Hmdb loader

Showing metabocard for 3-Hydroxycapric acid (HMDB0002203)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:41 UTC
Update Date2023-02-21 17:16:15 UTC
HMDB IDHMDB0002203
Secondary Accession Numbers
  • HMDB02203
Metabolite Identification
Common Name3-Hydroxycapric acid
Description3-Hydroxycapric acid (CAS: 14292-26-3) is a normally occurring carboxylic acid in human blood plasma. Medium- and long-chain 3-hydroxymonocarboxylic acids represent intermediates in the beta-oxidation of fatty acids. They accumulate in the plasma of patients with an inherited deficiency of long-chain 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35) (PMID: 1912723 ). 3-Hydroxyacyl-CoA dehydrogenase (HADH) deficiency has been described in diverse clinical cases: juvenile-onset recurrent myoglobinuria, hypoketotic hypoglycemic encephalopathy, hypertrophic/dilatative cardiomyopathy, sudden infant death, and fulminant hepatic failure (OMIM: 231530 ). 3-Hydroxycapric acid has some shape-transforming action on the membrane of intact human erythrocytes (PMID: 7318031 ).
Structure
Data?1676999775
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002203 (3-Hydroxycapric acid)


  Mrv1652303062020152D          

 13 12  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
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
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
  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for HMDB0002203 (3-Hydroxycapric acid)

HMDB0002203
     RDKit          3D
3-Hydroxycapric acid
 33 32  0  0  0  0  0  0  0  0999 V2000
    4.3136    0.9773   -0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0728    0.0818    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089   -1.0193    0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289   -0.6242   -0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0086    0.1958    0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3826    0.5672    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -0.6213   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308   -0.3342   -0.4953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7035    0.4010   -1.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5454    0.2272    0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679    0.4352   -0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2388    1.5897   -0.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7731   -0.5965   -0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966    1.2898   -0.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652    0.4247   -1.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6849    1.8983   -0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8456    0.6846    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0677   -0.4092    0.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173   -1.6219   -0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -1.7126    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607   -1.5973   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6765   -0.1449   -1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8730   -0.3797    1.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5445    1.1259    0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315    1.1768   -0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149    1.2659    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688   -1.2581   -0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -1.2440    0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0790   -1.3520   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004    1.2909   -1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1809    1.2393    0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6620   -0.3932    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5989   -1.5632   -0.1698 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
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
M  END
Download

3D SDF for HMDB0002203 (3-Hydroxycapric acid)


  Mrv1652303062020152D          

 13 12  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
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
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
  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002203

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O3/c1-2-3-4-5-6-7-9(11)8-10(12)13/h9,11H,2-8H2,1H3,(H,12,13)/t9-/m0/s1

> <INCHI_KEY>
FYSSBMZUBSBFJL-VIFPVBQESA-N

> <FORMULA>
C10H20O3

> <MOLECULAR_WEIGHT>
188.267

> <EXACT_MASS>
188.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
22.155625801533407

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
2.358359720666666

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.288498288675335

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.671850167040888

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7985874263168293

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
50.99309999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
S-3-hydroxydecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0002203 (3-Hydroxycapric acid)

HMDB0002203
     RDKit          3D
3-Hydroxycapric acid
 33 32  0  0  0  0  0  0  0  0999 V2000
    4.3136    0.9773   -0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0728    0.0818    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089   -1.0193    0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289   -0.6242   -0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0086    0.1958    0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3826    0.5672    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -0.6213   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308   -0.3342   -0.4953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7035    0.4010   -1.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5454    0.2272    0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679    0.4352   -0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2388    1.5897   -0.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7731   -0.5965   -0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966    1.2898   -0.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652    0.4247   -1.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6849    1.8983   -0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8456    0.6846    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0677   -0.4092    0.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173   -1.6219   -0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -1.7126    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607   -1.5973   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6765   -0.1449   -1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8730   -0.3797    1.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5445    1.1259    0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315    1.1768   -0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149    1.2659    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688   -1.2581   -0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -1.2440    0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0790   -1.3520   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004    1.2909   -1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1809    1.2393    0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6620   -0.3932    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5989   -1.5632   -0.1698 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
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
M  END
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PDB for HMDB0002203 (3-Hydroxycapric acid)

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    8666.8688663.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.2048663.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8669.5368663.832   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8670.8728663.064   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   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0002203 (3-Hydroxycapric acid)

COMPND    HMDB0002203
HETATM    1  C1  UNL     1       4.314   0.977  -0.888  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.073   0.082   0.312  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.109  -1.019   0.057  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.729  -0.624  -0.337  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.009   0.196   0.678  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.383   0.567   0.221  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.233  -0.621  -0.052  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.631  -0.334  -0.495  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.703   0.401  -1.655  1.00  0.00           O  
HETATM   10  C9  UNL     1      -3.545   0.227   0.538  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.868   0.435  -0.101  1.00  0.00           C  
HETATM   12  O2  UNL     1      -5.239   1.590  -0.511  1.00  0.00           O  
HETATM   13  O3  UNL     1      -5.773  -0.597  -0.290  1.00  0.00           O  
HETATM   14  H1  UNL     1       5.397   1.290  -0.933  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.065   0.425  -1.818  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.685   1.898  -0.798  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.846   0.685   1.210  1.00  0.00           H  
HETATM   18  H5  UNL     1       5.068  -0.409   0.530  1.00  0.00           H  
HETATM   19  H6  UNL     1       3.517  -1.622  -0.809  1.00  0.00           H  
HETATM   20  H7  UNL     1       3.045  -1.713   0.921  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.161  -1.597  -0.425  1.00  0.00           H  
HETATM   22  H9  UNL     1       1.676  -0.145  -1.327  1.00  0.00           H  
HETATM   23  H10 UNL     1       0.873  -0.380   1.633  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.544   1.126   0.959  1.00  0.00           H  
HETATM   25  H12 UNL     1      -0.232   1.177  -0.712  1.00  0.00           H  
HETATM   26  H13 UNL     1      -0.815   1.266   0.961  1.00  0.00           H  
HETATM   27  H14 UNL     1      -0.769  -1.258  -0.833  1.00  0.00           H  
HETATM   28  H15 UNL     1      -1.299  -1.244   0.864  1.00  0.00           H  
HETATM   29  H16 UNL     1      -3.079  -1.352  -0.764  1.00  0.00           H  
HETATM   30  H17 UNL     1      -3.100   1.291  -1.429  1.00  0.00           H  
HETATM   31  H18 UNL     1      -3.181   1.239   0.889  1.00  0.00           H  
HETATM   32  H19 UNL     1      -3.662  -0.393   1.440  1.00  0.00           H  
HETATM   33  H20 UNL     1      -5.599  -1.563  -0.170  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17   18
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8   27   28
CONECT    8    9   10   29
CONECT    9   30
CONECT   10   11   31   32
CONECT   11   12   12   13
CONECT   13   33
END
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SMILES for HMDB0002203 (3-Hydroxycapric acid)

CCCCCCC[C@H](O)CC(O)=O
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INCHI for HMDB0002203 (3-Hydroxycapric acid)

InChI=1S/C10H20O3/c1-2-3-4-5-6-7-9(11)8-10(12)13/h9,11H,2-8H2,1H3,(H,12,13)/t9-/m0/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3-HydroxycaprateGenerator
(S)-3-HydroxydecanoateHMDB
(+)-3-HydroxydecanoateHMDB
(+)-3-Hydroxydecanoic acidHMDB
(3S)-3-HydroxydecanoateHMDB
(3S)-3-Hydroxydecanoic acidHMDB
(±)-3-hydroxydecanoateHMDB
(±)-3-hydroxydecanoic acidHMDB
3(S)-HydroxydecanoateHMDB
3(S)-Hydroxydecanoic acidHMDB
3-HydroxidecanoateHMDB
3-Hydroxidecanoic acidHMDB
3-HydroxydecanoateHMDB
3-Hydroxydecanoic acidHMDB
FA(10:0(3-OH))HMDB
FA(10:0(3S-OH))HMDB
L-beta-HydroxydecanoateHMDB
L-beta-Hydroxydecanoic acidHMDB
L-Β-hydroxydecanoateHMDB
L-Β-hydroxydecanoic acidHMDB
S-3-HydroxydecanoateHMDB
S-3-Hydroxydecanoic acidHMDB
beta-HydroxycaprateHMDB
beta-Hydroxycapric acidHMDB
beta-HydroxydecanoateHMDB
beta-Hydroxydecanoic acidHMDB
Β-hydroxycaprateHMDB
Β-hydroxycapric acidHMDB
Β-hydroxydecanoateHMDB
Β-hydroxydecanoic acidHMDB
3-Hydroxycapric acidHMDB
Chemical FormulaC10H20O3
Average Molecular Weight188.267
Monoisotopic Molecular Weight188.141244504
IUPAC Name(3S)-3-hydroxydecanoic acid
Traditional NameS-3-hydroxydecanoic acid
CAS Registry Number19526-23-9
SMILES
CCCCCCC[C@H](O)CC(O)=O
InChI Identifier
InChI=1S/C10H20O3/c1-2-3-4-5-6-7-9(11)8-10(12)13/h9,11H,2-8H2,1H3,(H,12,13)/t9-/m0/s1
InChI KeyFYSSBMZUBSBFJL-VIFPVBQESA-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.74 g/LALOGPS
logP2.6ALOGPS
logP2.36ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity50.99 m³·mol⁻¹ChemAxon
Polarizability22.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+147.43930932474
DeepCCS[M-H]-143.41430932474
DeepCCS[M-2H]-180.88830932474
DeepCCS[M+Na]+156.55330932474
AllCCS[M+H]+147.732859911
AllCCS[M+H-H2O]+143.932859911
AllCCS[M+NH4]+151.232859911
AllCCS[M+Na]+152.232859911
AllCCS[M-H]-146.732859911
AllCCS[M+Na-2H]-148.132859911
AllCCS[M+HCOO]-149.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.6.06 minutes32390414
Predicted by Siyang on May 30, 202211.6304 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.06 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid48.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1856.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid304.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid142.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid183.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid274.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid497.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid493.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)99.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid998.2 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid389.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1273.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid321.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid328.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate396.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA207.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water87.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxycapric acidCCCCCCC[C@H](O)CC(O)=O2633.0Standard polar33892256
3-Hydroxycapric acidCCCCCCC[C@H](O)CC(O)=O1487.9Standard non polar33892256
3-Hydroxycapric acidCCCCCCC[C@H](O)CC(O)=O1569.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxycapric acid,1TMS,isomer #1CCCCCCC[C@@H](CC(=O)O)O[Si](C)(C)C1582.5Semi standard non polar33892256
3-Hydroxycapric acid,1TMS,isomer #2CCCCCCC[C@H](O)CC(=O)O[Si](C)(C)C1570.1Semi standard non polar33892256
3-Hydroxycapric acid,2TMS,isomer #1CCCCCCC[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1665.8Semi standard non polar33892256
3-Hydroxycapric acid,1TBDMS,isomer #1CCCCCCC[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C1804.3Semi standard non polar33892256
3-Hydroxycapric acid,1TBDMS,isomer #2CCCCCCC[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C1799.5Semi standard non polar33892256
3-Hydroxycapric acid,2TBDMS,isomer #1CCCCCCC[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2122.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Hydroxycapric acid GC-MS (2 TMS)splash10-0f89-3950000000-4dc7506e884d7c6679d52019-10-24HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Hydroxycapric acid GC-MS (Non-derivatized)splash10-0f89-3950000000-4dc7506e884d7c6679d52019-10-24HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxycapric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxycapric acid LC-ESI-IT , negative-QTOFsplash10-0a4i-9000000000-616c6c1304ee3dc8333d2019-10-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 10V, Negative-QTOFsplash10-000i-2900000000-b48a55f35e3a261db7a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 20V, Negative-QTOFsplash10-0a4i-9400000000-9bf57a4f1bdff00e64dc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 40V, Negative-QTOFsplash10-0006-9000000000-24256337cd6db4163a772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 10V, Positive-QTOFsplash10-052r-9800000000-05fd88a0d973888af6c82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 20V, Positive-QTOFsplash10-0a4i-9000000000-6e5509a032d59c16205c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 40V, Positive-QTOFsplash10-0a4l-9000000000-2cfe9add86e448abe6752021-09-23Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified6.00540 +/- 5.405 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal		 details
UrineDetected and Quantified5.405 +/- 9.609 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal		 details
UrineDetected and Quantified29.426 +/- 23.421 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal		 details
UrineDetected and Quantified31.829 +/- 13.212 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal		 details
UrineDetected and Quantified88.279 +/- 75.668 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and QuantifiedND-25 uMChildren (1-13 years old)Male3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified171.754-696.0255 umol/mmol creatinineInfant (0-1 year old)Not Specified3-Hydroxydicarboxylic aciduria details
Associated Disorders and Diseases
Disease References
3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency
  1. Thompson GN, Hsu BY, Pitt JJ, Treacy E, Stanley CA: Fasting hypoketotic coma in a child with deficiency of mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase. N Engl J Med. 1997 Oct 23;337(17):1203-7. doi: 10.1056/NEJM199710233371704. [PubMed:9337379 ]
Colorectal cancer
  1. 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 ]
  2. 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 ]
3-Hydroxydicarboxylic aciduria
  1. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Urinary 3-hydroxydicarboxylic acids in pathophysiology of metabolic disorders with dicarboxylic aciduria. Metabolism. 1991 Jul;40(7):676-82. [PubMed:1870421 ]
  2. 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 ]
Associated OMIM IDs
  • 605911 (3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency)
  • 114500 (Colorectal cancer)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022904
KNApSAcK IDNot Available
Chemspider ID4472224
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMyrmicacin
METLIN ID6544
PubChem Compound5312799
PDB IDNot Available
ChEBI ID37371
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKondo, Kiyoshi; Ryu, Yuchin. 3-Hydroxydecanoic acid. Jpn. Kokai Tokkyo Koho (1972), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Grupe A, Spiteller G: New polar acid metabolites in human urine. J Chromatogr. 1981 Dec 11;226(2):301-14. [PubMed:7320161 ]
  2. Dorland L, Ketting D, Bruinvis L, Duran M: Medium- and long-chain 3-hydroxymonocarboxylic acids: analysis by gas chromatography combined with mass spectrometry. Biomed Chromatogr. 1991 Jul;5(4):161-4. [PubMed:1912723 ]
  3. Kanaho Y, Sato T, Fujii T, Iwanami Y, Iwadare T, Orito K: Shape-transforming action of myrmicacin (3-hydroxydecanoic acid) and some related compounds on the membrane of intact human erythrocytes. Chem Pharm Bull (Tokyo). 1981 Oct;29(10):3063-6. [PubMed:7318031 ]
  4. 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 ]