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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:03:48 UTC

Update Date

2021-09-23 20:03:50 UTC

HMDB ID

HMDB0302718

Secondary Accession Numbers

None

Metabolite Identification

Common Name

beta-Chamigrene

Description

Beta-chamigrene is a member of the class of compounds known as chamigranes. Chamigranes are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. They are predominantly isolated from algae. Beta-chamigrene can be found in lovage, which makes beta-chamigrene a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302718
     RDKit          3D
beta-Chamigrene
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.3726    1.5424    1.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6009    1.1224    0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4005    1.9703   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876    1.1151   -1.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.2433   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401   -1.0076   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -1.6573    1.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392   -2.1726   -1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1120   -0.1645    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7881   -0.8182    1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0451   -0.0551    1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7134    0.3090    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905    1.0793    0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1354   -0.0879   -1.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6532    0.1452   -1.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2024    0.9814    2.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7939    2.5245    2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0750    2.6365    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780    2.6675   -0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831    1.6370   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7622    1.0860   -2.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3125   -0.1029    0.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9998   -0.8170   -1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -2.1626    0.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112   -0.8986    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0961   -2.4416    1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1274   -1.9062   -2.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0789   -2.6642   -0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -2.9347   -0.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3104   -0.9523    2.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284   -1.8268    0.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4334    0.2085    2.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8249    2.0747   -0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990    0.5391   -0.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3896    1.1367    1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068   -1.1372   -1.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192    0.5407   -1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3077   -0.4645   -2.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5021    1.1990   -1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  9  2  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
M  END


  Mrv0541 02241220582D          

 15 16  0  0  0  0            999 V2000
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9232   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2523   -0.7392    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  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302718

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CCC2(CC1)C(=C)CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-12-7-10-15(11-8-12)13(2)6-5-9-14(15,3)4/h7H,2,5-6,8-11H2,1,3-4H3

> <INCHI_KEY>
WLNGPDPILFYWKF-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
25.669563749612525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7,7-trimethyl-11-methylidenespiro[5.5]undec-2-ene

> <ALOGPS_LOGP>
6.03

> <JCHEM_LOGP>
4.532337415333334

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
67.3789

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-chamigrene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302718
     RDKit          3D
beta-Chamigrene
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.3726    1.5424    1.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6009    1.1224    0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4005    1.9703   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876    1.1151   -1.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.2433   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401   -1.0076   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -1.6573    1.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392   -2.1726   -1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1120   -0.1645    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7881   -0.8182    1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0451   -0.0551    1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7134    0.3090    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905    1.0793    0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1354   -0.0879   -1.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6532    0.1452   -1.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2024    0.9814    2.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7939    2.5245    2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0750    2.6365    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780    2.6675   -0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831    1.6370   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7622    1.0860   -2.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3125   -0.1029    0.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9998   -0.8170   -1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -2.1626    0.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112   -0.8986    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0961   -2.4416    1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1274   -1.9062   -2.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0789   -2.6642   -0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -2.9347   -0.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3104   -0.9523    2.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284   -1.8268    0.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4334    0.2085    2.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8249    2.0747   -0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990    0.5391   -0.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3896    1.1367    1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068   -1.1372   -1.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192    0.5407   -1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3077   -0.4645   -2.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5021    1.1990   -1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  9  2  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  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      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.954   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590  -2.103   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.338  -1.380   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8   13                                             
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0302718
HETATM    1  C1  UNL     1      -0.373   1.542   1.800  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.601   1.122   0.580  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.400   1.970  -0.345  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.188   1.115  -1.298  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.500  -0.243  -0.747  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.340  -1.008  -0.235  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.793  -1.657   1.081  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.039  -2.173  -1.156  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.112  -0.165   0.039  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.788  -0.818   1.057  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.045  -0.055   1.270  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.713   0.309   0.181  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.990   1.079   0.243  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.135  -0.088  -1.117  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.653   0.145  -1.225  1.00  0.00           C  
HETATM   16  H1  UNL     1       0.202   0.981   2.536  1.00  0.00           H  
HETATM   17  H2  UNL     1      -0.794   2.525   2.085  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.075   2.637   0.264  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.778   2.667  -0.940  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.183   1.637  -1.433  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.762   1.086  -2.323  1.00  0.00           H  
HETATM   22  H7  UNL     1      -3.313  -0.103   0.018  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.000  -0.817  -1.574  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.751  -2.163   0.838  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.011  -0.899   1.846  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.096  -2.442   1.406  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.127  -1.906  -2.227  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.079  -2.664  -0.911  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.834  -2.935  -0.971  1.00  0.00           H  
HETATM   30  H15 UNL     1       0.310  -0.952   2.040  1.00  0.00           H  
HETATM   31  H16 UNL     1       1.128  -1.827   0.715  1.00  0.00           H  
HETATM   32  H17 UNL     1       2.433   0.209   2.238  1.00  0.00           H  
HETATM   33  H18 UNL     1       3.825   2.075  -0.220  1.00  0.00           H  
HETATM   34  H19 UNL     1       4.699   0.539  -0.446  1.00  0.00           H  
HETATM   35  H20 UNL     1       4.390   1.137   1.258  1.00  0.00           H  
HETATM   36  H21 UNL     1       2.407  -1.137  -1.399  1.00  0.00           H  
HETATM   37  H22 UNL     1       2.619   0.541  -1.908  1.00  0.00           H  
HETATM   38  H23 UNL     1       0.308  -0.465  -2.087  1.00  0.00           H  
HETATM   39  H24 UNL     1       0.502   1.199  -1.538  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3    9
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6   22   23
CONECT    6    7    8    9
CONECT    7   24   25   26
CONECT    8   27   28   29
CONECT    9   10   15
CONECT   10   11   30   31
CONECT   11   12   12   32
CONECT   12   13   14
CONECT   13   33   34   35
CONECT   14   15   36   37
CONECT   15   38   39
END

HMDB0302718
     RDKit          3D
beta-Chamigrene
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.3726    1.5424    1.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6009    1.1224    0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4005    1.9703   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876    1.1151   -1.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.2433   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401   -1.0076   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -1.6573    1.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392   -2.1726   -1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1120   -0.1645    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7881   -0.8182    1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0451   -0.0551    1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7134    0.3090    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905    1.0793    0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1354   -0.0879   -1.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6532    0.1452   -1.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2024    0.9814    2.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7939    2.5245    2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0750    2.6365    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780    2.6675   -0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831    1.6370   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7622    1.0860   -2.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3125   -0.1029    0.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9998   -0.8170   -1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -2.1626    0.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112   -0.8986    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0961   -2.4416    1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1274   -1.9062   -2.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0789   -2.6642   -0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -2.9347   -0.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3104   -0.9523    2.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284   -1.8268    0.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4334    0.2085    2.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8249    2.0747   -0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990    0.5391   -0.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3896    1.1367    1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068   -1.1372   -1.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192    0.5407   -1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3077   -0.4645   -2.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5021    1.1990   -1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  9  2  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
b-Chamigrene	Generator
Β-chamigrene	Generator
(S)-Isochamigrene	MeSH
Chamigrene	MeSH
Isochamigrene	MeSH

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

IUPAC Name

3,7,7-trimethyl-11-methylidenespiro[5.5]undec-2-ene

Traditional Name

β-chamigrene

CAS Registry Number

Not Available

SMILES

CC1=CCC2(CC1)C(=C)CCCC2(C)C

InChI Identifier

InChI=1S/C15H24/c1-12-7-10-15(11-8-12)13(2)6-5-9-14(15,3)4/h7H,2,5-6,8-11H2,1,3-4H3

InChI Key

WLNGPDPILFYWKF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chamigranes. These are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. They are predominantly isolated from algae.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Chamigranes

Alternative Parents

Substituents

Chamigrane sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

carbobicyclic compound (CHEBI:61744 )
sesquiterpene (CHEBI:61744 )
a sesquiterpenoid (CPD-8241 )

Ontology

Not Available

Lovage (FooDB: FOOD00100)

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	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
logP	6.03	ALOGPS
logP	4.53	ChemAxon
logS	-5.1	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.38 m³·mol⁻¹	ChemAxon
Polarizability	25.67 Å³	ChemAxon
Number of Rings	2	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
AllCCS	[M+H]+	148.877	32859911
AllCCS	[M+H-H2O]+	144.877	32859911
AllCCS	[M+Na]+	153.674	32859911
AllCCS	[M+NH4]+	152.601	32859911
AllCCS	[M-H]-	157.484	32859911
AllCCS	[M+Na-2H]-	158.088	32859911
AllCCS	[M+HCOO]-	158.855	32859911
DeepCCS	[M+H]+	153.562	30932474
DeepCCS	[M-H]-	151.204	30932474
DeepCCS	[M-2H]-	185.267	30932474
DeepCCS	[M+Na]+	160.052	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chamigrene 10V, Positive-QTOF	splash10-0a4i-1390000000-abb55af960fe631eb394	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chamigrene 20V, Positive-QTOF	splash10-0bt9-5920000000-ec816ab398dec7756e43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chamigrene 40V, Positive-QTOF	splash10-0j4r-7900000000-857b09b117205c443b05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chamigrene 10V, Negative-QTOF	splash10-0udi-0090000000-48e732fd8f0cbce7aaa3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chamigrene 20V, Negative-QTOF	splash10-0udi-0190000000-f76a7363e71b7bda6bf9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chamigrene 40V, Negative-QTOF	splash10-000i-1910000000-b6c52ddc600dc5a74696	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chamigrene 10V, Positive-QTOF	splash10-0a4i-4980000000-56f15a9b6005ed8834b9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chamigrene 20V, Positive-QTOF	splash10-053i-8910000000-5247d2ce35ab0532f831	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chamigrene 40V, Positive-QTOF	splash10-0006-9200000000-37263daab0322d802418	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chamigrene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chamigrene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Chamigrene 40V, Negative-QTOF	splash10-0udi-0090000000-8c28a556bc5a47f43e10	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB005917

KNApSAcK ID

C00003116

Chemspider ID

27047

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

29073

PDB ID

Not Available

ChEBI ID

61744

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

Not Available

Showing metabocard for beta-Chamigrene (HMDB0302718)

MOL for HMDB0302718 (beta-Chamigrene)

3D MOL for HMDB0302718 (beta-Chamigrene)

3D SDF for HMDB0302718 (beta-Chamigrene)

3D-SDF for HMDB0302718 (beta-Chamigrene)

PDB for HMDB0302718 (beta-Chamigrene)

3D PDB for HMDB0302718 (beta-Chamigrene)

SMILES for HMDB0302718 (beta-Chamigrene)

INCHI for HMDB0302718 (beta-Chamigrene)

Structure for HMDB0302718 (beta-Chamigrene)

3D Structure for HMDB0302718 (beta-Chamigrene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra