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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:39:13 UTC

Update Date

2022-03-07 02:54:35 UTC

HMDB ID

HMDB0035643

Secondary Accession Numbers

HMDB35643

Metabolite Identification

Common Name

beta-Sinensal

Description

beta-Sinensal, also known as FEMA 3141, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. beta-Sinensal is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). beta-Sinensal can be found in citrus, lemon, and sweet orange, which makes beta-sinensal a potential biomarker for the consumption of these food products. beta-Sinensal is used as a food additive (EAFUS: Everything Added to Food in the United States) and also 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

HMDB0035643
     RDKit          3D
beta-Sinensal
 38 37  0  0  0  0  0  0  0  0999 V2000
   -4.2670   -2.4810    2.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9282   -1.5133    1.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2122   -0.3518    1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8786    0.6153    0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7496   -0.2807    1.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1709    0.9969    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6945    0.9356    0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886    0.9676   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3644    1.0688   -1.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325    0.9056    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2977   -0.2862   -0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7434   -0.2681   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6580   -0.1989   -1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1442   -0.1418   -2.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0760   -0.1813   -0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4165   -0.2333    0.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2001   -2.4278    2.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7932   -3.3425    2.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0111   -1.5868    1.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9512    0.5552    0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3387    1.4819    0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3189   -1.1746    0.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5190   -0.3634    2.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3782    1.0145   -0.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6148    1.8882    1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375    0.8626    1.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8740    2.0216   -1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205    0.1778   -1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4796    0.9899   -2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.8076   -0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075    0.8570    1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0836   -0.3935   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8770   -1.2000    0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0436   -0.3129    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307    0.1156   -3.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7619   -1.0886   -2.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4185    0.6909   -2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8201   -0.1262   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  3
  3  5  1  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
  5 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
    3.9150   -1.7006    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.8468   -0.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326   -0.9258   -0.6179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8913   -0.4782    0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558   -0.5018   -0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4789    0.1146    1.5713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4421    1.2193   -0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867    0.6615    1.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958    0.9740    0.7454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9733    1.4589   -1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095   -0.0731   -1.4967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0817   -2.1797   -1.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4676    0.6735    0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427    0.5133   -0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5972   -0.8946   -0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7216   -2.9086   -0.3879 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  2 13  2  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  1  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>
HMDB0035643

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-5-13(2)8-6-9-14(3)10-7-11-15(4)12-16/h5,9,11-12H,1-2,6-8,10H2,3-4H3/b14-9+,15-11+

> <INCHI_KEY>
NOPLRNXKHZRXHT-YFVJMOTDSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.34

> <EXACT_MASS>
218.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.94294032396855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,6E)-2,6-dimethyl-10-methylidenedodeca-2,6,11-trienal

> <ALOGPS_LOGP>
4.81

> <JCHEM_LOGP>
4.229890758333334

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.173217367722673

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
72.9734

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.92e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-sinensal

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035643
     RDKit          3D
beta-Sinensal
 38 37  0  0  0  0  0  0  0  0999 V2000
   -4.2670   -2.4810    2.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9282   -1.5133    1.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2122   -0.3518    1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8786    0.6153    0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7496   -0.2807    1.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1709    0.9969    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6945    0.9356    0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886    0.9676   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3644    1.0688   -1.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325    0.9056    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2977   -0.2862   -0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7434   -0.2681   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6580   -0.1989   -1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1442   -0.1418   -2.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0760   -0.1813   -0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4165   -0.2333    0.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2001   -2.4278    2.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7932   -3.3425    2.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0111   -1.5868    1.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9512    0.5552    0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3387    1.4819    0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3189   -1.1746    0.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5190   -0.3634    2.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3782    1.0145   -0.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6148    1.8882    1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375    0.8626    1.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8740    2.0216   -1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205    0.1778   -1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4796    0.9899   -2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.8076   -0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075    0.8570    1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0836   -0.3935   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8770   -1.2000    0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0436   -0.3129    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307    0.1156   -3.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7619   -1.0886   -2.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4185    0.6909   -2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8201   -0.1262   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  3
  3  5  1  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
  5 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       3.915  -1.701   0.004  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.585   1.847  -0.480  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.133  -0.926  -0.618  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.891  -0.478   0.691  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.956  -0.502  -0.528  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.479   0.115   1.571  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.442   1.219  -0.996  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.887   0.662   1.510  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.596   0.974   0.745  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.973   1.459  -1.042  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.910  -0.073  -1.497  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.082  -2.180  -1.162  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.468   0.674   0.159  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.143   0.513  -0.254  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.597  -0.895  -0.719  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.722  -2.909  -0.388  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    HMDB0035643
HETATM    1  C1  UNL     1      -4.267  -2.481   2.144  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.928  -1.513   1.556  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.212  -0.352   1.059  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.879   0.615   0.471  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.750  -0.281   1.225  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.171   0.997   0.652  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.695   0.936   0.887  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.189   0.968  -0.106  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.364   1.069  -1.489  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.633   0.906   0.159  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.298  -0.286  -0.492  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.743  -0.268  -0.172  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.658  -0.199  -1.131  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.144  -0.142  -2.522  1.00  0.00           C  
HETATM   15  C15 UNL     1       6.076  -0.181  -0.817  1.00  0.00           C  
HETATM   16  O1  UNL     1       6.416  -0.233   0.387  1.00  0.00           O  
HETATM   17  H1  UNL     1      -3.200  -2.428   2.264  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.793  -3.343   2.513  1.00  0.00           H  
HETATM   19  H3  UNL     1      -6.011  -1.587   1.444  1.00  0.00           H  
HETATM   20  H4  UNL     1      -5.951   0.555   0.353  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.339   1.482   0.100  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.319  -1.175   0.732  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.519  -0.363   2.309  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.378   1.014  -0.437  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.615   1.888   1.109  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.337   0.863   1.907  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.874   2.022  -1.669  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.021   0.178  -1.712  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.480   0.990  -2.194  1.00  0.00           H  
HETATM   30  H14 UNL     1       2.143   1.808  -0.213  1.00  0.00           H  
HETATM   31  H15 UNL     1       1.808   0.857   1.244  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.084  -0.394  -1.552  1.00  0.00           H  
HETATM   33  H17 UNL     1       1.877  -1.200   0.014  1.00  0.00           H  
HETATM   34  H18 UNL     1       4.044  -0.313   0.868  1.00  0.00           H  
HETATM   35  H19 UNL     1       5.031   0.116  -3.173  1.00  0.00           H  
HETATM   36  H20 UNL     1       3.762  -1.089  -2.892  1.00  0.00           H  
HETATM   37  H21 UNL     1       3.418   0.691  -2.649  1.00  0.00           H  
HETATM   38  H22 UNL     1       6.820  -0.126  -1.573  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   19
CONECT    3    4    4    5
CONECT    4   20   21
CONECT    5    6   22   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

HMDB0035643
     RDKit          3D
beta-Sinensal
 38 37  0  0  0  0  0  0  0  0999 V2000
   -4.2670   -2.4810    2.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9282   -1.5133    1.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2122   -0.3518    1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8786    0.6153    0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7496   -0.2807    1.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1709    0.9969    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6945    0.9356    0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886    0.9676   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3644    1.0688   -1.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325    0.9056    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2977   -0.2862   -0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7434   -0.2681   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6580   -0.1989   -1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1442   -0.1418   -2.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0760   -0.1813   -0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4165   -0.2333    0.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2001   -2.4278    2.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7932   -3.3425    2.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0111   -1.5868    1.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9512    0.5552    0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3387    1.4819    0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3189   -1.1746    0.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5190   -0.3634    2.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3782    1.0145   -0.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6148    1.8882    1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375    0.8626    1.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8740    2.0216   -1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205    0.1778   -1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4796    0.9899   -2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.8076   -0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075    0.8570    1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0836   -0.3935   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8770   -1.2000    0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0436   -0.3129    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307    0.1156   -3.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7619   -1.0886   -2.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4185    0.6909   -2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8201   -0.1262   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  3
  3  5  1  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
  5 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
2,6-Dimethyl-10-methylene-2,6,11-dodecatrienal	Kegg
b-Sinensal	Generator
Β-sinensal	Generator
(2E,6E)-2,6-Dimethyl-10-methylene-2,6,11-dodecatrienal	HMDB
(e,e)-2,6-Dimethyl-10-methylene-2,6,11-dodecatrienal	HMDB
Tianchengquan	HMDB
trans,trans-2,6-Dimethyl-10-methylene-2,6,11-dodecatrienal	HMDB
trans-Β-sinensal	HMDB
FEMA 3141	HMDB
beta-Sinensal	HMDB

Chemical Formula

C₁₅H₂₂O

Average Molecular Weight

218.34

Monoisotopic Molecular Weight

218.167065328

IUPAC Name

(2E,6E)-2,6-dimethyl-10-methylidenedodeca-2,6,11-trienal

Traditional Name

β-sinensal

CAS Registry Number

3779-62-2

SMILES

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

InChI Identifier

InChI=1S/C15H22O/c1-5-13(2)8-6-9-14(3)10-7-11-15(4)12-16/h5,9,11-12H,1-2,6-8,10H2,3-4H3/b14-9+,15-11+

InChI Key

NOPLRNXKHZRXHT-YFVJMOTDSA-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:10444 )
Sesquiterpenoids (C15) (C09730 )

Ontology

Physiological effect

Organoleptic effect

Odor

sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0035643)
Membrane (HMDB: HMDB0035643)

Not Available

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	0.49 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.624 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0069 g/L	ALOGPS
logP	4.81	ALOGPS
logP	4.23	ChemAxon
logS	-4.5	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	8	ChemAxon
Refractivity	72.97 m³·mol⁻¹	ChemAxon
Polarizability	26.94 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
DeepCCS	[M+H]+	164.113	30932474
DeepCCS	[M-H]-	161.755	30932474
DeepCCS	[M-2H]-	194.641	30932474
DeepCCS	[M+Na]+	170.206	30932474
AllCCS	[M+H]+	158.0	32859911
AllCCS	[M+H-H2O]+	154.4	32859911
AllCCS	[M+NH4]+	161.4	32859911
AllCCS	[M+Na]+	162.4	32859911
AllCCS	[M-H]-	155.1	32859911
AllCCS	[M+Na-2H]-	156.0	32859911
AllCCS	[M+HCOO]-	157.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Sinensal	C\C(CC\C=C(/C)C=O)=C/CCC(=C)C=C	2238.0	Standard polar	33892256
beta-Sinensal	C\C(CC\C=C(/C)C=O)=C/CCC(=C)C=C	1643.2	Standard non polar	33892256
beta-Sinensal	C\C(CC\C=C(/C)C=O)=C/CCC(=C)C=C	1688.4	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 - beta-Sinensal GC-MS (Non-derivatized) - 70eV, Positive	splash10-0v4i-9720000000-3063da13936103208041	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-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 - beta-Sinensal 10V, Positive-QTOF	splash10-014i-3490000000-33f122d22f63dd620d69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sinensal 20V, Positive-QTOF	splash10-0159-9820000000-edcb7278d53f79d1de69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sinensal 40V, Positive-QTOF	splash10-0udi-9100000000-0facb41da0d98b774dec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sinensal 10V, Negative-QTOF	splash10-014i-0090000000-eb12bc38ac78dda6e698	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sinensal 20V, Negative-QTOF	splash10-014i-1290000000-53d6fb8a58a5ba180ff7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sinensal 40V, Negative-QTOF	splash10-0pbi-9820000000-9f1482668f17c500dab4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sinensal 10V, Negative-QTOF	splash10-014i-0890000000-5cf22b4f248740f722c6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sinensal 20V, Negative-QTOF	splash10-01bi-2930000000-e0f5a8034d4108fef165	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sinensal 40V, Negative-QTOF	splash10-07vi-3900000000-fff8b9311f58d26b3f6a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sinensal 10V, Positive-QTOF	splash10-030r-6910000000-ad60edf8298d563cc50e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sinensal 20V, Positive-QTOF	splash10-052f-9400000000-2e70007be9ae3daf67ae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sinensal 40V, Positive-QTOF	splash10-0006-9200000000-d9203176cd55062f58ff	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

5281535

PDB ID

Not Available

ChEBI ID

10444

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1050371

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 beta-Sinensal (HMDB0035643)

MOL for HMDB0035643 (beta-Sinensal)

3D MOL for HMDB0035643 (beta-Sinensal)

3D SDF for HMDB0035643 (beta-Sinensal)

3D-SDF for HMDB0035643 (beta-Sinensal)

PDB for HMDB0035643 (beta-Sinensal)

3D PDB for HMDB0035643 (beta-Sinensal)

SMILES for HMDB0035643 (beta-Sinensal)

INCHI for HMDB0035643 (beta-Sinensal)

Structure for HMDB0035643 (beta-Sinensal)

3D Structure for HMDB0035643 (beta-Sinensal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra