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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 23:37:49 UTC

Update Date

2021-09-26 23:18:03 UTC

HMDB ID

HMDB0260107

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene

Description

(1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Based on a literature review very few articles have been published on (1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene. This compound has been identified in human blood as reported by (PMID: 31557052 ). (1s,4s,9r,10s,13r,14r)-5,5,9,14-tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0260107
     RDKit          3D
(1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexad...
 52 55  0  0  0  0  0  0  0  0999 V2000
    4.5601    1.5559   -0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3504    0.9696    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0659    1.4819   -0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2242    0.2650   -0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055    0.6641   -1.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0630    0.5279   -1.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5847    0.4430   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0409    0.4522   -0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7925    0.3860   -1.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5251    1.7758    0.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6145   -0.5958    0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9177   -1.2952    1.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4531   -1.0794    1.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8664   -0.7502    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9499   -1.9645   -0.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5522   -0.2682    0.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3044   -1.3425    1.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7801   -1.1830    1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3321   -0.4992    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3596   -0.6850   -0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3397    0.7745   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2716    1.9589   -1.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092    2.3918    0.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5018    1.1774    1.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    2.1058    0.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656    2.0857   -1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6094    1.7305   -2.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7633    0.0713   -2.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3986   -0.3862   -2.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4090   -2.0590    2.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2527   -0.2589    2.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0031   -2.0303    2.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171   -1.9440   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9953   -2.0747   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044   -2.8615    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9604   -1.3615    2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743   -2.3715    0.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3039   -2.1600    1.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -0.5765    2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3141   -0.9146   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789   -0.3689   -1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0451   -1.7240   -1.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
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  6  7  1  0
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 19  2  1  0
 16  4  1  0
 20  4  1  0
 14  7  1  0
  1 21  1  0
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 17 46  1  0
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 18 48  1  0
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 19 50  1  0
 20 51  1  0
 20 52  1  0
M  END


  Mrv1652309122101382D          

 20 23  0  0  0  0            999 V2000
    0.0435   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566   -0.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794    0.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2893    0.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5946    0.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    1.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582    0.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7638    0.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3206   -0.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0719   -0.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7095   -0.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883   -0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431   -1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8140   -0.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700   -1.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6141    1.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3527    1.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4 17  1  0  0  0  0
 12 18  1  0  0  0  0
  8 19  1  0  0  0  0
  8 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0260107

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC23CC1CCC2C1(C)CC=CC(C)(C)C1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C20H32/c1-14-12-20-11-8-16-18(2,3)9-5-10-19(16,4)17(20)7-6-15(14)13-20/h5,9,14-17H,6-8,10-13H2,1-4H3

> <INCHI_KEY>
AJMOAIFBRXSMBT-UHFFFAOYSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.476

> <EXACT_MASS>
272.25040103

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
34.13448943240268

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,5,9,14-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-6-ene

> <ALOGPS_LOGP>
6.18

> <JCHEM_LOGP>
5.601862319666666

> <ALOGPS_LOGS>
-7.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
86.98549999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.67e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,5,9,14-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-6-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0260107
     RDKit          3D
(1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexad...
 52 55  0  0  0  0  0  0  0  0999 V2000
    4.5601    1.5559   -0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3504    0.9696    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0659    1.4819   -0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2242    0.2650   -0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055    0.6641   -1.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0630    0.5279   -1.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5847    0.4430   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0409    0.4522   -0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7925    0.3860   -1.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5251    1.7758    0.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6145   -0.5958    0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8664   -0.7502    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9499   -1.9645   -0.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5522   -0.2682    0.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3044   -1.3425    1.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7801   -1.1830    1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3321   -0.4992    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3596   -0.6850   -0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3397    0.7745   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2716    1.9589   -1.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5018    1.1774    1.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7633    0.0713   -2.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4302    0.5782    1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3039   -2.1600    1.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3141   -0.9146   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789   -0.3689   -1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0451   -1.7240   -1.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
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  8 10  1  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
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 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19  2  1  0
 16  4  1  0
 20  4  1  0
 14  7  1  0
  1 21  1  0
  1 22  1  0
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  2 24  1  0
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  3 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
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 11 38  1  0
 12 39  1  0
 13 40  1  0
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 15 42  1  0
 15 43  1  0
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 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  C   UNK     0       0.081  -0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.599  -0.263   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.761   0.870   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.273   0.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.843   1.624   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.354   1.935   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.389   0.779   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.892   1.111   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.932  -0.025   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.468  -1.493   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.964  -1.825   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.924  -0.689   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.392  -1.066   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.934  -2.642   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.356  -2.939   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.310  -1.708   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.386  -0.839   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.477  -2.163   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.613   2.626   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.992   2.190   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13   17                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   19   20                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13   18                                             
CONECT   13   12    4   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16    4                                                       
CONECT   18   12                                                            
CONECT   19    8                                                            
CONECT   20    8                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0260107
HETATM    1  C1  UNL     1       4.560   1.556  -0.336  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.350   0.970   0.368  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.066   1.482  -0.165  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.224   0.265  -0.586  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.405   0.664  -1.742  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.063   0.528  -1.646  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.585   0.443  -0.229  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.041   0.452  -0.111  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.793   0.386  -1.422  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.525   1.776   0.520  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.614  -0.596   0.759  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.918  -1.295   1.598  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.453  -1.079   1.742  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.866  -0.750   0.378  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.950  -1.965  -0.486  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.552  -0.268   0.608  1.00  0.00           C  
HETATM   17  C17 UNL     1       1.304  -1.343   1.343  1.00  0.00           C  
HETATM   18  C18 UNL     1       2.780  -1.183   1.343  1.00  0.00           C  
HETATM   19  C19 UNL     1       3.332  -0.499   0.121  1.00  0.00           C  
HETATM   20  C20 UNL     1       2.360  -0.685  -1.000  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.340   0.774  -0.450  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.272   1.959  -1.339  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.009   2.392   0.222  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.502   1.177   1.456  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.507   2.106   0.558  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.266   2.086  -1.088  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.609   1.730  -2.070  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.763   0.071  -2.640  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.616   1.375  -2.126  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.399  -0.386  -2.202  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.174   1.376   0.268  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.870   0.153  -1.211  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.436  -0.374  -2.106  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.799   1.360  -1.959  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.742   2.049   1.260  1.00  0.00           H  
HETATM   36  H16 UNL     1      -4.490   1.655   1.012  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.516   2.579  -0.244  1.00  0.00           H  
HETATM   38  H18 UNL     1      -4.695  -0.813   0.708  1.00  0.00           H  
HETATM   39  H19 UNL     1      -3.409  -2.059   2.215  1.00  0.00           H  
HETATM   40  H20 UNL     1      -1.253  -0.259   2.481  1.00  0.00           H  
HETATM   41  H21 UNL     1      -1.003  -2.030   2.078  1.00  0.00           H  
HETATM   42  H22 UNL     1      -0.317  -1.944  -1.381  1.00  0.00           H  
HETATM   43  H23 UNL     1      -1.995  -2.075  -0.831  1.00  0.00           H  
HETATM   44  H24 UNL     1      -0.704  -2.862   0.091  1.00  0.00           H  
HETATM   45  H25 UNL     1       0.430   0.578   1.351  1.00  0.00           H  
HETATM   46  H26 UNL     1       0.960  -1.361   2.411  1.00  0.00           H  
HETATM   47  H27 UNL     1       1.074  -2.371   0.959  1.00  0.00           H  
HETATM   48  H28 UNL     1       3.304  -2.160   1.430  1.00  0.00           H  
HETATM   49  H29 UNL     1       3.118  -0.576   2.224  1.00  0.00           H  
HETATM   50  H30 UNL     1       4.314  -0.915  -0.157  1.00  0.00           H  
HETATM   51  H31 UNL     1       2.779  -0.369  -1.983  1.00  0.00           H  
HETATM   52  H32 UNL     1       2.045  -1.724  -1.025  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   19   24
CONECT    3    4   25   26
CONECT    4    5   16   20
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8   14   31
CONECT    8    9   10   11
CONECT    9   32   33   34
CONECT   10   35   36   37
CONECT   11   12   12   38
CONECT   12   13   39
CONECT   13   14   40   41
CONECT   14   15   16
CONECT   15   42   43   44
CONECT   16   17   45
CONECT   17   18   46   47
CONECT   18   19   48   49
CONECT   19   20   50
CONECT   20   51   52
END

HMDB0260107
     RDKit          3D
(1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexad...
 52 55  0  0  0  0  0  0  0  0999 V2000
    4.5601    1.5559   -0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3504    0.9696    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0659    1.4819   -0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2242    0.2650   -0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055    0.6641   -1.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0630    0.5279   -1.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5847    0.4430   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0409    0.4522   -0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7925    0.3860   -1.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5251    1.7758    0.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6145   -0.5958    0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9177   -1.2952    1.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4531   -1.0794    1.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8664   -0.7502    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9499   -1.9645   -0.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5522   -0.2682    0.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3044   -1.3425    1.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7801   -1.1830    1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3321   -0.4992    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3596   -0.6850   -0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3397    0.7745   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2716    1.9589   -1.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092    2.3918    0.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5018    1.1774    1.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    2.1058    0.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656    2.0857   -1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6094    1.7305   -2.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7633    0.0713   -2.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6162    1.3747   -2.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3986   -0.3862   -2.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1742    1.3757    0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8704    0.1530   -1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4357   -0.3744   -2.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7990    1.3599   -1.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7419    2.0494    1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4904    1.6551    1.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156    2.5789   -0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6955   -0.8128    0.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4090   -2.0590    2.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2527   -0.2589    2.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0031   -2.0303    2.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171   -1.9440   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9953   -2.0747   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044   -2.8615    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4302    0.5782    1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9604   -1.3615    2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743   -2.3715    0.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3039   -2.1600    1.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -0.5765    2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3141   -0.9146   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789   -0.3689   -1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0451   -1.7240   -1.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19  2  1  0
 16  4  1  0
 20  4  1  0
 14  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂

Average Molecular Weight

272.476

Monoisotopic Molecular Weight

272.25040103

IUPAC Name

5,5,9,14-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-6-ene

Traditional Name

5,5,9,14-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-6-ene

CAS Registry Number

Not Available

SMILES

CC1CC23CC1CCC2C1(C)CC=CC(C)(C)C1CC3

InChI Identifier

InChI=1S/C20H32/c1-14-12-20-11-8-16-18(2,3)9-5-10-19(16,4)17(20)7-6-15(14)13-20/h5,9,14-17H,6-8,10-13H2,1-4H3

InChI Key

AJMOAIFBRXSMBT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	6.18	ALOGPS
logP	5.6	ChemAxon
logS	-7	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	86.99 m³·mol⁻¹	ChemAxon
Polarizability	34.13 Å³	ChemAxon
Number of Rings	4	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
AllCCS	[M+H]+	170.169	32859911
AllCCS	[M+H-H2O]+	166.922	32859911
AllCCS	[M+Na]+	174.046	32859911
AllCCS	[M+NH4]+	173.18	32859911
AllCCS	[M-H]-	180.718	32859911
AllCCS	[M+Na-2H]-	180.822	32859911
AllCCS	[M+HCOO]-	181.07	32859911
DeepCCS	[M-2H]-	200.717	30932474
DeepCCS	[M+Na]+	176.282	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.92 minutes	32390414
Predicted by Siyang on May 30, 2022	23.9798 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.56 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2909.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	803.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	290.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	419.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	697.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	957.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	995.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1946.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	633.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1802.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	727.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	615.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	526.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	694.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene	CC1CC23CC1CCC2C1(C)CC=CC(C)(C)C1CC3	2423.4	Standard polar	33892256
(1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene	CC1CC23CC1CCC2C1(C)CC=CC(C)(C)C1CC3	1997.3	Standard non polar	33892256
(1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene	CC1CC23CC1CCC2C1(C)CC=CC(C)(C)C1CC3	2023.3	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 - (1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-0690000000-5bd41317e0cda2822535	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76058540

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene (HMDB0260107)

MOL for HMDB0260107 ((1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene)

3D MOL for HMDB0260107 ((1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene)

3D SDF for HMDB0260107 ((1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene)

3D-SDF for HMDB0260107 ((1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene)

PDB for HMDB0260107 ((1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene)

3D PDB for HMDB0260107 ((1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene)

SMILES for HMDB0260107 ((1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene)

INCHI for HMDB0260107 ((1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene)

Structure for HMDB0260107 ((1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene)

3D Structure for HMDB0260107 ((1S,4S,9R,10S,13R,14R)-5,5,9,14-Tetramethyltetracyclo[11.2.1.01,10.04,9]hexadec-6-ene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra