Human Metabolome Database Version 3.5

Showing metabocard for 5-Aminolevulinic acid (HMDB01149)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:59 -0700
HMDB ID HMDB01149
Secondary Accession Numbers None
Metabolite Identification
Common 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. 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C5H9NO3
Average Molecular Weight 131.1299
Monoisotopic Molecular Weight 131.058243159
IUPAC Name 5-amino-4-oxopentanoic acid
Traditional IUPAC Name aminolevulinic acid
CAS Registry Number 106-60-5
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 Key ZGXJTSGNIOSYLO-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Delta 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 Parent Delta Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycine, serine and threonine metabolism
  • Component of Porphyrin and chlorophyll metabolism
Application Not Available
Cellular locations
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 156 - 158 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1000 mg/mL at 25 °C Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 173 g/L ALOGPS
LogP -2.85 ALOGPS
LogP -3.3 ChemAxon
LogS 0.12 ALOGPS
pKa (strongest acidic) 4.05 ChemAxon
pKa (strongest basic) 7.84 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 80.39 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 30.45 ChemAxon
Polarizability 12.62 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Testes
  • Kidney
  • Skin
  • Spleen
  • Stratum Corneum
Pathways
Name SMPDB Link KEGG Link
Glycine and Serine Metabolism SMP00004 map00260 Link_out
Porphyrin Metabolism SMP00024 map00860 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.35 +/- 0.09 uM Newborn (0-30 days old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
1.97 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
1.28 +/- 0.57 umol/mmol creatinine Children (1-13 year old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
1.45 +/- 0.72 umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
2.9 (1.2-4.4) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022452
KNApSAcK ID Not Available
Chemspider ID 134 Link_out
KEGG Compound ID C00430 Link_out
BioCyc ID 5-AMINO-LEVULINATE Link_out
BiGG ID 34963 Link_out
Wikipedia Link 5-Aminolevulinic acid Link_out
NuGOwiki Link HMDB01149 Link_out
Metagene Link HMDB01149 Link_out
METLIN ID 6037 Link_out
PubChem Compound 137 Link_out
PDB ID Not Available
ChEBI ID 17549 Link_out
References
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)
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 Link_out
  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 Link_out
  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 Link_out
  4. Sassa S: Diagnosis and therapy of acute intermittent porphyria. Blood Rev. 1996 Mar;10(1):53-8. Pubmed: 8861279 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  16. Lerda D: Study of sperm characteristics in persons occupationally exposed to lead. Am J Ind Med. 1992;22(4):567-71. Pubmed: 1442789 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: 5-aminolevulinate synthase, erythroid-specific, mitochondrial
Reactions:
Succinyl-CoA + Glycine unknown 5-Aminolevulinic acid + Coenzyme A + CO(2) details
Succinyl-CoA + Glycine unknown 5-Aminolevulinic acid + Coenzyme A + Carbon dioxide details
Gene Name: ALAS2
Uniprot ID: P22557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-aminolevulinate synthase, nonspecific, mitochondrial
Reactions:
Succinyl-CoA + Glycine unknown 5-Aminolevulinic acid + Coenzyme A + CO(2) details
Succinyl-CoA + Glycine unknown 5-Aminolevulinic acid + Coenzyme A + Carbon dioxide details
Gene Name: ALAS1
Uniprot ID: P13196 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Delta-aminolevulinic acid dehydratase
Reactions:
5-Aminolevulinic acid unknown Porphobilinogen + Water details
Gene Name: ALAD
Uniprot ID: P13716 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA