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Showing NP-Card for 5-Aminolevulinic acid (NP0000055)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-15 04:56:49 UTC
NP-MRD IDNP0000055
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Aminolevulinic acid
Description5-Aminolevulinic acid, also known as 5-aminolevulinate or 5-amino-4-oxopentanoate, belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom. 5-Aminolevulinic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 5-Aminolevulinic acid exists in all living species, ranging from bacteria to humans. 5-Aminolevulinic acid can be biosynthesized from glycine and succinyl-CoA by the enzyme 5-aminolevulinate synthase. The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. In humans, 5-aminolevulinic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. Outside of the human body, 5-Aminolevulinic acid has been detected, but not quantified in several different foods, such as american butterfish, vaccinium (blueberry, cranberry, huckleberry), amaranths, purple mangosteens, and garden cress. 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 is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000055 (5-Aminolevulinic acid)

855
  Mrv1652305271900002D          

  9  8  0  0  0  0            999 V2000
    3.5217   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  9  1  0  0  0  0
  3  9  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
Download

3D MOL for NP0000055 (5-Aminolevulinic acid)

HMDB0001149
     RDKit          3D
5-Aminolevulinic acid
 18 17  0  0  0  0  0  0  0  0999 V2000
    3.3712   -0.2443    0.5214 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1332    0.3423    0.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784   -0.1856    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378   -1.0591   -0.7350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3732    0.3565    0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4234   -0.3051   -0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7640    0.2655   -0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8720    1.1718    0.6201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8953   -0.1668   -0.8995 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0597    0.3175    0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066   -1.2576    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903    0.2644    1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2058    1.4502    0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6628    0.3081    1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3884    1.4503    0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616   -1.3889   -0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1438   -0.1916   -1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1985   -1.1274   -0.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  9 18  1  0
M  END
Download

3D SDF for NP0000055 (5-Aminolevulinic acid)

855
  Mrv1652305271900002D          

  9  8  0  0  0  0            999 V2000
    3.5217   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  9  1  0  0  0  0
  3  9  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000055

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C5H9NO3

> <MOLECULAR_WEIGHT>
131.1299

> <EXACT_MASS>
131.058243159

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.548276397155476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-amino-4-oxopentanoic acid

> <ALOGPS_LOGP>
-2.85

> <JCHEM_LOGP>
-3.2526454527445376

> <ALOGPS_LOGS>
0.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.164001067559852

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.053151638897345

> <JCHEM_PKA_STRONGEST_BASIC>
7.835220055699867

> <JCHEM_POLAR_SURFACE_AREA>
80.39

> <JCHEM_REFRACTIVITY>
30.447799999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aminolevulinic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000055 (5-Aminolevulinic acid)

HMDB0001149
     RDKit          3D
5-Aminolevulinic acid
 18 17  0  0  0  0  0  0  0  0999 V2000
    3.3712   -0.2443    0.5214 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1332    0.3423    0.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784   -0.1856    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378   -1.0591   -0.7350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3732    0.3565    0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4234   -0.3051   -0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7640    0.2655   -0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8720    1.1718    0.6201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8953   -0.1668   -0.8995 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0597    0.3175    0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066   -1.2576    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903    0.2644    1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2058    1.4502    0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6628    0.3081    1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3884    1.4503    0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616   -1.3889   -0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1438   -0.1916   -1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1985   -1.1274   -0.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  9 18  1  0
M  END
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PDB for NP0000055 (5-Aminolevulinic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 855                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       6.574  -1.925   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.908  -0.385   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.575   1.925   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       3.907  -0.385   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.907   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.241  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.574  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.240   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.575   0.385   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    8                                                            
CONECT    5    6    7                                                       
CONECT    6    5    9                                                       
CONECT    7    1    5    8                                                  
CONECT    8    4    7                                                       
CONECT    9    2    3    6                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0000055 (5-Aminolevulinic acid)

COMPND    HMDB0001149
HETATM    1  N1  UNL     1       3.371  -0.244   0.521  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.133   0.342   0.840  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.978  -0.186   0.086  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.138  -1.059  -0.735  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.373   0.356   0.338  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.423  -0.305  -0.525  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.764   0.266  -0.244  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.872   1.172   0.620  1.00  0.00           O  
HETATM    9  O3  UNL     1      -3.895  -0.167  -0.900  1.00  0.00           O  
HETATM   10  H1  UNL     1       4.060   0.317   0.023  1.00  0.00           H  
HETATM   11  H2  UNL     1       3.407  -1.258   0.393  1.00  0.00           H  
HETATM   12  H3  UNL     1       1.890   0.264   1.919  1.00  0.00           H  
HETATM   13  H4  UNL     1       2.206   1.450   0.637  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.663   0.308   1.407  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.388   1.450   0.081  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.462  -1.389  -0.241  1.00  0.00           H  
HETATM   17  H8  UNL     1      -1.144  -0.192  -1.591  1.00  0.00           H  
HETATM   18  H9  UNL     1      -4.199  -1.127  -0.946  1.00  0.00           H  
CONECT    1    2   10   11
CONECT    2    3   12   13
CONECT    3    4    4    5
CONECT    5    6   14   15
CONECT    6    7   16   17
CONECT    7    8    8    9
CONECT    9   18
END
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SMILES for NP0000055 (5-Aminolevulinic acid)

NCC(=O)CCC(O)=O
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INCHI for NP0000055 (5-Aminolevulinic acid)

InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
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View in JSmol
Synonyms
ValueSource
5-ALAChEBI
5-Amino-4-oxopentanoateChEBI
5-Amino-4-oxovaleric acidChEBI
5-AminolevulinateChEBI
Aminolevulinic acidChEBI
DALAChEBI
delta-ALAChEBI
delta-Aminolevulinic acidChEBI
5-Amino-4-oxopentanoic acidGenerator
5-Amino-4-oxovalerateGenerator
AminolevulinateGenerator
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
5 AminolevulinateHMDB
Acid, Delta-aminolevulinicHMDB
LevulanHMDB
5 AminolaevulinateHMDB
Acid hydrochloride, aminolevulinicHMDB
Bertek brand OF aminolevulinic acid hydrochlorideHMDB
Hydrochloride, aminolevulinic acidHMDB
Acid, aminolevulinicHMDB
Aminolevulinic acid hydrochlorideHMDB
Delta Aminolevulinic acidHMDB
Chemical FormulaC5H9NO3
Average Mass131.1299 Da
Monoisotopic Mass131.05824 Da
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 KeyZGXJTSGNIOSYLO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaPlant
Avena sativa L.FooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chlorella vulgarisLOTUS Database
ColumbaFooDB
ColumbidaeFooDB
Daphnia pulexLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Escherichia coliBacteria
Gallus gallusFooDB
Homo sapiensLOTUS Database
Homo sapiens (Urine)Animalia
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Paraburkholderia phymatum-
PhasianidaeFooDB
Phasianus colchicusFooDB
Rhodobacter sphaeroides--
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Zea mays L.FooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives 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
  • Amino acid
  • Ketone
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organooxygen compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point156 - 158 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 25 °CNot Available
LogP-1.5https://pubchem.ncbi.nlm.nih.gov/compound/Aminolevulinic-acid#section=LogP
Predicted Properties
PropertyValueSource
Water Solubility173 g/LALOGPS
logP-2.8ALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.45 m³·mol⁻¹ChemAxon
Polarizability12.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001149
DrugBank IDDB00855
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030562
KNApSAcK IDC00007378
Chemspider ID134
KEGG Compound IDC00430
BioCyc ID5-AMINO-LEVULINATE
BiGG ID34963
Wikipedia LinkAminolevulinic_acid
METLIN ID6037
PubChem Compound137
PDB IDNot Available
ChEBI ID17549
Good Scents IDNot Available
References
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. [PubMed: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. [PubMed: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. [PubMed:12699472 ]
  4. Sassa S: Diagnosis and therapy of acute intermittent porphyria. Blood Rev. 1996 Mar;10(1):53-8. [PubMed: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. [PubMed:16643481 ]
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