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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-09-22 17:43:45 UTC

HMDB ID

HMDB0000888

Secondary Accession Numbers

HMDB00888

Metabolite Identification

Common Name

Undecanedioic acid

Description

Undecanedioic acid has been found in parts of human aortas with advanced atherosclerotic lesions associated with intercellular matrix macromolecules and specifically with elastin, and may be the result of an increased hydrolysis of esters and (or) a decreased esterification. (PMID:131675 ). Undecanedioic acid has been found (among other unusual dicarboxylic acids) in the urine from patients under hopantenate therapy during episodes of Reye's-like syndrome. (PMID:2331533 ).

Structure

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

HMDB0000888
     RDKit          3D
Undecanedioic acid
 35 34  0  0  0  0  0  0  0  0999 V2000
   -4.8357    0.2911    1.3495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3308   -0.0165    0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6543   -0.4426    0.2110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543    0.0602   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342    0.4439   -0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3653   -0.5272    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9316   -0.1053    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2260    0.0214   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2272    0.4268   -0.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0263   -0.5543    0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4446   -0.0230    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3401   -0.9485    0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7207   -0.4027    0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9879    0.6826    0.3576 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7227   -1.0778    1.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3798    0.2669    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0337    0.7642   -1.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6261   -0.9343   -1.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1347    1.4551   -0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6570    0.5881   -1.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8949   -0.7778    1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3339   -1.4928   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9957    0.8837    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948   -0.8669    1.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6961    0.8565   -1.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116   -0.9042   -1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6613    0.4181   -1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3383    1.4476   -0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829   -1.4964   -0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6090   -0.7795    0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4670    0.9780    0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8812    0.0698   -0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9994   -1.0340    1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3483   -1.9697    0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7337   -1.1944    2.6219 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  2  0
 13 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
M  END

Undecanoic acid.mol
  Mrv1652305271900312D          

 15 14  0  0  0  0            999 V2000
    3.2151    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296    0.0000    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
  1 12  2  0  0  0  0
  1 13  1  0  0  0  0
 11 14  2  0  0  0  0
 11 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000888

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H20O4/c12-10(13)8-6-4-2-1-3-5-7-9-11(14)15/h1-9H2,(H,12,13)(H,14,15)

> <INCHI_KEY>
LWBHHRRTOZQPDM-UHFFFAOYSA-N

> <FORMULA>
C11H20O4

> <MOLECULAR_WEIGHT>
216.2741

> <EXACT_MASS>
216.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
24.739435290762287

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
undecanedioic acid

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.7134976876666665

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.253049650892543

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.650989659564581

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
55.744

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
undecanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000888
     RDKit          3D
Undecanedioic acid
 35 34  0  0  0  0  0  0  0  0999 V2000
   -4.8357    0.2911    1.3495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3308   -0.0165    0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6543   -0.4426    0.2110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543    0.0602   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342    0.4439   -0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3653   -0.5272    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9316   -0.1053    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2260    0.0214   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2272    0.4268   -0.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0263   -0.5543    0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4446   -0.0230    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3401   -0.9485    0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7207   -0.4027    0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9879    0.6826    0.3576 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7227   -1.0778    1.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3798    0.2669    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0337    0.7642   -1.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6261   -0.9343   -1.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1347    1.4551   -0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6570    0.5881   -1.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8949   -0.7778    1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3339   -1.4928   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9957    0.8837    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948   -0.8669    1.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6961    0.8565   -1.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116   -0.9042   -1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6613    0.4181   -1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3383    1.4476   -0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829   -1.4964   -0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6090   -0.7795    0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4670    0.9780    0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8812    0.0698   -0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9994   -1.0340    1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3483   -1.9697    0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7337   -1.1944    2.6219 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  2  0
 13 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Undecanoic acid.mol                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       6.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.334   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.667  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.001   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.668   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.002  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.668   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       7.335   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -6.002  -2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -7.335   0.000   0.000  0.00  0.00           O+0
CONECT    1    2   12   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
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   14   15                                                  
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14   11                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0000888
HETATM    1  O1  UNL     1      -4.836   0.291   1.350  1.00  0.00           O  
HETATM    2  C1  UNL     1      -5.331  -0.016   0.253  1.00  0.00           C  
HETATM    3  O2  UNL     1      -6.654  -0.443   0.211  1.00  0.00           O  
HETATM    4  C2  UNL     1      -4.554   0.060  -0.989  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.134   0.444  -0.733  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.365  -0.527   0.101  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.932  -0.105   0.358  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.226   0.021  -0.947  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.227   0.427  -0.790  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.026  -0.554   0.013  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.445  -0.023   0.084  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.340  -0.949   0.879  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.721  -0.403   0.931  1.00  0.00           C  
HETATM   14  O3  UNL     1       5.988   0.683   0.358  1.00  0.00           O  
HETATM   15  O4  UNL     1       6.723  -1.078   1.606  1.00  0.00           O  
HETATM   16  H1  UNL     1      -7.380   0.267   0.387  1.00  0.00           H  
HETATM   17  H2  UNL     1      -5.034   0.764  -1.731  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.626  -0.934  -1.532  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.135   1.455  -0.271  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.657   0.588  -1.746  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.895  -0.778   1.018  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.334  -1.493  -0.509  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.996   0.884   0.893  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.495  -0.867   1.030  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.696   0.857  -1.519  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.312  -0.904  -1.513  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.661   0.418  -1.830  1.00  0.00           H  
HETATM   28  H13 UNL     1       1.338   1.448  -0.412  1.00  0.00           H  
HETATM   29  H14 UNL     1       2.083  -1.496  -0.587  1.00  0.00           H  
HETATM   30  H15 UNL     1       1.609  -0.779   0.994  1.00  0.00           H  
HETATM   31  H16 UNL     1       3.467   0.978   0.563  1.00  0.00           H  
HETATM   32  H17 UNL     1       3.881   0.070  -0.920  1.00  0.00           H  
HETATM   33  H18 UNL     1       3.999  -1.034   1.937  1.00  0.00           H  
HETATM   34  H19 UNL     1       4.348  -1.970   0.441  1.00  0.00           H  
HETATM   35  H20 UNL     1       6.734  -1.194   2.622  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   16
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8   23   24
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   14   15
CONECT   15   35
END

HMDB0000888
     RDKit          3D
Undecanedioic acid
 35 34  0  0  0  0  0  0  0  0999 V2000
   -4.8357    0.2911    1.3495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3308   -0.0165    0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6543   -0.4426    0.2110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543    0.0602   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342    0.4439   -0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3653   -0.5272    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9316   -0.1053    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2260    0.0214   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2272    0.4268   -0.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0263   -0.5543    0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4446   -0.0230    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3401   -0.9485    0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7207   -0.4027    0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9879    0.6826    0.3576 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7227   -1.0778    1.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3798    0.2669    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0337    0.7642   -1.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6261   -0.9343   -1.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1347    1.4551   -0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6570    0.5881   -1.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8949   -0.7778    1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3339   -1.4928   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9957    0.8837    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948   -0.8669    1.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6961    0.8565   -1.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116   -0.9042   -1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6613    0.4181   -1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3383    1.4476   -0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829   -1.4964   -0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6090   -0.7795    0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4670    0.9780    0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8812    0.0698   -0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9994   -1.0340    1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3483   -1.9697    0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7337   -1.1944    2.6219 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  2  0
 13 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,11-Undecanedioic acid	ChEBI
1,9-Nonanedicarboxylic acid	ChEBI
Hendecanedioic acid	ChEBI
Undecanedionic acid	ChEBI
1,11-Undecanedioate	Generator
1,9-Nonanedicarboxylate	Generator
Hendecanedioate	Generator
Undecanedionate	Generator
Undecanedioate	Generator

Chemical Formula

C₁₁H₂₀O₄

Average Molecular Weight

216.2741

Monoisotopic Molecular Weight

216.136159128

IUPAC Name

undecanedioic acid

Traditional Name

undecanedioic acid

CAS Registry Number

1852-04-6

SMILES

OC(=O)CCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C11H20O4/c12-10(13)8-6-4-2-1-3-5-7-9-11(14)15/h1-9H2,(H,12,13)(H,14,15)

InChI Key

LWBHHRRTOZQPDM-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

alpha,omega-dicarboxylic acid (CHEBI:73713 )
Dicarboxylic acids (LMFA01170007 )

Ontology

Not Available

Non-excretory biofluid

Blood (PMID: 2308028)
Saliva (PMID: 22308371)

Urine (HMDB: HMDB0000888)

Excreta

Feces (PMID: 26848182)

Cellular substructure

Membrane (HMDB: HMDB0000888)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000888)

Source

Endogenous

Endogenous (HMDB: HMDB0000888)

Animal

Animal (HMDB: HMDB0000888)

Exogenous

Food

Food (HMDB: HMDB0000888)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Guinea hen (FooDB: FOOD00373)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000888)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000888)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0000888)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000888)

Nutrient

Nutrient (HMDB: HMDB0000888)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	108 - 110 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5.1 mg/mL	YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.44 g/L	ALOGPS
logP	2.41	ALOGPS
logP	2.71	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	55.74 m³·mol⁻¹	ChemAxon
Polarizability	24.74 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
DarkChem	[M+H]+	152.604	31661259
DarkChem	[M-H]-	149.575	31661259
AllCCS	[M+H]+	150.532	32859911
AllCCS	[M-H]-	153.092	32859911
DeepCCS	[M+H]+	149.811	30932474
DeepCCS	[M-H]-	145.873	30932474
DeepCCS	[M-2H]-	183.169	30932474
DeepCCS	[M+Na]+	158.851	30932474
AllCCS	[M+H]+	150.5	32859911
AllCCS	[M+H-H2O]+	147.0	32859911
AllCCS	[M+NH4]+	153.8	32859911
AllCCS	[M+Na]+	154.7	32859911
AllCCS	[M-H]-	153.1	32859911
AllCCS	[M+Na-2H]-	154.1	32859911
AllCCS	[M+HCOO]-	155.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Undecanedioic acid	OC(=O)CCCCCCCCCC(O)=O	2813.4	Standard polar	33892256
Undecanedioic acid	OC(=O)CCCCCCCCCC(O)=O	1682.9	Standard non polar	33892256
Undecanedioic acid	OC(=O)CCCCCCCCCC(O)=O	1867.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Undecanedioic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCCCC(=O)O	1908.4	Semi standard non polar	33892256
Undecanedioic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCCCC(=O)O[Si](C)(C)C	2008.9	Semi standard non polar	33892256
Undecanedioic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCC(=O)O	2160.3	Semi standard non polar	33892256
Undecanedioic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2499.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Undecanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9800000000-db85d280b172836331b1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Undecanedioic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00dr-9770000000-a2d73ceb282e8a18157e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Undecanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Undecanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Undecanedioic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Undecanedioic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Undecanedioic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Undecanedioic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-014i-0290000000-7ae807700c28584d2e28	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Undecanedioic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-0f6t-2900000000-3f0c97ba1c386d655464	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Undecanedioic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-0fr2-9230000000-6e48936ad64fc2b1149b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Undecanedioic acid 90V, Positive-QTOF	splash10-0pc0-9400000000-6a74432b9f7f56219843	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Undecanedioic acid 75V, Positive-QTOF	splash10-0udi-3900000000-e126e8f774ea9180ce4d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Undecanedioic acid 75V, Negative-QTOF	splash10-0udi-3900000000-cb662d0a491d85433784	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Undecanedioic acid 90V, Negative-QTOF	splash10-0pc0-9400000000-001aea13ac806299ab1f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Undecanedioic acid 45V, Negative-QTOF	splash10-0udj-0910000000-9adbb3ad23909d9d4e78	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Undecanedioic acid 60V, Negative-QTOF	splash10-0udi-0910000000-1d421e549e1033a05df1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Undecanedioic acid 30V, Negative-QTOF	splash10-0fr2-0940000000-35fc1c6ae29a4b119c97	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Undecanedioic acid 15V, Negative-QTOF	splash10-014j-0690000000-83bc5df70a0bb38f9135	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecanedioic acid 10V, Positive-QTOF	splash10-00kb-0930000000-92c504d7493b68533709	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecanedioic acid 20V, Positive-QTOF	splash10-00r2-1910000000-84e296521dd0030ce164	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecanedioic acid 40V, Positive-QTOF	splash10-01td-9500000000-a014eaf3810192591c95	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecanedioic acid 10V, Negative-QTOF	splash10-014i-0390000000-8d3496492a9c0c8977b1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecanedioic acid 20V, Negative-QTOF	splash10-014j-1970000000-690951ba65eb6d7209ee	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecanedioic acid 40V, Negative-QTOF	splash10-0a4l-9400000000-c06fbfff105dafce2635	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecanedioic acid 10V, Positive-QTOF	splash10-00kb-1920000000-1af20d2caa8369d83f79	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecanedioic acid 20V, Positive-QTOF	splash10-0aps-9300000000-1eeafdbc57daff924152	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecanedioic acid 40V, Positive-QTOF	splash10-0a4l-9100000000-0a7400e1d784601b32e5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecanedioic acid 10V, Negative-QTOF	splash10-014i-0390000000-9163a48488a98a354cde	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecanedioic acid 20V, Negative-QTOF	splash10-0002-1920000000-ee6e1dd82e64cf1046a3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Undecanedioic acid 40V, Negative-QTOF	splash10-054p-8900000000-7c2f170d31d14a2e1a37	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.44(0.28-0.54) uM	Infant (0-1 year old)	Not Specified	Normal	2308028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.79-4.8 uM	Infant (0-1 year old)	Female	3-Hydroxydicarboxylic aciduria	2308028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Iron deficiency	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

3-Hydroxydicarboxylic aciduria
Hagenfeldt L, von Dobeln U, Holme E, Alm J, Brandberg G, Enocksson E, Lindeberg L: 3-Hydroxydicarboxylic aciduria--a fatty acid oxidation defect with severe prognosis. J Pediatr. 1990 Mar;116(3):387-92. [PubMed:2308028 ]
Iron deficiency
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Ulcerative colitis
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022300

KNApSAcK ID

Not Available

Chemspider ID

15037

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5846

PubChem Compound

15816

PDB ID

Not Available

ChEBI ID

73713

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1296061

References

Synthesis Reference

Durham, Lois J.; McLeod, Donald J.; Cason, James. Hendecanedioic acid. Organic Syntheses (1958), 38 34-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

Claire M, Jacotot B, Robert L: Characterization of lipids associated with macromolecules of the intercellular matrix of human aorta. Connect Tissue Res. 1976;4(2):61-71. [PubMed:131675 ]
Matsumoto M, Kuhara T, Inoue Y, Shinka T, Matsumoto I, Kajita M: Mass spectrometric identification of 2-hydroxydodecanedioic acid and its homologues in urine from patients with hopantenate therapy during clinical episode. Biomed Environ Mass Spectrom. 1990 Mar;19(3):171-5. [PubMed:2331533 ]

Showing metabocard for Undecanedioic acid (HMDB0000888)

MOL for HMDB0000888 (Undecanedioic acid)

3D MOL for HMDB0000888 (Undecanedioic acid)

3D SDF for HMDB0000888 (Undecanedioic acid)

3D-SDF for HMDB0000888 (Undecanedioic acid)

PDB for HMDB0000888 (Undecanedioic acid)

3D PDB for HMDB0000888 (Undecanedioic acid)

SMILES for HMDB0000888 (Undecanedioic acid)

INCHI for HMDB0000888 (Undecanedioic acid)

Structure for HMDB0000888 (Undecanedioic acid)

3D Structure for HMDB0000888 (Undecanedioic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra