MiMeDB: Showing metabocard for 3-Hydroxydodecanoic acid (MMDBc0000341)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:35:43 UTC

Update Date

2024-04-30 19:31:51 UTC

Metabolite ID

MMDBc0000341

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>
MMDBc0000341

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₂H₂₄O₃

Average Mass

216.321

Monoisotopic Mass

216.172544633

IUPAC Name

(3S)-3-hydroxydodecanoic acid

Traditional Name

(S)-3-hydroxylauric acid

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-5930000000-267beffaa56f4c3885ab	2019-10-24	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-5930000000-267beffaa56f4c3885ab	2019-10-24	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0aor-9050000000-f8825f9349ee9a2ec34e	2019-10-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-9000000000-3d142f4358076fbe5192	2019-10-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4i-9000000000-54e9a813b1c73a4dee86	2019-10-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-9640000000-6ae3522b4ab714ac01d9	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9000000000-f44f1941ba69e47860fb	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-7aa76d51356623cc325f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-066r-7090000000-c136666cfe0af2c7d044	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-918089033fd82836fb6f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-efd0e0c3d7b6aa45f62c	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2019-10-24	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)		2019-10-24	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Fatty acid oxidation disorder	Slight Increase	Association	Human Blood	HMDB	10657369

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	3	Human ; Human feces; Human stool; Human supragingival plaque; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human 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	HMDB	10657369
Human Blood	Detected and Quantified	0.3	0.2	0.6	uM	Adult (>18 years old)	Both	Normal	HMDB	10657369
Human Blood	Detected and Quantified	0.4	0.2	1.4	uM			Normal	HMDB	10657369
Human Placenta	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	23454028
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000387

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

References

Synthesis Reference

Not Available

General References

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 ]
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. doi: 10.1002/jcla.10033. [PubMed:11948802 ]
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 (MMDBc0000341)

MOL for #<Metabolite:0x00007fdb48012a40>

3D MOL for #<Metabolite:0x00007fdb48012a40>

3D SDF for #<Metabolite:0x00007fdb48012a40>

3D-SDF for #<Metabolite:0x00007fdb48012a40>

PDB for #<Metabolite:0x00007fdb48012a40>

3D PDB for #<Metabolite:0x00007fdb48012a40>

SMILES for #<Metabolite:0x00007fdb48012a40>

INCHI for #<Metabolite:0x00007fdb48012a40>

Structure for #<Metabolite:0x00007fdb48012a40>

3D Structure for #<Metabolite:0x00007fdb48012a40>