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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:17:02 UTC

Update Date

2022-03-07 02:56:00 UTC

HMDB ID

HMDB0038935

Secondary Accession Numbers

HMDB38935

Metabolite Identification

Common Name

Kamahine C

Description

Kamahine C belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. Based on a literature review a significant number of articles have been published on Kamahine C.

Structure

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

HMDB0038935
     RDKit          3D
Kamahine C
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.0913    2.5894   -1.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1659    1.5171   -0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7267    1.7643    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8732    0.6845    1.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3355    0.9482    2.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -0.6751    1.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758   -0.8160    1.3640 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4416   -0.0944    0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750   -0.8774   -0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7039   -0.6152    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9850   -0.5433   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120    0.7085    1.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    0.6224    2.6019 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888    1.0577    0.7090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527    0.1530   -0.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2809   -0.0881   -1.9831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000   -0.8491   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3421   -2.2439   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0795   -0.4941   -0.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302    2.5193   -2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1048    3.5977   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9296    2.5341   -2.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0611    2.7741    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835   -1.4750    1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7978   -0.4143   -1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251   -1.9442   -0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078   -1.4353    1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8654   -1.0886   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2451    0.4991   -0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855   -1.0352    0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693    1.4624    0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9050   -0.0718    2.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6715    0.6177   -2.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7834   -2.3142   -1.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3024   -2.8045   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377   -2.7781    0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1562    0.0072   -1.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6397    0.0619    0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6537   -1.4605   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 15  2  1  0
 17  6  1  0
 14  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  6 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END


  Mrv0541 02241216452D          

 19 21  0  0  0  0            999 V2000
    0.9221   -0.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4305   -0.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1065    0.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7824   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    1.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6143    0.3995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3685   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002   -1.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3685   -1.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1065    1.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1841    1.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0617    2.4895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992    1.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6148    0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5981    0.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7824   -1.9359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060   -1.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060   -0.7067    0.0000 O   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
  2  7  1  0  0  0  0
  2 15  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  2  0  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  5 15  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 19  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 18  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038935

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC2(OC1O)OC1C(=O)C=C(C)C2(O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O5/c1-7-6-13(19-11(7)16)14(17)8(2)5-9(15)10(18-13)12(14,3)4/h5,7,10-11,16-17H,6H2,1-4H3

> <INCHI_KEY>
NKEIHMMKFOXWAO-UHFFFAOYSA-N

> <FORMULA>
C14H20O5

> <MOLECULAR_WEIGHT>
268.3056

> <EXACT_MASS>
268.13107375

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.555742414939495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,5'-dihydroxy-4,4',8,8-tetramethyl-7-oxaspiro[bicyclo[3.2.1]octane-6,2'-oxolan]-3-en-2-one

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
1.4984571329999996

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.376880907660592

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.766169251690608

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0615141186759685

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
67.1147

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,5'-dihydroxy-4,4',8,8-tetramethyl-7-oxaspiro[bicyclo[3.2.1]octane-6,2'-oxolan]-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038935
     RDKit          3D
Kamahine C
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.0913    2.5894   -1.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1659    1.5171   -0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7267    1.7643    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8732    0.6845    1.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3355    0.9482    2.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -0.6751    1.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758   -0.8160    1.3640 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4416   -0.0944    0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750   -0.8774   -0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7039   -0.6152    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9850   -0.5433   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120    0.7085    1.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    0.6224    2.6019 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888    1.0577    0.7090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527    0.1530   -0.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2809   -0.0881   -1.9831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000   -0.8491   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3421   -2.2439   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0795   -0.4941   -0.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302    2.5193   -2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1048    3.5977   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9296    2.5341   -2.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0611    2.7741    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835   -1.4750    1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7978   -0.4143   -1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251   -1.9442   -0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078   -1.4353    1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8654   -1.0886   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2451    0.4991   -0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855   -1.0352    0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693    1.4624    0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9050   -0.0718    2.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6715    0.6177   -2.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7834   -2.3142   -1.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3024   -2.8045   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377   -2.7781    0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1562    0.0072   -1.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6397    0.0619    0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6537   -1.4605   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 15  2  1  0
 17  6  1  0
 14  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  6 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  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  O   UNK     0       1.721  -1.319   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.804  -0.056   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.065   0.746   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.327  -0.171   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.344   1.893   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.147   0.746   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.688  -0.630   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -2.008   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.688  -3.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.114  -4.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.065   2.467   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.344   3.156   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.115   4.647   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.492   3.156   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.148   1.434   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.983   1.549   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.327  -3.614   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.065  -2.811   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.065  -1.319   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   15                                             
CONECT    3    2    4   11                                                  
CONECT    4    3                                                            
CONECT    5    6   12   15                                                  
CONECT    6    5    7                                                       
CONECT    7    2    6    8   19                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9                                                            
CONECT   11    3   12                                                       
CONECT   12    5   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    2    5   14   16                                             
CONECT   16   15                                                            
CONECT   17   18                                                            
CONECT   18    9   17   19                                                  
CONECT   19    7   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0038935
HETATM    1  C1  UNL     1      -1.091   2.589  -1.470  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.166   1.517  -0.464  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.727   1.764   0.731  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.873   0.684   1.694  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.336   0.948   2.826  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.480  -0.675   1.321  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.076  -0.816   1.364  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.442  -0.094   0.322  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.575  -0.877  -0.346  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.704  -0.615   0.629  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.985  -0.543  -0.167  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.312   0.708   1.218  1.00  0.00           C  
HETATM   13  O3  UNL     1       2.250   0.622   2.602  1.00  0.00           O  
HETATM   14  O4  UNL     1       1.089   1.058   0.709  1.00  0.00           O  
HETATM   15  C11 UNL     1      -0.653   0.153  -0.685  1.00  0.00           C  
HETATM   16  O5  UNL     1      -0.281  -0.088  -1.983  1.00  0.00           O  
HETATM   17  C12 UNL     1      -1.700  -0.849  -0.189  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.342  -2.244  -0.588  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.079  -0.494  -0.597  1.00  0.00           C  
HETATM   20  H1  UNL     1      -0.130   2.519  -2.057  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.105   3.598  -1.043  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.930   2.534  -2.223  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.061   2.774   0.952  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.983  -1.475   1.865  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.798  -0.414  -1.339  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.325  -1.944  -0.443  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.708  -1.435   1.376  1.00  0.00           H  
HETATM   28  H9  UNL     1       3.865  -1.089  -1.137  1.00  0.00           H  
HETATM   29  H10 UNL     1       4.245   0.499  -0.439  1.00  0.00           H  
HETATM   30  H11 UNL     1       4.785  -1.035   0.424  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.069   1.462   0.928  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.905  -0.072   2.882  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.672   0.618  -2.561  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.783  -2.314  -1.529  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.302  -2.805  -0.752  1.00  0.00           H  
HETATM   36  H17 UNL     1      -0.838  -2.778   0.256  1.00  0.00           H  
HETATM   37  H18 UNL     1      -3.156   0.007  -1.574  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.640   0.062   0.199  1.00  0.00           H  
HETATM   39  H20 UNL     1      -3.654  -1.460  -0.713  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   15
CONECT    3    4   23
CONECT    4    5    5    6
CONECT    6    7   17   24
CONECT    7    8
CONECT    8    9   14   15
CONECT    9   10   25   26
CONECT   10   11   12   27
CONECT   11   28   29   30
CONECT   12   13   14   31
CONECT   13   32
CONECT   15   16   17
CONECT   16   33
CONECT   17   18   19
CONECT   18   34   35   36
CONECT   19   37   38   39
END

HMDB0038935
     RDKit          3D
Kamahine C
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.0913    2.5894   -1.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1659    1.5171   -0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7267    1.7643    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8732    0.6845    1.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3355    0.9482    2.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -0.6751    1.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758   -0.8160    1.3640 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4416   -0.0944    0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750   -0.8774   -0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7039   -0.6152    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9850   -0.5433   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120    0.7085    1.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    0.6224    2.6019 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888    1.0577    0.7090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527    0.1530   -0.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2809   -0.0881   -1.9831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000   -0.8491   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3421   -2.2439   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0795   -0.4941   -0.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302    2.5193   -2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1048    3.5977   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9296    2.5341   -2.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0611    2.7741    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835   -1.4750    1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7978   -0.4143   -1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251   -1.9442   -0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078   -1.4353    1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8654   -1.0886   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2451    0.4991   -0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855   -1.0352    0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693    1.4624    0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9050   -0.0718    2.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6715    0.6177   -2.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7834   -2.3142   -1.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3024   -2.8045   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377   -2.7781    0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1562    0.0072   -1.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6397    0.0619    0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6537   -1.4605   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 15  2  1  0
 17  6  1  0
 14  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  6 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₂₀O₅

Average Molecular Weight

268.3056

Monoisotopic Molecular Weight

268.13107375

IUPAC Name

5,5'-dihydroxy-4,4',8,8-tetramethyl-7-oxaspiro[bicyclo[3.2.1]octane-6,2'-oxolan]-3-en-2-one

Traditional Name

5,5'-dihydroxy-4,4',8,8-tetramethyl-7-oxaspiro[bicyclo[3.2.1]octane-6,2'-oxolan]-3-en-2-one

CAS Registry Number

144841-11-2

SMILES

CC1CC2(OC1O)OC1C(=O)C=C(C)C2(O)C1(C)C

InChI Identifier

InChI=1S/C14H20O5/c1-7-6-13(19-11(7)16)14(17)8(2)5-9(15)10(18-13)12(14,3)4/h5,7,10-11,16-17H,6H2,1-4H3

InChI Key

NKEIHMMKFOXWAO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Cyclohexenone
Tetrahydrofuran
Tertiary alcohol
Ketone
Hemiacetal
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038935)
Cytoplasm (HMDB: HMDB0038935)

Source

Exogenous

Food

Food (HMDB: HMDB0038935)

Not Available

Nutrient (HMDB: HMDB0038935)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038935)

Emulsifier (HMDB: HMDB0038935)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	152 - 154 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	169.9 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	11.8 g/L	ALOGPS
logP	0.4	ALOGPS
logP	1.5	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.77	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.11 m³·mol⁻¹	ChemAxon
Polarizability	27.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	161.013	31661259
DarkChem	[M-H]-	158.221	31661259
DeepCCS	[M+H]+	165.987	30932474
DeepCCS	[M-H]-	163.629	30932474
DeepCCS	[M-2H]-	196.516	30932474
DeepCCS	[M+Na]+	172.081	30932474
AllCCS	[M+H]+	160.9	32859911
AllCCS	[M+H-H2O]+	157.3	32859911
AllCCS	[M+NH4]+	164.2	32859911
AllCCS	[M+Na]+	165.1	32859911
AllCCS	[M-H]-	167.0	32859911
AllCCS	[M+Na-2H]-	167.0	32859911
AllCCS	[M+HCOO]-	167.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Kamahine C	CC1CC2(OC1O)OC1C(=O)C=C(C)C2(O)C1(C)C	3122.6	Standard polar	33892256
Kamahine C	CC1CC2(OC1O)OC1C(=O)C=C(C)C2(O)C1(C)C	1857.1	Standard non polar	33892256
Kamahine C	CC1CC2(OC1O)OC1C(=O)C=C(C)C2(O)C1(C)C	2064.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Kamahine C,1TMS,isomer #1	CC1=CC(=O)C2OC3(CC(C)C(O[Si](C)(C)C)O3)C1(O)C2(C)C	2004.8	Semi standard non polar	33892256
Kamahine C,1TMS,isomer #2	CC1=CC(=O)C2OC3(CC(C)C(O)O3)C1(O[Si](C)(C)C)C2(C)C	2040.9	Semi standard non polar	33892256
Kamahine C,1TMS,isomer #3	CC1=CC(O[Si](C)(C)C)=C2OC3(CC(C)C(O)O3)C1(O)C2(C)C	2056.5	Semi standard non polar	33892256
Kamahine C,2TMS,isomer #1	CC1=CC(=O)C2OC3(CC(C)C(O[Si](C)(C)C)O3)C1(O[Si](C)(C)C)C2(C)C	2068.3	Semi standard non polar	33892256
Kamahine C,2TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=C2OC3(CC(C)C(O[Si](C)(C)C)O3)C1(O)C2(C)C	2081.3	Semi standard non polar	33892256
Kamahine C,2TMS,isomer #3	CC1=CC(O[Si](C)(C)C)=C2OC3(CC(C)C(O)O3)C1(O[Si](C)(C)C)C2(C)C	2101.9	Semi standard non polar	33892256
Kamahine C,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2OC3(CC(C)C(O[Si](C)(C)C)O3)C1(O[Si](C)(C)C)C2(C)C	2125.9	Semi standard non polar	33892256
Kamahine C,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2OC3(CC(C)C(O[Si](C)(C)C)O3)C1(O[Si](C)(C)C)C2(C)C	2084.5	Standard non polar	33892256
Kamahine C,1TBDMS,isomer #1	CC1=CC(=O)C2OC3(CC(C)C(O[Si](C)(C)C(C)(C)C)O3)C1(O)C2(C)C	2236.2	Semi standard non polar	33892256
Kamahine C,1TBDMS,isomer #2	CC1=CC(=O)C2OC3(CC(C)C(O)O3)C1(O[Si](C)(C)C(C)(C)C)C2(C)C	2268.9	Semi standard non polar	33892256
Kamahine C,1TBDMS,isomer #3	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3(CC(C)C(O)O3)C1(O)C2(C)C	2280.2	Semi standard non polar	33892256
Kamahine C,2TBDMS,isomer #1	CC1=CC(=O)C2OC3(CC(C)C(O[Si](C)(C)C(C)(C)C)O3)C1(O[Si](C)(C)C(C)(C)C)C2(C)C	2540.2	Semi standard non polar	33892256
Kamahine C,2TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3(CC(C)C(O[Si](C)(C)C(C)(C)C)O3)C1(O)C2(C)C	2542.7	Semi standard non polar	33892256
Kamahine C,2TBDMS,isomer #3	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3(CC(C)C(O)O3)C1(O[Si](C)(C)C(C)(C)C)C2(C)C	2589.4	Semi standard non polar	33892256
Kamahine C,3TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3(CC(C)C(O[Si](C)(C)C(C)(C)C)O3)C1(O[Si](C)(C)C(C)(C)C)C2(C)C	2853.8	Semi standard non polar	33892256
Kamahine C,3TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3(CC(C)C(O[Si](C)(C)C(C)(C)C)O3)C1(O[Si](C)(C)C(C)(C)C)C2(C)C	2778.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Kamahine C GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udm-9410000000-f12b287974758c4afe51	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kamahine C GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-7943000000-77949c82a5bd89949c04	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kamahine C GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kamahine C 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 - Kamahine C 10V, Positive-QTOF	splash10-014i-1290000000-1762737c3b46b27e6c8f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kamahine C 20V, Positive-QTOF	splash10-0gb9-3190000000-48c6f6aaa21096b1c001	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kamahine C 40V, Positive-QTOF	splash10-0006-9400000000-01757d917cf6bb68ac3a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kamahine C 10V, Negative-QTOF	splash10-01b9-0190000000-1596b5c2888bc24b87c8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kamahine C 20V, Negative-QTOF	splash10-01ba-3290000000-be8baec56e42c374c54f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kamahine C 40V, Negative-QTOF	splash10-0lkc-9610000000-fe65a6fe3171ab4a121b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kamahine C 10V, Positive-QTOF	splash10-0uxr-0090000000-5fb63fd4ff0f7bac4e4e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kamahine C 20V, Positive-QTOF	splash10-0gb9-0490000000-bad3e6c557a66c7661f2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kamahine C 40V, Positive-QTOF	splash10-0udi-8910000000-0e24534f73b842569957	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kamahine C 10V, Negative-QTOF	splash10-014i-0090000000-eed592965a7585f56cb6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kamahine C 20V, Negative-QTOF	splash10-001i-0920000000-1d427f3b075b5232db88	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kamahine C 40V, Negative-QTOF	splash10-0159-3900000000-49759c2e9b2daa1901df	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB018410

KNApSAcK ID

Not Available

Chemspider ID

35014695

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85086233

PDB ID

Not Available

ChEBI ID

169469

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1872891

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 Kamahine C (HMDB0038935)

MOL for HMDB0038935 (Kamahine C)

3D MOL for HMDB0038935 (Kamahine C)

3D SDF for HMDB0038935 (Kamahine C)

3D-SDF for HMDB0038935 (Kamahine C)

PDB for HMDB0038935 (Kamahine C)

3D PDB for HMDB0038935 (Kamahine C)

SMILES for HMDB0038935 (Kamahine C)

INCHI for HMDB0038935 (Kamahine C)

Structure for HMDB0038935 (Kamahine C)

3D Structure for HMDB0038935 (Kamahine C)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra