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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:29:41 UTC

Update Date

2022-03-07 02:55:40 UTC

HMDB ID

HMDB0038215

Secondary Accession Numbers

HMDB0013693
HMDB13693
HMDB38215

Metabolite Identification

Common Name

alpha-Sinensal

Description

alpha-Sinensal, also known as α-sinensal or (2E,6E,9E)-2,6,10-trimethyl-2,6,9,11-dodecatetraenal, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. alpha-Sinensal is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). alpha-Sinensal is a constituent of orange oil. It plays an important role in the overall flavour and aroma of orange fruit.

Structure

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

HMDB0038215
     RDKit          3D
alpha-Sinensal
 38 37  0  0  0  0  0  0  0  0999 V2000
   -5.4155    1.8482    1.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1204    1.7177    1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007    0.9334    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3061    0.1928   -0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1677    0.8558   -0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159    0.0687   -1.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6635   -1.0011   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508   -1.1327   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2759   -0.1030   -1.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3718   -2.2847   -0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4734   -1.8930    0.7503 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5046   -1.0907    0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8282    0.1481    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304    0.7723    1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8497    0.8725   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4705    0.3735   -1.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7601    2.4666    2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1723    1.4087    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4526    2.2386    1.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0451   -0.9054   -0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0770    0.5282   -1.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3711    0.2428   -0.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899    1.4103    0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9802    0.7904   -1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2861   -0.3999   -1.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1307   -1.7567    0.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4342    0.8265   -1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -0.4742   -1.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7206    0.0751   -2.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7904   -2.8507   -1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6367   -2.9500    0.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9856   -2.8571    1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962   -1.3953    1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0503   -1.5103   -0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870    1.0656    1.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417    1.7382    1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1809    0.1474    2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1085    1.8834   -0.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
M  END


  Mrv1652304022019523D          

 16 15  0  0  0  0            999 V2000
   -5.4892    1.4405    1.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8002   -0.7397    0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -1.6480   -0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -1.2756    1.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6610    1.6625    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1019   -0.0163   -1.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2059    0.2618    0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9880    0.9912   -1.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6847    0.3506   -1.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7046    0.1023   -1.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105    0.7218    0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9553    0.5173    0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7958    0.6638   -0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2763   -0.3656   -1.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5884    0.0194    0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2971    1.6027    0.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  2 13  1  0  0  0  0
  3 14  1  0  0  0  0
  4 15  1  0  0  0  0
  5 13  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 13  2  0  0  0  0
  9 14  2  0  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 12 15  1  0  0  0  0
 12 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038215

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(CC\C=C(/C)C=O)=C/C\C=C(/C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-5-13(2)8-6-9-14(3)10-7-11-15(4)12-16/h5,8-9,11-12H,1,6-7,10H2,2-4H3/b13-8+,14-9+,15-11+

> <INCHI_KEY>
PFSTYGCNVAVZBK-JQGMZEBDSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.34

> <EXACT_MASS>
218.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.108021386460486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,6E,9E)-2,6,10-trimethyldodeca-2,6,9,11-tetraenal

> <ALOGPS_LOGP>
5.06

> <JCHEM_LOGP>
4.171957088

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.173218683361245

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
74.04589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-sinensal

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038215
     RDKit          3D
alpha-Sinensal
 38 37  0  0  0  0  0  0  0  0999 V2000
   -5.4155    1.8482    1.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1204    1.7177    1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007    0.9334    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3061    0.1928   -0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1677    0.8558   -0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159    0.0687   -1.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6635   -1.0011   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508   -1.1327   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2759   -0.1030   -1.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3718   -2.2847   -0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4734   -1.8930    0.7503 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5046   -1.0907    0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8282    0.1481    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304    0.7723    1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8497    0.8725   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4705    0.3735   -1.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7601    2.4666    2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1723    1.4087    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4526    2.2386    1.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0451   -0.9054   -0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0770    0.5282   -1.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3711    0.2428   -0.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899    1.4103    0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9802    0.7904   -1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2861   -0.3999   -1.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1307   -1.7567    0.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4342    0.8265   -1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -0.4742   -1.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7206    0.0751   -2.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7904   -2.8507   -1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6367   -2.9500    0.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9856   -2.8571    1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962   -1.3953    1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0503   -1.5103   -0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870    1.0656    1.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417    1.7382    1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1809    0.1474    2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1085    1.8834   -0.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
M  END

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0      -5.489   1.440   1.519  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.800  -0.740   0.390  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.042  -1.648  -0.478  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.247  -1.276   1.544  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.661   1.663   0.524  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.102  -0.016  -1.738  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.206   0.262   0.312  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.988   0.991  -1.102  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.685   0.351  -1.681  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.705   0.102  -1.113  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.611   0.722   0.342  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.955   0.517   0.915  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.796   0.664  -0.095  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.276  -0.366  -1.118  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.588   0.019   0.913  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.297   1.603   0.397  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    1   13                                                       
CONECT    6    8    9                                                       
CONECT    7   10   11                                                       
CONECT    8    6   13                                                       
CONECT    9    6   14                                                       
CONECT   10    7   14                                                       
CONECT   11    7   15                                                       
CONECT   12   15   16                                                       
CONECT   13    2    5    8                                                  
CONECT   14    3    9   10                                                  
CONECT   15    4   11   12                                                  
CONECT   16   12                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0038215
HETATM    1  C1  UNL     1      -5.416   1.848   1.269  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.120   1.718   1.100  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.501   0.933   0.047  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.306   0.193  -0.950  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.168   0.856  -0.051  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.516   0.069  -1.108  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.664  -1.001  -0.583  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.651  -1.133  -0.800  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.276  -0.103  -1.642  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.372  -2.285  -0.198  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.473  -1.893   0.750  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.505  -1.091   0.054  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.828   0.148   0.392  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.130   0.772   1.522  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.850   0.873  -0.337  1.00  0.00           C  
HETATM   16  O1  UNL     1       5.471   0.373  -1.311  1.00  0.00           O  
HETATM   17  H1  UNL     1      -5.760   2.467   2.100  1.00  0.00           H  
HETATM   18  H2  UNL     1      -6.172   1.409   0.672  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.453   2.239   1.806  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.045  -0.905  -0.887  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.077   0.528  -1.996  1.00  0.00           H  
HETATM   22  H6  UNL     1      -5.371   0.243  -0.720  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.590   1.410   0.698  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.980   0.790  -1.757  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.286  -0.400  -1.753  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.131  -1.757   0.037  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.434   0.827  -1.072  1.00  0.00           H  
HETATM   28  H12 UNL     1       2.267  -0.474  -1.969  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.721   0.075  -2.592  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.790  -2.851  -1.084  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.637  -2.950   0.327  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.986  -2.857   1.046  1.00  0.00           H  
HETATM   33  H17 UNL     1       2.096  -1.395   1.658  1.00  0.00           H  
HETATM   34  H18 UNL     1       4.050  -1.510  -0.784  1.00  0.00           H  
HETATM   35  H19 UNL     1       2.087   1.066   1.266  1.00  0.00           H  
HETATM   36  H20 UNL     1       3.642   1.738   1.791  1.00  0.00           H  
HETATM   37  H21 UNL     1       3.181   0.147   2.438  1.00  0.00           H  
HETATM   38  H22 UNL     1       5.109   1.883  -0.055  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   19
CONECT    3    4    5    5
CONECT    4   20   21   22
CONECT    5    6   23
CONECT    6    7   24   25
CONECT    7    8    8   26
CONECT    8    9   10
CONECT    9   27   28   29
CONECT   10   11   30   31
CONECT   11   12   32   33
CONECT   12   13   13   34
CONECT   13   14   15
CONECT   14   35   36   37
CONECT   15   16   16   38
END

HMDB0038215
     RDKit          3D
alpha-Sinensal
 38 37  0  0  0  0  0  0  0  0999 V2000
   -5.4155    1.8482    1.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1204    1.7177    1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007    0.9334    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3061    0.1928   -0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1677    0.8558   -0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159    0.0687   -1.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6635   -1.0011   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508   -1.1327   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2759   -0.1030   -1.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3718   -2.2847   -0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4734   -1.8930    0.7503 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5046   -1.0907    0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8282    0.1481    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304    0.7723    1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8497    0.8725   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4705    0.3735   -1.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7601    2.4666    2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1723    1.4087    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4526    2.2386    1.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0451   -0.9054   -0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0770    0.5282   -1.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3711    0.2428   -0.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899    1.4103    0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9802    0.7904   -1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2861   -0.3999   -1.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1307   -1.7567    0.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4342    0.8265   -1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -0.4742   -1.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7206    0.0751   -2.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7904   -2.8507   -1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6367   -2.9500    0.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9856   -2.8571    1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962   -1.3953    1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0503   -1.5103   -0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870    1.0656    1.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417    1.7382    1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1809    0.1474    2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1085    1.8834   -0.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Sinensal	Generator
Α-sinensal	Generator
(2E,6E,9E)-2,6,10-Trimethyl-2,6,9,11-dodecatetraenal	HMDB
(e,e,e)-2,6,10-Trimethyldodeca-2,6,9,11-tetraen-1-al	HMDB
2,6,10-Trimethyl-(2E,6E,9E)-2,6,9,11-dodecatetraenal	HMDB
2,6,10-Trimethyl-(e,e,e)-2,6,9,11-dodecatetraenal	HMDB
2,6,10-Trimethyl-2,6,9,11-dodecatetraenal	HMDB
alpha-Sinensal	HMDB

Chemical Formula

C₁₅H₂₂O

Average Molecular Weight

218.34

Monoisotopic Molecular Weight

218.167065328

IUPAC Name

(2E,6E,9E)-2,6,10-trimethyldodeca-2,6,9,11-tetraenal

Traditional Name

α-sinensal

CAS Registry Number

17909-77-2

SMILES

C\C(CC\C=C(/C)C=O)=C/C\C=C(/C)C=C

InChI Identifier

InChI=1S/C15H22O/c1-5-13(2)8-6-9-14(3)10-7-11-15(4)12-16/h5,8-9,11-12H,1,6-7,10H2,2-4H3/b13-8+,14-9+,15-11+

InChI Key

PFSTYGCNVAVZBK-JQGMZEBDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Medium-chain 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

sesquiterpenoid (CHEBI:10332 )
Sesquiterpenoids (C15) (C09729 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0038215)
Membrane (HMDB: HMDB0038215)

Source

Exogenous

Exogenous (HMDB: HMDB0038215)

Food

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Citrus (FooDB: FOOD00859)

Endogenous

Endogenous (HMDB: HMDB0038215)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	180.00 °C. @ 1.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.57 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.790 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	5.06	ALOGPS
logP	4.17	ChemAxon
logS	-4.1	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	7	ChemAxon
Refractivity	74.05 m³·mol⁻¹	ChemAxon
Polarizability	27.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	156.512	31661259
DarkChem	[M-H]-	155.41	31661259
DeepCCS	[M+H]+	164.361	30932474
DeepCCS	[M-H]-	162.003	30932474
DeepCCS	[M-2H]-	194.889	30932474
DeepCCS	[M+Na]+	170.454	30932474
AllCCS	[M+H]+	157.1	32859911
AllCCS	[M+H-H2O]+	153.5	32859911
AllCCS	[M+NH4]+	160.5	32859911
AllCCS	[M+Na]+	161.5	32859911
AllCCS	[M-H]-	155.0	32859911
AllCCS	[M+Na-2H]-	155.8	32859911
AllCCS	[M+HCOO]-	156.9	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.	8.52 minutes	32390414
Predicted by Siyang on May 30, 2022	18.9113 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.3 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2568.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	577.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	233.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	378.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	119.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	685.8 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	778.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1656.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	605.0 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	1191.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	606.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	410.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	345.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	596.8 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Sinensal	C\C(CC\C=C(/C)C=O)=C/C\C=C(/C)C=C	2303.4	Standard polar	33892256
alpha-Sinensal	C\C(CC\C=C(/C)C=O)=C/C\C=C(/C)C=C	1689.1	Standard non polar	33892256
alpha-Sinensal	C\C(CC\C=C(/C)C=O)=C/C\C=C(/C)C=C	1742.7	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 - alpha-Sinensal GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udl-9630000000-44fc0ab88fd372513051	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Sinensal GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Sinensal 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 - alpha-Sinensal 10V, Positive-QTOF	splash10-014i-3590000000-5eff757743c8c1ad43ca	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Sinensal 20V, Positive-QTOF	splash10-0gc0-9720000000-4c5c846303f21f30b570	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Sinensal 40V, Positive-QTOF	splash10-0udi-9100000000-a33955da910d70157f2e	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Sinensal 10V, Negative-QTOF	splash10-014i-0090000000-70cf9ab627666ef51adf	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Sinensal 20V, Negative-QTOF	splash10-014i-1290000000-ef81e35e2dea73f32699	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Sinensal 40V, Negative-QTOF	splash10-0pbi-9820000000-f920da939dd7d7f44d51	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Sinensal 10V, Positive-QTOF	splash10-02u0-5910000000-948d6ab8a9b9a963d81a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Sinensal 20V, Positive-QTOF	splash10-052f-9500000000-2527dc92fcb7c9f17055	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Sinensal 40V, Positive-QTOF	splash10-054o-9200000000-107c1c1b69f678dd2e4f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Sinensal 10V, Negative-QTOF	splash10-014i-0890000000-3a3db1e2c2c2b7999336	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Sinensal 20V, Negative-QTOF	splash10-01bi-2930000000-b1d4d2bb9e84aac665fa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Sinensal 40V, Negative-QTOF	splash10-082i-3900000000-6d208aa38d4b4c1be98d	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281534

PDB ID

Not Available

ChEBI ID

10332

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1009441

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for alpha-Sinensal (HMDB0038215)

MOL for HMDB0038215 (alpha-Sinensal)

3D MOL for HMDB0038215 (alpha-Sinensal)

3D SDF for HMDB0038215 (alpha-Sinensal)

3D-SDF for HMDB0038215 (alpha-Sinensal)

PDB for HMDB0038215 (alpha-Sinensal)

3D PDB for HMDB0038215 (alpha-Sinensal)

SMILES for HMDB0038215 (alpha-Sinensal)

INCHI for HMDB0038215 (alpha-Sinensal)

Structure for HMDB0038215 (alpha-Sinensal)

3D Structure for HMDB0038215 (alpha-Sinensal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra