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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 02:51:03 UTC

HMDB ID

HMDB0010735

Secondary Accession Numbers

HMDB10735

Metabolite Identification

Common Name

Trans-Hexa-dec-2-enoic acid

Description

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. Trans-hexa-dec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-hexa-dec-2-enoic acid converted from (R)-3-Hydroxy-hexadecanoic acid via two enzymes; fatty-acid Synthase and 3- Hydroxypalmitoyl- [acyl-carrier-protein] dehydratase (EC: 2.3.1.85 and EC: 4.2.1.61).

Structure

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

HMDB0010735
     RDKit          3D
Trans-Hexa-dec-2-enoic acid
 48 47  0  0  0  0  0  0  0  0999 V2000
    6.1887    2.4869    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9550    2.5913   -0.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2896    1.2766   -0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8431    0.5610    0.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924   -0.7474    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198   -1.5153    1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0821   -2.7961    0.8639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8947   -2.6256   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685   -1.8258    0.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3893   -1.6314   -0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4081   -0.8264    0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6498   -0.6083   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6430    0.1979    0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8787    0.4345   -0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2902    1.6502   -0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4929    1.9221   -1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2004    0.9763   -1.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8599    3.2235   -1.5666 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0642    2.1167   -0.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4975    3.5085    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0971    1.8007    1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2846    2.9792   -1.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2800    3.3569   -0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3852    1.4962   -1.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9225    0.6181   -1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433    0.2805    1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738    1.1369    1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3231   -0.4760   -0.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9323   -1.3888   -0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0186   -0.8955    1.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5553   -1.7679    1.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7058   -3.2994    1.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305   -3.4965    0.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1306   -2.1935   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4683   -3.6343   -0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4049   -2.2706    1.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2333   -0.7907    0.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904   -2.6091   -0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638   -1.0958   -1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737   -1.3412    1.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9577    0.1428    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553   -0.0972   -1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1398   -1.5539   -0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1987    1.1525    0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9070   -0.4119    1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4624   -0.4041   -0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6786    2.4662   -0.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1983    3.9269   -1.8916 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  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 18 48  1  0
M  END

  Mrv1652307301920022D          

 20 19  0  0  0  0            999 V2000
    4.7586    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7612    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4756    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4756    4.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1901    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    4.8099    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7612    2.7474    0.0000 H   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  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 16  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0010735

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h14-15H,2-13H2,1H3,(H,17,18)/b15-14+

> <INCHI_KEY>
ZVRMGCSSSYZGSM-CCEZHUSRSA-N

> <FORMULA>
C16H30O2

> <MOLECULAR_WEIGHT>
254.4082

> <EXACT_MASS>
254.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
33.74415362299203

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-hexadec-2-enoic acid

> <JCHEM_LOGP>
6.254406267333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.0255044264493

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
78.17689999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
hexadecenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010735
     RDKit          3D
Trans-Hexa-dec-2-enoic acid
 48 47  0  0  0  0  0  0  0  0999 V2000
    6.1887    2.4869    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9550    2.5913   -0.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2896    1.2766   -0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8431    0.5610    0.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924   -0.7474    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198   -1.5153    1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0821   -2.7961    0.8639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8947   -2.6256   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685   -1.8258    0.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3893   -1.6314   -0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4081   -0.8264    0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6498   -0.6083   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6430    0.1979    0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8787    0.4345   -0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2902    1.6502   -0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4929    1.9221   -1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2004    0.9763   -1.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8599    3.2235   -1.5666 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0642    2.1167   -0.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4975    3.5085    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0971    1.8007    1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2846    2.9792   -1.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2800    3.3569   -0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3852    1.4962   -1.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9225    0.6181   -1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433    0.2805    1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738    1.1369    1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3231   -0.4760   -0.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9323   -1.3888   -0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0186   -0.8955    1.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5553   -1.7679    1.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7058   -3.2994    1.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305   -3.4965    0.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1306   -2.1935   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4683   -3.6343   -0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4049   -2.2706    1.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2333   -0.7907    0.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904   -2.6091   -0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638   -1.0958   -1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737   -1.3412    1.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9577    0.1428    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553   -0.0972   -1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1398   -1.5539   -0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1987    1.1525    0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9070   -0.4119    1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4624   -0.4041   -0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6786    2.4662   -0.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1983    3.9269   -1.8916 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  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 18 48  1  0
M  END

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       8.883   6.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.216   7.438   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.217   6.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.885   6.668   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.552   6.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.219   6.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.887   6.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.221   7.438   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.554   6.668   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.888   7.438   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      28.888   8.978   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      30.222   6.668   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0      26.221   8.978   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0      27.554   5.128   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
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   15   19                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0010735
HETATM    1  C1  UNL     1       6.189   2.487   0.394  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.955   2.591  -0.446  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.290   1.277  -0.699  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.843   0.561   0.531  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.192  -0.747   0.081  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.720  -1.515   1.293  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.082  -2.796   0.864  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.895  -2.626  -0.029  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.169  -1.826   0.683  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.389  -1.631  -0.190  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.408  -0.826   0.583  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.650  -0.608  -0.257  1.00  0.00           C  
HETATM   13  C13 UNL     1      -4.643   0.198   0.546  1.00  0.00           C  
HETATM   14  C14 UNL     1      -5.879   0.435  -0.244  1.00  0.00           C  
HETATM   15  C15 UNL     1      -6.290   1.650  -0.533  1.00  0.00           C  
HETATM   16  C16 UNL     1      -7.493   1.922  -1.304  1.00  0.00           C  
HETATM   17  O1  UNL     1      -8.200   0.976  -1.732  1.00  0.00           O  
HETATM   18  O2  UNL     1      -7.860   3.223  -1.567  1.00  0.00           O  
HETATM   19  H1  UNL     1       7.064   2.117  -0.216  1.00  0.00           H  
HETATM   20  H2  UNL     1       6.497   3.509   0.722  1.00  0.00           H  
HETATM   21  H3  UNL     1       6.097   1.801   1.235  1.00  0.00           H  
HETATM   22  H4  UNL     1       5.285   2.979  -1.452  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.280   3.357  -0.043  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.385   1.496  -1.339  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.922   0.618  -1.300  1.00  0.00           H  
HETATM   26  H8  UNL     1       4.743   0.281   1.139  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.174   1.137   1.166  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.323  -0.476  -0.528  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.932  -1.389  -0.435  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.019  -0.895   1.852  1.00  0.00           H  
HETATM   31  H13 UNL     1       3.555  -1.768   1.977  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.706  -3.299   1.803  1.00  0.00           H  
HETATM   33  H15 UNL     1       2.831  -3.496   0.449  1.00  0.00           H  
HETATM   34  H16 UNL     1       1.131  -2.194  -1.009  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.468  -3.634  -0.215  1.00  0.00           H  
HETATM   36  H18 UNL     1      -0.405  -2.271   1.654  1.00  0.00           H  
HETATM   37  H19 UNL     1       0.233  -0.791   0.873  1.00  0.00           H  
HETATM   38  H20 UNL     1      -1.790  -2.609  -0.493  1.00  0.00           H  
HETATM   39  H21 UNL     1      -1.064  -1.096  -1.091  1.00  0.00           H  
HETATM   40  H22 UNL     1      -2.674  -1.341   1.518  1.00  0.00           H  
HETATM   41  H23 UNL     1      -1.958   0.143   0.866  1.00  0.00           H  
HETATM   42  H24 UNL     1      -3.355  -0.097  -1.188  1.00  0.00           H  
HETATM   43  H25 UNL     1      -4.140  -1.554  -0.526  1.00  0.00           H  
HETATM   44  H26 UNL     1      -4.199   1.152   0.874  1.00  0.00           H  
HETATM   45  H27 UNL     1      -4.907  -0.412   1.437  1.00  0.00           H  
HETATM   46  H28 UNL     1      -6.462  -0.404  -0.596  1.00  0.00           H  
HETATM   47  H29 UNL     1      -5.679   2.466  -0.163  1.00  0.00           H  
HETATM   48  H30 UNL     1      -7.198   3.927  -1.892  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8   32   33
CONECT    8    9   34   35
CONECT    9   10   36   37
CONECT   10   11   38   39
CONECT   11   12   40   41
CONECT   12   13   42   43
CONECT   13   14   44   45
CONECT   14   15   15   46
CONECT   15   16   47
CONECT   16   17   17   18
CONECT   18   48
END

HMDB0010735
     RDKit          3D
Trans-Hexa-dec-2-enoic acid
 48 47  0  0  0  0  0  0  0  0999 V2000
    6.1887    2.4869    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9550    2.5913   -0.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2896    1.2766   -0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8431    0.5610    0.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924   -0.7474    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198   -1.5153    1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0821   -2.7961    0.8639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8947   -2.6256   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685   -1.8258    0.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3893   -1.6314   -0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4081   -0.8264    0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6498   -0.6083   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6430    0.1979    0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8787    0.4345   -0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2902    1.6502   -0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4929    1.9221   -1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2004    0.9763   -1.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8599    3.2235   -1.5666 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0642    2.1167   -0.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4975    3.5085    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0971    1.8007    1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2846    2.9792   -1.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2800    3.3569   -0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3852    1.4962   -1.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9225    0.6181   -1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433    0.2805    1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738    1.1369    1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3231   -0.4760   -0.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9323   -1.3888   -0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0186   -0.8955    1.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5553   -1.7679    1.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7058   -3.2994    1.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305   -3.4965    0.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1306   -2.1935   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4683   -3.6343   -0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4049   -2.2706    1.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2333   -0.7907    0.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904   -2.6091   -0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638   -1.0958   -1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737   -1.3412    1.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9577    0.1428    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553   -0.0972   -1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1398   -1.5539   -0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1987    1.1525    0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9070   -0.4119    1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4624   -0.4041   -0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6786    2.4662   -0.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1983    3.9269   -1.8916 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  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 18 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
trans-Hexa-dec-2-enoate	Generator
(2E)-Hexadecenoic acid	ChEBI
(e)-2-Hexadecenoic acid	ChEBI
2-Palmitoleic acid	ChEBI
2-trans-Hexadecenoic acid	ChEBI
Gaidic acid	ChEBI
t-16:1D2	ChEBI
t-2-Hexadecenoic acid	ChEBI
trans-2-Hexadecenoic acid	ChEBI
trans-Delta(2)-Hexadecenoic acid	ChEBI
trans-Hexadec-2-enoic acid	ChEBI
(2E)-Hexadecenoate	Generator
(e)-2-Hexadecenoate	Generator
2-Palmitoleate	Generator
2-trans-Hexadecenoate	Generator
Gaidate	Generator
t-2-Hexadecenoate	Generator
trans-2-Hexadecenoate	Generator
trans-delta(2)-Hexadecenoate	Generator
trans-δ(2)-hexadecenoate	Generator
trans-δ(2)-hexadecenoic acid	Generator
trans-Hexadec-2-enoate	Generator
Hexadecenoic acid, (e)-isomer	MeSH, HMDB
cis-Hexadecenoic acid	MeSH, HMDB
Hexadecenoic acid	MeSH, HMDB
Hexadecenoic acid, (Z)-isomer	MeSH, HMDB
trans-Hexadecenoic acid	MeSH, HMDB

Chemical Formula

C₁₆H₃₀O₂

Average Molecular Weight

254.4082

Monoisotopic Molecular Weight

254.224580204

IUPAC Name

(2E)-hexadec-2-enoic acid

Traditional Name

hexadecenoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCCCCCCCC)=C(\[H])C(O)=O

InChI Identifier

InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h14-15H,2-13H2,1H3,(H,17,18)/b15-14+

InChI Key

ZVRMGCSSSYZGSM-CCEZHUSRSA-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
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha,beta-unsaturated monocarboxylic acid (CHEBI:37252 )
hexadecenoic acid (CHEBI:37252 )
Unsaturated fatty acids (LMFA01030054 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0010735)
Membrane (HMDB: HMDB0010735)

Source

Exogenous

Exogenous (HMDB: HMDB0010735)

Endogenous

Endogenous (HMDB: HMDB0010735)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Biosynthesis (PathBank: SMP0002360)
Fatty Acid Biosynthesis (PathBank: SMP0087409)

Role

Not Available

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	167.864	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001848

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00022 g/L	ALOGPS
logP	6.25	ChemAxon
pKa (Strongest Acidic)	5.03	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	78.18 m³·mol⁻¹	ChemAxon
Polarizability	33.74 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	168.493	31661259
DarkChem	[M-H]-	169.478	31661259
DeepCCS	[M+H]+	171.81	30932474
DeepCCS	[M-H]-	169.259	30932474
DeepCCS	[M-2H]-	203.249	30932474
DeepCCS	[M+Na]+	179.485	30932474
AllCCS	[M+H]+	169.9	32859911
AllCCS	[M+H-H2O]+	166.6	32859911
AllCCS	[M+NH4]+	172.9	32859911
AllCCS	[M+Na]+	173.7	32859911
AllCCS	[M-H]-	170.8	32859911
AllCCS	[M+Na-2H]-	172.1	32859911
AllCCS	[M+HCOO]-	173.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trans-Hexa-dec-2-enoic acid	[H]\C(CCCCCCCCCCCCC)=C(\[H])C(O)=O	2919.7	Standard polar	33892256
Trans-Hexa-dec-2-enoic acid	[H]\C(CCCCCCCCCCCCC)=C(\[H])C(O)=O	1926.3	Standard non polar	33892256
Trans-Hexa-dec-2-enoic acid	[H]\C(CCCCCCCCCCCCC)=C(\[H])C(O)=O	1977.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Trans-Hexa-dec-2-enoic acid,1TMS,isomer #1	CCCCCCCCCCCCC/C=C/C(=O)O[Si](C)(C)C	2099.5	Semi standard non polar	33892256
Trans-Hexa-dec-2-enoic acid,1TBDMS,isomer #1	CCCCCCCCCCCCC/C=C/C(=O)O[Si](C)(C)C(C)(C)C	2333.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Trans-Hexa-dec-2-enoic acid GC-MS (1 TMS)	splash10-017j-5900000000-58442a5c08ea8c4926d0	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Trans-Hexa-dec-2-enoic acid GC-MS (Non-derivatized)	splash10-017j-5900000000-58442a5c08ea8c4926d0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trans-Hexa-dec-2-enoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-01p6-9820000000-ca98f4a0dd8ff557bc6c	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trans-Hexa-dec-2-enoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-022i-9551000000-39e4b8ad34555c61b4ad	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trans-Hexa-dec-2-enoic 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 - Trans-Hexa-dec-2-enoic acid 10V, Positive-QTOF	splash10-0a4r-0190000000-1228a4503bc27bed1ebf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-Hexa-dec-2-enoic acid 20V, Positive-QTOF	splash10-0a4l-3960000000-1370ead704dcac4cec1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-Hexa-dec-2-enoic acid 40V, Positive-QTOF	splash10-052f-9700000000-85e6708e40be2971ffc9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-Hexa-dec-2-enoic acid 10V, Negative-QTOF	splash10-0udi-0090000000-bb3d892e7f48a711d0ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-Hexa-dec-2-enoic acid 20V, Negative-QTOF	splash10-0zfr-0090000000-6a46dea6de3429b73374	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-Hexa-dec-2-enoic acid 40V, Negative-QTOF	splash10-0a4l-9440000000-668a65146f3042b031de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-Hexa-dec-2-enoic acid 10V, Negative-QTOF	splash10-0udi-0090000000-37cfc189faecac3c9577	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-Hexa-dec-2-enoic acid 20V, Negative-QTOF	splash10-0udi-0090000000-b570c7cdc86145fba021	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-Hexa-dec-2-enoic acid 40V, Negative-QTOF	splash10-00n0-1960000000-8371cc75a9113569270b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-Hexa-dec-2-enoic acid 10V, Positive-QTOF	splash10-0a4r-4490000000-61560c3648170efe9274	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-Hexa-dec-2-enoic acid 20V, Positive-QTOF	splash10-0ab9-9520000000-26416932e2aa67751576	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trans-Hexa-dec-2-enoic acid 40V, Positive-QTOF	splash10-0aor-9100000000-9eed9d946622d4a4c83c	2021-09-24	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004789

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

5282743

PDB ID

Not Available

ChEBI ID

Not Available

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 Trans-Hexa-dec-2-enoic acid (HMDB0010735)

MOL for HMDB0010735 (Trans-Hexa-dec-2-enoic acid)

3D MOL for HMDB0010735 (Trans-Hexa-dec-2-enoic acid)

3D SDF for HMDB0010735 (Trans-Hexa-dec-2-enoic acid)

3D-SDF for HMDB0010735 (Trans-Hexa-dec-2-enoic acid)

PDB for HMDB0010735 (Trans-Hexa-dec-2-enoic acid)

3D PDB for HMDB0010735 (Trans-Hexa-dec-2-enoic acid)

SMILES for HMDB0010735 (Trans-Hexa-dec-2-enoic acid)

INCHI for HMDB0010735 (Trans-Hexa-dec-2-enoic acid)

Structure for HMDB0010735 (Trans-Hexa-dec-2-enoic acid)

3D Structure for HMDB0010735 (Trans-Hexa-dec-2-enoic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes