MiMeDB: Showing metabocard for (R)-3-Hydroxy-hexadecanoic acid (MMDBc0047818)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:44:11 UTC

Update Date

2024-04-30 20:30:52 UTC

Metabolite ID

MMDBc0047818

Metabolite Identification

Common Name

(R)-3-Hydroxy-hexadecanoic acid

Description

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. (R)-3-Hydroxy-hexadecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, (R)-3-Hydroxy-hexadecanoic 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

HMDB0010734
     RDKit          3D
(R)-3-Hydroxy-hexadecanoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
   -7.4421    1.2927    0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0999    0.6618    0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6048    0.0149    1.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2411   -0.6427    1.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2385    0.3681    0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8513   -0.2616    0.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9223   -1.3068   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6847   -2.0330   -0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4843   -1.3868   -1.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855   -0.3010   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4399    0.1429   -1.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0698    1.2476   -0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086    1.7713   -1.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3532    0.7134   -1.3553 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4811    1.2426   -1.9764 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6969   -0.0266   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2168    0.8314    0.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3462    2.0563    0.7953 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5699    0.2868    2.1844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1941    0.4732    0.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3471    1.8341    1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6778    1.9881   -0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4272    1.4840    0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2473   -0.0914   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3109   -0.7949    1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4908    0.7852    2.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9130   -1.0996    2.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3763   -1.4828    0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4974    0.7903   -0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1594    1.2086    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5463   -0.7243    1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930    0.5932    0.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -0.8835   -1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6562   -2.0954    0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -2.5902    0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678   -2.9544   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1082   -0.9618   -2.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2238   -2.1845   -1.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    0.6523   -0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4918   -0.5655    0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1100   -0.7366   -1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1580    0.4622   -2.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.0822   -0.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717    0.8287    0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6570    2.6876   -0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9925    2.0809   -2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9384   -0.0457   -2.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9889    0.4503   -2.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8322   -0.5904    0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360   -0.8230   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5573    0.3033    2.4364 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
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  6
 15 48  1  0
 16 49  1  0
 16 50  1  0
 19 51  1  0
M  END


  Mrv0541 02241201182D          

 20 19  0  0  1  0            999 V2000
   12.6193   -7.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3337   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0482   -7.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7627   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4771   -7.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1916   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9061   -7.2511    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.6206   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3351   -7.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0495   -7.6636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3351   -6.4261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9048   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1903   -7.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4759   -7.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2489   -6.5239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4929   -6.4742    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7614   -7.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0469   -7.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3325   -7.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6180   -7.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 15  1  1  0  0  0
  7 16  1  6  0  0  0
 17 14  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047818

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15(17)14-16(18)19/h15,17H,2-14H2,1H3,(H,18,19)/t15-/m1/s1

> <INCHI_KEY>
CBWALJHXHCJYTE-OAHLLOKOSA-N

> <FORMULA>
C16H32O3

> <MOLECULAR_WEIGHT>
272.4235

> <EXACT_MASS>
272.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.10668172681193

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.75

> <JCHEM_LOGP>
5.025771710666666

> <ALOGPS_LOGS>
-4.69

> <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>
78.59909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(R)-3-hydroxypalmitic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010734
     RDKit          3D
(R)-3-Hydroxy-hexadecanoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
   -7.4421    1.2927    0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0999    0.6618    0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6048    0.0149    1.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2411   -0.6427    1.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2385    0.3681    0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8513   -0.2616    0.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9223   -1.3068   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6847   -2.0330   -0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4843   -1.3868   -1.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855   -0.3010   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4399    0.1429   -1.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0698    1.2476   -0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086    1.7713   -1.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3532    0.7134   -1.3553 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4811    1.2426   -1.9764 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6969   -0.0266   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2168    0.8314    0.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3462    2.0563    0.7953 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5699    0.2868    2.1844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1941    0.4732    0.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3471    1.8341    1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6778    1.9881   -0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4272    1.4840    0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2473   -0.0914   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3109   -0.7949    1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4908    0.7852    2.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9130   -1.0996    2.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3763   -1.4828    0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4974    0.7903   -0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1594    1.2086    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5463   -0.7243    1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930    0.5932    0.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -0.8835   -1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6562   -2.0954    0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -2.5902    0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678   -2.9544   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1082   -0.9618   -2.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2238   -2.1845   -1.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    0.6523   -0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4918   -0.5655    0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1100   -0.7366   -1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1580    0.4622   -2.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.0822   -0.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717    0.8287    0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6570    2.6876   -0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9925    2.0809   -2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9384   -0.0457   -2.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9889    0.4503   -2.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8322   -0.5904    0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360   -0.8230   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5573    0.3033    2.4364 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
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  6
 15 48  1  0
 16 49  1  0
 16 50  1  0
 19 51  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      23.556 -13.535   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.890 -14.305   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.223 -13.535   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.557 -14.305   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.891 -13.535   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.224 -14.305   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.558 -13.535   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.892 -14.305   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.226 -13.535   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      35.559 -14.305   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      34.226 -11.995   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      22.222 -14.305   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.889 -13.536   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.555 -14.306   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      30.331 -12.178   0.000  0.00  0.00           O+0
HETATM   16  H   UNK     0      32.653 -12.085   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0      18.221 -13.536   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.888 -14.306   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.554 -13.536   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.220 -14.306   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15   16                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   17                                                       
CONECT   15    7                                                            
CONECT   16    7                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0010734
HETATM    1  C1  UNL     1      -7.442   1.293   0.684  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.100   0.662   0.391  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.605   0.015   1.678  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.241  -0.643   1.436  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.238   0.368   0.993  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.851  -0.262   0.779  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.922  -1.307  -0.274  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.685  -2.033  -0.618  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.484  -1.387  -1.228  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.186  -0.301  -0.521  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.440   0.143  -1.316  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.070   1.248  -0.503  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.309   1.771  -1.171  1.00  0.00           C  
HETATM   14  C14 UNL     1       5.353   0.713  -1.355  1.00  0.00           C  
HETATM   15  O1  UNL     1       6.481   1.243  -1.976  1.00  0.00           O  
HETATM   16  C15 UNL     1       5.697  -0.027  -0.090  1.00  0.00           C  
HETATM   17  C16 UNL     1       6.217   0.831   0.972  1.00  0.00           C  
HETATM   18  O2  UNL     1       6.346   2.056   0.795  1.00  0.00           O  
HETATM   19  O3  UNL     1       6.570   0.287   2.184  1.00  0.00           O  
HETATM   20  H1  UNL     1      -8.194   0.473   0.776  1.00  0.00           H  
HETATM   21  H2  UNL     1      -7.347   1.834   1.648  1.00  0.00           H  
HETATM   22  H3  UNL     1      -7.678   1.988  -0.125  1.00  0.00           H  
HETATM   23  H4  UNL     1      -5.427   1.484   0.065  1.00  0.00           H  
HETATM   24  H5  UNL     1      -6.247  -0.091  -0.405  1.00  0.00           H  
HETATM   25  H6  UNL     1      -6.311  -0.795   1.931  1.00  0.00           H  
HETATM   26  H7  UNL     1      -5.491   0.785   2.442  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.913  -1.100   2.379  1.00  0.00           H  
HETATM   28  H9  UNL     1      -4.376  -1.483   0.699  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.497   0.790  -0.019  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.159   1.209   1.705  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.546  -0.724   1.774  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.193   0.593   0.581  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.436  -0.883  -1.200  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.656  -2.095   0.129  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.356  -2.590   0.350  1.00  0.00           H  
HETATM   36  H17 UNL     1      -0.968  -2.954  -1.261  1.00  0.00           H  
HETATM   37  H18 UNL     1       0.108  -0.962  -2.232  1.00  0.00           H  
HETATM   38  H19 UNL     1       1.224  -2.185  -1.568  1.00  0.00           H  
HETATM   39  H20 UNL     1       0.599   0.652  -0.505  1.00  0.00           H  
HETATM   40  H21 UNL     1       1.492  -0.566   0.477  1.00  0.00           H  
HETATM   41  H22 UNL     1       3.110  -0.737  -1.354  1.00  0.00           H  
HETATM   42  H23 UNL     1       2.158   0.462  -2.331  1.00  0.00           H  
HETATM   43  H24 UNL     1       2.365   2.082  -0.376  1.00  0.00           H  
HETATM   44  H25 UNL     1       3.272   0.829   0.504  1.00  0.00           H  
HETATM   45  H26 UNL     1       4.657   2.688  -0.688  1.00  0.00           H  
HETATM   46  H27 UNL     1       3.992   2.081  -2.211  1.00  0.00           H  
HETATM   47  H28 UNL     1       4.938  -0.046  -2.065  1.00  0.00           H  
HETATM   48  H29 UNL     1       6.989   0.450  -2.328  1.00  0.00           H  
HETATM   49  H30 UNL     1       4.832  -0.590   0.310  1.00  0.00           H  
HETATM   50  H31 UNL     1       6.436  -0.823  -0.398  1.00  0.00           H  
HETATM   51  H32 UNL     1       7.557   0.303   2.436  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   35   36
CONECT    9   10   37   38
CONECT   10   11   39   40
CONECT   11   12   41   42
CONECT   12   13   43   44
CONECT   13   14   45   46
CONECT   14   15   16   47
CONECT   15   48
CONECT   16   17   49   50
CONECT   17   18   18   19
CONECT   19   51
END

HMDB0010734
     RDKit          3D
(R)-3-Hydroxy-hexadecanoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
   -7.4421    1.2927    0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0999    0.6618    0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6048    0.0149    1.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2411   -0.6427    1.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2385    0.3681    0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8513   -0.2616    0.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9223   -1.3068   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6847   -2.0330   -0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4843   -1.3868   -1.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855   -0.3010   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4399    0.1429   -1.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0698    1.2476   -0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086    1.7713   -1.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3532    0.7134   -1.3553 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4811    1.2426   -1.9764 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6969   -0.0266   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2168    0.8314    0.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3462    2.0563    0.7953 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5699    0.2868    2.1844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1941    0.4732    0.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3471    1.8341    1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6778    1.9881   -0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4272    1.4840    0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2473   -0.0914   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3109   -0.7949    1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4908    0.7852    2.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9130   -1.0996    2.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3763   -1.4828    0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4974    0.7903   -0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1594    1.2086    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5463   -0.7243    1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930    0.5932    0.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -0.8835   -1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6562   -2.0954    0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -2.5902    0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678   -2.9544   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1082   -0.9618   -2.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2238   -2.1845   -1.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    0.6523   -0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4918   -0.5655    0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1100   -0.7366   -1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1580    0.4622   -2.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.0822   -0.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717    0.8287    0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6570    2.6876   -0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9925    2.0809   -2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9384   -0.0457   -2.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9889    0.4503   -2.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8322   -0.5904    0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360   -0.8230   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5573    0.3033    2.4364 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
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  6
 15 48  1  0
 16 49  1  0
 16 50  1  0
 19 51  1  0
M  END

Synonyms

Value	Source
(R)-3-Hydroxy-hexadecanoate	Generator
(R)-beta-Hydroxypalmitic acid	ChEBI
(R)-b-Hydroxypalmitate	Generator
(R)-b-Hydroxypalmitic acid	Generator
(R)-beta-Hydroxypalmitate	Generator
(R)-β-hydroxypalmitate	Generator
(R)-β-hydroxypalmitic acid	Generator
3-Hydroxypalmitic acid	MeSH, HMDB
beta-Hydroxypalmitic acid	MeSH, HMDB
3-Hydroxypalmitic acid, (+-)-isomer	MeSH, HMDB
beta-Hydroxypalmitate	MeSH, HMDB

Molecular Formula

C₁₆H₃₂O₃

Average Mass

272.4235

Monoisotopic Mass

272.23514489

IUPAC Name

(3R)-3-hydroxyhexadecanoic acid

Traditional Name

(R)-3-hydroxypalmitic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15(17)14-16(18)19/h15,17H,2-14H2,1H3,(H,18,19)/t15-/m1/s1

InChI Key

CBWALJHXHCJYTE-OAHLLOKOSA-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:38247 )
3-hydroxypalmitic acid (CHEBI:38247 )
Hydroxy fatty acids (LMFA01050366 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0056 g/L	ALOGPS
logP	5.75	ALOGPS
logP	5.03	ChemAxon
logS	-4.7	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	14	ChemAxon
Refractivity	78.6 m³·mol⁻¹	ChemAxon
Polarizability	35.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9340000000-7f3268f819048bc0fb4c	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-009i-9231100000-2ee529fc9d520d001aee	2017-10-06	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0090000000-170f4b78f38f50653281	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3590000000-72735537a44743fc49f3	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-18c6bb5829efbdfd8324	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-69dd00738d6e82b5a71a	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0adi-2090000000-a29b15501f484eac1a95	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9240000000-34c29dc88bb32e93e509	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1090000000-b8b5369541b20493e1ab	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9020000000-0763938b2406df6b3db3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9020000000-405e88be7cf7e93b3269	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-2190000000-13586bde632215e51549	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9430000000-96b8600a3183721e0024	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-ac851687758f1e0f9afd	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191709	Fatty acid synthase	Enzyme	P49327	Homo sapiens
MMDBp0195915	3-oxoacyl-[acyl-carrier-protein] synthase, mitochondrial	Enzyme	Q9NWU1	Homo sapiens

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0010734

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027881

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15569776

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [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. doi: 10.1194/jlr.R600022-JLR200. 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. doi: 10.1194/jlr.R700005-JLR200. 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.

Showing metabocard for (R)-3-Hydroxy-hexadecanoic acid (MMDBc0047818)

MOL for #<Metabolite:0x00007fecece6a6c8>

3D MOL for #<Metabolite:0x00007fecece6a6c8>

3D SDF for #<Metabolite:0x00007fecece6a6c8>

3D-SDF for #<Metabolite:0x00007fecece6a6c8>

PDB for #<Metabolite:0x00007fecece6a6c8>

3D PDB for #<Metabolite:0x00007fecece6a6c8>

SMILES for #<Metabolite:0x00007fecece6a6c8>

INCHI for #<Metabolite:0x00007fecece6a6c8>

Structure for #<Metabolite:0x00007fecece6a6c8>

3D Structure for #<Metabolite:0x00007fecece6a6c8>