b3f56a5View in 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-c0d571fa1aa74cf69ea6View in 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-d0a9f31de64870117dfeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-00di-1911000000-117a44ade2fd70812e5cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-00dr-2900000000-635a7d4012b9ef5150f9View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-5900000000-cf9a0266243b1a1d0f73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-995eb11961b16f254be2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-64b1ef51cceb8d346f52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-01q9-1900000000-a5686c059e357bc14e96View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9300000000-8e219c18bb0fd0837d82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0avr-9000000000-b0d0d9b25a36e5c49f2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-96cc61ad07db2c38c952View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9000000000-7b8165e702ac7e6d5f34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-01p9-8900000000-0b739a89ed524e47e3a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-1ffb96adb6268888f722View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4900000000-1669ed2d77c2a1921a2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0292-9300000000-c07de16859b85d8fb54cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-9000000000-316eb66f80f8b40f4ae2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4900000000-1669ed2d77c2a1921a2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0292-9300000000-c07de16859b85d8fb54cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-9000000000-316eb66f80f8b40f4ae2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-e2f3aecb5b3f533e4905View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu0-9600000000-fc4f9eaeca47b90745aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-304beef010b4b4fdbb53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-e2f3aecb5b3f533e4905View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu0-9600000000-fc4f9eaeca47b90745aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-304beef010b4b4fdbb53View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
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  • Murata K, Sakai T, Morita Y, Iwata T, Dakeishi M: Critical dose of lead affecting delta-aminolevulinic acid levels. J Occup Health. 2003 Jul;45(4):209-14. Pubmed: 14646278
  • Santos MA, Belo VG, Santos G: Effectiveness of photodynamic therapy with topical 5-aminolevulinic acid and intense pulsed light versus intense pulsed light alone in the treatment of acne vulgaris: comparative study. Dermatol Surg. 2005 Aug;31(8 Pt 1):910-5. Pubmed: 16042935
  • Sassa S: Diagnosis and therapy of acute intermittent porphyria. Blood Rev. 1996 Mar;10(1):53-8. Pubmed: 8861279
  • Srivastava G, Borthwick IA, Maguire DJ, Elferink CJ, Bawden MJ, Mercer JF, May BK: Regulation of 5-aminolevulinate synthase mRNA in different rat tissues. J Biol Chem. 1988 Apr 15;263(11):5202-9. Pubmed: 3356687
  • Tauber S, Stepp H, Meier R, Bone A, Hofstetter A, Stief C: Integral spectrophotometric analysis of 5-aminolaevulinic acid-induced fluorescence cytology of the urinary bladder. BJU Int. 2006 May;97(5):992-6. Pubmed: 16643481
  • Tschudy DP, Valsamis M, Magnussen CR: Acute intermittent porphyria: clinical and selected research aspects. Ann Intern Med. 1975 Dec;83(6):851-64. Pubmed: 1106284
  • van den Akker JT, Boot K, Vernon DI, Brown SB, Groenendijk L, van Rhoon GC, Sterenborg HJ: Effect of elevating the skin temperature during topical ALA application on in vitro ALA penetration through mouse skin and in vivo PpIX production in human skin. Photochem Photobiol Sci. 2004 Mar;3(3):263-7. Epub 2004 Feb 13. Pubmed: 14993942
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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  • Winkler A, Muller-Goymann CC: Comparative permeation studies for delta-aminolevulinic acid and its n-butylester through stratum corneum and artificial skin constructs. Eur J Pharm Biopharm. 2002 May;53(3):281-7. Pubmed: 11976015
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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.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID17549
HMDB IDHMDB01149
Pubchem Compound ID137
Kegg IDC00430
ChemSpider ID134
Wikipedia5-Aminolevulinic acid
BioCyc ID5-AMINO-LEVULINATE
EcoCyc ID5-AMINO-LEVULINATE