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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:26:49 UTC

Update Date

2022-03-07 02:55:39 UTC

HMDB ID

HMDB0038164

Secondary Accession Numbers

HMDB38164

Metabolite Identification

Common Name

Vulgarone B

Description

Vulgarone 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 significant number of articles have been published on Vulgarone B.

Structure

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

HMDB0038164
     RDKit          3D
Vulgarone B
 38 40  0  0  0  0  0  0  0  0999 V2000
    2.7522    1.7684   -0.8621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9868    0.9011    0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428    0.5881    1.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4360   -0.2735    2.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6649   -0.6179    3.2294 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044   -0.6904    1.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3160    0.5351    0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6964    0.3082   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7242   -1.1464   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1207   -1.6922    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1822   -2.0179   -0.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3534   -1.3017   -1.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2463   -0.6711   -0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    0.5601    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554    1.6947   -0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5995    0.9291    1.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3423    2.5437   -0.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3438    1.1497   -1.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0231    2.3358   -1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2621    0.9407    1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4694   -1.3548    1.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0883    1.4608    1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4143    0.5537   -1.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879   -2.6755   -0.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685   -1.0402   -0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030   -1.8671    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6223   -2.8568   -0.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891   -2.4926   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0567   -0.6204   -2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -2.1045   -1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -1.4454    0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2062   -0.4111   -0.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8073    2.2216   -0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7106    1.2913   -1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517    2.4591   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4897    1.4470    0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0282    1.5810    2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552    0.0104    1.9338 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
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  8  2  1  0
  9  6  1  0
 14  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END

  Mrv0541 01251306422D          

 16 18  0  0  0  0            999 V2000
   -2.3866   -1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1011   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1011   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271   -1.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271   -3.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228   -3.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228   -1.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8155   -3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -0.7661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2107   -0.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105   -3.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6146   -4.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  7  1  0  0  0  0
  1  6  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  5  1  0  0  0  0
  6  7  1  0  0  0  0
  3 12  1  0  0  0  0
  1 13  2  0  0  0  0
  5 14  1  0  0  0  0
  4  5  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038164

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=O)C2C3C1C2(C)CCCC3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-9-8-10(16)12-13-11(9)15(12,4)7-5-6-14(13,2)3/h8,11-13H,5-7H2,1-4H3

> <INCHI_KEY>
KTPOZFYJWLGJGH-UHFFFAOYSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.3346

> <EXACT_MASS>
218.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.01711263797589

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6,6,11-tetramethyltricyclo[5.4.0.0²,⁸]undec-10-en-9-one

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
3.5376527893333325

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.686840391516764

> <JCHEM_PKA_STRONGEST_BASIC>
-4.7608041158443495

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
66.3384

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6,6,11-tetramethyltricyclo[5.4.0.0²,⁸]undec-10-en-9-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038164
     RDKit          3D
Vulgarone B
 38 40  0  0  0  0  0  0  0  0999 V2000
    2.7522    1.7684   -0.8621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9868    0.9011    0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428    0.5881    1.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4360   -0.2735    2.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6649   -0.6179    3.2294 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044   -0.6904    1.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3160    0.5351    0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6964    0.3082   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7242   -1.1464   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1207   -1.6922    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1822   -2.0179   -0.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3534   -1.3017   -1.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2463   -0.6711   -0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    0.5601    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554    1.6947   -0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5995    0.9291    1.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3423    2.5437   -0.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3438    1.1497   -1.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0231    2.3358   -1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2621    0.9407    1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4694   -1.3548    1.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0883    1.4608    1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4143    0.5537   -1.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879   -2.6755   -0.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685   -1.0402   -0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030   -1.8671    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6223   -2.8568   -0.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891   -2.4926   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0567   -0.6204   -2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -2.1045   -1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -1.4454    0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2062   -0.4111   -0.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8073    2.2216   -0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7106    1.2913   -1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517    2.4591   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4897    1.4470    0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0282    1.5810    2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552    0.0104    1.9338 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
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  8  2  1  0
  9  6  1  0
 14  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END

HEADER    PROTEIN                                 25-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JAN-13         0                                  
HETATM    1  C   UNK     0      -4.455  -2.970   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.789  -3.740   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.789  -5.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.455  -6.050   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.917  -2.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.121  -3.740   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.121  -5.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.917  -6.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.416  -5.898   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.252  -4.510   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.416  -3.123   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.122  -6.050   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.455  -1.430   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.260  -1.278   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.006  -7.329   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.147  -7.574   0.000  0.00  0.00           C+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    7    5                                                  
CONECT    5    6   11   14    4                                             
CONECT    6    1    5    7                                                  
CONECT    7    4    8    6                                                  
CONECT    8    7    9   15   16                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5                                                       
CONECT   12    3                                                            
CONECT   13    1                                                            
CONECT   14    5                                                            
CONECT   15    8                                                            
CONECT   16    8                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0038164
HETATM    1  C1  UNL     1       2.752   1.768  -0.862  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.987   0.901   0.037  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.343   0.588   1.274  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.436  -0.274   2.063  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.665  -0.618   3.229  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.204  -0.690   1.302  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.316   0.535   0.636  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.696   0.308  -0.457  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.724  -1.146  -0.062  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.121  -1.692   0.002  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.182  -2.018  -0.842  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.353  -1.302  -1.467  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.246  -0.671  -0.433  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.718   0.560   0.177  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.855   1.695  -0.847  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.600   0.929   1.362  1.00  0.00           C  
HETATM   17  H1  UNL     1       3.342   2.544  -0.346  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.344   1.150  -1.564  1.00  0.00           H  
HETATM   19  H3  UNL     1       2.023   2.336  -1.511  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.262   0.941   1.713  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.469  -1.355   1.810  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.088   1.461   1.234  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.414   0.554  -1.470  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.188  -2.676  -0.546  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.868  -1.040  -0.503  1.00  0.00           H  
HETATM   26  H10 UNL     1       2.403  -1.867   1.064  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.622  -2.857  -0.231  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.389  -2.493  -1.656  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.057  -0.620  -2.269  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.976  -2.105  -1.958  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.530  -1.445   0.300  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.206  -0.411  -0.970  1.00  0.00           H  
HETATM   33  H17 UNL     1      -2.807   2.222  -0.686  1.00  0.00           H  
HETATM   34  H18 UNL     1      -1.711   1.291  -1.852  1.00  0.00           H  
HETATM   35  H19 UNL     1      -1.052   2.459  -0.635  1.00  0.00           H  
HETATM   36  H20 UNL     1      -3.490   1.447   0.964  1.00  0.00           H  
HETATM   37  H21 UNL     1      -2.028   1.581   2.069  1.00  0.00           H  
HETATM   38  H22 UNL     1      -2.855   0.010   1.934  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    8
CONECT    3    4   20
CONECT    4    5    5    6
CONECT    6    7    9   21
CONECT    7    8   14   22
CONECT    8    9   23
CONECT    9   10   11
CONECT   10   24   25   26
CONECT   11   12   27   28
CONECT   12   13   29   30
CONECT   13   14   31   32
CONECT   14   15   16
CONECT   15   33   34   35
CONECT   16   36   37   38
END

HMDB0038164
     RDKit          3D
Vulgarone B
 38 40  0  0  0  0  0  0  0  0999 V2000
    2.7522    1.7684   -0.8621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9868    0.9011    0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428    0.5881    1.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4360   -0.2735    2.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6649   -0.6179    3.2294 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044   -0.6904    1.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3160    0.5351    0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6964    0.3082   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7242   -1.1464   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1207   -1.6922    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1822   -2.0179   -0.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3534   -1.3017   -1.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2463   -0.6711   -0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    0.5601    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554    1.6947   -0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5995    0.9291    1.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3423    2.5437   -0.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3438    1.1497   -1.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0231    2.3358   -1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2621    0.9407    1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4694   -1.3548    1.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0883    1.4608    1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4143    0.5537   -1.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879   -2.6755   -0.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685   -1.0402   -0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030   -1.8671    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6223   -2.8568   -0.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891   -2.4926   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0567   -0.6204   -2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -2.1045   -1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -1.4454    0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2062   -0.4111   -0.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8073    2.2216   -0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7106    1.2913   -1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517    2.4591   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4897    1.4470    0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0282    1.5810    2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552    0.0104    1.9338 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
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  8  2  1  0
  9  6  1  0
 14  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-oxo-a-Longipinene	HMDB
Longiverbenone (vulgarone b)	HMDB
Vulgarone b	MeSH

Chemical Formula

C₁₅H₂₂O

Average Molecular Weight

218.3346

Monoisotopic Molecular Weight

218.167065326

IUPAC Name

2,6,6,11-tetramethyltricyclo[5.4.0.0²,⁸]undec-10-en-9-one

Traditional Name

2,6,6,11-tetramethyltricyclo[5.4.0.0²,⁸]undec-10-en-9-one

CAS Registry Number

64180-68-3

SMILES

CC1=CC(=O)C2C3C1C2(C)CCCC3(C)C

InChI Identifier

InChI=1S/C15H22O/c1-9-8-10(16)12-13-11(9)15(12,4)7-5-6-14(13,2)3/h8,11-13H,5-7H2,1-4H3

InChI Key

KTPOZFYJWLGJGH-UHFFFAOYSA-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

Longipinane sesquiterpenoid
Sesquiterpenoid
Cyclohexenone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038164)

Source

Endogenous

Endogenous (HMDB: HMDB0038164)

Plant

Plant (HMDB: HMDB0038164)

Animal

Animal (HMDB: HMDB0038164)

Exogenous

Food

Food (HMDB: HMDB0038164)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0038164)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038164)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038164)

Lipid metabolism pathway (HMDB: HMDB0038164)

Cellular process

Cell signaling (HMDB: HMDB0038164)

Biochemical process

Lipid transport (HMDB: HMDB0038164)

Role

Biological role

Energy source (HMDB: HMDB0038164)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038164)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	35.5 - 36 °C	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	0.036 g/L	ALOGPS
logP	2.9	ALOGPS
logP	3.54	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	19.69	ChemAxon
pKa (Strongest Basic)	-4.8	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	0	ChemAxon
Refractivity	66.34 m³·mol⁻¹	ChemAxon
Polarizability	26.02 Å³	ChemAxon
Number of Rings	3	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]+	152.729	31661259
DarkChem	[M-H]-	146.917	31661259
DeepCCS	[M+H]+	158.791	30932474
DeepCCS	[M-H]-	156.433	30932474
DeepCCS	[M-2H]-	189.446	30932474
DeepCCS	[M+Na]+	164.884	30932474
AllCCS	[M+H]+	149.0	32859911
AllCCS	[M+H-H2O]+	145.2	32859911
AllCCS	[M+NH4]+	152.5	32859911
AllCCS	[M+Na]+	153.5	32859911
AllCCS	[M-H]-	158.7	32859911
AllCCS	[M+Na-2H]-	159.0	32859911
AllCCS	[M+HCOO]-	159.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vulgarone B	CC1=CC(=O)C2C3C1C2(C)CCCC3(C)C	2097.4	Standard polar	33892256
Vulgarone B	CC1=CC(=O)C2C3C1C2(C)CCCC3(C)C	1635.9	Standard non polar	33892256
Vulgarone B	CC1=CC(=O)C2C3C1C2(C)CCCC3(C)C	1658.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vulgarone B,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C3C1C2(C)CCCC3(C)C	1803.1	Semi standard non polar	33892256
Vulgarone B,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C3C1C2(C)CCCC3(C)C	1659.2	Standard non polar	33892256
Vulgarone B,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C3C1C2(C)CCCC3(C)C	2026.4	Semi standard non polar	33892256
Vulgarone B,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C3C1C2(C)CCCC3(C)C	1872.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vulgarone B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0v03-9540000000-b86ee707cf9a538a1f75	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vulgarone B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vulgarone 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 - Vulgarone B 10V, Positive-QTOF	splash10-014i-0090000000-cadf05f7f87042708f2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarone B 20V, Positive-QTOF	splash10-014i-0090000000-5a75390c9e8f5a1d3b19	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarone B 40V, Positive-QTOF	splash10-0udr-0590000000-f44747939c085888e732	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarone B 10V, Negative-QTOF	splash10-014i-0090000000-722ea9b9ad2a2de2b652	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarone B 20V, Negative-QTOF	splash10-014i-0090000000-722ea9b9ad2a2de2b652	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarone B 40V, Negative-QTOF	splash10-0gb9-0390000000-bfe962fa072e7037c9bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarone B 10V, Positive-QTOF	splash10-014i-0090000000-1b3b626a2fdf64c8bc97	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarone B 20V, Positive-QTOF	splash10-014i-0190000000-da01ec6223a7ac5900e0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarone B 40V, Positive-QTOF	splash10-014l-8390000000-ff8ce2860f559d2022e1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarone B 10V, Negative-QTOF	splash10-014i-0090000000-868e2fb00a2cfbf6c529	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarone B 20V, Negative-QTOF	splash10-014i-0090000000-868e2fb00a2cfbf6c529	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarone B 40V, Negative-QTOF	splash10-014i-0090000000-868e2fb00a2cfbf6c529	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB017394

KNApSAcK ID

C00021325

Chemspider ID

462030

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

530428

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1866121

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 Vulgarone B (HMDB0038164)

MOL for HMDB0038164 (Vulgarone B)

3D MOL for HMDB0038164 (Vulgarone B)

3D SDF for HMDB0038164 (Vulgarone B)

3D-SDF for HMDB0038164 (Vulgarone B)

PDB for HMDB0038164 (Vulgarone B)

3D PDB for HMDB0038164 (Vulgarone B)

SMILES for HMDB0038164 (Vulgarone B)

INCHI for HMDB0038164 (Vulgarone B)

Structure for HMDB0038164 (Vulgarone B)

3D Structure for HMDB0038164 (Vulgarone B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra