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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:24:03 UTC

Update Date

2022-03-07 03:17:45 UTC

HMDB ID

HMDB0060482

Secondary Accession Numbers

HMDB60482

Metabolite Identification

Common Name

Hexadecenal

Description

Among the 19 human ALDHs, ALDH3A2 is the only known ALDH that catalyzes the oxidation of long-chain fatty aldehydes including C16 aldehydes (hexadecanal and trans-2-hexadecenal) generated through sphingolipid metabolism. (PMID: 23721920 ) We recently identified that two products within the sphingolipid pathway, sphingosine-1-PO4 and hexadecenal, directly regulate BAK and BAX activation, respectively. (PMID: 23750296 ) Sphingosine-1-phosphate lyase (SPL) is the only known enzyme that irreversibly cleaves sphingosine-1-phosphate (S1P) into phosphoethanolamine and (2E)-hexadecenal during the final step of sphingolipid catabolism. (PMID: 22444536 ) Sphingosine 1-phosphate, a bioactive signaling molecule with diverse cellular functions, is irreversibly degraded by the endoplasmic reticulum enzyme sphingosine 1-phosphate lyase, generating trans-2-hexadecenal and phosphoethanolamine. We recently demonstrated that trans-2-hexadecenal causes cytoskeletal reorganization, detachment, and apoptosis in multiple cell types via a JNK-dependent pathway. (PMID: 22727907 )

Structure

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

HMDB0060482
     RDKit          3D
Hexadecenal
 47 46  0  0  0  0  0  0  0  0999 V2000
    6.4416   -1.6066   -0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300   -2.0544    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1745   -0.7661    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711   -1.1473    0.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9040    0.1144    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807    0.9413   -0.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1715    2.2310   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599    2.3640   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407    2.1006    0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459    2.2544    1.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9387    1.3127    0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870   -0.1129    0.6253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435   -1.1048   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8045   -1.0310    0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4450   -2.0972    0.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8841   -2.0392    0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5215   -0.9991    0.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1961   -2.2849    0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5888   -0.6135    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6177   -1.5530   -1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6175   -2.7262   -0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0389   -2.5468    1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6082   -0.1218    0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2519   -0.3025   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3028   -1.7878   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7402   -1.6219    1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8783   -0.3602    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2486    0.6487    1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    0.2700   -1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9793    1.1314   -1.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344    2.7769   -1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215    2.9185    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8222    1.6059   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5920    3.3826   -0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2560    1.2126    1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2123    2.9515    1.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3184    1.9845    2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4297    3.2969    1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443    1.5355   -0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0073    1.4599    0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8102   -0.2921    1.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5080   -0.2414    0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1544   -0.8743   -1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9384   -2.1112   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3980   -0.1579   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9127   -3.0174    0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3790   -2.9219    1.0243 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
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
M  END


  Mrv0541 05161318242D          

 17 16  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
  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
M  END
> <DATABASE_ID>
HMDB0060482

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCC\C=C\C=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h14-16H,2-13H2,1H3/b15-14+

> <INCHI_KEY>
KLJFYXOVGVXZKT-CCEZHUSRSA-N

> <FORMULA>
C16H30O

> <MOLECULAR_WEIGHT>
238.4088

> <EXACT_MASS>
238.229665582

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
32.5234321586139

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-hexadec-2-enal

> <ALOGPS_LOGP>
6.97

> <JCHEM_LOGP>
6.095790015

> <ALOGPS_LOGS>
-6.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.203792945095838

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
77.25149999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.59e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-trans-hexadecenal

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060482
     RDKit          3D
Hexadecenal
 47 46  0  0  0  0  0  0  0  0999 V2000
    6.4416   -1.6066   -0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300   -2.0544    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1745   -0.7661    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711   -1.1473    0.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9040    0.1144    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807    0.9413   -0.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1715    2.2310   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599    2.3640   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407    2.1006    0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459    2.2544    1.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9387    1.3127    0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870   -0.1129    0.6253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435   -1.1048   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8045   -1.0310    0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4450   -2.0972    0.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8841   -2.0392    0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5215   -0.9991    0.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1961   -2.2849    0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5888   -0.6135    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6177   -1.5530   -1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6175   -2.7262   -0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0389   -2.5468    1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6082   -0.1218    0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2519   -0.3025   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3028   -1.7878   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7402   -1.6219    1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8783   -0.3602    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2486    0.6487    1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    0.2700   -1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9793    1.1314   -1.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344    2.7769   -1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215    2.9185    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8222    1.6059   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5920    3.3826   -0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2560    1.2126    1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2123    2.9515    1.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3184    1.9845    2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4297    3.2969    1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443    1.5355   -0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0073    1.4599    0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8102   -0.2921    1.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5080   -0.2414    0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1544   -0.8743   -1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9384   -2.1112   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3980   -0.1579   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9127   -3.0174    0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3790   -2.9219    1.0243 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
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
M  END

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         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
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                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0060482
HETATM    1  C1  UNL     1       6.442  -1.607  -0.274  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.030  -2.054   0.010  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.174  -0.766   0.089  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.771  -1.147   0.367  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.904   0.114   0.490  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.881   0.941  -0.733  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.172   2.231  -0.754  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.260   2.364  -0.453  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.641   2.101   0.943  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.146   2.254   1.177  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.939   1.313   0.331  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.587  -0.113   0.625  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.343  -1.105  -0.186  1.00  0.00           C  
HETATM   14  C14 UNL     1      -4.804  -1.031   0.003  1.00  0.00           C  
HETATM   15  C15 UNL     1      -5.445  -2.097   0.460  1.00  0.00           C  
HETATM   16  C16 UNL     1      -6.884  -2.039   0.651  1.00  0.00           C  
HETATM   17  O1  UNL     1      -7.522  -0.999   0.391  1.00  0.00           O  
HETATM   18  H1  UNL     1       7.196  -2.285   0.210  1.00  0.00           H  
HETATM   19  H2  UNL     1       6.589  -0.613   0.152  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.618  -1.553  -1.382  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.617  -2.726  -0.758  1.00  0.00           H  
HETATM   22  H5  UNL     1       5.039  -2.547   1.011  1.00  0.00           H  
HETATM   23  H6  UNL     1       4.608  -0.122   0.877  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.252  -0.302  -0.925  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.303  -1.788  -0.377  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.740  -1.622   1.386  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.878  -0.360   0.631  1.00  0.00           H  
HETATM   28  H11 UNL     1       2.249   0.649   1.382  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.556   0.270  -1.593  1.00  0.00           H  
HETATM   30  H13 UNL     1       2.979   1.131  -1.029  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.434   2.777  -1.738  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.722   2.918   0.004  1.00  0.00           H  
HETATM   33  H16 UNL     1      -0.822   1.606  -1.109  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.592   3.383  -0.812  1.00  0.00           H  
HETATM   35  H18 UNL     1      -0.256   1.213   1.368  1.00  0.00           H  
HETATM   36  H19 UNL     1      -0.212   2.951   1.587  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.318   1.985   2.238  1.00  0.00           H  
HETATM   38  H21 UNL     1      -2.430   3.297   1.038  1.00  0.00           H  
HETATM   39  H22 UNL     1      -2.844   1.536  -0.758  1.00  0.00           H  
HETATM   40  H23 UNL     1      -4.007   1.460   0.580  1.00  0.00           H  
HETATM   41  H24 UNL     1      -2.810  -0.292   1.715  1.00  0.00           H  
HETATM   42  H25 UNL     1      -1.508  -0.241   0.425  1.00  0.00           H  
HETATM   43  H26 UNL     1      -3.154  -0.874  -1.275  1.00  0.00           H  
HETATM   44  H27 UNL     1      -2.938  -2.111  -0.025  1.00  0.00           H  
HETATM   45  H28 UNL     1      -5.398  -0.158  -0.207  1.00  0.00           H  
HETATM   46  H29 UNL     1      -4.913  -3.017   0.695  1.00  0.00           H  
HETATM   47  H30 UNL     1      -7.379  -2.922   1.024  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   37   38
CONECT   11   12   39   40
CONECT   12   13   41   42
CONECT   13   14   43   44
CONECT   14   15   15   45
CONECT   15   16   46
CONECT   16   17   17   47
END

HMDB0060482
     RDKit          3D
Hexadecenal
 47 46  0  0  0  0  0  0  0  0999 V2000
    6.4416   -1.6066   -0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300   -2.0544    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1745   -0.7661    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711   -1.1473    0.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9040    0.1144    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807    0.9413   -0.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1715    2.2310   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599    2.3640   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407    2.1006    0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459    2.2544    1.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9387    1.3127    0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870   -0.1129    0.6253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435   -1.1048   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8045   -1.0310    0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4450   -2.0972    0.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8841   -2.0392    0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5215   -0.9991    0.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1961   -2.2849    0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5888   -0.6135    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6177   -1.5530   -1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6175   -2.7262   -0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0389   -2.5468    1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6082   -0.1218    0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2519   -0.3025   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3028   -1.7878   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7402   -1.6219    1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8783   -0.3602    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2486    0.6487    1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    0.2700   -1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9793    1.1314   -1.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344    2.7769   -1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215    2.9185    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8222    1.6059   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5920    3.3826   -0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2560    1.2126    1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2123    2.9515    1.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3184    1.9845    2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4297    3.2969    1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443    1.5355   -0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0073    1.4599    0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8102   -0.2921    1.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5080   -0.2414    0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1544   -0.8743   -1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9384   -2.1112   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3980   -0.1579   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9127   -3.0174    0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3790   -2.9219    1.0243 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
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E)-Hexadecenal	ChEBI
2-trans-Hexadecenal	ChEBI
(2E)-Hexadec-2-enal	HMDB
2-(D5)-Hexadecenal	HMDB
2-(15,15,16,16,16-D5)-Hexadecenal	HMDB
2-Hexadecenal	MeSH

Chemical Formula

C₁₆H₃₀O

Average Molecular Weight

238.4088

Monoisotopic Molecular Weight

238.229665582

IUPAC Name

(2E)-hexadec-2-enal

Traditional Name

2-trans-hexadecenal

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCC\C=C\C=O

InChI Identifier

InChI=1S/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h14-16H,2-13H2,1H3/b15-14+

InChI Key

KLJFYXOVGVXZKT-CCEZHUSRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty aldehydes. These are long chain aldehydes with a chain of at least 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty aldehydes

Direct Parent

Fatty aldehydes

Alternative Parents

Substituents

Fatty aldehyde
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

enal (CHEBI:17585 )
trans-2,3-unsaturated fatty aldehyde (CHEBI:17585 )
hexadecenal (CHEBI:17585 )
Fatty aldehydes (C06123 )
Fatty aldehydes (LMFA06000089 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.6e-05 g/L	ALOGPS
logP	6.97	ALOGPS
logP	6.1	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	77.25 m³·mol⁻¹	ChemAxon
Polarizability	32.52 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]+	164.466	31661259
DarkChem	[M-H]-	163.788	31661259
DeepCCS	[M+H]+	167.732	30932474
DeepCCS	[M-H]-	163.712	30932474
DeepCCS	[M-2H]-	201.3	30932474
DeepCCS	[M+Na]+	176.963	30932474
AllCCS	[M+H]+	166.4	32859911
AllCCS	[M+H-H2O]+	163.1	32859911
AllCCS	[M+NH4]+	169.5	32859911
AllCCS	[M+Na]+	170.4	32859911
AllCCS	[M-H]-	168.4	32859911
AllCCS	[M+Na-2H]-	169.7	32859911
AllCCS	[M+HCOO]-	171.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	10.32 minutes	32390414
Predicted by Siyang on May 30, 2022	25.2853 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.36 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3075.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	804.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	306.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	515.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	559.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1102.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1054.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	130.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2310.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	669.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2035.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	881.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	600.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	879.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	735.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hexadecenal	CCCCCCCCCCCCC\C=C\C=O	2258.8	Standard polar	33892256
Hexadecenal	CCCCCCCCCCCCC\C=C\C=O	1842.8	Standard non polar	33892256
Hexadecenal	CCCCCCCCCCCCC\C=C\C=O	1875.2	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 - Hexadecenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-07im-9700000000-2c13204d06f7eb271721	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexadecenal 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 - Hexadecenal 10V, Positive-QTOF	splash10-000i-0190000000-fd969cd7262af491d84d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexadecenal 20V, Positive-QTOF	splash10-059i-7970000000-0d33189fbc54287fc6f1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexadecenal 40V, Positive-QTOF	splash10-0a4l-9800000000-1d27dc6f4cbaa7f9fe16	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexadecenal 10V, Negative-QTOF	splash10-000i-0090000000-108c8ba671de7d698e9c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexadecenal 20V, Negative-QTOF	splash10-052r-0090000000-9e187c8e1c3bcb512ec4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexadecenal 40V, Negative-QTOF	splash10-052f-8970000000-e2bbec2b313129e521a6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexadecenal 10V, Positive-QTOF	splash10-05uj-9520000000-c5fcf67323e03a2ca0b0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexadecenal 20V, Positive-QTOF	splash10-0a5a-9200000000-911dd1c303ce58c3deb6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexadecenal 40V, Positive-QTOF	splash10-0a4m-9000000000-c2477e88688a37257f1d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexadecenal 10V, Negative-QTOF	splash10-000i-0090000000-755d6a2b1ffd2f706c0b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexadecenal 20V, Negative-QTOF	splash10-000i-0090000000-a540059de9ca8fde48be	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexadecenal 40V, Negative-QTOF	splash10-00y0-9720000000-1d971990b816f176c9af	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C06123

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280541

PDB ID

Not Available

ChEBI ID

17585

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
Kitamura T, Naganuma T, Abe K, Nakahara K, Ohno Y, Kihara A: Substrate specificity, plasma membrane localization, and lipid modification of the aldehyde dehydrogenase ALDH3B1. Biochim Biophys Acta. 2013 Aug;1831(8):1395-401. doi: 10.1016/j.bbalip.2013.05.007. Epub 2013 May 27. [PubMed:23721920 ]
Renault TT, Chipuk JE: Inter-organellar communication with mitochondria regulates both the intrinsic and extrinsic pathways of apoptosis. Commun Integr Biol. 2013 Mar 1;6(2):e22872. doi: 10.4161/cib.22872. [PubMed:23750296 ]
Luth A, Neuber C, Kleuser B: Novel methods for the quantification of (2E)-hexadecenal by liquid chromatography with detection by either ESI QTOF tandem mass spectrometry or fluorescence measurement. Anal Chim Acta. 2012 Apr 13;722:70-9. doi: 10.1016/j.aca.2012.01.063. Epub 2012 Feb 13. [PubMed:22444536 ]
Upadhyaya P, Kumar A, Byun HS, Bittman R, Saba JD, Hecht SS: The sphingolipid degradation product trans-2-hexadecenal forms adducts with DNA. Biochem Biophys Res Commun. 2012 Jul 20;424(1):18-21. doi: 10.1016/j.bbrc.2012.06.012. Epub 2012 Jun 19. [PubMed:22727907 ]
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. Sphingosine-1-phosphate lyase 1

General function:: Involved in carboxy-lyase activity
Specific function:: Cleaves phosphorylated sphingoid bases (PSBs), such as sphingosine-1-phosphate, into fatty aldehydes and phosphoethanolamine. Elevates stress-induced ceramide production and apoptosis.
Gene Name:: SGPL1
Uniprot ID:: O95470
Molecular weight:: 63523.265

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Sphingosine 1-phosphate → O-Phosphoethanolamine + Hexadecenal	details

Showing metabocard for Hexadecenal (HMDB0060482)

MOL for HMDB0060482 (Hexadecenal)

3D MOL for HMDB0060482 (Hexadecenal)

3D SDF for HMDB0060482 (Hexadecenal)

3D-SDF for HMDB0060482 (Hexadecenal)

PDB for HMDB0060482 (Hexadecenal)

3D PDB for HMDB0060482 (Hexadecenal)

SMILES for HMDB0060482 (Hexadecenal)

INCHI for HMDB0060482 (Hexadecenal)

Structure for HMDB0060482 (Hexadecenal)

3D Structure for HMDB0060482 (Hexadecenal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions