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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:16:52 UTC

Update Date

2022-03-07 02:55:10 UTC

HMDB ID

HMDB0037038

Secondary Accession Numbers

HMDB37038

Metabolite Identification

Common Name

Cyclodehydroisolubimin

Description

Cyclodehydroisolubimin belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Based on a literature review a significant number of articles have been published on Cyclodehydroisolubimin.

Structure

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

HMDB0037038
     RDKit          3D
Cyclodehydroisolubimin
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.3596    1.5074   -0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1009    0.2229   -0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2351   -0.7372   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7424   -0.2905   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -0.9427    1.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0933   -1.2248    0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598    0.0286    0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    0.7633   -0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.9816    1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0079    1.8502    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8514    1.2685   -1.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5776   -0.0908   -0.9536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0671   -0.7789   -2.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8565   -0.7293   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2227   -0.4110    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3510   -0.7291    1.2514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3362    0.2585    1.8669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3934    1.8842   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6045    2.2709   -0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9192   -1.7320    0.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5698   -0.9062   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1079   -0.3360    0.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5142   -1.0632   -1.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4238   -0.2105    1.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569   -1.8564    1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131   -1.6039    1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0973   -2.0251   -0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9672    1.5587    0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5098    1.2115   -1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658    1.5450    1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0906    1.9169    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659    2.8811    0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9077   -1.8441   -1.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840   -0.3133   -2.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -0.7661   -2.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6665   -0.3491   -1.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8538   -1.8375   -0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9245   -0.4187    2.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8992    1.0468    2.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  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
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  8  4  1  0
 17  9  1  0
 12  7  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
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
M  END


  Mrv0541 05061309312D          

 17 19  0  0  0  0            999 V2000
   -0.3223    2.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0966    2.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0569   -0.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4796    0.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3193   -0.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9893   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8459    0.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6113   -0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400   -1.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3383    2.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406    1.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605   -0.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1275   -1.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999   -0.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393   -2.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -1.6427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  4  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  3  1  0  0  0  0
 14  8  1  0  0  0  0
 15  5  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  2  0  0  0  0
 17  9  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037038

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1CCC2(C1)C1COC2(C)CC(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-10(2)11-4-5-15(7-11)12-6-13(16)8-14(15,3)17-9-12/h11-12H,1,4-9H2,2-3H3

> <INCHI_KEY>
YHIWYGHFGRMQMO-UHFFFAOYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.750686650954655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-4'-(prop-1-en-2-yl)-6-oxaspiro[bicyclo[3.2.1]octane-8,1'-cyclopentane]-3-one

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
2.467303798333333

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.248828573544372

> <JCHEM_PKA_STRONGEST_BASIC>
-4.173271438940905

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
67.0365

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-4'-(prop-1-en-2-yl)-6-oxaspiro[bicyclo[3.2.1]octane-8,1'-cyclopentane]-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037038
     RDKit          3D
Cyclodehydroisolubimin
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.3596    1.5074   -0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1009    0.2229   -0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2351   -0.7372   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7424   -0.2905   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -0.9427    1.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0933   -1.2248    0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598    0.0286    0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    0.7633   -0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.9816    1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0079    1.8502    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8514    1.2685   -1.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5776   -0.0908   -0.9536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0671   -0.7789   -2.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8565   -0.7293   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2227   -0.4110    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3510   -0.7291    1.2514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3362    0.2585    1.8669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3934    1.8842   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6045    2.2709   -0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9192   -1.7320    0.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5698   -0.9062   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1079   -0.3360    0.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5142   -1.0632   -1.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4238   -0.2105    1.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569   -1.8564    1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131   -1.6039    1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0973   -2.0251   -0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9672    1.5587    0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5098    1.2115   -1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658    1.5450    1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0906    1.9169    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659    2.8811    0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9077   -1.8441   -1.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840   -0.3133   -2.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -0.7661   -2.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6665   -0.3491   -1.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8538   -1.8375   -0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9245   -0.4187    2.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8992    1.0468    2.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  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
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  8  4  1  0
 17  9  1  0
 12  7  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
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  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      -0.602   4.677   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.047   4.361   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.106  -0.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.895   1.474   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.596  -0.037   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.713  -1.011   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.579   1.179   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.008  -1.737   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.381  -2.363   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.631   3.754   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.449   2.225   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.980  -1.040   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.971  -2.537   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.194  -1.737   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.933  -0.219   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.740  -3.871   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.223  -3.066   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   14                                                            
CONECT    4    5   11                                                       
CONECT    5    4   15                                                       
CONECT    6   12   13                                                       
CONECT    7   11   15                                                       
CONECT    8   13   14                                                       
CONECT    9   12   17                                                       
CONECT   10    1    2   11                                                  
CONECT   11    4    7   10                                                  
CONECT   12    6    9   15                                                  
CONECT   13    6    8   16                                                  
CONECT   14    3    8   15   17                                             
CONECT   15    5    7   12   14                                             
CONECT   16   13                                                            
CONECT   17    9   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0037038
HETATM    1  C1  UNL     1       3.360   1.507  -0.509  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.101   0.223  -0.405  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.235  -0.737  -0.344  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.742  -0.290  -0.345  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.382  -0.943   1.001  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.093  -1.225   0.738  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.560   0.029   0.145  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.654   0.763  -0.398  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.265   0.982   1.071  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.008   1.850   0.056  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.851   1.268  -1.176  1.00  0.00           O  
HETATM   12  C11 UNL     1      -1.578  -0.091  -0.954  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.067  -0.779  -2.171  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.857  -0.729  -0.507  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.223  -0.411   0.886  1.00  0.00           C  
HETATM   16  O2  UNL     1      -4.351  -0.729   1.251  1.00  0.00           O  
HETATM   17  C15 UNL     1      -2.336   0.259   1.867  1.00  0.00           C  
HETATM   18  H1  UNL     1       4.393   1.884  -0.550  1.00  0.00           H  
HETATM   19  H2  UNL     1       2.605   2.271  -0.563  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.919  -1.732   0.065  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.570  -0.906  -1.392  1.00  0.00           H  
HETATM   22  H5  UNL     1       5.108  -0.336   0.203  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.514  -1.063  -1.111  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.424  -0.210   1.824  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.957  -1.856   1.172  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.613  -1.604   1.613  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.097  -2.025  -0.058  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.967   1.559   0.342  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.510   1.212  -1.375  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.566   1.545   1.684  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.091   1.917   0.278  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.566   2.881   0.068  1.00  0.00           H  
HETATM   33  H16 UNL     1      -0.908  -1.844  -1.921  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.184  -0.313  -2.631  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.884  -0.766  -2.933  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.667  -0.349  -1.169  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.854  -1.837  -0.635  1.00  0.00           H  
HETATM   38  H21 UNL     1      -1.924  -0.419   2.629  1.00  0.00           H  
HETATM   39  H22 UNL     1      -2.899   1.047   2.438  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3    4
CONECT    3   20   21   22
CONECT    4    5    8   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8    9   12
CONECT    8   28   29
CONECT    9   10   17   30
CONECT   10   11   31   32
CONECT   11   12
CONECT   12   13   14
CONECT   13   33   34   35
CONECT   14   15   36   37
CONECT   15   16   16   17
CONECT   17   38   39
END

HMDB0037038
     RDKit          3D
Cyclodehydroisolubimin
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.3596    1.5074   -0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1009    0.2229   -0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2351   -0.7372   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7424   -0.2905   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -0.9427    1.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0933   -1.2248    0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598    0.0286    0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    0.7633   -0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.9816    1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0079    1.8502    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8514    1.2685   -1.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5776   -0.0908   -0.9536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0671   -0.7789   -2.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8565   -0.7293   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2227   -0.4110    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3510   -0.7291    1.2514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3362    0.2585    1.8669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3934    1.8842   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6045    2.2709   -0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9192   -1.7320    0.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5698   -0.9062   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1079   -0.3360    0.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5142   -1.0632   -1.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4238   -0.2105    1.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569   -1.8564    1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131   -1.6039    1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0973   -2.0251   -0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9672    1.5587    0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5098    1.2115   -1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658    1.5450    1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0906    1.9169    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659    2.8811    0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9077   -1.8441   -1.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840   -0.3133   -2.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -0.7661   -2.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6665   -0.3491   -1.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8538   -1.8375   -0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9245   -0.4187    2.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8992    1.0468    2.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  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
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  8  4  1  0
 17  9  1  0
 12  7  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
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,10-Epoxy-11-spirovetiven-2-one	HMDB
Sulfonium, dodecyldimethyl- iodide	HMDB

Chemical Formula

C₁₅H₂₂O₂

Average Molecular Weight

234.334

Monoisotopic Molecular Weight

234.161979948

IUPAC Name

5-methyl-4'-(prop-1-en-2-yl)-6-oxaspiro[bicyclo[3.2.1]octane-8,1'-cyclopentane]-3-one

Traditional Name

5-methyl-4'-(prop-1-en-2-yl)-6-oxaspiro[bicyclo[3.2.1]octane-8,1'-cyclopentane]-3-one

CAS Registry Number

72055-93-7

SMILES

CC(=C)C1CCC2(C1)C1COC2(C)CC(=O)C1

InChI Identifier

InChI=1S/C15H22O2/c1-10(2)11-4-5-15(7-11)12-6-13(16)8-14(15,3)17-9-12/h11-12H,1,4-9H2,2-3H3

InChI Key

YHIWYGHFGRMQMO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Oxepane
Tetrahydrofuran
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0037038)
Cell membrane (HMDB: HMDB0037038)

Cellular substructure

Extracellular (HMDB: HMDB0037038)
Membrane (HMDB: HMDB0037038)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037038)

Source

Endogenous

Endogenous (HMDB: HMDB0037038)

Plant

Plant (HMDB: HMDB0037038)

Animal

Animal (HMDB: HMDB0037038)

Exogenous

Food

Food (HMDB: HMDB0037038)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0037038)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0037038)

Cellular process

Cell signaling (HMDB: HMDB0037038)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0037038)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0037038)

Nutrient

Nutrient (HMDB: HMDB0037038)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037038)

Emulsifier (HMDB: HMDB0037038)

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
Water Solubility	0.067 g/L	ALOGPS
logP	2.59	ALOGPS
logP	2.47	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	18.25	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.04 m³·mol⁻¹	ChemAxon
Polarizability	26.75 Å³	ChemAxon
Number of Rings	3	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]+	155.989	31661259
DarkChem	[M-H]-	152.685	31661259
DeepCCS	[M+H]+	155.793	30932474
DeepCCS	[M-H]-	153.435	30932474
DeepCCS	[M-2H]-	186.54	30932474
DeepCCS	[M+Na]+	161.887	30932474
AllCCS	[M+H]+	155.5	32859911
AllCCS	[M+H-H2O]+	151.7	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.9	32859911
AllCCS	[M-H]-	163.3	32859911
AllCCS	[M+Na-2H]-	163.4	32859911
AllCCS	[M+HCOO]-	163.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclodehydroisolubimin	CC(=C)C1CCC2(C1)C1COC2(C)CC(=O)C1	2541.3	Standard polar	33892256
Cyclodehydroisolubimin	CC(=C)C1CCC2(C1)C1COC2(C)CC(=O)C1	1747.7	Standard non polar	33892256
Cyclodehydroisolubimin	CC(=C)C1CCC2(C1)C1COC2(C)CC(=O)C1	1874.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclodehydroisolubimin,1TMS,isomer #1	C=C(C)C1CCC2(C1)C1C=C(O[Si](C)(C)C)CC2(C)OC1	1845.1	Semi standard non polar	33892256
Cyclodehydroisolubimin,1TMS,isomer #1	C=C(C)C1CCC2(C1)C1C=C(O[Si](C)(C)C)CC2(C)OC1	1759.3	Standard non polar	33892256
Cyclodehydroisolubimin,1TMS,isomer #2	C=C(C)C1CCC2(C1)C1COC2(C)C=C(O[Si](C)(C)C)C1	1850.0	Semi standard non polar	33892256
Cyclodehydroisolubimin,1TMS,isomer #2	C=C(C)C1CCC2(C1)C1COC2(C)C=C(O[Si](C)(C)C)C1	1765.1	Standard non polar	33892256
Cyclodehydroisolubimin,1TBDMS,isomer #1	C=C(C)C1CCC2(C1)C1C=C(O[Si](C)(C)C(C)(C)C)CC2(C)OC1	2083.5	Semi standard non polar	33892256
Cyclodehydroisolubimin,1TBDMS,isomer #1	C=C(C)C1CCC2(C1)C1C=C(O[Si](C)(C)C(C)(C)C)CC2(C)OC1	1962.2	Standard non polar	33892256
Cyclodehydroisolubimin,1TBDMS,isomer #2	C=C(C)C1CCC2(C1)C1COC2(C)C=C(O[Si](C)(C)C(C)(C)C)C1	2082.3	Semi standard non polar	33892256
Cyclodehydroisolubimin,1TBDMS,isomer #2	C=C(C)C1CCC2(C1)C1COC2(C)C=C(O[Si](C)(C)C(C)(C)C)C1	1959.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclodehydroisolubimin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9440000000-0ed03726272da8f88c91	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclodehydroisolubimin 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 - Cyclodehydroisolubimin 10V, Positive-QTOF	splash10-000i-0190000000-a6b5746e34222663523a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 20V, Positive-QTOF	splash10-00kr-4790000000-63ef827ae210e3b13e2a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 40V, Positive-QTOF	splash10-014m-9310000000-ce9ff938014642822401	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 10V, Negative-QTOF	splash10-001i-0090000000-d38cd97eac084545e563	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 20V, Negative-QTOF	splash10-001i-0090000000-4c5832e665dfd95f5da4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 40V, Negative-QTOF	splash10-0pvi-2940000000-91a5c066609e1c584a59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 10V, Positive-QTOF	splash10-000i-0390000000-cd7fca1e3e1027ed0ca0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 20V, Positive-QTOF	splash10-00kr-1960000000-e23513ff9fcec61a4338	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 40V, Positive-QTOF	splash10-0fsc-6490000000-792c5d642efcba5375c8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 10V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 20V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclodehydroisolubimin 40V, Negative-QTOF	splash10-001i-1290000000-0ccac9941aa10f30d4f4	2021-09-25	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

FDB016020

KNApSAcK ID

C00021575

Chemspider ID

35014354

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14258974

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

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 Cyclodehydroisolubimin (HMDB0037038)

MOL for HMDB0037038 (Cyclodehydroisolubimin)

3D MOL for HMDB0037038 (Cyclodehydroisolubimin)

3D SDF for HMDB0037038 (Cyclodehydroisolubimin)

3D-SDF for HMDB0037038 (Cyclodehydroisolubimin)

PDB for HMDB0037038 (Cyclodehydroisolubimin)

3D PDB for HMDB0037038 (Cyclodehydroisolubimin)

SMILES for HMDB0037038 (Cyclodehydroisolubimin)

INCHI for HMDB0037038 (Cyclodehydroisolubimin)

Structure for HMDB0037038 (Cyclodehydroisolubimin)

3D Structure for HMDB0037038 (Cyclodehydroisolubimin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra