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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-10-15 12:12:16 UTC

Update Date

2022-03-07 02:51:02 UTC

HMDB ID

HMDB0010731

Secondary Accession Numbers

HMDB10731

Metabolite Identification

Common Name

(R)-3-Hydroxy-tetradecanoic acid

Description

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. (R)-3-Hydroxy-tetradecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, (R)-3-Hydroxy-tetradecanoic acid is converted from 3-Oxo-tetradecanoic acid via fatty-acid Synthase and 3-oxoacyl- [acyl-carrier-protein] reductase. (EC: 2.3.1.85 and EC:2.3.1.41).

Structure

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

HMDB0010731
     RDKit          3D
(R)-3-Hydroxy-tetradecanoic acid
 45 44  0  0  0  0  0  0  0  0999 V2000
   -5.6504   -0.2742   -1.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1873   -0.4211   -1.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3166    0.1026   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6218   -0.6899    0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0079   -0.3605    1.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5564   -0.3811    1.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6855    0.5828    1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626    0.3407    1.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7074    1.2753    1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7010    1.1463   -0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0813   -0.2144   -0.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4626   -0.6450   -0.5476 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6600   -1.9177   -1.0772 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5320    0.2659   -1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8882   -0.1685   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0690   -1.1829    0.0532 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0338    0.5082   -1.0810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0800   -1.2320   -1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2115    0.0945   -2.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8131    0.4707   -0.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9435   -1.4940   -2.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8947    0.1613   -2.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5543    1.1503   -0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937   -0.0594   -1.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4553   -1.8124    0.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7685   -0.6827    0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5328   -1.0142    2.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3937    0.6797    2.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595   -0.2562    3.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865   -1.4486    1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7755    0.5690    0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0014    1.6176    1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7809    0.5530    2.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -0.7014    1.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7359    1.0503    1.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5012    2.3358    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4098    1.8989   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151    1.3949   -0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0514   -0.2060   -2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3731   -0.9785   -0.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5815   -0.6977    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676   -2.4504   -0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3643    1.3262   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5184    0.2710   -2.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1705    1.4940   -0.8299 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
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  1
 13 42  1  0
 14 43  1  0
 14 44  1  0
 17 45  1  0
M  END

FTT
  Mrv0541 02231216262D          

 18 17  0  0  0  0            999 V2000
   -4.6445    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9300   -0.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2154    0.1646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5010   -0.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7864    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -0.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571   -0.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152   -0.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6442   -0.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3591   -0.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2154    0.9897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6445    0.9897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2154   -0.4193    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 15  2  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 16  1  1  0  0  0
  3 18  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0010731

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)/t13-/m1/s1

> <INCHI_KEY>
ATRNZOYKSNPPBF-CYBMUJFWSA-N

> <FORMULA>
C14H28O3

> <MOLECULAR_WEIGHT>
244.3703

> <EXACT_MASS>
244.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.856556396012678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3-hydroxytetradecanoic acid

> <ALOGPS_LOGP>
4.69

> <JCHEM_LOGP>
4.136634380666667

> <ALOGPS_LOGS>
-3.91

> <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>
69.3971

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-tetradecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010731
     RDKit          3D
(R)-3-Hydroxy-tetradecanoic acid
 45 44  0  0  0  0  0  0  0  0999 V2000
   -5.6504   -0.2742   -1.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1873   -0.4211   -1.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3166    0.1026   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6218   -0.6899    0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0079   -0.3605    1.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5564   -0.3811    1.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6855    0.5828    1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626    0.3407    1.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7074    1.2753    1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7010    1.1463   -0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0813   -0.2144   -0.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4626   -0.6450   -0.5476 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6600   -1.9177   -1.0772 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5320    0.2659   -1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8882   -0.1685   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0690   -1.1829    0.0532 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0338    0.5082   -1.0810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0800   -1.2320   -1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2115    0.0945   -2.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8131    0.4707   -0.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9435   -1.4940   -2.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8947    0.1613   -2.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5543    1.1503   -0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937   -0.0594   -1.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4553   -1.8124    0.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7685   -0.6827    0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5328   -1.0142    2.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3937    0.6797    2.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595   -0.2562    3.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865   -1.4486    1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7755    0.5690    0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0014    1.6176    1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7809    0.5530    2.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -0.7014    1.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7359    1.0503    1.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5012    2.3358    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4098    1.8989   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151    1.3949   -0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0514   -0.2060   -2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3731   -0.9785   -0.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5815   -0.6977    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676   -2.4504   -0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3643    1.3262   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5184    0.2710   -2.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1705    1.4940   -0.8299 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
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  1
 13 42  1  0
 14 43  1  0
 14 44  1  0
 17 45  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: FTT                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -8.670   0.307   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.336  -0.463   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.002   0.307   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.669  -0.463   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.335   0.307   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.001  -0.463   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.667   0.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.667  -0.463   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.001   0.307   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.334  -0.463   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.668   0.307   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.002  -0.463   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.336   0.307   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.669  -0.463   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -10.004  -0.463   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -6.002   1.847   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -8.670   1.847   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0      -6.002  -0.783   0.000  0.00  0.00           H+0
CONECT    1    2   15   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   16   18                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    1                                                            
CONECT   16    3                                                            
CONECT   17    1                                                            
CONECT   18    3                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0010731
HETATM    1  C1  UNL     1      -5.650  -0.274  -1.583  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.187  -0.421  -1.934  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.317   0.103  -0.740  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.622  -0.690   0.470  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.008  -0.360   1.764  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.556  -0.381   1.978  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.685   0.583   1.252  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.763   0.341   1.700  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.707   1.275   1.013  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.701   1.146  -0.478  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.081  -0.214  -0.968  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.463  -0.645  -0.548  1.00  0.00           C  
HETATM   13  O1  UNL     1       3.660  -1.918  -1.077  1.00  0.00           O  
HETATM   14  C13 UNL     1       4.532   0.266  -1.110  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.888  -0.169  -0.689  1.00  0.00           C  
HETATM   16  O2  UNL     1       6.069  -1.183   0.053  1.00  0.00           O  
HETATM   17  O3  UNL     1       7.034   0.508  -1.081  1.00  0.00           O  
HETATM   18  H1  UNL     1      -6.080  -1.232  -1.192  1.00  0.00           H  
HETATM   19  H2  UNL     1      -6.211   0.094  -2.468  1.00  0.00           H  
HETATM   20  H3  UNL     1      -5.813   0.471  -0.772  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.943  -1.494  -2.068  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.895   0.161  -2.809  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.554   1.150  -0.617  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.294  -0.059  -1.150  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.455  -1.812   0.257  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.769  -0.683   0.552  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.533  -1.014   2.548  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.394   0.680   2.096  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.359  -0.256   3.100  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.186  -1.449   1.776  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.776   0.569   0.188  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.001   1.618   1.588  1.00  0.00           H  
HETATM   33  H16 UNL     1       0.781   0.553   2.788  1.00  0.00           H  
HETATM   34  H17 UNL     1       1.023  -0.701   1.525  1.00  0.00           H  
HETATM   35  H18 UNL     1       2.736   1.050   1.362  1.00  0.00           H  
HETATM   36  H19 UNL     1       1.501   2.336   1.257  1.00  0.00           H  
HETATM   37  H20 UNL     1       2.410   1.899  -0.881  1.00  0.00           H  
HETATM   38  H21 UNL     1       0.715   1.395  -0.931  1.00  0.00           H  
HETATM   39  H22 UNL     1       2.051  -0.206  -2.069  1.00  0.00           H  
HETATM   40  H23 UNL     1       1.373  -0.979  -0.578  1.00  0.00           H  
HETATM   41  H24 UNL     1       3.582  -0.698   0.533  1.00  0.00           H  
HETATM   42  H25 UNL     1       4.168  -2.450  -0.417  1.00  0.00           H  
HETATM   43  H26 UNL     1       4.364   1.326  -0.799  1.00  0.00           H  
HETATM   44  H27 UNL     1       4.518   0.271  -2.222  1.00  0.00           H  
HETATM   45  H28 UNL     1       7.171   1.494  -0.830  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   37   38
CONECT   11   12   39   40
CONECT   12   13   14   41
CONECT   13   42
CONECT   14   15   43   44
CONECT   15   16   16   17
CONECT   17   45
END

HMDB0010731
     RDKit          3D
(R)-3-Hydroxy-tetradecanoic acid
 45 44  0  0  0  0  0  0  0  0999 V2000
   -5.6504   -0.2742   -1.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1873   -0.4211   -1.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3166    0.1026   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6218   -0.6899    0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0079   -0.3605    1.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5564   -0.3811    1.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6855    0.5828    1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626    0.3407    1.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7074    1.2753    1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7010    1.1463   -0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0813   -0.2144   -0.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4626   -0.6450   -0.5476 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6600   -1.9177   -1.0772 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5320    0.2659   -1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8882   -0.1685   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0690   -1.1829    0.0532 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0338    0.5082   -1.0810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0800   -1.2320   -1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2115    0.0945   -2.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8131    0.4707   -0.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9435   -1.4940   -2.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8947    0.1613   -2.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5543    1.1503   -0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937   -0.0594   -1.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4553   -1.8124    0.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7685   -0.6827    0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5328   -1.0142    2.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3937    0.6797    2.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595   -0.2562    3.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865   -1.4486    1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7755    0.5690    0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0014    1.6176    1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7809    0.5530    2.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -0.7014    1.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7359    1.0503    1.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5012    2.3358    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4098    1.8989   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151    1.3949   -0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0514   -0.2060   -2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3731   -0.9785   -0.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5815   -0.6977    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676   -2.4504   -0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3643    1.3262   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5184    0.2710   -2.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1705    1.4940   -0.8299 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
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  1
 13 42  1  0
 14 43  1  0
 14 44  1  0
 17 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R)-3-Hydroxy-tetradecanoate	Generator
(-)-3-Hydroxymyristic acid	HMDB
(3R)-Hydroxymyristic acid	HMDB
(R)-(-)-3-Hydroxytetradecanoic acid	HMDB
(R)-3-Hydroxymyristic acid	HMDB
beta-Hydroxymyristic acid	HMDB
beta-Hydroxytetradecanoic acid	HMDB
D-(-)-beta-Hydroxymyristic acid	HMDB
(-)-3-Hydroxymyristate	HMDB
(3R)-Hydroxymyristate	HMDB
(R)-(-)-3-Hydroxytetradecanoate	HMDB
(R)-3-Hydroxymyristate	HMDB
b-Hydroxymyristate	HMDB
b-Hydroxymyristic acid	HMDB
beta-Hydroxymyristate	HMDB
Β-hydroxymyristate	HMDB
Β-hydroxymyristic acid	HMDB
b-Hydroxytetradecanoate	HMDB
b-Hydroxytetradecanoic acid	HMDB
beta-Hydroxytetradecanoate	HMDB
Β-hydroxytetradecanoate	HMDB
Β-hydroxytetradecanoic acid	HMDB
D-(-)-b-Hydroxymyristate	HMDB
D-(-)-b-Hydroxymyristic acid	HMDB
D-(-)-beta-Hydroxymyristate	HMDB
D-(-)-Β-hydroxymyristate	HMDB
D-(-)-Β-hydroxymyristic acid	HMDB
(R)-3-Hydroxytetradecanoic acid	HMDB
(R)-3-Hydroxytetradecanoate	HMDB

Chemical Formula

C₁₄H₂₈O₃

Average Molecular Weight

244.3703

Monoisotopic Molecular Weight

244.203844762

IUPAC Name

(3R)-3-hydroxytetradecanoic acid

Traditional Name

3-hydroxy-tetradecanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)/t13-/m1/s1

InChI Key

ATRNZOYKSNPPBF-CYBMUJFWSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

(3R)-3-hydroxy fatty acid (CHEBI:42539 )
3-hydroxytetradecanoic acid (CHEBI:42539 )
Hydroxy fatty acids (LMFA01050322 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0010731)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0010731)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0010731)

Source

Exogenous

Exogenous (HMDB: HMDB0010731)

Food

Food (HMDB: HMDB0010731)

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)

Endogenous

Endogenous (HMDB: HMDB0010731)

Process

Role

Biological role

Energy source (HMDB: HMDB0010731)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0010731)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0010731)

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	0.03 g/L	ALOGPS
logP	4.69	ALOGPS
logP	4.14	ChemAxon
logS	-3.9	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	12	ChemAxon
Refractivity	69.4 m³·mol⁻¹	ChemAxon
Polarizability	30.86 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	162.227	31661259
DarkChem	[M-H]-	163.651	31661259
DeepCCS	[M+H]+	157.58	30932474
DeepCCS	[M-H]-	154.945	30932474
DeepCCS	[M-2H]-	190.861	30932474
DeepCCS	[M+Na]+	165.461	30932474
AllCCS	[M+H]+	166.0	32859911
AllCCS	[M+H-H2O]+	162.7	32859911
AllCCS	[M+NH4]+	169.1	32859911
AllCCS	[M+Na]+	170.0	32859911
AllCCS	[M-H]-	164.9	32859911
AllCCS	[M+Na-2H]-	165.9	32859911
AllCCS	[M+HCOO]-	167.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-3-Hydroxy-tetradecanoic acid	[H][C@@](O)(CCCCCCCCCCC)CC(O)=O	3043.7	Standard polar	33892256
(R)-3-Hydroxy-tetradecanoic acid	[H][C@@](O)(CCCCCCCCCCC)CC(O)=O	1864.5	Standard non polar	33892256
(R)-3-Hydroxy-tetradecanoic acid	[H][C@@](O)(CCCCCCCCCCC)CC(O)=O	1974.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-3-Hydroxy-tetradecanoic acid,1TMS,isomer #1	CCCCCCCCCCC[C@H](CC(=O)O)O[Si](C)(C)C	1982.4	Semi standard non polar	33892256
(R)-3-Hydroxy-tetradecanoic acid,1TMS,isomer #2	CCCCCCCCCCC[C@@H](O)CC(=O)O[Si](C)(C)C	1965.6	Semi standard non polar	33892256
(R)-3-Hydroxy-tetradecanoic acid,2TMS,isomer #1	CCCCCCCCCCC[C@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2052.4	Semi standard non polar	33892256
(R)-3-Hydroxy-tetradecanoic acid,1TBDMS,isomer #1	CCCCCCCCCCC[C@H](CC(=O)O)O[Si](C)(C)C(C)(C)C	2217.4	Semi standard non polar	33892256
(R)-3-Hydroxy-tetradecanoic acid,1TBDMS,isomer #2	CCCCCCCCCCC[C@@H](O)CC(=O)O[Si](C)(C)C(C)(C)C	2208.6	Semi standard non polar	33892256
(R)-3-Hydroxy-tetradecanoic acid,2TBDMS,isomer #1	CCCCCCCCCCC[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2514.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9500000000-d3837d6527b09790d09e	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-9142000000-2b802003b701914b13b7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid 10V, Positive-QTOF	splash10-004j-0290000000-3cbad25621cd84dd55dc	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid 20V, Positive-QTOF	splash10-057j-4960000000-28121e72e39700d4f373	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid 40V, Positive-QTOF	splash10-052f-9300000000-77f13667a638fc0db127	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid 10V, Negative-QTOF	splash10-0006-1490000000-041e325e3e96f0f26837	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid 20V, Negative-QTOF	splash10-0a5d-4950000000-ceff7e67442b0ca855ab	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid 40V, Negative-QTOF	splash10-0a4l-9600000000-2a651411e77e87c314c5	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid 10V, Negative-QTOF	splash10-0006-1090000000-576941859c2295d4cb14	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid 20V, Negative-QTOF	splash10-0a4i-9110000000-be27ca1efc0330f18073	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid 40V, Negative-QTOF	splash10-0a4l-9110000000-b5cfa3eff2f2e135cf70	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid 10V, Positive-QTOF	splash10-002b-4390000000-0cbb960da18db3e0e662	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid 20V, Positive-QTOF	splash10-0pb9-9310000000-0ff6d44ab8d422fb3b9b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-Hydroxy-tetradecanoic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-29ad8b4130f67f29eb80	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Fatty Acid Biosynthesis		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02767

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027878

KNApSAcK ID

Not Available

Chemspider ID

4450466

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5288266

PDB ID

FTT

ChEBI ID

42539

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Fatty acid synthase

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: P49327
Molecular weight:: 273424.06

Showing metabocard for (R)-3-Hydroxy-tetradecanoic acid (HMDB0010731)

MOL for HMDB0010731 ((R)-3-Hydroxy-tetradecanoic acid)

3D MOL for HMDB0010731 ((R)-3-Hydroxy-tetradecanoic acid)

3D SDF for HMDB0010731 ((R)-3-Hydroxy-tetradecanoic acid)

3D-SDF for HMDB0010731 ((R)-3-Hydroxy-tetradecanoic acid)

PDB for HMDB0010731 ((R)-3-Hydroxy-tetradecanoic acid)

3D PDB for HMDB0010731 ((R)-3-Hydroxy-tetradecanoic acid)

SMILES for HMDB0010731 ((R)-3-Hydroxy-tetradecanoic acid)

INCHI for HMDB0010731 ((R)-3-Hydroxy-tetradecanoic acid)

Structure for HMDB0010731 ((R)-3-Hydroxy-tetradecanoic acid)

3D Structure for HMDB0010731 ((R)-3-Hydroxy-tetradecanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes