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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:21:09 UTC

Update Date

2021-09-26 23:06:10 UTC

HMDB ID

HMDB0253144

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hexaminolevulinate

Description

Hexaminolevulinate 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. PpIX and PAPs are reported to accumulate preferentially in neoplastic cells as compared to normal urothelium, partly due to altered enzymatic activity in the neoplastic cells. Hexaminolevulinate is an ester of the heme precursor, aminolevulinic acid. Hexaminolevulinate is a very strong basic compound (based on its pKa). Hexaminolevulinate is an optical imaging drug. After bladder instillation of hexaminolevulinate hydrochloride intravesical solution for approximately 1 hour and subsequent illumination with blue light at wavelengths 360 – 450nm, the porphyrins will fluoresce red. On May 28, 2010, the U.S. Food and Drug Administration (FDA) granted approval for hexaminolevulinate hydrochloride (Cysview for Intravesical Solution, Photocure ASA), as an optical imaging agent for use in combination with the Karl Storz Photodynamic Diagnostic D-Light C (PDD) System for cystoscopic detection of non-muscle invasive papillary cancer of the bladder for patients suspected or known to have lesion(s) on the basis of a prior cystoscopy. Adequate reproductive and developmental toxicity studies in animals have not been performed to evaluate the effects of hexaminolevulinate hydrochloride on fertility. In vitro studies have shown increased porphyrin fluorescence in normal urothelium after exposure to hexaminolevulinate hydrochloride intravesical solution. No studies in animals have been conducted to evaluate the carcinogenic potential of hexaminolevulinate hydrochloride. Similar processes may occur in inflamed cells. This compound has been identified in human blood as reported by (PMID: 31557052 ). Hexaminolevulinate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Hexaminolevulinate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0253144
     RDKit          3D
Hexaminolevulinate
 36 35  0  0  0  0  0  0  0  0999 V2000
    6.4995    0.4101    0.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2845   -0.2748    0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0512    0.6095    0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8849   -0.1786   -0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5581    0.5594   -0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5173   -0.3246   -0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7943    0.1947   -0.6087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7682   -0.6133   -1.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4060   -1.7313   -1.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1946   -0.3080   -1.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278   -1.0186   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3780   -0.7522   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1195   -1.6243   -0.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9705    0.5103    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0333    1.4248    0.7970 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2907   -0.3385    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8949    1.1111   -0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1823    0.9419    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1119   -1.2905    0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4288   -0.3307   -1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9762    0.8207    1.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1968    1.5585   -0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1035   -0.3495   -1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8436   -1.1842    0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3881    0.7597    1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6418    1.5447   -0.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5030   -1.2743   -0.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7742   -0.6018   -1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4220    0.7827   -1.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5998   -0.7144   -2.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7463   -2.1302   -0.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -0.7327    0.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7677    0.2870    1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4754    1.0353   -0.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7870    2.1968    0.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441    1.0252    1.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
M  END

  Mrv1572009171518002D          

 17 16  0  0  0  0            999 V2000
    7.6861   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9716    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8281   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3991   -0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8295    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5440   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1150   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2585    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4005    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9729   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2571   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5426    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9716    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8281   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1137    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9562    0.0495    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3991   -0.7177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 13  1  0  0  0  0
  2 13  2  0  0  0  0
  3 14  2  0  0  0  0
  4 15  1  0  0  0  0
  4 16  1  0  0  0  0
  4 17  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253144

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]N([H])CC(=O)CCC(=O)OCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C11H21NO3/c1-2-3-4-5-8-15-11(14)7-6-10(13)9-12/h2-9,12H2,1H3

> <INCHI_KEY>
RYQOILLJDKPETL-UHFFFAOYSA-N

> <FORMULA>
C11H21NO3

> <MOLECULAR_WEIGHT>
215.293

> <EXACT_MASS>
215.15214354

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.960932917333498

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
hexyl 5-amino-4-oxopentanoate

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
1.3659431133333326

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.10674862594475

> <JCHEM_PKA_STRONGEST_BASIC>
7.834133913242029

> <JCHEM_POLAR_SURFACE_AREA>
69.39

> <JCHEM_REFRACTIVITY>
58.2925

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexyl 5-amino-4-oxopentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253144
     RDKit          3D
Hexaminolevulinate
 36 35  0  0  0  0  0  0  0  0999 V2000
    6.4995    0.4101    0.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2845   -0.2748    0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0512    0.6095    0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8849   -0.1786   -0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5581    0.5594   -0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5173   -0.3246   -0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7943    0.1947   -0.6087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7682   -0.6133   -1.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4060   -1.7313   -1.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1946   -0.3080   -1.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278   -1.0186   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3780   -0.7522   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1195   -1.6243   -0.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9705    0.5103    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0333    1.4248    0.7970 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2907   -0.3385    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8949    1.1111   -0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1823    0.9419    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1119   -1.2905    0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4288   -0.3307   -1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9762    0.8207    1.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1968    1.5585   -0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1035   -0.3495   -1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8436   -1.1842    0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3881    0.7597    1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6418    1.5447   -0.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5030   -1.2743   -0.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7742   -0.6018   -1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4220    0.7827   -1.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5998   -0.7144   -2.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7463   -2.1302   -0.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -0.7327    0.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7677    0.2870    1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4754    1.0353   -0.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7870    2.1968    0.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441    1.0252    1.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
M  END

HEADER    PROTEIN                                 17-SEP-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-15         0                                  
HETATM    1  O   UNK     0      14.347  -0.385   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.014   1.925   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.012  -1.925   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       6.345  -0.385   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      18.348   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.682  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.015  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.016   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.681   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.349  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.680  -0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.346   0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.014   0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.012  -0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.679   0.385   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       5.518   0.092   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       6.345  -1.340   0.000  0.00  0.00           H+0
CONECT    1    9   13                                                       
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   15   16   17                                                  
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    1    7                                                       
CONECT   10    8                                                            
CONECT   11   12   13                                                       
CONECT   12   11   14                                                       
CONECT   13    1    2   11                                                  
CONECT   14    3   12   15                                                  
CONECT   15    4   14                                                       
CONECT   16    4                                                            
CONECT   17    4                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0253144
HETATM    1  C1  UNL     1       6.499   0.410   0.641  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.284  -0.275   0.093  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.051   0.609   0.346  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.885  -0.179  -0.216  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.558   0.559  -0.051  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.517  -0.325  -0.654  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.794   0.195  -0.609  1.00  0.00           O  
HETATM    8  C7  UNL     1      -1.768  -0.613  -1.185  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.406  -1.731  -1.694  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.195  -0.308  -1.269  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.928  -1.019  -0.143  1.00  0.00           C  
HETATM   12  C10 UNL     1      -5.378  -0.752  -0.225  1.00  0.00           C  
HETATM   13  O3  UNL     1      -6.119  -1.624  -0.701  1.00  0.00           O  
HETATM   14  C11 UNL     1      -5.971   0.510   0.237  1.00  0.00           C  
HETATM   15  N1  UNL     1      -5.033   1.425   0.797  1.00  0.00           N  
HETATM   16  H1  UNL     1       7.291  -0.338   0.877  1.00  0.00           H  
HETATM   17  H2  UNL     1       6.895   1.111  -0.090  1.00  0.00           H  
HETATM   18  H3  UNL     1       6.182   0.942   1.580  1.00  0.00           H  
HETATM   19  H4  UNL     1       5.112  -1.291   0.441  1.00  0.00           H  
HETATM   20  H5  UNL     1       5.429  -0.331  -1.016  1.00  0.00           H  
HETATM   21  H6  UNL     1       3.976   0.821   1.423  1.00  0.00           H  
HETATM   22  H7  UNL     1       4.197   1.559  -0.241  1.00  0.00           H  
HETATM   23  H8  UNL     1       3.104  -0.350  -1.295  1.00  0.00           H  
HETATM   24  H9  UNL     1       2.844  -1.184   0.262  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.388   0.760   1.020  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.642   1.545  -0.568  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.503  -1.274  -0.039  1.00  0.00           H  
HETATM   28  H13 UNL     1       0.774  -0.602  -1.700  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.422   0.783  -1.272  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.600  -0.714  -2.221  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.746  -2.130  -0.305  1.00  0.00           H  
HETATM   32  H17 UNL     1      -3.497  -0.733   0.811  1.00  0.00           H  
HETATM   33  H18 UNL     1      -6.768   0.287   1.008  1.00  0.00           H  
HETATM   34  H19 UNL     1      -6.475   1.035  -0.630  1.00  0.00           H  
HETATM   35  H20 UNL     1      -4.787   2.197   0.135  1.00  0.00           H  
HETATM   36  H21 UNL     1      -4.244   1.025   1.322  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   13   14
CONECT   14   15   33   34
CONECT   15   35   36
END

HMDB0253144
     RDKit          3D
Hexaminolevulinate
 36 35  0  0  0  0  0  0  0  0999 V2000
    6.4995    0.4101    0.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2845   -0.2748    0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0512    0.6095    0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8849   -0.1786   -0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5581    0.5594   -0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5173   -0.3246   -0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7943    0.1947   -0.6087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7682   -0.6133   -1.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4060   -1.7313   -1.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1946   -0.3080   -1.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278   -1.0186   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3780   -0.7522   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1195   -1.6243   -0.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9705    0.5103    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0333    1.4248    0.7970 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2907   -0.3385    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8949    1.1111   -0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1823    0.9419    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1119   -1.2905    0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4288   -0.3307   -1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9762    0.8207    1.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1968    1.5585   -0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1035   -0.3495   -1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8436   -1.1842    0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3881    0.7597    1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6418    1.5447   -0.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5030   -1.2743   -0.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7742   -0.6018   -1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4220    0.7827   -1.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5998   -0.7144   -2.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7463   -2.1302   -0.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -0.7327    0.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7677    0.2870    1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4754    1.0353   -0.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7870    2.1968    0.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441    1.0252    1.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hexaminolevulinic acid	Generator
Hexyl-aminolevulinate	MeSH
5-ALAHE	MeSH
5-Aminolevulinic acid hexyl ester	MeSH
Hexaminolevulinate hydrochloride	MeSH
ALA hexyl ester	MeSH
(14C)-Hexaminolevulinate	MeSH
Aminolevulinic acid hexylester	MeSH
Hexylaminolevulinate	MeSH
Hexa ala	MeSH

Chemical Formula

C₁₁H₂₁NO₃

Average Molecular Weight

215.293

Monoisotopic Molecular Weight

215.15214354

IUPAC Name

hexyl 5-amino-4-oxopentanoate

Traditional Name

hexyl 5-amino-4-oxopentanoate

CAS Registry Number

Not Available

SMILES

[H]N([H])CC(=O)CCC(=O)OCCCCCC

InChI Identifier

InChI=1S/C11H21NO3/c1-2-3-4-5-8-15-11(14)7-6-10(13)9-12/h2-9,12H2,1H3

InChI Key

RYQOILLJDKPETL-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Delta amino acids and derivatives

Alternative Parents

Substituents

Delta amino acid or derivatives
Gamma-keto acid
Fatty acid ester
Keto acid
Fatty acyl
Alpha-aminoketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0253144)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.55	ALOGPS
logP	1.37	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	16.11	ChemAxon
pKa (Strongest Basic)	7.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.39 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	58.29 m³·mol⁻¹	ChemAxon
Polarizability	24.96 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	148.073	30932474
DeepCCS	[M-H]-	145.678	30932474
DeepCCS	[M-2H]-	179.104	30932474
DeepCCS	[M+Na]+	154.021	30932474
AllCCS	[M+H]+	151.7	32859911
AllCCS	[M+H-H2O]+	148.3	32859911
AllCCS	[M+NH4]+	154.8	32859911
AllCCS	[M+Na]+	155.7	32859911
AllCCS	[M-H]-	154.0	32859911
AllCCS	[M+Na-2H]-	155.1	32859911
AllCCS	[M+HCOO]-	156.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hexaminolevulinate	[H]N([H])CC(=O)CCC(=O)OCCCCCC	1968.5	Standard polar	33892256
Hexaminolevulinate	[H]N([H])CC(=O)CCC(=O)OCCCCCC	1462.6	Standard non polar	33892256
Hexaminolevulinate	[H]N([H])CC(=O)CCC(=O)OCCCCCC	1627.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hexaminolevulinate,1TMS,isomer #1	CCCCCCOC(=O)CC=C(CN)O[Si](C)(C)C	1841.6	Semi standard non polar	33892256
Hexaminolevulinate,1TMS,isomer #1	CCCCCCOC(=O)CC=C(CN)O[Si](C)(C)C	1843.4	Standard non polar	33892256
Hexaminolevulinate,1TMS,isomer #1	CCCCCCOC(=O)CC=C(CN)O[Si](C)(C)C	2791.8	Standard polar	33892256
Hexaminolevulinate,1TMS,isomer #2	CCCCCCOC(=O)CCC(=CN)O[Si](C)(C)C	1868.4	Semi standard non polar	33892256
Hexaminolevulinate,1TMS,isomer #2	CCCCCCOC(=O)CCC(=CN)O[Si](C)(C)C	1786.1	Standard non polar	33892256
Hexaminolevulinate,1TMS,isomer #2	CCCCCCOC(=O)CCC(=CN)O[Si](C)(C)C	2827.3	Standard polar	33892256
Hexaminolevulinate,1TMS,isomer #3	CCCCCCOC(=O)CCC(=O)CN[Si](C)(C)C	1860.6	Semi standard non polar	33892256
Hexaminolevulinate,1TMS,isomer #3	CCCCCCOC(=O)CCC(=O)CN[Si](C)(C)C	1863.8	Standard non polar	33892256
Hexaminolevulinate,1TMS,isomer #3	CCCCCCOC(=O)CCC(=O)CN[Si](C)(C)C	2357.1	Standard polar	33892256
Hexaminolevulinate,2TMS,isomer #1	CCCCCCOC(=O)CC=C(CN[Si](C)(C)C)O[Si](C)(C)C	1986.7	Semi standard non polar	33892256
Hexaminolevulinate,2TMS,isomer #1	CCCCCCOC(=O)CC=C(CN[Si](C)(C)C)O[Si](C)(C)C	2006.8	Standard non polar	33892256
Hexaminolevulinate,2TMS,isomer #1	CCCCCCOC(=O)CC=C(CN[Si](C)(C)C)O[Si](C)(C)C	2162.2	Standard polar	33892256
Hexaminolevulinate,2TMS,isomer #2	CCCCCCOC(=O)CCC(=CN[Si](C)(C)C)O[Si](C)(C)C	2037.2	Semi standard non polar	33892256
Hexaminolevulinate,2TMS,isomer #2	CCCCCCOC(=O)CCC(=CN[Si](C)(C)C)O[Si](C)(C)C	1998.4	Standard non polar	33892256
Hexaminolevulinate,2TMS,isomer #2	CCCCCCOC(=O)CCC(=CN[Si](C)(C)C)O[Si](C)(C)C	2245.3	Standard polar	33892256
Hexaminolevulinate,2TMS,isomer #3	CCCCCCOC(=O)CCC(=O)CN([Si](C)(C)C)[Si](C)(C)C	2074.3	Semi standard non polar	33892256
Hexaminolevulinate,2TMS,isomer #3	CCCCCCOC(=O)CCC(=O)CN([Si](C)(C)C)[Si](C)(C)C	2039.9	Standard non polar	33892256
Hexaminolevulinate,2TMS,isomer #3	CCCCCCOC(=O)CCC(=O)CN([Si](C)(C)C)[Si](C)(C)C	2178.0	Standard polar	33892256
Hexaminolevulinate,3TMS,isomer #1	CCCCCCOC(=O)CC=C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2178.6	Semi standard non polar	33892256
Hexaminolevulinate,3TMS,isomer #1	CCCCCCOC(=O)CC=C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2124.3	Standard non polar	33892256
Hexaminolevulinate,3TMS,isomer #1	CCCCCCOC(=O)CC=C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2086.0	Standard polar	33892256
Hexaminolevulinate,3TMS,isomer #2	CCCCCCOC(=O)CCC(=CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2194.7	Semi standard non polar	33892256
Hexaminolevulinate,3TMS,isomer #2	CCCCCCOC(=O)CCC(=CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2045.1	Standard non polar	33892256
Hexaminolevulinate,3TMS,isomer #2	CCCCCCOC(=O)CCC(=CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2159.4	Standard polar	33892256
Hexaminolevulinate,1TBDMS,isomer #1	CCCCCCOC(=O)CC=C(CN)O[Si](C)(C)C(C)(C)C	2076.8	Semi standard non polar	33892256
Hexaminolevulinate,1TBDMS,isomer #1	CCCCCCOC(=O)CC=C(CN)O[Si](C)(C)C(C)(C)C	2029.8	Standard non polar	33892256
Hexaminolevulinate,1TBDMS,isomer #1	CCCCCCOC(=O)CC=C(CN)O[Si](C)(C)C(C)(C)C	2805.0	Standard polar	33892256
Hexaminolevulinate,1TBDMS,isomer #2	CCCCCCOC(=O)CCC(=CN)O[Si](C)(C)C(C)(C)C	2093.9	Semi standard non polar	33892256
Hexaminolevulinate,1TBDMS,isomer #2	CCCCCCOC(=O)CCC(=CN)O[Si](C)(C)C(C)(C)C	2003.9	Standard non polar	33892256
Hexaminolevulinate,1TBDMS,isomer #2	CCCCCCOC(=O)CCC(=CN)O[Si](C)(C)C(C)(C)C	2854.7	Standard polar	33892256
Hexaminolevulinate,1TBDMS,isomer #3	CCCCCCOC(=O)CCC(=O)CN[Si](C)(C)C(C)(C)C	2079.0	Semi standard non polar	33892256
Hexaminolevulinate,1TBDMS,isomer #3	CCCCCCOC(=O)CCC(=O)CN[Si](C)(C)C(C)(C)C	2093.7	Standard non polar	33892256
Hexaminolevulinate,1TBDMS,isomer #3	CCCCCCOC(=O)CCC(=O)CN[Si](C)(C)C(C)(C)C	2404.7	Standard polar	33892256
Hexaminolevulinate,2TBDMS,isomer #1	CCCCCCOC(=O)CC=C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2411.3	Semi standard non polar	33892256
Hexaminolevulinate,2TBDMS,isomer #1	CCCCCCOC(=O)CC=C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2379.9	Standard non polar	33892256
Hexaminolevulinate,2TBDMS,isomer #1	CCCCCCOC(=O)CC=C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2385.4	Standard polar	33892256
Hexaminolevulinate,2TBDMS,isomer #2	CCCCCCOC(=O)CCC(=CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2459.9	Semi standard non polar	33892256
Hexaminolevulinate,2TBDMS,isomer #2	CCCCCCOC(=O)CCC(=CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2372.1	Standard non polar	33892256
Hexaminolevulinate,2TBDMS,isomer #2	CCCCCCOC(=O)CCC(=CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2439.7	Standard polar	33892256
Hexaminolevulinate,2TBDMS,isomer #3	CCCCCCOC(=O)CCC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2473.5	Semi standard non polar	33892256
Hexaminolevulinate,2TBDMS,isomer #3	CCCCCCOC(=O)CCC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2386.4	Standard non polar	33892256
Hexaminolevulinate,2TBDMS,isomer #3	CCCCCCOC(=O)CCC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2377.8	Standard polar	33892256
Hexaminolevulinate,3TBDMS,isomer #1	CCCCCCOC(=O)CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2831.9	Semi standard non polar	33892256
Hexaminolevulinate,3TBDMS,isomer #1	CCCCCCOC(=O)CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2625.2	Standard non polar	33892256
Hexaminolevulinate,3TBDMS,isomer #1	CCCCCCOC(=O)CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2413.0	Standard polar	33892256
Hexaminolevulinate,3TBDMS,isomer #2	CCCCCCOC(=O)CCC(=CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2835.6	Semi standard non polar	33892256
Hexaminolevulinate,3TBDMS,isomer #2	CCCCCCOC(=O)CCC(=CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2554.8	Standard non polar	33892256
Hexaminolevulinate,3TBDMS,isomer #2	CCCCCCOC(=O)CCC(=CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2467.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hexaminolevulinate GC-MS (Non-derivatized) - 70eV, Positive	splash10-06sr-9200000000-0e60df2b518c68b3624f	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexaminolevulinate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexaminolevulinate 10V, Positive-QTOF	splash10-014j-5960000000-c8065381f077c431e7a7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexaminolevulinate 20V, Positive-QTOF	splash10-000i-9300000000-2706cef2f317ae5993d0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexaminolevulinate 40V, Positive-QTOF	splash10-052o-9000000000-f583e5a926627ca1fb3e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexaminolevulinate 10V, Negative-QTOF	splash10-03di-3970000000-ab8cc2993819621ed672	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexaminolevulinate 20V, Negative-QTOF	splash10-03e9-5910000000-cd8d02bcb6b2beaad9c1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexaminolevulinate 40V, Negative-QTOF	splash10-0bu0-9300000000-20a2e5ce02294399d2e0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexaminolevulinate 10V, Positive-QTOF	splash10-00kr-9440000000-61642b6e21ff9abe93f7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexaminolevulinate 20V, Positive-QTOF	splash10-000i-9300000000-2722f1c4a1c7ab12e7c2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexaminolevulinate 40V, Positive-QTOF	splash10-0a4i-9000000000-613317a8ad1e5967a2b2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexaminolevulinate 10V, Negative-QTOF	splash10-03di-3980000000-0dc686a50b7880b62248	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexaminolevulinate 20V, Negative-QTOF	splash10-0a5a-9300000000-ff621ef3ab87f5c7de76	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexaminolevulinate 40V, Negative-QTOF	splash10-00dj-9000000000-865d828e91128ff959eb	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06261

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6433083

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Hexaminolevulinate (HMDB0253144)

MOL for HMDB0253144 (Hexaminolevulinate)

3D MOL for HMDB0253144 (Hexaminolevulinate)

3D SDF for HMDB0253144 (Hexaminolevulinate)

3D-SDF for HMDB0253144 (Hexaminolevulinate)

PDB for HMDB0253144 (Hexaminolevulinate)

3D PDB for HMDB0253144 (Hexaminolevulinate)

SMILES for HMDB0253144 (Hexaminolevulinate)

INCHI for HMDB0253144 (Hexaminolevulinate)

Structure for HMDB0253144 (Hexaminolevulinate)

3D Structure for HMDB0253144 (Hexaminolevulinate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra