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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-22 22:04:33 UTC

Update Date

2022-03-07 02:49:31 UTC

HMDB ID

HMDB0006294

Secondary Accession Numbers

HMDB0155887
HMDB06294

Metabolite Identification

Common Name

16-Hydroxyhexadecanoic acid

Description

16-Hydroxyhexadecanoic acid, also known as 16-hydroxypalmitic acid, is a hydroxylated fatty acid where the terminal (omega) carbon has been hydroxylated. In animal tissues, a family of enzymes termed cytochromes P450s are involved in fatty acid oxidation, hydroxylating with high specificity at the energetically unfavourable terminal (omega) or omega-1 carbons. Hydroxy fatty acids primarily come from the consumption of plant products (vegetables or fruits) or cow’s milk. Omega hydroxy fatty acids are found in the structure of suberin, a lipid polyester present in plant cell walls, and of cutin, a lipid polyester which is a component of the plant cuticle. These apoplastic structures are important plant-environment interfaces that act as barriers limiting water and nutrient loss and protecting plants from radiation and pathogens. 16-Hydroxyhexadecanoic acid and 18-hydroxystearic acid are particularly abundant in cutin in the plant cuticle. 16-Hydroxyhexadecanoic acid has been proposed as a biomarker of beer consumption.

Structure

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

HMDB0006294
     RDKit          3D
16-Hydroxyhexadecanoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
    9.8498    1.6232   -0.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9916    0.7045   -0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4223   -0.5927   -0.4216 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5778    1.0774   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6519   -0.1010   -0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2431    0.4047    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215   -0.7112    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8623   -0.0738    0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593   -1.1213    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461   -0.3320    0.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7067   -1.2980    0.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9935   -0.5431    0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2945    0.4562   -0.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5872    1.1955   -0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7189    0.2346   -0.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0619    0.9186   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1019   -0.2091   -0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4908    0.3378    0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3697   -0.7319    0.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0051   -1.3107    0.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2820    1.8025   -0.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4026    1.6116    0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9297   -0.8186    0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7237   -0.5811   -1.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625    0.9497    1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0220    1.1064   -0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4347   -1.4738    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2530   -1.2332   -0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8671    0.5061    1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7282    0.6491   -0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533   -1.7106   -0.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8707   -1.7290    1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5059    0.1066    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    0.4210   -0.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160   -2.0028    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -1.8631   -0.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8326   -1.2546    0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311    0.0273    1.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4514    1.1477   -0.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -0.1262   -1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4941    1.8026    0.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7302    1.9056   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574   -0.2689   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6549   -0.5497    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0520    1.3187    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2805    1.6619   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0709   -0.6597   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8347   -0.9966    0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7178    0.9864   -0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5098    0.9056    1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8909   -1.5686    0.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  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
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 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  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
M  END

  Mrv1652309182019222D          

 19 18  0  0  0  0            999 V2000
 9999.167010000.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.882110000.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.452310000.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.597010000.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.737410000.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.312210000.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.022510000.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.025810000.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.307610000.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.741510000.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.590610000.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.457110000.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.875710000.3299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.590610001.5672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.170710000.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.886410000.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.602010000.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.315710000.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.031410000.7416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006294

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCCCCCCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H32O3/c17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(18)19/h17H,1-15H2,(H,18,19)

> <INCHI_KEY>
UGAGPNKCDRTDHP-UHFFFAOYSA-N

> <FORMULA>
C16H32O3

> <MOLECULAR_WEIGHT>
272.4235

> <EXACT_MASS>
272.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.411821666366656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-hydroxyhexadecanoic acid

> <ALOGPS_LOGP>
5.77

> <JCHEM_LOGP>
4.819904161

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.84394282199214

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019704603348

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9922594590354228

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
79.01229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-hydroxyhexadecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006294
     RDKit          3D
16-Hydroxyhexadecanoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
    9.8498    1.6232   -0.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9916    0.7045   -0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4223   -0.5927   -0.4216 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5778    1.0774   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6519   -0.1010   -0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2431    0.4047    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215   -0.7112    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8623   -0.0738    0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593   -1.1213    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461   -0.3320    0.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7067   -1.2980    0.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9935   -0.5431    0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2945    0.4562   -0.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5872    1.1955   -0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7189    0.2346   -0.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0619    0.9186   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1019   -0.2091   -0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4908    0.3378    0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3697   -0.7319    0.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0051   -1.3107    0.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2820    1.8025   -0.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4026    1.6116    0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9297   -0.8186    0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7237   -0.5811   -1.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625    0.9497    1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0220    1.1064   -0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4347   -1.4738    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2530   -1.2332   -0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8671    0.5061    1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7282    0.6491   -0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533   -1.7106   -0.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8707   -1.7290    1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5059    0.1066    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    0.4210   -0.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160   -2.0028    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -1.8631   -0.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8326   -1.2546    0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311    0.0273    1.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4514    1.1477   -0.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -0.1262   -1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4941    1.8026    0.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7302    1.9056   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574   -0.2689   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6549   -0.5497    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0520    1.3187    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2805    1.6619   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0709   -0.6597   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8347   -0.9966    0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7178    0.9864   -0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5098    0.9056    1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8909   -1.5686    0.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  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
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 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  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
M  END

HEADER    PROTEIN                                 18-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-20         0                                  
HETATM    1  C   UNK     0    8665.1128667.283   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.4478668.051   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8663.7788668.051   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8667.7818667.283   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8662.4438667.283   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.1168668.051   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8661.1098668.051   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8670.4488667.283   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8659.7748667.283   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8671.7848668.051   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8658.4368668.051   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8673.1208667.283   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8657.1018667.283   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8658.4368669.592   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8674.4528668.051   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8675.7888667.283   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8677.1248668.051   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8678.4568667.283   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8679.7928668.051   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13   14                                                  
CONECT   12   10   15                                                       
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0006294
HETATM    1  O1  UNL     1       9.850   1.623  -0.258  1.00  0.00           O  
HETATM    2  C1  UNL     1       8.992   0.705  -0.266  1.00  0.00           C  
HETATM    3  O2  UNL     1       9.422  -0.593  -0.422  1.00  0.00           O  
HETATM    4  C2  UNL     1       7.578   1.077  -0.108  1.00  0.00           C  
HETATM    5  C3  UNL     1       6.652  -0.101  -0.134  1.00  0.00           C  
HETATM    6  C4  UNL     1       5.243   0.405   0.036  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.222  -0.711   0.025  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.862  -0.074   0.202  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.759  -1.121   0.204  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.446  -0.332   0.391  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.707  -1.298   0.405  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.993  -0.543   0.604  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.294   0.456  -0.469  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.587   1.196  -0.243  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.719   0.235  -0.220  1.00  0.00           C  
HETATM   16  C14 UNL     1      -6.062   0.919  -0.010  1.00  0.00           C  
HETATM   17  C15 UNL     1      -7.102  -0.209  -0.014  1.00  0.00           C  
HETATM   18  C16 UNL     1      -8.491   0.338   0.187  1.00  0.00           C  
HETATM   19  O3  UNL     1      -9.370  -0.732   0.172  1.00  0.00           O  
HETATM   20  H1  UNL     1       9.005  -1.311   0.131  1.00  0.00           H  
HETATM   21  H2  UNL     1       7.282   1.802  -0.901  1.00  0.00           H  
HETATM   22  H3  UNL     1       7.403   1.612   0.858  1.00  0.00           H  
HETATM   23  H4  UNL     1       6.930  -0.819   0.667  1.00  0.00           H  
HETATM   24  H5  UNL     1       6.724  -0.581  -1.121  1.00  0.00           H  
HETATM   25  H6  UNL     1       5.162   0.950   1.009  1.00  0.00           H  
HETATM   26  H7  UNL     1       5.022   1.106  -0.767  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.435  -1.474   0.799  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.253  -1.233  -0.951  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.867   0.506   1.141  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.728   0.649  -0.629  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.753  -1.711  -0.711  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.871  -1.729   1.124  1.00  0.00           H  
HETATM   33  H14 UNL     1       0.506   0.107   1.419  1.00  0.00           H  
HETATM   34  H15 UNL     1       0.354   0.421  -0.392  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.616  -2.003   1.256  1.00  0.00           H  
HETATM   36  H17 UNL     1      -0.714  -1.863  -0.558  1.00  0.00           H  
HETATM   37  H18 UNL     1      -2.833  -1.255   0.776  1.00  0.00           H  
HETATM   38  H19 UNL     1      -1.931   0.027   1.578  1.00  0.00           H  
HETATM   39  H20 UNL     1      -1.451   1.148  -0.665  1.00  0.00           H  
HETATM   40  H21 UNL     1      -2.457  -0.126  -1.426  1.00  0.00           H  
HETATM   41  H22 UNL     1      -3.494   1.803   0.682  1.00  0.00           H  
HETATM   42  H23 UNL     1      -3.730   1.906  -1.087  1.00  0.00           H  
HETATM   43  H24 UNL     1      -4.757  -0.269  -1.215  1.00  0.00           H  
HETATM   44  H25 UNL     1      -4.655  -0.550   0.531  1.00  0.00           H  
HETATM   45  H26 UNL     1      -6.052   1.319   1.025  1.00  0.00           H  
HETATM   46  H27 UNL     1      -6.281   1.662  -0.774  1.00  0.00           H  
HETATM   47  H28 UNL     1      -7.071  -0.660  -1.036  1.00  0.00           H  
HETATM   48  H29 UNL     1      -6.835  -0.997   0.688  1.00  0.00           H  
HETATM   49  H30 UNL     1      -8.718   0.986  -0.697  1.00  0.00           H  
HETATM   50  H31 UNL     1      -8.510   0.906   1.137  1.00  0.00           H  
HETATM   51  H32 UNL     1      -8.891  -1.569   0.394  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8   27   28
CONECT    8    9   29   30
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   35   36
CONECT   12   13   37   38
CONECT   13   14   39   40
CONECT   14   15   41   42
CONECT   15   16   43   44
CONECT   16   17   45   46
CONECT   17   18   47   48
CONECT   18   19   49   50
CONECT   19   51
END

HMDB0006294
     RDKit          3D
16-Hydroxyhexadecanoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
    9.8498    1.6232   -0.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9916    0.7045   -0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4223   -0.5927   -0.4216 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5778    1.0774   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6519   -0.1010   -0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2431    0.4047    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215   -0.7112    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8623   -0.0738    0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593   -1.1213    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461   -0.3320    0.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7067   -1.2980    0.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9935   -0.5431    0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2945    0.4562   -0.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5872    1.1955   -0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7189    0.2346   -0.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0619    0.9186   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1019   -0.2091   -0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4908    0.3378    0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3697   -0.7319    0.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0051   -1.3107    0.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2820    1.8025   -0.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4026    1.6116    0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9297   -0.8186    0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7237   -0.5811   -1.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625    0.9497    1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0220    1.1064   -0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4347   -1.4738    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2530   -1.2332   -0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8671    0.5061    1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7282    0.6491   -0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533   -1.7106   -0.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8707   -1.7290    1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5059    0.1066    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    0.4210   -0.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160   -2.0028    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -1.8631   -0.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8326   -1.2546    0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311    0.0273    1.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4514    1.1477   -0.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -0.1262   -1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4941    1.8026    0.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7302    1.9056   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574   -0.2689   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6549   -0.5497    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0520    1.3187    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2805    1.6619   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0709   -0.6597   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8347   -0.9966    0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7178    0.9864   -0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5098    0.9056    1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8909   -1.5686    0.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  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
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 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  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
16-Hydroxy-hexadecanoic acid	ChEBI
16-Hydroxypalmitic acid	ChEBI
16-OH 16:0	ChEBI
Juniperic acid	ChEBI
Omega-hydroxypalmitic acid	ChEBI
16-Hydroxy-hexadecanoate	Generator
16-Hydroxypalmitate	Generator
Juniperate	Generator
Omega-hydroxypalmitate	Generator
16-Hydroxyhexadecanoate	Generator
16-Hydroxy hexadecanoate	HMDB
FA(16:0(16-OH))	HMDB
Lanopalmitic acid	HMDB
Omega-hydroxyhexadecanoic acid	HMDB
Ω-hydroxyhexadecanoic acid	HMDB
Ω-hydroxypalmitic acid	HMDB
16-Hydroxyhexadecanoic acid	ChEBI, HMDB

Chemical Formula

C₁₆H₃₂O₃

Average Molecular Weight

272.4235

Monoisotopic Molecular Weight

272.23514489

IUPAC Name

16-hydroxyhexadecanoic acid

Traditional Name

16-hydroxyhexadecanoic acid

CAS Registry Number

506-13-8

SMILES

OCCCCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C16H32O3/c17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(18)19/h17H,1-15H2,(H,18,19)

InChI Key

UGAGPNKCDRTDHP-UHFFFAOYSA-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
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:55328 )
omega-hydroxy fatty acid (CHEBI:55328 )
Hydroxy fatty acids (LMFA01050051 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0006294)

Endogenous

Endogenous (HMDB: HMDB0006294)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	94.00 to 98.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	414.00 to 415.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2.87 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.904 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	168.988	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.001 g/L	ALOGPS
logP	5.77	ALOGPS
logP	4.82	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-2	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	15	ChemAxon
Refractivity	79.01 m³·mol⁻¹	ChemAxon
Polarizability	35.41 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]+	172.025	31661259
DarkChem	[M-H]-	170.311	31661259
DeepCCS	[M+H]+	167.021	30932474
DeepCCS	[M-H]-	163.001	30932474
DeepCCS	[M-2H]-	200.594	30932474
DeepCCS	[M+Na]+	176.294	30932474
AllCCS	[M+H]+	171.1	32859911
AllCCS	[M+H-H2O]+	168.1	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.7	32859911
AllCCS	[M-H]-	173.0	32859911
AllCCS	[M+Na-2H]-	174.0	32859911
AllCCS	[M+HCOO]-	175.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
16-Hydroxyhexadecanoic acid	OCCCCCCCCCCCCCCCC(O)=O	3310.4	Standard polar	33892256
16-Hydroxyhexadecanoic acid	OCCCCCCCCCCCCCCCC(O)=O	2142.8	Standard non polar	33892256
16-Hydroxyhexadecanoic acid	OCCCCCCCCCCCCCCCC(O)=O	2256.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
16-Hydroxyhexadecanoic acid,1TMS,isomer #1	C[Si](C)(C)OCCCCCCCCCCCCCCCC(=O)O	2354.8	Semi standard non polar	33892256
16-Hydroxyhexadecanoic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCO	2312.2	Semi standard non polar	33892256
16-Hydroxyhexadecanoic acid,2TMS,isomer #1	C[Si](C)(C)OCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C	2404.5	Semi standard non polar	33892256
16-Hydroxyhexadecanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCCCCCCCCCCCCC(=O)O	2579.6	Semi standard non polar	33892256
16-Hydroxyhexadecanoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCO	2563.8	Semi standard non polar	33892256
16-Hydroxyhexadecanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2921.0	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 - 16-Hydroxyhexadecanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7930000000-ad8cf0089b491fa1e5cd	2018-04-09	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Hydroxyhexadecanoic 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 - 16-Hydroxyhexadecanoic acid 10V, Positive-QTOF	splash10-0a4i-0090000000-468101d8a11af1e19fb2	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 20V, Positive-QTOF	splash10-0a4i-1390000000-b96e5d9bf93a0533f50a	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 40V, Positive-QTOF	splash10-001l-7910000000-de85d9f11917d3bd2f54	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 10V, Negative-QTOF	splash10-00di-0090000000-355bea410e278c7b034e	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 20V, Negative-QTOF	splash10-0uk9-1090000000-a82fa5c9114086d0e61e	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 40V, Negative-QTOF	splash10-0a4l-9250000000-93d26870cf342252967f	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 10V, Positive-QTOF	splash10-0ab9-2290000000-578204c997b44c45b07a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 20V, Positive-QTOF	splash10-0a4i-9440000000-a06fb9b2d3c16ea9e814	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 40V, Positive-QTOF	splash10-0a4m-9000000000-9ad19ca2f1345bd8f812	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 10V, Negative-QTOF	splash10-00di-0090000000-09835f7bfaa31d64d09c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 20V, Negative-QTOF	splash10-0fk9-0090000000-9e380c8ffde0c8460bc6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 40V, Negative-QTOF	splash10-0006-9320000000-be3d31d993db22a6eb07	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10466

PDB ID

Not Available

ChEBI ID

55328

Food Biomarker Ontology

Not Available

VMH ID

WHHDCA

MarkerDB ID

Not Available

Good Scents ID

rw1157321

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 16-Hydroxyhexadecanoic acid (HMDB0006294)

MOL for HMDB0006294 (16-Hydroxyhexadecanoic acid)

3D MOL for HMDB0006294 (16-Hydroxyhexadecanoic acid)

3D SDF for HMDB0006294 (16-Hydroxyhexadecanoic acid)

3D-SDF for HMDB0006294 (16-Hydroxyhexadecanoic acid)

PDB for HMDB0006294 (16-Hydroxyhexadecanoic acid)

3D PDB for HMDB0006294 (16-Hydroxyhexadecanoic acid)

SMILES for HMDB0006294 (16-Hydroxyhexadecanoic acid)

INCHI for HMDB0006294 (16-Hydroxyhexadecanoic acid)

Structure for HMDB0006294 (16-Hydroxyhexadecanoic acid)

3D Structure for HMDB0006294 (16-Hydroxyhexadecanoic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra