NP-MRD: Showing NP-Card for 3-Hydroxytetradecanedioic acid (NP0000472)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:15:47 UTC

NP-MRD ID

NP0000472

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Hydroxytetradecanedioic acid

Description

3-Hydroxytetradecanedioic acid is an unusual 3-hydroxydicarboxylic acid human metabolite found occasionally in urine. (PMID 2925825 ) High levels of 3-Hydroxytetradecanedioic acid (and other 3-hydroxydicarboxylic acids) were detected in the urine of a patient with 3-hydroxydicarboxylic aciduria (PMID 1507493 ), due to acute intoxication associated with hopantenate occurs owing to pantothenic acid deficiency or the inhibition of CoA-requiring reactions during stress, i.E., Infection, prolonged fasting, or malnutrition (PMID 2026687 ), and in a patient with thanatophoric dysplasia due to enhanced but incomplete oxidation of fatty acid, a consequence of a heterozygous point mutation, S249C in the fibroblast growth factor receptor 3 gene. (PMID 11879084 ).

Structure

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

HMDB0000394
     RDKit          3D
3-Hydroxytetradecanedioic acid
 45 44  0  0  0  0  0  0  0  0999 V2000
    7.6412   -0.3821    0.5414 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2654   -0.2344   -0.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2092   -0.1080   -1.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8188   -0.2073   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064   -0.3406    0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5386   -0.3021   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6941   -0.4398    1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2198   -0.3983    0.8572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8532    0.9060    0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6069    1.0233   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380    0.8835    1.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9618    1.0398    0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260    0.0160   -0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7348    0.1319   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9687   -0.8773   -1.9019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7944    0.0407    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7845   -1.2232    0.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7315   -1.6626    1.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9553   -1.9428    1.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0578    0.3467   -2.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5373   -1.0509   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5012    0.7339   -1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2781    0.5716    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2788   -1.2099    0.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -1.1705   -0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837    0.6105   -0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9429    0.3163    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9210   -1.4370    1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -0.6869    1.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -1.1819    0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911    1.7127    0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.1249   -0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922    0.2435   -0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477    2.0075   -0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571    1.7027    1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4675   -0.1209    1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6721    0.9170    1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1408    2.0876    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291   -0.9831   -0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6960    0.2082   -1.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9091    1.1042   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2253   -0.5052   -2.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913    0.9270    0.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8139    0.1825   -0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5998   -2.0970    0.2190 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 19 45  1  0
M  END

3-Hydroxytetradecanedioic acid.mol
  Mrv1652305261923572D          

 19 18  0  0  0  0            999 V2000
    3.9296    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6441   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.2062    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 15  2  0  0  0  0
  1 16  1  0  0  0  0
 14 17  2  0  0  0  0
 14 18  1  0  0  0  0
  3 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000472

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CCCCCCCCCCC(O)=O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H26O5/c15-12(11-14(18)19)9-7-5-3-1-2-4-6-8-10-13(16)17/h12,15H,1-11H2,(H,16,17)(H,18,19)

> <INCHI_KEY>
CEDZIURHISELSQ-UHFFFAOYSA-N

> <FORMULA>
C14H26O5

> <MOLECULAR_WEIGHT>
274.3532

> <EXACT_MASS>
274.178023942

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
31.841668448650115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxytetradecanedioic acid

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
2.8163926156666674

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.135176336436662

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.488693485812775

> <JCHEM_PKA_STRONGEST_BASIC>
-2.798587426318786

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
71.0625

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxytetradecanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000394
     RDKit          3D
3-Hydroxytetradecanedioic acid
 45 44  0  0  0  0  0  0  0  0999 V2000
    7.6412   -0.3821    0.5414 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2654   -0.2344   -0.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2092   -0.1080   -1.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8188   -0.2073   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064   -0.3406    0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5386   -0.3021   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6941   -0.4398    1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2198   -0.3983    0.8572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8532    0.9060    0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6069    1.0233   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380    0.8835    1.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9618    1.0398    0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260    0.0160   -0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7348    0.1319   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9687   -0.8773   -1.9019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7944    0.0407    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7845   -1.2232    0.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7315   -1.6626    1.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9553   -1.9428    1.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0578    0.3467   -2.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5373   -1.0509   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5012    0.7339   -1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2781    0.5716    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2788   -1.2099    0.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -1.1705   -0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837    0.6105   -0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9429    0.3163    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9210   -1.4370    1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -0.6869    1.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -1.1819    0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911    1.7127    0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.1249   -0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922    0.2435   -0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477    2.0075   -0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571    1.7027    1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4675   -0.1209    1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6721    0.9170    1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1408    2.0876    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291   -0.9831   -0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6960    0.2082   -1.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9091    1.1042   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2253   -0.5052   -2.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913    0.9270    0.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8139    0.1825   -0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5998   -2.0970    0.2190 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 19 45  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3-Hydroxytetradecanedioic acid.mol                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       7.335   1.925   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.335   0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.002  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.002  -1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.668  -2.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.334  -1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.001  -2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.667  -1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.667  -2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.001  -1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.334  -2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.668  -1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.002  -2.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.335  -1.925   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.002   2.695   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.669   2.695   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -7.335  -0.385   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -8.669  -2.695   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.668   0.385   0.000  0.00  0.00           O+0
CONECT    1    2   15   16                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   17   18                                                  
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17   14                                                            
CONECT   18   14                                                            
CONECT   19    3                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0000394
HETATM    1  O1  UNL     1       7.641  -0.382   0.541  1.00  0.00           O  
HETATM    2  C1  UNL     1       7.265  -0.234  -0.667  1.00  0.00           C  
HETATM    3  O2  UNL     1       8.209  -0.108  -1.640  1.00  0.00           O  
HETATM    4  C2  UNL     1       5.819  -0.207  -0.945  1.00  0.00           C  
HETATM    5  C3  UNL     1       5.006  -0.341   0.335  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.539  -0.302  -0.051  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.694  -0.440   1.178  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.220  -0.398   0.857  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.853   0.906   0.229  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.607   1.023  -0.134  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.538   0.883   1.011  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.962   1.040   0.543  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.326   0.016  -0.475  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.735   0.132  -0.945  1.00  0.00           C  
HETATM   15  O3  UNL     1      -4.969  -0.877  -1.902  1.00  0.00           O  
HETATM   16  C13 UNL     1      -5.794   0.041   0.108  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.784  -1.223   0.854  1.00  0.00           C  
HETATM   18  O4  UNL     1      -4.732  -1.663   1.351  1.00  0.00           O  
HETATM   19  O5  UNL     1      -6.955  -1.943   1.012  1.00  0.00           O  
HETATM   20  H1  UNL     1       8.058   0.347  -2.548  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.537  -1.051  -1.626  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.501   0.734  -1.435  1.00  0.00           H  
HETATM   23  H4  UNL     1       5.278   0.572   0.935  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.279  -1.210   0.935  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.302  -1.170  -0.698  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.384   0.610  -0.631  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.943   0.316   1.958  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.921  -1.437   1.618  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.597  -0.687   1.702  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.068  -1.182   0.069  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.091   1.713   0.954  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.438   1.125  -0.683  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.792   0.244  -0.911  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.748   2.007  -0.624  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.357   1.703   1.749  1.00  0.00           H  
HETATM   36  H17 UNL     1      -1.468  -0.121   1.490  1.00  0.00           H  
HETATM   37  H18 UNL     1      -3.672   0.917   1.416  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.141   2.088   0.188  1.00  0.00           H  
HETATM   39  H20 UNL     1      -3.129  -0.983  -0.090  1.00  0.00           H  
HETATM   40  H21 UNL     1      -2.696   0.208  -1.408  1.00  0.00           H  
HETATM   41  H22 UNL     1      -4.909   1.104  -1.500  1.00  0.00           H  
HETATM   42  H23 UNL     1      -5.225  -0.505  -2.780  1.00  0.00           H  
HETATM   43  H24 UNL     1      -5.691   0.927   0.800  1.00  0.00           H  
HETATM   44  H25 UNL     1      -6.814   0.183  -0.360  1.00  0.00           H  
HETATM   45  H26 UNL     1      -7.600  -2.097   0.219  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8   27   28
CONECT    8    9   29   30
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   35   36
CONECT   12   13   37   38
CONECT   13   14   39   40
CONECT   14   15   16   41
CONECT   15   42
CONECT   16   17   43   44
CONECT   17   18   18   19
CONECT   19   45
END

HMDB0000394
     RDKit          3D
3-Hydroxytetradecanedioic acid
 45 44  0  0  0  0  0  0  0  0999 V2000
    7.6412   -0.3821    0.5414 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2654   -0.2344   -0.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2092   -0.1080   -1.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8188   -0.2073   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064   -0.3406    0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5386   -0.3021   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6941   -0.4398    1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2198   -0.3983    0.8572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8532    0.9060    0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6069    1.0233   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380    0.8835    1.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9618    1.0398    0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260    0.0160   -0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7348    0.1319   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9687   -0.8773   -1.9019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7944    0.0407    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7845   -1.2232    0.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7315   -1.6626    1.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9553   -1.9428    1.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0578    0.3467   -2.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5373   -1.0509   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5012    0.7339   -1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2781    0.5716    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2788   -1.2099    0.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -1.1705   -0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837    0.6105   -0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9429    0.3163    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9210   -1.4370    1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -0.6869    1.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -1.1819    0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911    1.7127    0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.1249   -0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922    0.2435   -0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477    2.0075   -0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571    1.7027    1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4675   -0.1209    1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6721    0.9170    1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1408    2.0876    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291   -0.9831   -0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6960    0.2082   -1.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9091    1.1042   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2253   -0.5052   -2.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913    0.9270    0.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8139    0.1825   -0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5998   -2.0970    0.2190 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 19 45  1  0
M  END

View in JSmol

Synonyms

Value	Source
3-Hydroxytetradecanedioate	Generator
3-Hydroxy-tetradecanedioate	HMDB

Chemical Formula

C₁₄H₂₆O₅

Average Mass

274.3532 Da

Monoisotopic Mass

274.17802 Da

IUPAC Name

3-hydroxytetradecanedioic acid

Traditional Name

3-hydroxytetradecanedioic acid

CAS Registry Number

73179-89-2

SMILES

OC(CCCCCCCCCCC(O)=O)CC(O)=O

InChI Identifier

InChI=1S/C14H26O5/c15-12(11-14(18)19)9-7-5-3-1-2-4-6-8-10-13(16)17/h12,15H,1-11H2,(H,16,17)(H,18,19)

InChI Key

CEDZIURHISELSQ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, simulated)	V.dorna83			2021-08-10	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Beta-hydroxy acid
Hydroxy acid
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Dicarboxylic acids (LMFA01170094 )

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	2.03	ALOGPS
logP	2.82	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	71.06 m³·mol⁻¹	ChemAxon
Polarizability	31.84 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

External Links

HMDB ID

HMDB0000394

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022012

KNApSAcK ID

Not Available

Chemspider ID

13628077

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5383

PubChem Compound

20848956

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lefevere MF, Verhaeghe BJ, Declerck DH, Van Bocxlaer JF, De Leenheer AP, De Sagher RM: Metabolic profiling of urinary organic acids by single and multicolumn capillary gas chromatography. J Chromatogr Sci. 1989 Jan;27(1):23-9. [PubMed:2925825 ]
Matsumoto M, Kuhara T, Inoue Y, Shinka T, Matsumoto I: Abnormal fatty acid metabolism in patients in hopantenate therapy during clinical episodes. J Chromatogr. 1991 Jan 2;562(1-2):139-45. [PubMed:2026687 ]
Okajima K, Asai K, Niwa T, Ohki S, Sobajima H, Tyson J, Malcolm S, Wada Y: Clinical and biochemical findings of a patient with thanatophoric dysplasia type I: additional finding of dicarboxylic aciduria. Cleft Palate Craniofac J. 2002 Mar;39(2):246-8. [PubMed:11879084 ]
Shimizu A, Nakanishi T: [Quantitative analysis of urinary organic acid]. Rinsho Byori. 1992 Jul;40(7):743-50. [PubMed:1507493 ]
Looby N, Roszkowska A, Reyes-Garces N, Yu M, Baczek T, Kulasingam V, Pawliszyn J, Chandran V: Serum metabolic fingerprinting of psoriasis and psoriatic arthritis patients using solid-phase microextraction-liquid chromatography-high-resolution mass spectrometry. Metabolomics. 2021 Jun 16;17(7):59. doi: 10.1007/s11306-021-01805-3. [PubMed:34137950 ]
Chawes BL, Giordano G, Pirillo P, Rago D, Rasmussen MA, Stokholm J, Bonnelykke K, Bisgaard H, Baraldi E: Neonatal Urine Metabolic Profiling and Development of Childhood Asthma. Metabolites. 2019 Sep 16;9(9). pii: metabo9090185. doi: 10.3390/metabo9090185. [PubMed:31527391 ]
Shi J, Zhou J, Ma H, Guo H, Ni Z, Duan J, Tao W, Qian D: An in vitro metabolomics approach to identify hepatotoxicity biomarkers in human L02 liver cells treated with pekinenal, a natural compound. Anal Bioanal Chem. 2016 Feb;408(5):1413-24. doi: 10.1007/s00216-015-9202-4. Epub 2015 Dec 29. [PubMed:26715247 ]

Showing NP-Card for 3-Hydroxytetradecanedioic acid (NP0000472)

MOL for NP0000472 (3-Hydroxytetradecanedioic acid)

3D MOL for NP0000472 (3-Hydroxytetradecanedioic acid)

3D SDF for NP0000472 (3-Hydroxytetradecanedioic acid)

3D-SDF for NP0000472 (3-Hydroxytetradecanedioic acid)

PDB for NP0000472 (3-Hydroxytetradecanedioic acid)

3D PDB for NP0000472 (3-Hydroxytetradecanedioic acid)

SMILES for NP0000472 (3-Hydroxytetradecanedioic acid)

INCHI for NP0000472 (3-Hydroxytetradecanedioic acid)

Structure for NP0000472 (3-Hydroxytetradecanedioic acid)

3D Structure for NP0000472 (3-Hydroxytetradecanedioic acid)