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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:52:22 UTC

Update Date

2022-03-07 02:55:49 UTC

HMDB ID

HMDB0038548

Secondary Accession Numbers

HMDB38548

Metabolite Identification

Common Name

Glandulone B

Description

Glandulone B belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on Glandulone B.

Structure

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

HMDB0038548
     RDKit          3D
Glandulone B
 34 34  0  0  0  0  0  0  0  0999 V2000
   -5.6293    0.1226    1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2046   -0.0018    0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3913   -0.8704    1.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -0.9958    0.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252   -1.8605    1.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4352   -0.1821   -0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0611   -0.2585   -0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4116    0.6789   -1.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7994   -1.0915   -0.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2322   -1.2388   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0603   -0.9366    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9420    0.0307    0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1420    0.8834   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7393    0.2898    1.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5773    1.2055    1.8010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2878    0.7042   -0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6720    0.8330   -0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4428    1.6780   -0.9635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7986    1.0440    1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2876    0.0946    0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8908   -0.7500    1.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7890   -1.4933    1.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0033    1.6922   -1.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4879    0.8328   -1.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684    0.3767   -2.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503   -1.7982    0.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152   -0.7456   -1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3147   -2.3532   -0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450   -1.5427    1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030    1.7071   -0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381    1.4007   -0.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2360    0.3126   -1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5553   -0.3533    2.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230    1.3264   -1.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  6 16  2  0
 16 17  1  0
 17 18  2  0
 17  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
M  END

  Mrv0541 02241217132D          

 18 18  0  0  0  0            999 V2000
   -0.0416    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8457    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1858    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833    1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1858   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8457    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882   -0.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5882   -0.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 17  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 15  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 13  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038548

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(C=O)=C/C\C=C(/C)C1=CC(=O)C(C)=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O3/c1-10(9-16)5-4-6-11(2)13-8-14(17)12(3)7-15(13)18/h5-9H,4H2,1-3H3/b10-5+,11-6+

> <INCHI_KEY>
TUGXTSKUBLGSJF-YOYBCKCWSA-N

> <FORMULA>
C15H16O3

> <MOLECULAR_WEIGHT>
244.2857

> <EXACT_MASS>
244.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.144043897371176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,5E)-2-methyl-6-(4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)hepta-2,5-dienal

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
2.8340136916666667

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.311538158982116

> <JCHEM_POLAR_SURFACE_AREA>
51.21

> <JCHEM_REFRACTIVITY>
74.33699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,5E)-2-methyl-6-(4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)hepta-2,5-dienal

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038548
     RDKit          3D
Glandulone B
 34 34  0  0  0  0  0  0  0  0999 V2000
   -5.6293    0.1226    1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2046   -0.0018    0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3913   -0.8704    1.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -0.9958    0.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252   -1.8605    1.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4352   -0.1821   -0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0611   -0.2585   -0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4116    0.6789   -1.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7994   -1.0915   -0.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2322   -1.2388   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0603   -0.9366    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9420    0.0307    0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1420    0.8834   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7393    0.2898    1.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5773    1.2055    1.8010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2878    0.7042   -0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6720    0.8330   -0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4428    1.6780   -0.9635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7986    1.0440    1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2876    0.0946    0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8908   -0.7500    1.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7890   -1.4933    1.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0033    1.6922   -1.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4879    0.8328   -1.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684    0.3767   -2.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503   -1.7982    0.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152   -0.7456   -1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3147   -2.3532   -0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450   -1.5427    1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030    1.7071   -0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381    1.4007   -0.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2360    0.3126   -1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5553   -0.3533    2.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230    1.3264   -1.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  6 16  2  0
 16 17  1  0
 17 18  2  0
 17  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.078   0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.308  -0.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.694   0.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.926  -0.769   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.926  -2.309   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.698   2.309   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.312   1.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.080   2.309   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.694   1.539   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.462   2.309   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.308  -2.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.308  -0.769   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.694   0.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.080  -0.769   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.312   0.001   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.698  -0.769   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.312   0.001   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.698  -0.769   0.000  0.00  0.00           O+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    1   11   13                                                  
CONECT   13    9   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15    7   14   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0038548
HETATM    1  C1  UNL     1      -5.629   0.123   1.100  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.205  -0.002   0.650  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.391  -0.870   1.205  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.976  -0.996   0.760  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.325  -1.860   1.376  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.435  -0.182  -0.288  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.061  -0.259  -0.750  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.412   0.679  -1.831  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.799  -1.091  -0.263  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.232  -1.239  -0.682  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.060  -0.937   0.514  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.942   0.031   0.547  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.142   0.883  -0.665  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.739   0.290   1.763  1.00  0.00           C  
HETATM   15  O2  UNL     1       5.577   1.205   1.801  1.00  0.00           O  
HETATM   16  C14 UNL     1      -2.288   0.704  -0.845  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.672   0.833  -0.415  1.00  0.00           C  
HETATM   18  O3  UNL     1      -4.443   1.678  -0.963  1.00  0.00           O  
HETATM   19  H1  UNL     1      -5.799   1.044   1.655  1.00  0.00           H  
HETATM   20  H2  UNL     1      -6.288   0.095   0.185  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.891  -0.750   1.726  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.789  -1.493   2.000  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.003   1.692  -1.525  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.488   0.833  -1.839  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.068   0.377  -2.823  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.550  -1.798   0.541  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.515  -0.746  -1.590  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.315  -2.353  -0.926  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.945  -1.543   1.431  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.403   1.707  -0.713  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.138   1.401  -0.520  1.00  0.00           H  
HETATM   32  H14 UNL     1       4.236   0.313  -1.588  1.00  0.00           H  
HETATM   33  H15 UNL     1       4.555  -0.353   2.608  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.923   1.326  -1.637  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   17
CONECT    3    4   22
CONECT    4    5    5    6
CONECT    6    7   16   16
CONECT    7    8    9    9
CONECT    8   23   24   25
CONECT    9   10   26
CONECT   10   11   27   28
CONECT   11   12   12   29
CONECT   12   13   14
CONECT   13   30   31   32
CONECT   14   15   15   33
CONECT   16   17   34
CONECT   17   18   18
END

HMDB0038548
     RDKit          3D
Glandulone B
 34 34  0  0  0  0  0  0  0  0999 V2000
   -5.6293    0.1226    1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2046   -0.0018    0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3913   -0.8704    1.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -0.9958    0.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252   -1.8605    1.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4352   -0.1821   -0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0611   -0.2585   -0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4116    0.6789   -1.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7994   -1.0915   -0.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2322   -1.2388   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0603   -0.9366    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9420    0.0307    0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1420    0.8834   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7393    0.2898    1.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5773    1.2055    1.8010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2878    0.7042   -0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6720    0.8330   -0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4428    1.6780   -0.9635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7986    1.0440    1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2876    0.0946    0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8908   -0.7500    1.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7890   -1.4933    1.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0033    1.6922   -1.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4879    0.8328   -1.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684    0.3767   -2.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503   -1.7982    0.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152   -0.7456   -1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3147   -2.3532   -0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450   -1.5427    1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030    1.7071   -0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381    1.4007   -0.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2360    0.3126   -1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5553   -0.3533    2.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230    1.3264   -1.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  6 16  2  0
 16 17  1  0
 17 18  2  0
 17  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₃

Average Molecular Weight

244.2857

Monoisotopic Molecular Weight

244.109944378

IUPAC Name

(2E,5E)-2-methyl-6-(4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)hepta-2,5-dienal

Traditional Name

(2E,5E)-2-methyl-6-(4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)hepta-2,5-dienal

CAS Registry Number

Not Available

SMILES

C\C(C=O)=C/C\C=C(/C)C1=CC(=O)C(C)=CC1=O

InChI Identifier

InChI=1S/C15H16O3/c1-10(9-16)5-4-6-11(2)13-8-14(17)12(3)7-15(13)18/h5-9H,4H2,1-3H3/b10-5+,11-6+

InChI Key

TUGXTSKUBLGSJF-YOYBCKCWSA-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

Bisabolane sesquiterpenoid
Sesquiterpenoid
Quinone
P-benzoquinone
Enal
Alpha,beta-unsaturated aldehyde
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038548)

Source

Endogenous

Endogenous (HMDB: HMDB0038548)

Animal

Animal (HMDB: HMDB0038548)

Exogenous

Food

Food (HMDB: HMDB0038548)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0038548)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038548)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038548)

Lipid metabolism pathway (HMDB: HMDB0038548)

Cellular process

Cell signaling (HMDB: HMDB0038548)

Biochemical process

Lipid transport (HMDB: HMDB0038548)

Role

Biological role

Energy source (HMDB: HMDB0038548)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038548)

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	0.03 g/L	ALOGPS
logP	2.86	ALOGPS
logP	2.83	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	51.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.34 m³·mol⁻¹	ChemAxon
Polarizability	26.14 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	167.39	30932474
DeepCCS	[M-H]-	165.032	30932474
DeepCCS	[M-2H]-	197.918	30932474
DeepCCS	[M+Na]+	173.483	30932474
AllCCS	[M+H]+	157.4	32859911
AllCCS	[M+H-H2O]+	153.6	32859911
AllCCS	[M+NH4]+	160.9	32859911
AllCCS	[M+Na]+	162.0	32859911
AllCCS	[M-H]-	160.2	32859911
AllCCS	[M+Na-2H]-	160.5	32859911
AllCCS	[M+HCOO]-	161.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glandulone B	C\C(C=O)=C/C\C=C(/C)C1=CC(=O)C(C)=CC1=O	3052.5	Standard polar	33892256
Glandulone B	C\C(C=O)=C/C\C=C(/C)C1=CC(=O)C(C)=CC1=O	2127.0	Standard non polar	33892256
Glandulone B	C\C(C=O)=C/C\C=C(/C)C1=CC(=O)C(C)=CC1=O	2100.9	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 - Glandulone B GC-MS (Non-derivatized) - 70eV, Positive	splash10-00or-5690000000-0daa5f49cfe64b33b1bb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glandulone B 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 - Glandulone B 10V, Positive-QTOF	splash10-0002-1290000000-77b75a60ceca6eafb208	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glandulone B 20V, Positive-QTOF	splash10-002b-5960000000-51175a5e35da4b7187bc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glandulone B 40V, Positive-QTOF	splash10-1000-9400000000-f65ba7e1c60381a1e488	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glandulone B 10V, Negative-QTOF	splash10-0006-0090000000-390802c46d10fe405142	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glandulone B 20V, Negative-QTOF	splash10-0006-1290000000-d29a28779572c8e180e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glandulone B 40V, Negative-QTOF	splash10-05i9-9630000000-02043224b1e51bc26b67	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glandulone B 10V, Positive-QTOF	splash10-000b-0890000000-6228d573b4a8c627282a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glandulone B 20V, Positive-QTOF	splash10-00vi-2930000000-8b5a78cf6a49c109a163	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glandulone B 40V, Positive-QTOF	splash10-03dj-3920000000-ef113f1f4429f81669ef	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glandulone B 10V, Negative-QTOF	splash10-0006-0090000000-b66eb7866e41c4ccda01	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glandulone B 20V, Negative-QTOF	splash10-014i-0590000000-4b539b098ca5f068cd76	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glandulone B 40V, Negative-QTOF	splash10-0002-2900000000-6e1430f642e368061d47	2021-09-23	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

FDB017934

KNApSAcK ID

Not Available

Chemspider ID

30777270

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752399

PDB ID

Not Available

ChEBI ID

174265

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). 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 Glandulone B (HMDB0038548)

MOL for HMDB0038548 (Glandulone B)

3D MOL for HMDB0038548 (Glandulone B)

3D SDF for HMDB0038548 (Glandulone B)

3D-SDF for HMDB0038548 (Glandulone B)

PDB for HMDB0038548 (Glandulone B)

3D PDB for HMDB0038548 (Glandulone B)

SMILES for HMDB0038548 (Glandulone B)

INCHI for HMDB0038548 (Glandulone B)

Structure for HMDB0038548 (Glandulone B)

3D Structure for HMDB0038548 (Glandulone B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra