Showing metabocard for 5-Aminolevulinic acid (MMDBc0029572)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:32:45 UTC
Update Date2024-10-13 12:08:49 UTC
Metabolite IDMMDBc0029572
Metabolite Identification
Common Name5-Aminolevulinic acid
Description5-Aminolevulinic acid is an intermediate in heme synthesis. This is the first compound in the porphyrin synthesis pathway. It is produced by the enzyme ALA synthase, from glycine and succinyl CoA. This reaction is known as the Shemin pathway.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f46c9fe4c70>

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
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3D MOL for #<Metabolite:0x00007f46c9fe4c70>

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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3D SDF for #<Metabolite:0x00007f46c9fe4c70>

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>
MMDBc0029572

> <DATABASE_NAME>
MIME

> <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

$$$$
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3D-SDF for #<Metabolite:0x00007f46c9fe4c70>

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 #<Metabolite:0x00007f46c9fe4c70>

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 #<Metabolite:0x00007f46c9fe4c70>

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 #<Metabolite:0x00007f46c9fe4c70>

NCC(=O)CCC(O)=O
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INCHI for #<Metabolite:0x00007f46c9fe4c70>

InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
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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
Molecular FormulaC5H9NO3
Average Mass131.1299
Monoisotopic Mass131.058243159
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