5-amino-4-oxopentanoic acid

• ChemBase编号: 733
• 分子式: C5H9NO3
• 平均质量: 131.12986
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 5-amino-4-oxopentanoic acid
• IUPAC传统名: aminolevulinic acid
• 商标名: Aladerm; Kerastick; Levulan; Levulan Kerastick
• 别名: 5-Aminolevulinic acid; δ-AMINOLEVULINIC ACID; ALA; delta-Aminolevulinic acid; Aminolevulinate; Aminolevulinic acid

登记号

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

理论计算性质

JChem

• Acid pKa: 4.0531516
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): -3.2572048
• LogD (pH = 7.4): -3.3702924
• Log P: -3.2526455
• 摩尔折射率: 30.4478 cm^3
• 极化性: 12.14889 Å^3
• 极化表面积: 80.39 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -2.85
• LOG S: 0.12
• 溶解度: 1.73e+02 g/l

分子性质

理化性质

• 溶解度: Very soluble
• 疏水性(logP): -1.5

安全信息

• 保存条件: 0°C
• RTECS编号: OI1640000

产品相关信息

• 纯度: ~98%

详细说明

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

参考文献

• 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