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Human Metabolome Database Version 3.5

Showing metabocard for 5-Aminolevulinic acid (HMDB01149)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
• Links
• References

enzymes (2)

• Blood
• Urine

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	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	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 Aladerm Amino-levulinic acid Aminolevulinate Aminolevulinic acid delta-Aminolevulinate delta-Aminolevulinic acid 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 Porphyrin Metabolism SMP00024 map00860
Normal Concentrations
	Biofluid Status Value Age Sex Condition Comments Blood Detected and Quantified 0.35 +/- 0.09 uM Newborn (0-30 days old) Both Normal Not Available Urine Detected and Quantified 1.97 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 1.28 +/- 0.57 umol/mmol creatinine Children (1-13 year old) Both Normal Not Available Urine Detected and Quantified 1.45 +/- 0.72 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 2.9 (1.2-4.4) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Abnormal Concentrations
	Not Available
Associated Disorders and Diseases
Disease References	None
Associated OMIM IDs	None
External Links
DrugBank 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
KEGG Compound ID	C00430
BioCyc ID	5-AMINO-LEVULINATE
BiGG ID	34963
Wikipedia Link	5-Aminolevulinic acid
NuGOwiki Link	HMDB01149
Metagene Link	HMDB01149
METLIN ID	6037
PubChem Compound	137
PDB ID	Not Available
ChEBI ID	17549
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	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 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 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 Sassa S: Diagnosis and therapy of acute intermittent porphyria. Blood Rev. 1996 Mar;10(1):53-8. Pubmed: 8861279 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 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 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 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 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 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 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 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 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 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 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 Lerda D: Study of sperm characteristics in persons occupationally exposed to lead. Am J Ind Med. 1992;22(4):567-71. Pubmed: 1442789 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 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 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

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Enzymes
Name: 5-aminolevulinate synthase, erythroid-specific, mitochondrial Reactions: succinyl-CoA + glycine = 5-aminolevulinate + CoA + CO2 [RN:R00830] Gene Name: ALAS2 Uniprot ID: P22557 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 5-aminolevulinate synthase, nonspecific, mitochondrial Reactions: succinyl-CoA + glycine = 5-aminolevulinate + CoA + CO2 [RN:R00830] Gene Name: ALAS1 Uniprot ID: P13196 Protein Sequence: FASTA Gene Sequence: FASTA

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