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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:14:41 UTC

Update Date

2022-03-07 02:56:19 UTC

HMDB ID

HMDB0039712

Secondary Accession Numbers

HMDB39712

Metabolite Identification

Common Name

gamma-Pinacene

Description

gamma-Pinacene, also known as γ-pinacene, belongs to the class of organic compounds known as cembrane diterpenoids. These are diterpenoids with a structure based a cembrane skeleton, which is characterized by the presence of an isopropyl group at C-1 and by three symmetrically disposed methyl groups a the t C-4, -8 and -12 positions. Based on a literature review a small amount of articles have been published on gamma-Pinacene.

Structure

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

HMDB0039712
     RDKit          3D
gamma-Pinacene
 52 52  0  0  0  0  0  0  0  0999 V2000
   -0.8095   -3.1753    1.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0129   -2.5405    0.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086   -2.0384    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095   -1.4064    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0043   -0.2280   -0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0773    0.2665   -1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6602    1.5024   -0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1659   -0.7541   -1.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8848    0.6513   -0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8001    1.2288    1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2370    2.2787    1.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1529    3.6682    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5003    1.9840    1.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631    0.6374    1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1863    0.2360    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0017    0.1059   -0.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057    1.2243   -1.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4802   -0.9743   -1.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0502   -2.1199   -0.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6080   -2.5366   -0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0969   -3.8384    2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5844   -3.8153    1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1456   -2.3624    2.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5001   -2.1796    2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0379   -1.9650   -0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6106    0.4417   -2.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9079    1.3401    0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5976    1.7824   -1.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9318    2.3361   -0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7817   -1.6945   -2.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8988   -0.3353   -2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7093   -0.9029   -0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1147    0.3154   -0.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057    1.5837   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040    1.7296    1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829    0.4995    1.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4227    4.0864   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2189    3.7716    0.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0776    4.3783    1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2810    2.7655    1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037   -0.1334    1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3384    0.6940    2.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6918   -0.6361    1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9241    1.0784    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5644    1.8956   -1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1958    1.8142   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876    0.8311   -2.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635   -1.0252   -2.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3101   -2.0384    0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6588   -2.9978   -0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276   -1.8461   -1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5329   -3.5829   -1.0489 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
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 17 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
M  END


  Mrv0541 05061311212D          

 20 20  0  0  0  0            999 V2000
    1.3899   -3.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5880    2.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5604   -1.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5917   -1.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3991    0.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5788    1.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917    0.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696    0.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954    0.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1733   -1.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3807   -1.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9935   -1.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9843   -2.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7678   -0.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0028   -0.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17  8  2  0  0  0  0
 17  9  1  0  0  0  0
 18  4  1  0  0  0  0
 18 10  1  0  0  0  0
 18 12  2  0  0  0  0
 19  5  1  0  0  0  0
 19 11  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  2  0  0  0  0
 20 15  1  0  0  0  0
 20 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039712

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=C\C=C(C)/CC\C=C(C)/CC\C=C(C)/CC\1

> <INCHI_IDENTIFIER>
InChI=1S/C20H32/c1-16(2)20-14-12-18(4)10-6-8-17(3)9-7-11-19(5)13-15-20/h8,11-12,14,16H,6-7,9-10,13,15H2,1-5H3/b17-8-,18-12-,19-11-,20-14-

> <INCHI_KEY>
UJUWZMUCEGGBOH-CXDHOTJMSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.4681

> <EXACT_MASS>
272.250401024

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
35.15532509437216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1Z,3Z,7Z,11Z)-1,7,11-trimethyl-4-(propan-2-yl)cyclotetradeca-1,3,7,11-tetraene

> <ALOGPS_LOGP>
7.15

> <JCHEM_LOGP>
6.481307531333332

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
95.158

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1Z,3Z,7Z,11Z)-4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0039712
     RDKit          3D
gamma-Pinacene
 52 52  0  0  0  0  0  0  0  0999 V2000
   -0.8095   -3.1753    1.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0129   -2.5405    0.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086   -2.0384    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095   -1.4064    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0043   -0.2280   -0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0773    0.2665   -1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6602    1.5024   -0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1659   -0.7541   -1.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8848    0.6513   -0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8001    1.2288    1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2370    2.2787    1.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1529    3.6682    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5003    1.9840    1.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631    0.6374    1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1863    0.2360    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0017    0.1059   -0.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057    1.2243   -1.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4802   -0.9743   -1.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0502   -2.1199   -0.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6080   -2.5366   -0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0969   -3.8384    2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5844   -3.8153    1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1456   -2.3624    2.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5001   -2.1796    2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0379   -1.9650   -0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6106    0.4417   -2.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9079    1.3401    0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5976    1.7824   -1.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9318    2.3361   -0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7817   -1.6945   -2.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8988   -0.3353   -2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7093   -0.9029   -0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1147    0.3154   -0.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057    1.5837   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040    1.7296    1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829    0.4995    1.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4227    4.0864   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2189    3.7716    0.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0776    4.3783    1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2810    2.7655    1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037   -0.1334    1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3384    0.6940    2.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6918   -0.6361    1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9241    1.0784    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5644    1.8956   -1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1958    1.8142   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876    0.8311   -2.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635   -1.0252   -2.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3101   -2.0384    0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6588   -2.9978   -0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276   -1.8461   -1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5329   -3.5829   -1.0489 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
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 17 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.594  -5.724   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.184  -5.083   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.964   3.886   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.513  -1.880   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.105  -1.880   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   0.469   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.745   1.751   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.814   1.964   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.225   1.323   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.663   0.042   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.365   0.683   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.923  -2.521   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.485  -1.239   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.444  -2.093   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.855  -2.734   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.704  -4.656   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.334   2.391   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.033  -1.453   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.005  -0.812   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.334  -3.161   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   19                                                            
CONECT    6    8   10                                                       
CONECT    7    9   11                                                       
CONECT    8    6   17                                                       
CONECT    9    7   17                                                       
CONECT   10    6   18                                                       
CONECT   11    7   19                                                       
CONECT   12   14   18                                                       
CONECT   13   15   19                                                       
CONECT   14   12   20                                                       
CONECT   15   13   20                                                       
CONECT   16    1    2   20                                                  
CONECT   17    3    8    9                                                  
CONECT   18    4   10   12                                                  
CONECT   19    5   11   13                                                  
CONECT   20   14   15   16                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0039712
HETATM    1  C1  UNL     1      -0.810  -3.175   1.817  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.013  -2.541   0.714  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.209  -2.038   0.965  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.110  -1.406   0.045  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.004  -0.228  -0.528  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.077   0.266  -1.486  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.660   1.502  -0.857  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.166  -0.754  -1.630  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.885   0.651  -0.266  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.800   1.229   1.138  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.237   2.279   1.046  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.153   3.668   0.733  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.500   1.984   1.240  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.963   0.637   1.553  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.186   0.236   0.763  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.002   0.106  -0.676  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.406   1.224  -1.611  1.00  0.00           C  
HETATM   18  C18 UNL     1      -2.480  -0.974  -1.243  1.00  0.00           C  
HETATM   19  C19 UNL     1      -2.050  -2.120  -0.442  1.00  0.00           C  
HETATM   20  C20 UNL     1      -0.608  -2.537  -0.656  1.00  0.00           C  
HETATM   21  H1  UNL     1      -0.097  -3.838   2.389  1.00  0.00           H  
HETATM   22  H2  UNL     1      -1.584  -3.815   1.396  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.146  -2.362   2.459  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.500  -2.180   2.038  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.038  -1.965  -0.203  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.611   0.442  -2.449  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.908   1.340   0.192  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.598   1.782  -1.398  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.932   2.336  -0.918  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.782  -1.695  -2.081  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.899  -0.335  -2.355  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.709  -0.903  -0.685  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.115   0.315  -0.506  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.006   1.584  -0.904  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.804   1.730   1.291  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.683   0.500   1.927  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.423   4.086  -0.140  1.00  0.00           H  
HETATM   38  H18 UNL     1       1.219   3.772   0.461  1.00  0.00           H  
HETATM   39  H19 UNL     1      -0.078   4.378   1.575  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.281   2.766   1.172  1.00  0.00           H  
HETATM   41  H21 UNL     1      -1.204  -0.133   1.575  1.00  0.00           H  
HETATM   42  H22 UNL     1      -2.338   0.694   2.629  1.00  0.00           H  
HETATM   43  H23 UNL     1      -3.692  -0.636   1.233  1.00  0.00           H  
HETATM   44  H24 UNL     1      -3.924   1.078   0.937  1.00  0.00           H  
HETATM   45  H25 UNL     1      -2.564   1.896  -1.797  1.00  0.00           H  
HETATM   46  H26 UNL     1      -4.196   1.814  -1.069  1.00  0.00           H  
HETATM   47  H27 UNL     1      -3.888   0.831  -2.511  1.00  0.00           H  
HETATM   48  H28 UNL     1      -2.364  -1.025  -2.319  1.00  0.00           H  
HETATM   49  H29 UNL     1      -2.310  -2.038   0.632  1.00  0.00           H  
HETATM   50  H30 UNL     1      -2.659  -2.998  -0.810  1.00  0.00           H  
HETATM   51  H31 UNL     1      -0.128  -1.846  -1.337  1.00  0.00           H  
HETATM   52  H32 UNL     1      -0.533  -3.583  -1.049  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3   20
CONECT    3    4   24
CONECT    4    5    5   25
CONECT    5    6    9
CONECT    6    7    8   26
CONECT    7   27   28   29
CONECT    8   30   31   32
CONECT    9   10   33   34
CONECT   10   11   35   36
CONECT   11   12   13   13
CONECT   12   37   38   39
CONECT   13   14   40
CONECT   14   15   41   42
CONECT   15   16   43   44
CONECT   16   17   18   18
CONECT   17   45   46   47
CONECT   18   19   48
CONECT   19   20   49   50
CONECT   20   51   52
END

HMDB0039712
     RDKit          3D
gamma-Pinacene
 52 52  0  0  0  0  0  0  0  0999 V2000
   -0.8095   -3.1753    1.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0129   -2.5405    0.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086   -2.0384    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095   -1.4064    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0043   -0.2280   -0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0773    0.2665   -1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6602    1.5024   -0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1659   -0.7541   -1.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8848    0.6513   -0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8001    1.2288    1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2370    2.2787    1.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1529    3.6682    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5003    1.9840    1.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631    0.6374    1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1863    0.2360    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0017    0.1059   -0.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057    1.2243   -1.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4802   -0.9743   -1.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0502   -2.1199   -0.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6080   -2.5366   -0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0969   -3.8384    2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5844   -3.8153    1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1456   -2.3624    2.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5001   -2.1796    2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0379   -1.9650   -0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6106    0.4417   -2.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9079    1.3401    0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5976    1.7824   -1.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9318    2.3361   -0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7817   -1.6945   -2.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8988   -0.3353   -2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7093   -0.9029   -0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1147    0.3154   -0.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057    1.5837   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040    1.7296    1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829    0.4995    1.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4227    4.0864   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2189    3.7716    0.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0776    4.3783    1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2810    2.7655    1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037   -0.1334    1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3384    0.6940    2.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6918   -0.6361    1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9241    1.0784    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5644    1.8956   -1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1958    1.8142   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876    0.8311   -2.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635   -1.0252   -2.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3101   -2.0384    0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6588   -2.9978   -0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276   -1.8461   -1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5329   -3.5829   -1.0489 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
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 17 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
g-Pinacene	Generator
Γ-pinacene	Generator

Chemical Formula

C₂₀H₃₂

Average Molecular Weight

272.4681

Monoisotopic Molecular Weight

272.250401024

IUPAC Name

(1Z,3Z,7Z,11Z)-1,7,11-trimethyl-4-(propan-2-yl)cyclotetradeca-1,3,7,11-tetraene

Traditional Name

(1Z,3Z,7Z,11Z)-4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene

CAS Registry Number

37905-11-6

SMILES

CC(C)C1=C\C=C(C)/CC\C=C(C)/CC\C=C(C)/CC\1

InChI Identifier

InChI=1S/C20H32/c1-16(2)20-14-12-18(4)10-6-8-17(3)9-7-11-19(5)13-15-20/h8,11-12,14,16H,6-7,9-10,13,15H2,1-5H3/b17-8-,18-12-,19-11-,20-14-

InChI Key

UJUWZMUCEGGBOH-CXDHOTJMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cembrane diterpenoids. These are diterpenoids with a structure based a cembrane skeleton, which is characterized by the presence of an isopropyl group at C-1 and by three symmetrically disposed methyl groups a the t C-4, -8 and -12 positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Cembrane diterpenoids

Alternative Parents

Substituents

Cembrane diterpenoid
Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0039712)
Cell membrane (HMDB: HMDB0039712)

Cellular substructure

Extracellular (HMDB: HMDB0039712)
Membrane (HMDB: HMDB0039712)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039712)

Source

Endogenous

Endogenous (HMDB: HMDB0039712)

Plant

Plant (HMDB: HMDB0039712)

Animal

Animal (HMDB: HMDB0039712)

Exogenous

Food

Food (HMDB: HMDB0039712)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0039712)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0039712)

Cellular process

Cell signaling (HMDB: HMDB0039712)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0039712)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0039712)

Nutrient

Nutrient (HMDB: HMDB0039712)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039712)

Emulsifier (HMDB: HMDB0039712)

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	5.4e-05 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0038 g/L	ALOGPS
logP	7.15	ALOGPS
logP	6.48	ChemAxon
logS	-4.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.16 m³·mol⁻¹	ChemAxon
Polarizability	35.16 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	166.965	31661259
DarkChem	[M-H]-	164.659	31661259
DeepCCS	[M+H]+	177.818	30932474
DeepCCS	[M-H]-	175.46	30932474
DeepCCS	[M-2H]-	208.346	30932474
DeepCCS	[M+Na]+	183.911	30932474
AllCCS	[M+H]+	168.7	32859911
AllCCS	[M+H-H2O]+	165.1	32859911
AllCCS	[M+NH4]+	172.0	32859911
AllCCS	[M+Na]+	172.9	32859911
AllCCS	[M-H]-	179.1	32859911
AllCCS	[M+Na-2H]-	179.7	32859911
AllCCS	[M+HCOO]-	180.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Pinacene	CC(C)C1=C\C=C(C)/CC\C=C(C)/CC\C=C(C)/CC\1	2223.0	Standard polar	33892256
gamma-Pinacene	CC(C)C1=C\C=C(C)/CC\C=C(C)/CC\C=C(C)/CC\1	1962.9	Standard non polar	33892256
gamma-Pinacene	CC(C)C1=C\C=C(C)/CC\C=C(C)/CC\C=C(C)/CC\1	2005.3	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-Pinacene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-1090000000-f1c9ded279d4e1f925bc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Pinacene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Pinacene 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-Pinacene 10V, Positive-QTOF	splash10-00di-0090000000-e2b89a7fe885d8742c86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pinacene 20V, Positive-QTOF	splash10-00di-1980000000-627bc4e5186ed5207695	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pinacene 40V, Positive-QTOF	splash10-0f79-1940000000-32d3090c65631ab97905	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pinacene 10V, Negative-QTOF	splash10-00di-0090000000-05bc311651d4369f26a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pinacene 20V, Negative-QTOF	splash10-00di-0090000000-51d4008db4ffd7caf30c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pinacene 40V, Negative-QTOF	splash10-0a4v-1390000000-572b22681cc4d88d538e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pinacene 10V, Negative-QTOF	splash10-00di-0090000000-4c81b77566a3712a2980	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pinacene 20V, Negative-QTOF	splash10-00di-0090000000-4c81b77566a3712a2980	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pinacene 40V, Negative-QTOF	splash10-0abi-0090000000-07fe9437e59eee3293a0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pinacene 10V, Positive-QTOF	splash10-00di-0090000000-d10590d89514cc99f1e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pinacene 20V, Positive-QTOF	splash10-00e9-0090000000-3609ade1f226129e72f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pinacene 40V, Positive-QTOF	splash10-0006-9000000000-1721daf5b5a2632b9ef7	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB019347

KNApSAcK ID

C00057376

Chemspider ID

30777362

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6004093

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1879641

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-Pinacene (HMDB0039712)

MOL for HMDB0039712 (gamma-Pinacene)

3D MOL for HMDB0039712 (gamma-Pinacene)

3D SDF for HMDB0039712 (gamma-Pinacene)

3D-SDF for HMDB0039712 (gamma-Pinacene)

PDB for HMDB0039712 (gamma-Pinacene)

3D PDB for HMDB0039712 (gamma-Pinacene)

SMILES for HMDB0039712 (gamma-Pinacene)

INCHI for HMDB0039712 (gamma-Pinacene)

Structure for HMDB0039712 (gamma-Pinacene)

3D Structure for HMDB0039712 (gamma-Pinacene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra