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5-Aminolevulinic acid

CAT: 0013-GTR19226794-01Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19226794-01Size:100 mg
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Description
5-Aminolevulinic acid (5-ALA) is a biochemical precursor in heme biosynthesis. As a prodrug, it is metabolized to protoporphyrin IX, a photosensitizer used in photodynamic therapy research for actinic keratosis and in studies targeting various cancer cells in vitro and in vivo.
CAS Number
106-60-5
Field of Research
Metabolism Research, Pharmacology & Drug Discovery
Smiles
NCC (=O) CCC (O) =O
Molecular Formula
C5H9NO3
Molecular Weight
131.13
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

5-Aminolevulinic Acid

5-aminolevulinic acid is the simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp. It has a role as an antineoplastic agent, a photosensitizing agent, a dermatologic drug, a prodrug, a mouse metabolite, a Saccharomyces cerevisiae metabolite, a plant metabolite, an Escherichia coli metabolite and a human metabolite. It is a delta-amino acid and a 4-oxo monocarboxylic acid. It is functionally related to a 4-oxopentanoic acid. It is a conjugate base of a 5-ammoniolevulinic acid. It is a conjugate acid of a 5-aminolevulinate. It is a tautomer of a 5-ammoniolevulinate.

CAS Number106-60-5
PubChem CID137
IUPAC Name5-amino-4-oxopentanoic acid
Molecular FormulaC5H9NO3
Molecular Weight131.13
XLogP-3.8
Topological Polar Surface Area80.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Heavy Atom Count9
Formal Charge0
Complexity121
SMILES
C(CC(=O)O)C(=O)CN
InChI
InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
InChIKey
ZGXJTSGNIOSYLO-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 5-Aminolevulinic Acid
CAS: 106-60-5
CID: 137
Formula: C5H9NO3
MW: 131.13
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight131.13
XLogP3-3.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass131.058243149
Monoisotopic Mass131.058243149
Topological Polar Surface Area80.4 Ų
Heavy Atom Count9
Formal Charge0
Complexity121
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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