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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2015-03-09 22:57:11 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Aminolevulinic acid
Description5-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. Aminolevulinic acid plus blue light illumination using a blue light photodynamic therapy illuminator is indicated for the treatment of minimally to moderately thick actinic keratoses of the face or scalp.
  1. 5-Amino-4-oxo-Pentanoate
  2. 5-Amino-4-oxo-Pentanoic acid
  3. 5-Amino-4-oxopentanoate
  4. 5-Amino-4-oxopentanoic acid
  5. 5-Amino-4-oxovalerate
  6. 5-Amino-4-oxovaleric acid
  7. 5-Amino-Levulinate
  8. 5-Amino-Levulinic acid
  9. 5-Aminolaevulinate
  10. 5-Aminolaevulinic acid
  11. 5-Aminolevulinate
  12. Aladerm
  13. Amino-levulinic acid
  14. Aminolevulinate
  15. Aminolevulinic acid
  16. delta-Aminolevulinate
  17. delta-Aminolevulinic acid
  18. Kerastick
Chemical FormulaC5H9NO3
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
IUPAC Name5-amino-4-oxopentanoic acid
Traditional Nameaminolevulinic acid
CAS Registry Number106-60-5
InChI Identifier
Chemical 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.
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
  • 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 FrameworkAliphatic acyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
  • Component of Glycine, serine and threonine metabolism
  • Component of Porphyrin and chlorophyll metabolism
ApplicationNot Available
Cellular locations
  • Mitochondria
Physical Properties
Experimental Properties
Melting Point156 - 158 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility173.0 mg/mLALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Kidney
  • Skin
  • Spleen
  • Stratum Corneum
  • Testes
Glycine and Serine MetabolismSMP00004map00260
Porphyrin MetabolismSMP00024map00860
Normal Concentrations
BloodDetected and Quantified0.35 +/- 0.09 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
UrineDetected and Quantified1.97 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.28 +/- 0.57 umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
UrineDetected and Quantified1.45 +/- 0.72 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
UrineDetected and Quantified2.9 (1.2-4.4) umol/mmol creatinineAdult (>18 years old)Both
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022452
KNApSAcK IDNot Available
Chemspider ID134
KEGG Compound IDC00430
BiGG ID34963
Wikipedia Link5-Aminolevulinic acid
NuGOwiki LinkHMDB01149
Metagene LinkHMDB01149
PubChem Compound137
PDB IDNot Available
ChEBI ID17549
Synthesis ReferenceGoli?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)
General References
  1. 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. [14646278 ]
  2. 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. [11864490 ]
  3. 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. [12699472 ]
  4. Sassa S: Diagnosis and therapy of acute intermittent porphyria. Blood Rev. 1996 Mar;10(1):53-8. [8861279 ]
  5. 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. [16643481 ]
  6. 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. [15901802 ]
  7. Tschudy DP, Valsamis M, Magnussen CR: Acute intermittent porphyria: clinical and selected research aspects. Ann Intern Med. 1975 Dec;83(6):851-64. [1106284 ]
  8. 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. [11966640 ]
  9. 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. [1381933 ]
  10. 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. [3356687 ]
  11. 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. [4039724 ]
  12. 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. [16042935 ]
  13. 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. [10392465 ]
  14. 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. [10571277 ]
  15. 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. [14993942 ]
  16. Lerda D: Study of sperm characteristics in persons occupationally exposed to lead. Am J Ind Med. 1992;22(4):567-71. [1442789 ]
  17. 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. [11976015 ]
  18. 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. [15991884 ]
  19. 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. [16752943 ]
  20. 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. [9230710 ]


General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
Succinyl-CoA + Glycine → 5-Aminolevulinic acid + Coenzyme A + CO(2)details
Succinyl-CoA + Glycine → 5-Aminolevulinic acid + Coenzyme A + Carbon dioxidedetails
General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
Succinyl-CoA + Glycine → 5-Aminolevulinic acid + Coenzyme A + CO(2)details
Succinyl-CoA + Glycine → 5-Aminolevulinic acid + Coenzyme A + Carbon dioxidedetails
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:
Uniprot ID:
Molecular weight:
5-Aminolevulinic acid → Porphobilinogen + Waterdetails