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Record Information
Version	2.0
Creation Date	2012-05-31 13:46:24 -0600
Update Date	2015-09-13 12:56:10 -0600
Secondary Accession Numbers	ECMDB01149
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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xab7d778c> Close
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
Weight:	Average: 131.1299 Monoisotopic: 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
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	Delta amino acids and derivatives
Alternative Parents	Gamma-keto acids and derivatives Short-chain keto acids and derivatives Alpha-amino ketones Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
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 Framework	Aliphatic acyclic compounds
External Descriptors	delta-amino acid (CHEBI:17549 ) 4-oxo monocarboxylic acid (CHEBI:17549 ) Amino fatty acids (LMFA01100055 )
Physical Properties
State:	Solid
Charge:	0
Melting point:	156-158 °C
Experimental Properties:	Property Value Source Water Solubility: 1000 mg/mL at 25 oC [MEYLAN,WM et al. (1996)] PhysProp
Predicted Properties	Property Value Source Water Solubility 173 g/L ALOGPS logP -2.9 ALOGPS logP -3.3 ChemAxon logS 0.12 ALOGPS pKa (Strongest Acidic) 4.05 ChemAxon pKa (Strongest Basic) 7.84 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 80.39 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 30.45 m³·mol⁻¹ ChemAxon Polarizability 12.55 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	(S)-4-Amino-5-oxopentanoate <> 5-Aminolevulinic acid 2 5-Aminolevulinic acid <> Hydrogen ion +2 Water + Porphobilinogen 2 5-Aminolevulinic acid <> Porphobilinogen +2 Water 5-Aminolevulinic acid <> (S)-4-Amino-5-oxopentanoate 5-Aminolevulinic acid <> Hydrogen ion + Water + Porphobilinogen (S)-4-Amino-5-oxopentanoate > 5-Aminolevulinic acid 2 5-Aminolevulinic acid > Porphobilinogen +2 Water 8 (S)-4-Amino-5-oxopentanoate >8 5-Aminolevulinic acid 8 5-Aminolevulinic acid >4 Hydrogen ion +8 Water +4 Porphobilinogen (S)-4-Amino-5-oxopentanoate <>5 5-Aminolevulinic acid 5 5-Aminolevulinic acid <> (S)-4-Amino-5-oxopentanoate 2 5-Aminolevulinic acid <> Hydrogen ion +2 Water + Porphobilinogen 2 5-Aminolevulinic acid <> Porphobilinogen +2 Water (S)-4-Amino-5-oxopentanoate <>5 5-Aminolevulinic acid 2 5-Aminolevulinic acid <> Hydrogen ion +2 Water + Porphobilinogen
SMPDB Pathways:	Porphyrin metabolism PW000936
KEGG Pathways:	ABC transporters ec02010 Glycine, serine and threonine metabolism ec00260 Metabolic pathways eco01100 Porphyrin and chlorophyll metabolism ec00860
EcoCyc Pathways:	tetrapyrrole biosynthesis I PWY-5188
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) splash10-0fki-2910000000-12bd38ce6e25c61b8e60 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) splash10-00dr-4900000000-c11a861a1638dd2c20d8 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-00dr-2911000000-d5b5567862328f5a46cd View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-00dr-3900000000-538e027ec9932b3f56a5 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS; 1 MEOX) splash10-00di-9500000000-c0d571fa1aa74cf69ea6 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS; 1 MEOX) splash10-00di-9600000000-d0a9f31de64870117dfe View in MoNA GC-MS GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS) splash10-00di-1911000000-117a44ade2fd70812e5c View in MoNA GC-MS GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS) splash10-00dr-2900000000-635a7d4012b9ef5150f9 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0fki-2910000000-12bd38ce6e25c61b8e60 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00dr-4900000000-c11a861a1638dd2c20d8 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00dr-2911000000-d5b5567862328f5a46cd View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00dr-3900000000-538e027ec9932b3f56a5 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00di-9500000000-c0d571fa1aa74cf69ea6 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00di-9600000000-d0a9f31de64870117dfe View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-00di-1911000000-117a44ade2fd70812e5c View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-00dr-2900000000-635a7d4012b9ef5150f9 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-001i-9000000000-b1941f10190ebb6e1343 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-05ai-9200000000-6a559cb30668be35a1ed View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-0udi-5900000000-cf9a0266243b1a1d0f73 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-000i-9000000000-995eb11961b16f254be2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-0fb9-9000000000-64b1ef51cceb8d346f52 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive splash10-01q9-1900000000-a5686c059e357bc14e96 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive splash10-000i-9300000000-8e219c18bb0fd0837d82 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive splash10-0avr-9000000000-b0d0d9b25a36e5c49f2a View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive splash10-0a4i-9000000000-96cc61ad07db2c38c952 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive splash10-0a4i-9000000000-7b8165e702ac7e6d5f34 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-01p9-8900000000-0b739a89ed524e47e3a2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative splash10-001i-0900000000-1ffb96adb6268888f722 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , negative splash10-001i-0900000000-1ffb96adb6268888f722 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-01q9-1900000000-a5686c059e357bc14e96 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-000i-9300000000-8e219c18bb0fd0837d82 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03di-4900000000-1669ed2d77c2a1921a2d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0292-9300000000-c07de16859b85d8fb54c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-067j-9000000000-316eb66f80f8b40f4ae2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03di-4900000000-1669ed2d77c2a1921a2d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0292-9300000000-c07de16859b85d8fb54c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-067j-9000000000-316eb66f80f8b40f4ae2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001i-2900000000-e2f3aecb5b3f533e4905 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0bu0-9600000000-fc4f9eaeca47b90745ae View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4l-9000000000-304beef010b4b4fdbb53 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001i-2900000000-e2f3aecb5b3f533e4905 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0bu0-9600000000-fc4f9eaeca47b90745ae View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4l-9000000000-304beef010b4b4fdbb53 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Bhardwaj RK, Herrera-Ruiz D, Sinko PJ, Gudmundsson OS, Knipp G: Delineation of human peptide transporter 1 (hPepT1)-mediated uptake and transport of substrates with varying transporter affinities utilizing stably transfected hPepT1/Madin-Darby canine kidney clones and Caco-2 cells. J Pharmacol Exp Ther. 2005 Sep;314(3):1093-100. Epub 2005 May 18. Pubmed: 15901802 Collaud S, Jichlinski P, Marti A, Aymon D, Gurny R, Lange N: An open pharmacokinetic study of hexylaminolevulinate-induced photodiagnosis after intravesical administration. Drugs R D. 2006;7(3):173-86. Pubmed: 16752943 Fritsch C, Batz J, Bolsen K, Schulte KW, Zumdick M, Ruzicka T, Goerz G: Ex vivo application of delta-aminolevulinic acid induces high and specific porphyrin levels in human skin tumors: possible basis for selective photodynamic therapy. Photochem Photobiol. 1997 Jul;66(1):114-8. Pubmed: 9230710 Gederaas OA, Rasch MH, Berg K, Lagerberg JW, Dubbelman TM: Photodynamically induced effects in colon carcinoma cells (WiDr) by endogenous photosensitizers generated by incubation with 5-aminolaevulinic acid. J Photochem Photobiol B. 1999 Apr;49(2-3):162-70. Pubmed: 10392465 Hexyl aminolevulinate: 5-ALA hexylester, 5-ALA hexylesther, aminolevulinic acid hexyl ester, hexaminolevulinate, hexyl 5-aminolevulinate, P 1206. Drugs R D. 2005;6(4):235-8. Pubmed: 15991884 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 Landry JL, Gelet A, Bouvier R, Dubernard JM, Martin X, Colombel M: Detection of bladder dysplasia using 5-aminolaevulinic acid-induced porphyrin fluorescence. BJU Int. 2003 May;91(7):623-6. Pubmed: 12699472 Lee S, Kollias N, McAuliffe DJ, Flotte TJ, Doukas AG: Topical drug delivery in humans with a single photomechanical wave. Pharm Res. 1999 Nov;16(11):1717-21. Pubmed: 10571277 Lerda D: Study of sperm characteristics in persons occupationally exposed to lead. Am J Ind Med. 1992;22(4):567-71. Pubmed: 1442789 Lipinski M, Jeromin L: Comparison of the bladder tumour antigen test with photodynamic diagnosis in patients with pathologically confirmed recurrent superficial urinary bladder tumours. BJU Int. 2002 May;89(7):757-9. Pubmed: 11966640 Lu L, Lin G, Xu M, Zou H, Wang Q: [Re-assessment of indicators for screening lead poisoning] Zhonghua Yu Fang Yi Xue Za Zhi. 1999 Sep;33(5):275-8. Pubmed: 11864490 Maines MD, Mayer RD: Inhibition of testicular cytochrome P-450-dependent steroid biosynthesis by cis-platinum. Reversal by human chorionic gonadotropin. J Biol Chem. 1985 May 25;260(10):6063-8. Pubmed: 4039724 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064 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 Zareba G, Chmielnicka J: Disturbances in heme biosynthesis in rabbits after administration per os of low doses of tin or lead. Biol Trace Elem Res. 1992 Aug;34(2):115-22. Pubmed: 1381933
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)
Links
External Links:	Resource Link CHEBI ID 17549 HMDB ID HMDB01149 Pubchem Compound ID 137 Kegg ID C00430 ChemSpider ID 134 Wikipedia 5-Aminolevulinic acid BioCyc ID 5-AMINO-LEVULINATE EcoCyc ID 5-AMINO-LEVULINATE

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