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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 23:27:03 UTC

Update Date

2022-03-07 02:55:39 UTC

HMDB ID

HMDB0038168

Secondary Accession Numbers

HMDB38168

Metabolite Identification

Common Name

gamma-Himachalene

Description

gamma-Himachalene, also known as γ-himachalene, belongs to the class of organic compounds known as himachalane and lippifoliane sesquiterpenoids. These are sesquiterpenoids with a structure based on either the himachalane or the lippifoliane skeleton. Thus, gamma-himachalene is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on gamma-Himachalene.

Structure

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

HMDB0038168
     RDKit          3D
gamma-Himachalene
 39 40  0  0  0  0  0  0  0  0999 V2000
    3.8279   -0.8186   -1.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5840   -0.2775   -0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4883   -1.0280   -0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752   -0.3642    0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0538    0.9240   -0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3025    1.7475   -0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4539    1.0741    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0836    1.6532   -0.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7654    2.9319    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442    1.2407   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9253    0.0285   -0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357   -1.0401   -0.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9006   -1.2638    0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4251   -2.7004    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -1.1689    1.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.5531   -2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6862   -0.3517   -0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236   -1.9326   -0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4522   -2.0285   -0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694   -0.1024    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2711    0.7665   -1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634    2.7627   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    1.8785   -1.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744    1.0157    1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3747    1.6299   -0.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287    2.8059    1.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5930    3.7706    0.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6860    3.2079    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0595    1.8728    0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867    0.3492   -1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7824   -0.3208    0.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683   -0.8979   -1.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155   -2.0062   -1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -3.3279    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4619   -2.8861    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3341   -3.0087   -1.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5686   -0.1373    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523   -1.6541    1.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9237   -1.7909    2.1962 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  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  7  2  1  0
 13  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

Himachalen-gamma
  Mrv1572001071617122D          
  Mrv0541 01101309102D          
 15 16  0  0  0  0            999 V2000
   -5.7020    2.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4165    1.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4165    0.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7020    0.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9876    0.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9876    1.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1310    2.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426    0.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5383    0.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1803    1.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5383    1.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426    2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1410    2.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8713    2.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5261   -0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  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
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12  6  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  8 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038168

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2C(CC1)C(C)=CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-11-7-8-13-12(2)6-5-9-15(3,4)14(13)10-11/h6,10,13-14H,5,7-9H2,1-4H3

> <INCHI_KEY>
PUWNTRHCKNHSAT-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.010863236120162

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,5,9-tetramethyl-2,4a,5,6,7,9a-hexahydro-1H-benzo[7]annulene

> <ALOGPS_LOGP>
5.57

> <JCHEM_LOGP>
4.461375721333334

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
68.5249

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-himachalene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038168
     RDKit          3D
gamma-Himachalene
 39 40  0  0  0  0  0  0  0  0999 V2000
    3.8279   -0.8186   -1.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5840   -0.2775   -0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4883   -1.0280   -0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752   -0.3642    0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0538    0.9240   -0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3025    1.7475   -0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4539    1.0741    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0836    1.6532   -0.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7654    2.9319    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442    1.2407   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9253    0.0285   -0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357   -1.0401   -0.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9006   -1.2638    0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4251   -2.7004    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -1.1689    1.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.5531   -2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6862   -0.3517   -0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236   -1.9326   -0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4522   -2.0285   -0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694   -0.1024    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2711    0.7665   -1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634    2.7627   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    1.8785   -1.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744    1.0157    1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3747    1.6299   -0.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287    2.8059    1.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5930    3.7706    0.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6860    3.2079    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0595    1.8728    0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867    0.3492   -1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7824   -0.3208    0.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683   -0.8979   -1.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155   -2.0062   -1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -3.3279    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4619   -2.8861    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3341   -3.0087   -1.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5686   -0.1373    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523   -1.6541    1.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9237   -1.7909    2.1962 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  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  7  2  1  0
 13  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Himachalen-gamma                                  
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0     -10.644   3.869   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.977   3.099   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.977   1.559   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.644   0.789   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.310   1.559   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.310   3.099   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -13.311   3.869   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.106   0.599   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.605   0.942   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.937   2.329   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.605   3.717   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.106   4.060   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.730   5.553   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.093   5.242   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.449  -0.902   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    5   12                                                  
CONECT    7    2                                                            
CONECT    8    5    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6   13   14                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    8                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0038168
HETATM    1  C1  UNL     1       3.828  -0.819  -1.082  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.584  -0.278  -0.515  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.488  -1.028  -0.537  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.275  -0.364   0.074  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.054   0.924  -0.660  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.303   1.748  -0.654  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.454   1.074   0.096  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.084   1.653  -0.007  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.765   2.932   0.686  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.344   1.241  -0.004  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.925   0.029  -0.605  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.936  -1.040  -0.923  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.901  -1.264   0.135  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.425  -2.700   0.008  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.571  -1.169   1.512  1.00  0.00           C  
HETATM   16  H1  UNL     1       3.866  -0.553  -2.156  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.686  -0.352  -0.521  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.824  -1.933  -0.923  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.452  -2.029  -0.954  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.569  -0.102   1.116  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.271   0.766  -1.712  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.163   2.763  -0.236  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.669   1.878  -1.690  1.00  0.00           H  
HETATM   24  H9  UNL     1       2.274   1.016   1.173  1.00  0.00           H  
HETATM   25  H10 UNL     1       3.375   1.630  -0.159  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.029   2.806   1.457  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.593   3.771   0.003  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.686   3.208   1.277  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.060   1.873   0.509  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.387   0.349  -1.585  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.782  -0.321   0.011  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.468  -0.898  -1.914  1.00  0.00           H  
HETATM   33  H18 UNL     1      -2.516  -2.006  -1.011  1.00  0.00           H  
HETATM   34  H19 UNL     1      -1.263  -3.328   0.424  1.00  0.00           H  
HETATM   35  H20 UNL     1       0.462  -2.886   0.614  1.00  0.00           H  
HETATM   36  H21 UNL     1      -0.334  -3.009  -1.054  1.00  0.00           H  
HETATM   37  H22 UNL     1      -1.569  -0.137   1.889  1.00  0.00           H  
HETATM   38  H23 UNL     1      -2.552  -1.654   1.494  1.00  0.00           H  
HETATM   39  H24 UNL     1      -0.924  -1.791   2.196  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    7
CONECT    3    4   19
CONECT    4    5   13   20
CONECT    5    6    8   21
CONECT    6    7   22   23
CONECT    7   24   25
CONECT    8    9   10   10
CONECT    9   26   27   28
CONECT   10   11   29
CONECT   11   12   30   31
CONECT   12   13   32   33
CONECT   13   14   15
CONECT   14   34   35   36
CONECT   15   37   38   39
END

HMDB0038168
     RDKit          3D
gamma-Himachalene
 39 40  0  0  0  0  0  0  0  0999 V2000
    3.8279   -0.8186   -1.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5840   -0.2775   -0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4883   -1.0280   -0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752   -0.3642    0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0538    0.9240   -0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3025    1.7475   -0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4539    1.0741    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0836    1.6532   -0.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7654    2.9319    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442    1.2407   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9253    0.0285   -0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357   -1.0401   -0.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9006   -1.2638    0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4251   -2.7004    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -1.1689    1.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.5531   -2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6862   -0.3517   -0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236   -1.9326   -0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4522   -2.0285   -0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694   -0.1024    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2711    0.7665   -1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634    2.7627   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    1.8785   -1.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744    1.0157    1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3747    1.6299   -0.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287    2.8059    1.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5930    3.7706    0.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6860    3.2079    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0595    1.8728    0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867    0.3492   -1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7824   -0.3208    0.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683   -0.8979   -1.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155   -2.0062   -1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -3.3279    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4619   -2.8861    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3341   -3.0087   -1.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5686   -0.1373    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523   -1.6541    1.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9237   -1.7909    2.1962 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  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  7  2  1  0
 13  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
g-Himachalene	Generator
Γ-himachalene	Generator
(1R,6S)-gamma-Himachalene	HMDB
Himachal-4,10-diene	HMDB

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.357

Monoisotopic Molecular Weight

204.187800773

IUPAC Name

3,5,5,9-tetramethyl-2,4a,5,6,7,9a-hexahydro-1H-benzo[7]annulene

Traditional Name

gamma-himachalene

CAS Registry Number

53111-25-4

SMILES

CC1=CC2C(CC1)C(C)=CCCC2(C)C

InChI Identifier

InChI=1S/C15H24/c1-11-7-8-13-12(2)6-5-9-15(3,4)14(13)10-11/h6,10,13-14H,5,7-9H2,1-4H3

InChI Key

PUWNTRHCKNHSAT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as himachalane and lippifoliane sesquiterpenoids. These are sesquiterpenoids with a structure based on either the himachalane or the lippifoliane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Himachalane and lippifoliane sesquiterpenoids

Alternative Parents

Substituents

Himachalane 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

himachalene (CHEBI:49224 )
Lippifoliane and himachalane sesquiterpenoids (LMPR0103480007 )
a sesquiterpenoid (CPD-8734 )

Ontology

Not Available

Urine (HMDB: HMDB0038168)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)

Cellular substructure

Membrane (HMDB: HMDB0038168)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038168)

Source

Endogenous

Endogenous (HMDB: HMDB0038168)

Plant

Plant (HMDB: HMDB0038168)

Animal

Animal (HMDB: HMDB0038168)

Exogenous

Food

Food (HMDB: HMDB0038168)

Milk and milk product

Fermented milk product

Cheese (FooDB: FOOD00617)

Herb and spice

Herb

Anise (FooDB: FOOD00137)

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0038168)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0038168)

Cellular process

Cell signaling (HMDB: HMDB0038168)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0038168)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0038168)

Nutrient

Nutrient (HMDB: HMDB0038168)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038168)

Emulsifier (HMDB: HMDB0038168)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	267.00 to 268.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.058 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.478 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0085 g/L	ALOGPS
logP	5.57	ALOGPS
logP	4.46	ChemAxon
logS	-4.4	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	68.52 m³·mol⁻¹	ChemAxon
Polarizability	26.01 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
DarkChem	[M+H]+	150.347	31661259
DarkChem	[M-H]-	146.27	31661259
DeepCCS	[M+H]+	151.032	30932474
DeepCCS	[M-H]-	148.659	30932474
DeepCCS	[M-2H]-	182.747	30932474
DeepCCS	[M+Na]+	157.488	30932474
AllCCS	[M+H]+	146.2	32859911
AllCCS	[M+H-H2O]+	142.2	32859911
AllCCS	[M+NH4]+	150.0	32859911
AllCCS	[M+Na]+	151.1	32859911
AllCCS	[M-H]-	156.4	32859911
AllCCS	[M+Na-2H]-	156.9	32859911
AllCCS	[M+HCOO]-	157.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Himachalene	CC1=CC2C(CC1)C(C)=CCCC2(C)C	1716.9	Standard polar	33892256
gamma-Himachalene	CC1=CC2C(CC1)C(C)=CCCC2(C)C	1491.1	Standard non polar	33892256
gamma-Himachalene	CC1=CC2C(CC1)C(C)=CCCC2(C)C	1477.3	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 - gamma-Himachalene GC-MS (Non-derivatized) - 70eV, Positive	splash10-01p2-1900000000-38b6680cd70b73d40c7b	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Himachalene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Himachalene 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 - gamma-Himachalene 10V, Positive-QTOF	splash10-0a4i-0290000000-a81f2e021a74d7e7a2bc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Himachalene 20V, Positive-QTOF	splash10-0a4i-3950000000-30bb0ea9f97a24b0a090	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Himachalene 40V, Positive-QTOF	splash10-029i-4900000000-3b643f45a326a4f18f4c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Himachalene 10V, Negative-QTOF	splash10-0udi-0090000000-080d7272458a2c9e6cb3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Himachalene 20V, Negative-QTOF	splash10-0udi-0190000000-77f27cd1c1698ff65b65	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Himachalene 40V, Negative-QTOF	splash10-01y9-1900000000-3b07b289b9d6c277e869	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Himachalene 10V, Positive-QTOF	splash10-0a4i-0190000000-8239d79b18cfbbeb1176	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Himachalene 20V, Positive-QTOF	splash10-052n-7930000000-5710676bde45ab96a8e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Himachalene 40V, Positive-QTOF	splash10-0006-9300000000-67cc55866990b74ec764	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Himachalene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Himachalene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Himachalene 40V, Negative-QTOF	splash10-0udi-0390000000-223e3a6874c2b06b6569	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details

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

FDB017399

KNApSAcK ID

C00021310

Chemspider ID

501668

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

577062

PDB ID

Not Available

ChEBI ID

49224

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1442231

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 gamma-Himachalene (HMDB0038168)

MOL for HMDB0038168 (gamma-Himachalene)

3D MOL for HMDB0038168 (gamma-Himachalene)

3D SDF for HMDB0038168 (gamma-Himachalene)

3D-SDF for HMDB0038168 (gamma-Himachalene)

PDB for HMDB0038168 (gamma-Himachalene)

3D PDB for HMDB0038168 (gamma-Himachalene)

SMILES for HMDB0038168 (gamma-Himachalene)

INCHI for HMDB0038168 (gamma-Himachalene)

Structure for HMDB0038168 (gamma-Himachalene)

3D Structure for HMDB0038168 (gamma-Himachalene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra