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Showing NP-Card for Pimelic acid (NP0001322)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-03 04:18:33 UTC
NP-MRD IDNP0001322
Natural Product DOIhttps://doi.org/10.57994/1430
Secondary Accession NumbersNone
Natural Product Identification
Common NamePimelic acid
DescriptionPimelic acid, also known as heptanedioic acid is a dicarboxylic acid. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid called lysine. Pimelic acid is one methylene longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides. Pimelic acid is essential for the synthesis of biotin (also called vitamin B7). Biotin is a heterocyclic, S-containing monocarboxylic acid that is made from two precursors, alanine and pimeloyl-CoA. Biotin is important in fatty acid synthesis, branched-chain amino acid catabolism, and gluconeogenesis. Biotin is found in a wide range of foods. Likewise, intestinal bacteria synthesize biotin, which is then absorbed by the host animal. Pimelic acid (which is the precursor for pimeloyl-CoA) is synthesized in many bacteria via a head-to-tail incorporation of acetate units through a modified fatty acid synthetic pathway using O-methyl esters disguised to resemble the canonical intermediates of the fatty acid synthetic pathway (PMID: 21435937 ). Some bacteria and yeast synthesize pimelic acid not by biosynthesis, but via cleavage of longer chain fatty acids (such as linolenic acid) via a cytochrome P450-like enzyme (PMID: 28196402 , 21435937 , 3236079 ). Pimelic acid is excreted in elevated amounts in the urine of individuals with mitochondrial beta-oxidation disorders and peroxisomal beta oxidation disorders (PMID: 1527989 )
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001322 (Pimelic acid)


  Mrv1652305271900262D          

 11 10  0  0  0  0            999 V2000
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0001322 (Pimelic acid)

HMDB0000857
     RDKit          3D
Pimelic acid
 23 22  0  0  0  0  0  0  0  0999 V2000
    2.4459    1.4973   -0.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0884    0.4275   -0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3959    0.4122   -0.7669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4569   -0.7846    0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0400   -0.6157    0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813   -0.2076   -0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2971   -0.1020    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2744    0.3129   -0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6445    0.4447   -0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5681    0.7831   -1.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8643    0.1931    1.0665 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1725    0.3452   -0.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0161   -1.1495    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5322   -1.6369   -0.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9223    0.0843    1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6817   -1.6073    1.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2783    0.7907   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0464   -0.9715   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6050   -1.1079    0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2053    0.6459    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2241   -0.4353   -1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9417    1.2830   -1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4407    0.6797    1.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
 11 23  1  0
M  END
Download

3D SDF for NP0001322 (Pimelic acid)


  Mrv1652305271900262D          

 11 10  0  0  0  0            999 V2000
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11)

> <INCHI_KEY>
WLJVNTCWHIRURA-UHFFFAOYSA-N

> <FORMULA>
C7H12O4

> <MOLECULAR_WEIGHT>
160.1678

> <EXACT_MASS>
160.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.309765941205747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
heptanedioic acid

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
0.9352230276666667

> <ALOGPS_LOGS>
-1.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.8101291244285145

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.045044284282043

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
37.339999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pimelic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001322 (Pimelic acid)

HMDB0000857
     RDKit          3D
Pimelic acid
 23 22  0  0  0  0  0  0  0  0999 V2000
    2.4459    1.4973   -0.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0884    0.4275   -0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3959    0.4122   -0.7669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4569   -0.7846    0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0400   -0.6157    0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813   -0.2076   -0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2971   -0.1020    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2744    0.3129   -0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6445    0.4447   -0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5681    0.7831   -1.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8643    0.1931    1.0665 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1725    0.3452   -0.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0161   -1.1495    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5322   -1.6369   -0.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9223    0.0843    1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6817   -1.6073    1.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2783    0.7907   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0464   -0.9715   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6050   -1.1079    0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2053    0.6459    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2241   -0.4353   -1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9417    1.2830   -1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4407    0.6797    1.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
 11 23  1  0
M  END
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PDB for NP0001322 (Pimelic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.596   4.771   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       6.930   2.461   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for NP0001322 (Pimelic acid)

COMPND    HMDB0000857
HETATM    1  O1  UNL     1       2.446   1.497  -0.393  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.088   0.428  -0.320  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.396   0.412  -0.767  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.457  -0.785   0.232  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.040  -0.616   0.657  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.081  -0.208  -0.406  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.297  -0.102   0.264  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.274   0.313  -0.815  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.644   0.445  -0.270  1.00  0.00           C  
HETATM   10  O3  UNL     1      -4.568   0.783  -1.047  1.00  0.00           O  
HETATM   11  O4  UNL     1      -3.864   0.193   1.066  1.00  0.00           O  
HETATM   12  H1  UNL     1       5.172   0.345  -0.103  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.016  -1.149   1.144  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.532  -1.637  -0.486  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.922   0.084   1.509  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.682  -1.607   1.056  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.278   0.791  -0.809  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.046  -0.972  -1.203  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.605  -1.108   0.640  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.205   0.646   1.069  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.224  -0.435  -1.623  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.942   1.283  -1.225  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.441   0.680   1.830  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7    8   19   20
CONECT    8    9   21   22
CONECT    9   10   10   11
CONECT   11   23
END
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SMILES for NP0001322 (Pimelic acid)

OC(=O)CCCCCC(O)=O
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INCHI for NP0001322 (Pimelic acid)

InChI=1S/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11)
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View in JSmol
Synonyms
ValueSource
1,5-Pentanedicarboxylic acidChEBI
6-Carboxyhexanoic acidChEBI
Heptanedioic acidChEBI
PimelateChEBI
6-CarboxyhexanoateKegg
1,5-PentanedicarboxylateGenerator
HeptanedioateGenerator
Acid, pimelicHMDB
Acids, pimelicHMDB
Pimelic acidsHMDB
1,7-HeptanedioateHMDB
1,7-Heptanedioic acidHMDB
HeptandioateHMDB
Heptandioic acidHMDB
Heptane-1,7-dioateHMDB
Heptane-1,7-dioic acidHMDB
PilerateHMDB
Pileric acidHMDB
Chemical FormulaC7H12O4
Average Mass160.1678 Da
Monoisotopic Mass160.07356 Da
IUPAC Nameheptanedioic acid
Traditional Namepimelic acid
CAS Registry Number111-16-0
SMILES
OC(=O)CCCCCC(O)=O
InChI Identifier
InChI=1S/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11)
InChI KeyWLJVNTCWHIRURA-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
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
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Daphnia magnaLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Ricinus communisKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point103 - 106 °CNot Available
Boiling Point342.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility50 mg/mLNot Available
LogP0.61Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility13.3 g/LALOGPS
logP0.51ALOGPS
logP0.94ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity37.34 m³·mol⁻¹ChemAxon
Polarizability16.31 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000857
DrugBank IDDB01856
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022283
KNApSAcK IDC00001199
Chemspider ID376
KEGG Compound IDC02656
BioCyc IDCPD-205
BiGG IDNot Available
Wikipedia LinkPimelic_acid
METLIN ID3280
PubChem Compound385
PDB IDNot Available
ChEBI ID30531
Good Scents IDrw1274891
References
General References
  1. Passi S, Picardo M, Mingrone G, Breathnach AS, Nazzaro-Porro M: Azelaic acid--biochemistry and metabolism. Acta Derm Venereol Suppl (Stockh). 1989;143:8-13. [PubMed:2505463 ]
  2. Pettit BR: The analysis of thiodiglycollic acid by selected ion monitoring. Clin Chim Acta. 1986 Apr 15;156(1):85-90. [PubMed:3698320 ]
  3. Niwa T, Ohki T, Maeda K, Saito A, Kobayashi K: Pattern of aliphatic dicarboxylic acids in uremic serum including a new organic acid, 2,4-dimethyladipic acid. Clin Chim Acta. 1979 Nov 15;99(1):71-83. [PubMed:498544 ]
  4. Cronan JE, Lin S: Synthesis of the alpha,omega-dicarboxylic acid precursor of biotin by the canonical fatty acid biosynthetic pathway. Curr Opin Chem Biol. 2011 Jun;15(3):407-13. doi: 10.1016/j.cbpa.2011.03.001. Epub 2011 Mar 23. [PubMed:21435937 ]
  5. Manandhar M, Cronan JE: Pimelic acid, the first precursor of the Bacillus subtilis biotin synthesis pathway, exists as the free acid and is assembled by fatty acid synthesis. Mol Microbiol. 2017 May;104(4):595-607. doi: 10.1111/mmi.13648. Epub 2017 Mar 3. [PubMed:28196402 ]
  6. Ohsugi M, Miyauchi K, Tachibana K, Nakao S: Formation of a biotin precursor, pimelic acid, in yeasts from C18 fatty acids. J Nutr Sci Vitaminol (Tokyo). 1988 Aug;34(4):343-52. doi: 10.3177/jnsv.34.343. [PubMed:3236079 ]
  7. Bennett MJ, Ragni MC, Hood I, Hale DE: Azelaic and pimelic acids: metabolic intermediates or artefacts? J Inherit Metab Dis. 1992;15(2):220-3. doi: 10.1007/BF01799635. [PubMed:1527989 ]