You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:59 UTC
HMDB IDHMDB01149
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.
Structure
Thumb
Synonyms
  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 IUPAC Nameaminolevulinic acid
CAS Registry Number106-60-5
SMILES
NCC(=O)CCC(O)=O
InChI Identifier
InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
InChI KeyZGXJTSGNIOSYLO-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassDelta Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Amino fatty acids(Lipidmaps)
  • amino acid zwitterion(ChEBI)
Substituents
  • Alpha Aminoketone
  • Carboxylic Acid
  • Gamma Keto Acid
  • Ketone
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentDelta Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycine, serine and threonine metabolism
  • Component of Porphyrin and chlorophyll metabolism
ApplicationNot Available
Cellular locations
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point156 - 158 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility173 g/LALOGPS
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 area80.39ChemAxon
rotatable bond count4ChemAxon
refractivity30.45ChemAxon
polarizability12.62ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Kidney
  • Skin
  • Spleen
  • Stratum Corneum
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004map00260
Porphyrin MetabolismSMP00024map00860
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.35 +/- 0.09 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
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...
details
UrineDetected and Quantified1.45 +/- 0.72 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified2.9 (1.2-4.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
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
BioCyc ID5-AMINO-LEVULINATE
BiGG ID34963
Wikipedia Link5-Aminolevulinic acid
NuGOwiki LinkHMDB01149
Metagene LinkHMDB01149
METLIN ID6037
PubChem Compound137
PDB IDNot Available
ChEBI ID17549
References
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. Pubmed: 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. Pubmed: 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. Pubmed: 12699472
  4. Sassa S: Diagnosis and therapy of acute intermittent porphyria. Blood Rev. 1996 Mar;10(1):53-8. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 14993942
  16. Lerda D: Study of sperm characteristics in persons occupationally exposed to lead. Am J Ind Med. 1992;22(4):567-71. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 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. Pubmed: 9230710

Enzymes

General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
ALAS2
Uniprot ID:
P22557
Molecular weight:
64632.86
Reactions
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:
ALAS1
Uniprot ID:
P13196
Molecular weight:
70580.325
Reactions
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:
ALAD
Uniprot ID:
P13716
Molecular weight:
36294.485
Reactions
5-Aminolevulinic acid → Porphobilinogen + Waterdetails