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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:55 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
ValueSource
5-ALAChEBI
5-amino-4-OxopentanoateChEBI
5-amino-4-Oxovaleric acidChEBI
5-AminolevulinateChEBI
DALAChEBI
delta-ALAChEBI
delta-Aminolevulinic acidChEBI
AminolevulinateGenerator
5-amino-4-Oxopentanoic acidGenerator
5-amino-4-OxovalerateGenerator
5-Aminolevulinic acidGenerator
δ-alaGenerator
delta-AminolevulinateGenerator
δ-aminolevulinateGenerator
δ-aminolevulinic acidGenerator
5-amino-4-oxo-PentanoateHMDB
5-amino-4-oxo-Pentanoic acidHMDB
5-amino-LevulinateHMDB
5-amino-Levulinic acidHMDB
5-AminolaevulinateHMDB
5-Aminolaevulinic acidHMDB
AladermHMDB
amino-Levulinic acidHMDB
KerastickHMDB
Chemical FormulaC5H9NO3
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
IUPAC Name5-amino-4-oxopentanoic acid
Traditional 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 KeyInChIKey=ZGXJTSGNIOSYLO-UHFFFAOYSA-N
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
Substituents
  • 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
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 Solubility173.0 mg/mLALOGPS
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 Area80.39 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.45 m3·mol-1ChemAxon
Polarizability12.55 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fki-2910000000-12bd38ce6e25c61b8e60View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dr-4900000000-c11a861a1638dd2c20d8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00dr-2911000000-d5b5567862328f5a46cdView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00dr-3900000000-538e027ec9932b3f56a5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS; 1 MEOX)splash10-00di-9500000000-c0d571fa1aa74cf69ea6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS; 1 MEOX)splash10-00di-9600000000-d0a9f31de64870117dfeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-00di-1911000000-117a44ade2fd70812e5cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-00dr-2900000000-635a7d4012b9ef5150f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-5900000000-cf9a0266243b1a1d0f73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-995eb11961b16f254be2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-64b1ef51cceb8d346f52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-01q9-1900000000-a5686c059e357bc14e96View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9300000000-8e219c18bb0fd0837d82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0avr-9000000000-b0d0d9b25a36e5c49f2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-96cc61ad07db2c38c952View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9000000000-7b8165e702ac7e6d5f34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-01p9-8900000000-0b739a89ed524e47e3a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-1ffb96adb6268888f722View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4900000000-1669ed2d77c2a1921a2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0292-9300000000-c07de16859b85d8fb54cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-9000000000-316eb66f80f8b40f4ae2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4900000000-1669ed2d77c2a1921a2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0292-9300000000-c07de16859b85d8fb54cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-9000000000-316eb66f80f8b40f4ae2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-e2f3aecb5b3f533e4905View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu0-9600000000-fc4f9eaeca47b90745aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-304beef010b4b4fdbb53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-e2f3aecb5b3f533e4905View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu0-9600000000-fc4f9eaeca47b90745aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-304beef010b4b4fdbb53View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Kidney
  • Skin
  • Spleen
  • Stratum Corneum
  • Testes
Pathways
NameSMPDB LinkKEGG Link
3-Phosphoglycerate dehydrogenase deficiencySMP00721Not Available
Acute Intermittent PorphyriaSMP00344Not Available
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseSMP00345Not Available
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)SMP00179Not Available
Dimethylglycine Dehydrogenase DeficiencySMP00242Not Available
Dimethylglycine Dehydrogenase DeficiencySMP00484Not Available
Glycine and Serine MetabolismSMP00004map00260
Hereditary Coproporphyria (HCP)SMP00342Not Available
Hyperglycinemia, non-ketoticSMP00485Not Available
Non Ketotic HyperglycinemiaSMP00223Not Available
Porphyria Variegata (PV)SMP00346Not Available
Porphyrin MetabolismSMP00024map00860
SarcosinemiaSMP00244Not Available
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 Quantified7.953 +/- 2.681 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified2.9 (1.2-4.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified19.24 +/- 16.586 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
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. [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 ]

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