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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:05:30 UTC

Update Date

2022-03-07 02:55:06 UTC

HMDB ID

HMDB0036908

Secondary Accession Numbers

HMDB36908

Metabolite Identification

Common Name

Sesquicineol

Description

Sesquicineol belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. Based on a literature review very few articles have been published on Sesquicineol.

Structure

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

HMDB0036908
     RDKit          3D
Sesquicineol
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.7253   -1.3656    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8485   -0.1929   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4202    1.1669    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5622   -0.3936   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289    0.7164   -0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4901    0.8742    0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4982   -0.2109    0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0663   -1.5080    0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112    0.2652    1.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164    0.4759    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6104    1.1925    1.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6442    1.3652   -0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7790    0.6421   -1.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2019   -0.5555   -0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2771   -1.5698   -0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3613   -0.8225    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064   -1.7872    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4740   -2.1148   -0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7979   -1.1286    0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5153    1.0935    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2632    1.7774   -0.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0266    1.7174    0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2495   -1.4271   -0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2510    1.6639   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2962    0.7445   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508    1.0204    1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0497    1.8479    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1851   -2.2927    0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0036   -1.4262    1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6834   -1.9340    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3276    0.9912    2.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6841    0.9486    1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5393    2.3028    1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6947    1.4181   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3378    2.3846   -0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0219    1.2809   -2.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4167    0.2578   -2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4407   -1.0737   -1.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -2.0215   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9225   -2.3694    0.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8083   -1.3966    0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1538   -0.5570   -0.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14  7  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END


  Mrv0541 02241219172D          

 16 17  0  0  0  0            999 V2000
   -0.1206   -0.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5530   -0.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9647   -0.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9647    0.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1077   -0.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -1.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5515   -1.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1450    1.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7140    1.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007    0.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154    1.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302    0.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    1.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302    0.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  3  1  0  0  0  0
  2 10  1  0  0  0  0
  2 11  1  0  0  0  0
  2  6  1  0  0  0  0
  2  4  1  0  0  0  0
  3  4  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036908

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCCC1(C)OC2(C)CCC1CC2

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-12(2)6-5-9-15(4)13-7-10-14(3,16-15)11-8-13/h6,13H,5,7-11H2,1-4H3

> <INCHI_KEY>
BAQRIYKLDIPFQB-UHFFFAOYSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.977268179616534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-dimethyl-3-(4-methylpent-3-en-1-yl)-2-oxabicyclo[2.2.2]octane

> <ALOGPS_LOGP>
5.17

> <JCHEM_LOGP>
4.086087611333333

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.207915181653882

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
69.5865

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3-dimethyl-3-(4-methylpent-3-en-1-yl)-2-oxabicyclo[2.2.2]octane

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036908
     RDKit          3D
Sesquicineol
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.7253   -1.3656    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8485   -0.1929   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4202    1.1669    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5622   -0.3936   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289    0.7164   -0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4901    0.8742    0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4982   -0.2109    0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0663   -1.5080    0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112    0.2652    1.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164    0.4759    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6104    1.1925    1.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6442    1.3652   -0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7790    0.6421   -1.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2019   -0.5555   -0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2771   -1.5698   -0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3613   -0.8225    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064   -1.7872    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4740   -2.1148   -0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7979   -1.1286    0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5153    1.0935    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2632    1.7774   -0.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0266    1.7174    0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2495   -1.4271   -0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2510    1.6639   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2962    0.7445   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508    1.0204    1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0497    1.8479    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1851   -2.2927    0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0036   -1.4262    1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6834   -1.9340    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3276    0.9912    2.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6841    0.9486    1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5393    2.3028    1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6947    1.4181   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3378    2.3846   -0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0219    1.2809   -2.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4167    0.2578   -2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4407   -1.0737   -1.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -2.0215   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9225   -2.3694    0.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8083   -1.3966    0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1538   -0.5570   -0.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14  7  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.225  -1.791   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   1.857   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.032  -0.577   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   0.145   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.801  -1.292   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.801   0.711   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.934  -0.575   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.130  -1.891   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.029  -2.629   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.004   2.629   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.333   2.626   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.001   1.857   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.335   2.626   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.670   1.857   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.004   2.626   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.670   0.315   0.000  0.00  0.00           C+0
CONECT    1    5    3                                                       
CONECT    2   10   11    6    4                                             
CONECT    3    1    4                                                       
CONECT    4    2    3    7                                                  
CONECT    5    1    8    9    6                                             
CONECT    6    2    5                                                       
CONECT    7    4    8                                                       
CONECT    8    5    7                                                       
CONECT    9    5                                                            
CONECT   10    2                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0036908
HETATM    1  C1  UNL     1       4.725  -1.366   0.144  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.849  -0.193  -0.101  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.420   1.167   0.021  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.562  -0.394  -0.426  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.629   0.716  -0.684  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.490   0.874   0.238  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.498  -0.211   0.387  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.066  -1.508   0.906  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.511   0.265   1.239  1.00  0.00           O  
HETATM   10  C9  UNL     1      -2.716   0.476   0.631  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.610   1.192   1.627  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.644   1.365  -0.596  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.779   0.642  -1.601  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.202  -0.555  -0.919  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.277  -1.570  -0.596  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.361  -0.822   0.160  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.606  -1.787   1.164  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.474  -2.115  -0.651  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.798  -1.129   0.005  1.00  0.00           H  
HETATM   20  H4  UNL     1       5.515   1.094   0.165  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.263   1.777  -0.892  1.00  0.00           H  
HETATM   22  H6  UNL     1       4.027   1.717   0.917  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.249  -1.427  -0.510  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.251   1.664  -0.597  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.296   0.744  -1.753  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.951   1.020   1.274  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.050   1.848   0.095  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.185  -2.293   0.129  1.00  0.00           H  
HETATM   29  H13 UNL     1       1.004  -1.426   1.454  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.683  -1.934   1.663  1.00  0.00           H  
HETATM   31  H15 UNL     1      -3.328   0.991   2.668  1.00  0.00           H  
HETATM   32  H16 UNL     1      -4.684   0.949   1.469  1.00  0.00           H  
HETATM   33  H17 UNL     1      -3.539   2.303   1.486  1.00  0.00           H  
HETATM   34  H18 UNL     1      -3.695   1.418  -0.990  1.00  0.00           H  
HETATM   35  H19 UNL     1      -2.338   2.385  -0.387  1.00  0.00           H  
HETATM   36  H20 UNL     1      -1.022   1.281  -2.061  1.00  0.00           H  
HETATM   37  H21 UNL     1      -2.417   0.258  -2.438  1.00  0.00           H  
HETATM   38  H22 UNL     1      -0.441  -1.074  -1.566  1.00  0.00           H  
HETATM   39  H23 UNL     1      -2.681  -2.021  -1.522  1.00  0.00           H  
HETATM   40  H24 UNL     1      -1.922  -2.369   0.053  1.00  0.00           H  
HETATM   41  H25 UNL     1      -3.808  -1.397   0.966  1.00  0.00           H  
HETATM   42  H26 UNL     1      -4.154  -0.557  -0.570  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4    4
CONECT    3   20   21   22
CONECT    4    5   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8    9   14
CONECT    8   28   29   30
CONECT    9   10
CONECT   10   11   12   16
CONECT   11   31   32   33
CONECT   12   13   34   35
CONECT   13   14   36   37
CONECT   14   15   38
CONECT   15   16   39   40
CONECT   16   41   42
END

HMDB0036908
     RDKit          3D
Sesquicineol
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.7253   -1.3656    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8485   -0.1929   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4202    1.1669    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5622   -0.3936   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289    0.7164   -0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4901    0.8742    0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4982   -0.2109    0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0663   -1.5080    0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112    0.2652    1.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164    0.4759    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6104    1.1925    1.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6442    1.3652   -0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7790    0.6421   -1.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2019   -0.5555   -0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2771   -1.5698   -0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3613   -0.8225    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064   -1.7872    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4740   -2.1148   -0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7979   -1.1286    0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5153    1.0935    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2632    1.7774   -0.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0266    1.7174    0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2495   -1.4271   -0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2510    1.6639   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2962    0.7445   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508    1.0204    1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0497    1.8479    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1851   -2.2927    0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0036   -1.4262    1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6834   -1.9340    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3276    0.9912    2.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6841    0.9486    1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5393    2.3028    1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6947    1.4181   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3378    2.3846   -0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0219    1.2809   -2.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4167    0.2578   -2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4407   -1.0737   -1.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -2.0215   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9225   -2.3694    0.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8083   -1.3966    0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1538   -0.5570   -0.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14  7  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,7-Epoxy-10-bisabolene	HMDB
3,7-oxido-10-Bisabolene	HMDB
BISABOL-10-ene,3,7-oxide	HMDB
Sesquicineole	HMDB

Chemical Formula

C₁₅H₂₆O

Average Molecular Weight

222.3663

Monoisotopic Molecular Weight

222.198365454

IUPAC Name

1,3-dimethyl-3-(4-methylpent-3-en-1-yl)-2-oxabicyclo[2.2.2]octane

Traditional Name

1,3-dimethyl-3-(4-methylpent-3-en-1-yl)-2-oxabicyclo[2.2.2]octane

CAS Registry Number

90131-02-5

SMILES

CC(C)=CCCC1(C)OC2(C)CCC1CC2

InChI Identifier

InChI=1S/C15H26O/c1-12(2)6-5-9-15(4)13-7-10-14(3,16-15)11-8-13/h6,13H,5,7-11H2,1-4H3

InChI Key

BAQRIYKLDIPFQB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Oxane
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0036908)

Exogenous

Food

Food (HMDB: HMDB0036908)

Exogenous (HMDB: HMDB0036908)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036908)

Role

Biological role

Energy source (HMDB: HMDB0036908)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036908)

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	0.77 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	0.0032 g/L	ALOGPS
logP	5.17	ALOGPS
logP	4.09	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	69.59 m³·mol⁻¹	ChemAxon
Polarizability	27.98 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]+	155.055	31661259
DarkChem	[M-H]-	149.725	31661259
DeepCCS	[M+H]+	153.517	30932474
DeepCCS	[M-H]-	151.159	30932474
DeepCCS	[M-2H]-	186.107	30932474
DeepCCS	[M+Na]+	161.172	30932474
AllCCS	[M+H]+	154.2	32859911
AllCCS	[M+H-H2O]+	150.4	32859911
AllCCS	[M+NH4]+	157.7	32859911
AllCCS	[M+Na]+	158.8	32859911
AllCCS	[M-H]-	163.4	32859911
AllCCS	[M+Na-2H]-	164.0	32859911
AllCCS	[M+HCOO]-	164.7	32859911

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. Predicted by Afia on May 17, 2022.	7.51 minutes	32390414
Predicted by Siyang on May 30, 2022	19.2922 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.74 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2822.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	608.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	237.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	331.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	324.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	939.6 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	866.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1581.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	496.6 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	1433.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	685.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	415.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	571.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	674.6 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	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sesquicineol	CC(C)=CCCC1(C)OC2(C)CCC1CC2	1768.6	Standard polar	33892256
Sesquicineol	CC(C)=CCCC1(C)OC2(C)CCC1CC2	1489.4	Standard non polar	33892256
Sesquicineol	CC(C)=CCCC1(C)OC2(C)CCC1CC2	1491.6	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 - Sesquicineol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9820000000-cb1899f7d3642d81bc22	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sesquicineol 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 - Sesquicineol 10V, Positive-QTOF	splash10-00di-1290000000-703873260a1d72003a76	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquicineol 20V, Positive-QTOF	splash10-00xr-5950000000-a0368877e3ddbd006a78	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquicineol 40V, Positive-QTOF	splash10-0gb9-9600000000-6b3e40b6d68df10c9288	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquicineol 10V, Negative-QTOF	splash10-00di-0090000000-807b2757d3268b602774	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquicineol 20V, Negative-QTOF	splash10-00di-0090000000-4ffa64cda84a0fbb1cb2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquicineol 40V, Negative-QTOF	splash10-0kg9-2920000000-efa42f5f5b1a5c649f2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquicineol 10V, Positive-QTOF	splash10-00di-2590000000-4d9084bd27124c95d8e0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquicineol 20V, Positive-QTOF	splash10-001l-9110000000-0f92ffaa130fe30067f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquicineol 40V, Positive-QTOF	splash10-0159-9000000000-3792bd4f5d313bbf5e0d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquicineol 10V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquicineol 20V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesquicineol 40V, Negative-QTOF	splash10-00di-0190000000-3627d8cd32c757adc546	2021-09-24	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

FDB015871

KNApSAcK ID

C00011918

Chemspider ID

302913

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

341779

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1566731

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Sesquicineol (HMDB0036908)

MOL for HMDB0036908 (Sesquicineol)

3D MOL for HMDB0036908 (Sesquicineol)

3D SDF for HMDB0036908 (Sesquicineol)

3D-SDF for HMDB0036908 (Sesquicineol)

PDB for HMDB0036908 (Sesquicineol)

3D PDB for HMDB0036908 (Sesquicineol)

SMILES for HMDB0036908 (Sesquicineol)

INCHI for HMDB0036908 (Sesquicineol)

Structure for HMDB0036908 (Sesquicineol)

3D Structure for HMDB0036908 (Sesquicineol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra