5-amino-4-oxopentanoic acid

• ChemBase ID: 733
• Molecular Formular: C5H9NO3
• Molecular Mass: 131.12986
• Monoisotopic Mass: 131.05824315
• SMILES: O=C(CCC(=O)O)CN
• Canonical SMILES: NCC(=O)CCC(=O)O
• InChI: InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
• InChIKey: ZGXJTSGNIOSYLO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-4-oxopentanoic acid
• IUPAC Traditional name: aminolevulinic acid
• Brand Name: Aladerm; Kerastick; Levulan; Levulan Kerastick
• Synonyms: 5-Aminolevulinic acid; δ-AMINOLEVULINIC ACID; ALA; delta-Aminolevulinic acid; Aminolevulinate; Aminolevulinic acid

Database IDs

• CAS Number: 5451-09-2; 106-60-5
• EC Number: 226-679-5
• PubChem SID: 160964196; 46506856
• PubChem CID: 137

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.0531516
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.2572048
• LogD (pH = 7.4): -3.3702924
• Log P: -3.2526455
• Molar Refractivity: 30.4478 cm^3
• Polarizability: 12.14889 Å^3
• Polar Surface Area: 80.39 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.85
• LOG S: 0.12
• Solubility (Water): 1.73e+02 g/l

PROPERTIES

Physical Property

• Solubility: Very soluble
• Hydrophobicity(logP): -1.5

Safety Information

• Storage Condition: 0°C
• RTECS: OI1640000

Product Information

• Purity: ~98%

DETAILS

MP Biomedicals - 02194621

Hydrochloride
Cell Culture Reagent
Purity: Approx. 98%

DrugBank - DB00855

• Drug Groups: approved
• Description: A compound produced from succinyl-CoA and glycine as an intermediate in heme synthesis. It is used as a photochemotherapy for actinic keratosis. [PubChem]
• Indication: 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.
• Pharmacology: The metabolism of aminolevulinic acid (ALA) is the first step in the biochemical pathway resulting in heme synthesis. Aminolevulinic acid is not a photosensitizer, but rather a metabolic precursor of protoporphyrin IX (PpIX), which is a photosensitizer. The synthesis of ALA is normally tightly controlled by feedback inhibition of the enzyme, ALA synthetase, presumably by intracellular heme levels. ALA, when provided to the cell, bypasses this control point and results in the accumulation of PpIX, which is converted into heme by ferrochelatase through the addition of iron to the PpIX nucleus.
• Toxicity: Solution overdose have not been reported.
• Affected Organisms: Humans and other mammals
• Biotransformation: Following topical administration, synthesis into protoporphyrin IX takes place in situ in the skin.
• Absorption: Oral bioavailability is 50-60%.
• Half Life: Mean half-life is 0.70 ± 0.18 h after the oral dose and 0.83 ± 0.05 h after the intravenous dose.
• References: Stummer W, Pichlmeier U, Meinel T, Wiestler OD, Zanella F, Reulen HJ: Fluorescence-guided surgery with 5-aminolevulinic acid for resection of malignant glioma: a randomised controlled multicentre phase III trial. Lancet Oncol. 2006 May;7(5):392-401. [Pubmed] ; Kennedy JC, Marcus SL, Pottier RH: Photodynamic therapy (PDT) and photodiagnosis (PD) using endogenous photosensitization induced by 5-aminolevulinic acid (ALA): mechanisms and clinical results. J Clin Laser Med Surg. 1996 Oct;14(5):289-304. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Stummer W, Pichlmeier U, Meinel T, Wiestler OD, Zanella F, Reulen HJ: Fluorescence-guided surgery with 5-aminolevulinic acid for resection of malignant glioma: a randomised controlled multicentre phase III trial. Lancet Oncol. 2006 May;7(5):392-401. Pubmed
• Kennedy JC, Marcus SL, Pottier RH: Photodynamic therapy (PDT) and photodiagnosis (PD) using endogenous photosensitization induced by 5-aminolevulinic acid (ALA): mechanisms and clinical results. J Clin Laser Med Surg. 1996 Oct;14(5):289-304. Pubmed