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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 17:43:42 UTC

HMDB ID

HMDB0000387

Secondary Accession Numbers

HMDB00387

Metabolite Identification

Common Name

3-Hydroxydodecanoic acid

Description

3-Hydroxydodecanoic acid (CAS: 1883-13-2) is a medium-chain fatty acid associated with fatty acid metabolic disorders (PMID: 11948802 ). Deficiency of medium-chain acyl-CoA dehydrogenase is characterized by an intolerance to prolonged fasting, recurrent episodes of hypoglycemic coma with medium-chain dicarboxylic aciduria, impaired ketogenesis, and low plasma and tissue carnitine levels (OMIM: 201450 ). 3-Hydroxydodecanoic acid is also a microbial metabolite found in Acinetobacter, Moraxella, and Pseudomonas (PMID: 21687748 ). 3-Hydroxydodecanoic acid has been identified in the human placenta (PMID: 32033212 ).

Structure

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

HMDB0000387
     RDKit          3D
3-Hydroxydodecanoic acid
 39 38  0  0  0  0  0  0  0  0999 V2000
    5.3256   -0.0322    1.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0297    0.9041    0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    0.3715   -0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7640    0.0456   -0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7653   -0.4992   -1.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509   -0.8258   -0.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    0.3640    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5002    0.0370    0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5321   -0.5142   -0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8273   -0.8378    0.4194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6916   -1.3378   -0.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5123    0.3363    1.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8361    1.4022    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9402    2.1863   -0.3767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1375    1.6039   -0.4191 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4371   -0.2327    1.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1091    0.4215    2.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8522   -1.0158    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9689    1.2299   -0.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5967    1.8373    0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5256   -0.5592   -1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9832    1.0911   -1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3688    0.9543    0.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9527   -0.7709    0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039    0.2598   -2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1353   -1.4016   -1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6937   -1.5669    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -1.3709   -1.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    0.7364    0.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2498    1.1790   -0.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9202    1.0055    1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247   -0.5939    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1864   -1.4408   -0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7413    0.2216   -1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7303   -1.6238    1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3204   -1.2556   -1.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9890    0.7341    1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5027   -0.0417    1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7585    0.7989   -0.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  1
 11 36  1  0
 12 37  1  0
 12 38  1  0
 15 39  1  0
M  END


  Mrv1652303062020102D          

 15 14  0  0  0  0            999 V2000
 9997.9637 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2489 9998.4815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.5339 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8190 9998.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1042 9998.0698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8190 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2489 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6785 9998.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3942 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5371 9998.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2528 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9666 9998.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6817 9998.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.1078 9998.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8234 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  8  9  1  0  0  0  0
 15 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
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000387

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCC[C@H](O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H24O3/c1-2-3-4-5-6-7-8-9-11(13)10-12(14)15/h11,13H,2-10H2,1H3,(H,14,15)/t11-/m0/s1

> <INCHI_KEY>
MUCMKTPAZLSKTL-NSHDSACASA-N

> <FORMULA>
C12H24O3

> <MOLECULAR_WEIGHT>
216.321

> <EXACT_MASS>
216.172544633

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.3795500663006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3-hydroxydodecanoic acid

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
3.2474970506666665

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.288498288670866

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.671850167040888

> <JCHEM_PKA_STRONGEST_BASIC>
-2.798587426318786

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
60.19509999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-3-hydroxylauric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000387
     RDKit          3D
3-Hydroxydodecanoic acid
 39 38  0  0  0  0  0  0  0  0999 V2000
    5.3256   -0.0322    1.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0297    0.9041    0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    0.3715   -0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7640    0.0456   -0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7653   -0.4992   -1.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509   -0.8258   -0.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    0.3640    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5002    0.0370    0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5321   -0.5142   -0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8273   -0.8378    0.4194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6916   -1.3378   -0.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5123    0.3363    1.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8361    1.4022    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9402    2.1863   -0.3767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1375    1.6039   -0.4191 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4371   -0.2327    1.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1091    0.4215    2.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8522   -1.0158    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9689    1.2299   -0.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5967    1.8373    0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5256   -0.5592   -1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9832    1.0911   -1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3688    0.9543    0.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9527   -0.7709    0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039    0.2598   -2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1353   -1.4016   -1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6937   -1.5669    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -1.3709   -1.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    0.7364    0.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2498    1.1790   -0.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9202    1.0055    1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247   -0.5939    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1864   -1.4408   -0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7413    0.2216   -1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7303   -1.6238    1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3204   -1.2556   -1.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9890    0.7341    1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5027   -0.0417    1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7585    0.7989   -0.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  1
 11 36  1  0
 12 37  1  0
 12 38  1  0
 15 39  1  0
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8662.8668663.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8661.5318663.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8660.1978663.064   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8658.8628663.832   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8657.5288663.064   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8658.8628665.373   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8661.5318665.373   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8664.2008663.832   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.5368663.064   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8669.5368663.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8670.8728663.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8672.2048663.835   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8673.5398663.068   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.8688663.832   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8668.2048663.064   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2                                                            
CONECT    8    1    9                                                       
CONECT    9    8   14                                                       
CONECT   10   15   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    9   15                                                       
CONECT   15   10   14                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0000387
HETATM    1  C1  UNL     1       5.326  -0.032   1.221  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.030   0.904   0.099  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.086   0.371  -0.927  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.764   0.046  -0.266  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.765  -0.499  -1.264  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.451  -0.826  -0.597  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.198   0.364   0.049  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.500   0.037   0.708  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.532  -0.514  -0.243  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.827  -0.838   0.419  1.00  0.00           C  
HETATM   11  O1  UNL     1      -4.692  -1.338  -0.568  1.00  0.00           O  
HETATM   12  C11 UNL     1      -4.512   0.336   1.048  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.836   1.402   0.068  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.940   2.186  -0.377  1.00  0.00           O  
HETATM   15  O3  UNL     1      -6.138   1.604  -0.419  1.00  0.00           O  
HETATM   16  H1  UNL     1       6.437  -0.233   1.239  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.109   0.422   2.223  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.852  -1.016   1.156  1.00  0.00           H  
HETATM   19  H4  UNL     1       5.969   1.230  -0.406  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.597   1.837   0.547  1.00  0.00           H  
HETATM   21  H6  UNL     1       4.526  -0.559  -1.365  1.00  0.00           H  
HETATM   22  H7  UNL     1       3.983   1.091  -1.756  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.369   0.954   0.202  1.00  0.00           H  
HETATM   24  H9  UNL     1       2.953  -0.771   0.461  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.604   0.260  -2.073  1.00  0.00           H  
HETATM   26  H11 UNL     1       2.135  -1.402  -1.767  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.694  -1.567   0.220  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.223  -1.371  -1.278  1.00  0.00           H  
HETATM   29  H14 UNL     1       0.472   0.736   0.877  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.250   1.179  -0.685  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.920   1.005   1.091  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.325  -0.594   1.576  1.00  0.00           H  
HETATM   33  H18 UNL     1      -2.186  -1.441  -0.758  1.00  0.00           H  
HETATM   34  H19 UNL     1      -2.741   0.222  -1.051  1.00  0.00           H  
HETATM   35  H20 UNL     1      -3.730  -1.624   1.198  1.00  0.00           H  
HETATM   36  H21 UNL     1      -4.320  -1.256  -1.472  1.00  0.00           H  
HETATM   37  H22 UNL     1      -3.989   0.734   1.940  1.00  0.00           H  
HETATM   38  H23 UNL     1      -5.503  -0.042   1.430  1.00  0.00           H  
HETATM   39  H24 UNL     1      -6.758   0.799  -0.497  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8   29   30
CONECT    8    9   31   32
CONECT    9   10   33   34
CONECT   10   11   12   35
CONECT   11   36
CONECT   12   13   37   38
CONECT   13   14   14   15
CONECT   15   39
END

HMDB0000387
     RDKit          3D
3-Hydroxydodecanoic acid
 39 38  0  0  0  0  0  0  0  0999 V2000
    5.3256   -0.0322    1.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0297    0.9041    0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    0.3715   -0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7640    0.0456   -0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7653   -0.4992   -1.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509   -0.8258   -0.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    0.3640    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5002    0.0370    0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5321   -0.5142   -0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8273   -0.8378    0.4194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6916   -1.3378   -0.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5123    0.3363    1.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8361    1.4022    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9402    2.1863   -0.3767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1375    1.6039   -0.4191 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4371   -0.2327    1.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1091    0.4215    2.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8522   -1.0158    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9689    1.2299   -0.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5967    1.8373    0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5256   -0.5592   -1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9832    1.0911   -1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3688    0.9543    0.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9527   -0.7709    0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039    0.2598   -2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1353   -1.4016   -1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6937   -1.5669    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -1.3709   -1.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    0.7364    0.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2498    1.1790   -0.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9202    1.0055    1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247   -0.5939    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1864   -1.4408   -0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7413    0.2216   -1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7303   -1.6238    1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3204   -1.2556   -1.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9890    0.7341    1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5027   -0.0417    1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7585    0.7989   -0.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  1
 11 36  1  0
 12 37  1  0
 12 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-3-Hydroxydodecanoic acid	ChEBI
(S)-3-OH Dodecanoic acid	ChEBI
(S)-3-OH Lauric acid	ChEBI
(S)-beta-Hydroxydodecanoic acid	ChEBI
(S)-beta-Hydroxylauric acid	ChEBI
(S)-beta-OH Dodecanoic acid	ChEBI
(S)-beta-OH Lauric acid	ChEBI
(S)-3-Hydroxydodecanoate	Generator
(S)-3-OH Dodecanoate	Generator
(S)-3-OH Laate	Generator
(S)-3-OH Laic acid	Generator
(S)-b-Hydroxydodecanoate	Generator
(S)-b-Hydroxydodecanoic acid	Generator
(S)-beta-Hydroxydodecanoate	Generator
(S)-Β-hydroxydodecanoate	Generator
(S)-Β-hydroxydodecanoic acid	Generator
(S)-b-Hydroxylaate	Generator
(S)-b-Hydroxylaic acid	Generator
(S)-beta-Hydroxylaate	Generator
(S)-beta-Hydroxylaic acid	Generator
(S)-Β-hydroxylaate	Generator
(S)-Β-hydroxylaic acid	Generator
(S)-b-OH Dodecanoate	Generator
(S)-b-OH Dodecanoic acid	Generator
(S)-beta-OH Dodecanoate	Generator
(S)-Β-OH dodecanoate	Generator
(S)-Β-OH dodecanoic acid	Generator
(S)-b-OH Laate	Generator
(S)-b-OH Laic acid	Generator
(S)-beta-OH Laate	Generator
(S)-beta-OH Laic acid	Generator
(S)-Β-OH laate	Generator
(S)-Β-OH laic acid	Generator
3-Hydroxydodecanoate	Generator
(S)-3-Hydroxylaate	HMDB
(S)-3-Hydroxylaic acid	HMDB
(3S)-3-Hydroxydodecanoate	HMDB
(3S)-3-Hydroxydodecanoic acid	HMDB
(±)-3-hydroxydodecanoate	HMDB
(±)-3-hydroxydodecanoic acid	HMDB
3-Hydroxylaurate	HMDB
3-Hydroxylauric acid	HMDB
DL-beta-Hydroxydodecanoate	HMDB
DL-beta-Hydroxydodecanoic acid	HMDB
DL-Β-hydroxydodecanoate	HMDB
DL-Β-hydroxydodecanoic acid	HMDB
FA(12:0(3-OH))	HMDB
FA(12:0(3S-OH))	HMDB
L-3-Hydroxydodecanoate	HMDB
L-3-Hydroxydodecanoic acid	HMDB
beta-Hydroxydodecanoate	HMDB
beta-Hydroxydodecanoic acid	HMDB
beta-Hydroxylaurate	HMDB
beta-Hydroxylauric acid	HMDB
Β-hydroxydodecanoate	HMDB
Β-hydroxydodecanoic acid	HMDB
Β-hydroxylaurate	HMDB
Β-hydroxylauric acid	HMDB
3-Hydroxydodecanoic acid	HMDB

Chemical Formula

C₁₂H₂₄O₃

Average Molecular Weight

216.321

Monoisotopic Molecular Weight

216.172544633

IUPAC Name

(3S)-3-hydroxydodecanoic acid

Traditional Name

(S)-3-hydroxylauric acid

CAS Registry Number

45162-48-9

SMILES

CCCCCCCCC[C@H](O)CC(O)=O

InChI Identifier

InChI=1S/C12H24O3/c1-2-3-4-5-6-7-8-9-11(13)10-12(14)15/h11,13H,2-10H2,1H3,(H,14,15)/t11-/m0/s1

InChI Key

MUCMKTPAZLSKTL-NSHDSACASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-hydroxylauric acid (CHEBI:36210 )
Hydroxy fatty acids (LMFA01050252 )

Ontology

Physiological effect

Health effect

Nutritional disorder

Fatty acid oxidation disorder (HMDB: HMDB0000387)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 10657369)

Cellular substructure

Organ

Placenta (HMDB: HMDB0000387)

Excreta

Biofluid or Excreta

Feces (PMID: 23454028)

Source

Endogenous

Endogenous (HMDB: HMDB0000387)

Microbe

Exogenous

Food

Food (HMDB: HMDB0000387)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Vegetable

Fruit vegetable

Olive (FooDB: FOOD00121)

Cereal and cereal product

Cereal

Rice (FooDB: FOOD00125)
White bread (FooDB: FOOD00987)

Leavened bread

Rye bread (FooDB: FOOD00809)

Nut

Almond (FooDB: FOOD00148)

Aquatic origin

Fish

Milk and milk product

Fermented milk product

Herb and spice

Oilseed crop

Coconut oil (FooDB: FOOD00941)

Exogenous (HMDB: HMDB0000387)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0000387)

Role

Biological role

Energy source (HMDB: HMDB0000387)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000387)

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.34 g/L	ALOGPS
logP	3.63	ALOGPS
logP	3.25	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	60.2 m³·mol⁻¹	ChemAxon
Polarizability	26.38 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	157.769	30932474
DeepCCS	[M-H]-	153.746	30932474
DeepCCS	[M-2H]-	191.32	30932474
DeepCCS	[M+Na]+	166.985	30932474
AllCCS	[M+H]+	156.6	32859911
AllCCS	[M+H-H2O]+	153.0	32859911
AllCCS	[M+NH4]+	159.8	32859911
AllCCS	[M+Na]+	160.8	32859911
AllCCS	[M-H]-	156.0	32859911
AllCCS	[M+Na-2H]-	157.1	32859911
AllCCS	[M+HCOO]-	158.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.74 minutes	32390414
Predicted by Siyang on May 30, 2022	13.3627 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.63 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	39.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2175.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	325.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	159.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	379.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	591.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	568.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	100.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1186.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	436.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1390.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	396.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	388.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	252.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	59.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxydodecanoic acid	CCCCCCCCC[C@H](O)CC(O)=O	2842.7	Standard polar	33892256
3-Hydroxydodecanoic acid	CCCCCCCCC[C@H](O)CC(O)=O	1679.3	Standard non polar	33892256
3-Hydroxydodecanoic acid	CCCCCCCCC[C@H](O)CC(O)=O	1772.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxydodecanoic acid,1TMS,isomer #1	CCCCCCCCC[C@@H](CC(=O)O)O[Si](C)(C)C	1780.9	Semi standard non polar	33892256
3-Hydroxydodecanoic acid,1TMS,isomer #2	CCCCCCCCC[C@H](O)CC(=O)O[Si](C)(C)C	1767.4	Semi standard non polar	33892256
3-Hydroxydodecanoic acid,2TMS,isomer #1	CCCCCCCCC[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1855.5	Semi standard non polar	33892256
3-Hydroxydodecanoic acid,1TBDMS,isomer #1	CCCCCCCCC[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C	2007.2	Semi standard non polar	33892256
3-Hydroxydodecanoic acid,1TBDMS,isomer #2	CCCCCCCCC[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C	2000.8	Semi standard non polar	33892256
3-Hydroxydodecanoic acid,2TBDMS,isomer #1	CCCCCCCCC[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2314.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (2 TMS)	splash10-001i-5930000000-267beffaa56f4c3885ab	2019-10-24	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (Non-derivatized)	splash10-001i-5930000000-267beffaa56f4c3885ab	2019-10-24	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxydodecanoic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-0aor-9050000000-f8825f9349ee9a2ec34e	2019-10-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-0a4i-9000000000-3d142f4358076fbe5192	2019-10-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-0a4i-9000000000-54e9a813b1c73a4dee86	2019-10-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid 10V, Positive-QTOF	splash10-014i-9640000000-6ae3522b4ab714ac01d9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid 20V, Positive-QTOF	splash10-0ab9-9000000000-f44f1941ba69e47860fb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid 40V, Positive-QTOF	splash10-0a4l-9000000000-7aa76d51356623cc325f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid 10V, Negative-QTOF	splash10-066r-7090000000-c136666cfe0af2c7d044	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid 20V, Negative-QTOF	splash10-0a4i-9000000000-918089033fd82836fb6f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxydodecanoic acid 40V, Negative-QTOF	splash10-0006-9000000000-efd0e0c3d7b6aa45f62c	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)	2019-10-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)	2019-10-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.3 (0.2-0.6) uM	Adult (>18 years old)	Both	Normal	10657369	details
Blood	Detected and Quantified	0.4 (0.2-1.4) uM	Not Available	Not Available	Normal	10657369	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.4 (0.2-1.4) uM	Adult (>18 years old)	Both	Fatty Acid Oxidation disorder with supplementation of MCT formula	10657369	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	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

Fatty Acid Oxidation disorder
Jones PM, Quinn R, Fennessey PV, Tjoa S, Goodman SI, Fiore S, Burlina AB, Rinaldo P, Boriack RL, Bennett MJ: Improved stable isotope dilution-gas chromatography-mass spectrometry method for serum or plasma free 3-hydroxy-fatty acids and its utility for the study of disorders of mitochondrial fatty acid beta-oxidation. Clin Chem. 2000 Feb;46(2):149-55. [PubMed:10657369 ]
Nonalcoholic fatty liver disease
Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022005

KNApSAcK ID

Not Available

Chemspider ID

4472230

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5376

PubChem Compound

5312805

PDB ID

Not Available

ChEBI ID

36210

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Iwata, Tsutomu; Iwamoto, Osamu; Sugiyama, Haruhiko. Process for preparing b-hydroxy fatty acid. Eur. Pat. Appl. (1990), 6 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Chickos JS, Way BA, Wilson J, Shaharuzzaman M, Laird J, Landt M: Analysis of 3-hydroxydodecanedioic acid for studies of fatty acid metabolic disorders: preparation of stable isotope standards. J Clin Lab Anal. 2002;16(2):115-20. [PubMed:11948802 ]
Jones PM, Quinn R, Fennessey PV, Tjoa S, Goodman SI, Fiore S, Burlina AB, Rinaldo P, Boriack RL, Bennett MJ: Improved stable isotope dilution-gas chromatography-mass spectrometry method for serum or plasma free 3-hydroxy-fatty acids and its utility for the study of disorders of mitochondrial fatty acid beta-oxidation. Clin Chem. 2000 Feb;46(2):149-55. [PubMed:10657369 ]
Jones PM, Moffitt M, Joseph D, Harthcock PA, Boriack RL, Ibdah JA, Strauss AW, Bennett MJ: Accumulation of free 3-hydroxy fatty acids in the culture media of fibroblasts from patients deficient in long-chain l-3-hydroxyacyl-CoA dehydrogenase: a useful diagnostic aid. Clin Chem. 2001;47(7):1190-4. [PubMed:11427448 ]
Ktsoyan ZA, Beloborodova NV, Sedrakyan AM, Osipov GA, Khachatryan ZA, Kelly D, Manukyan GP, Arakelova KA, Hovhannisyan AI, Olenin AY, Arakelyan AA, Ghazaryan KA, Aminov RI: Profiles of Microbial Fatty Acids in the Human Metabolome are Disease-Specific. Front Microbiol. 2011 Jan 20;1:148. doi: 10.3389/fmicb.2010.00148. eCollection 2010. [PubMed:21687748 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for 3-Hydroxydodecanoic acid (HMDB0000387)

MOL for HMDB0000387 (3-Hydroxydodecanoic acid)

3D MOL for HMDB0000387 (3-Hydroxydodecanoic acid)

3D SDF for HMDB0000387 (3-Hydroxydodecanoic acid)

3D-SDF for HMDB0000387 (3-Hydroxydodecanoic acid)

PDB for HMDB0000387 (3-Hydroxydodecanoic acid)

3D PDB for HMDB0000387 (3-Hydroxydodecanoic acid)

SMILES for HMDB0000387 (3-Hydroxydodecanoic acid)

INCHI for HMDB0000387 (3-Hydroxydodecanoic acid)

Structure for HMDB0000387 (3-Hydroxydodecanoic acid)

3D Structure for HMDB0000387 (3-Hydroxydodecanoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra