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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:21:09 UTC

Update Date

2022-03-07 02:56:21 UTC

HMDB ID

HMDB0039814

Secondary Accession Numbers

HMDB39814

Metabolite Identification

Common Name

Cyclocalopin E

Description

Cyclocalopin E belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Cyclocalopin E has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make cyclocalopin e a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cyclocalopin E.

Structure

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

HMDB0039814
     RDKit          3D
Cyclocalopin E
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.3943    2.0518    0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3690    0.6038    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7778    0.0664    0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -1.3092    0.3825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8116   -2.1430    0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0626   -3.3722   -0.0296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620   -1.6433   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299   -1.7655    0.9534 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5313   -1.0659    0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769   -2.0152   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2407   -0.6162    1.6716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958    0.6946    1.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056    1.2423    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0356    0.1307   -0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8322    0.5029   -1.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428   -0.3808   -2.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2094    0.8289   -0.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0239    1.0777   -1.8421 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    0.8775    0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8416   -0.0554    0.6964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900   -0.1596   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412    2.3666   -0.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775    2.3761   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4211    2.6439    0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361    0.4115    1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1160    0.3348   -0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4438    0.5849    0.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542   -2.1478   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0358   -2.5463    0.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -2.8671   -0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442   -1.6271   -0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7562    1.2286    2.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6173    2.1908    0.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542    1.3918    1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3887    1.4785   -1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -0.3863   -2.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0906    1.9180    0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1004   -0.5843   -0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7383    0.4511    1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -0.7751    1.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6424    0.0070   -1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 14 21  1  0
 21  2  1  0
 21  7  1  0
 14  9  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
M  END

  Mrv0541 05061311252D          

 21 24  0  0  0  0            999 V2000
    1.8749    1.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -0.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9239   -2.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2455   -0.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9464    0.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1229    0.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7911   -0.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4274   -0.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7535   -0.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2971    0.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2077   -0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625    0.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0313   -0.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219   -1.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9273   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    1.3195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909    1.0976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4855   -1.5594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4006   -0.1330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0999   -1.6005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -1.5800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  2  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19  5  1  0  0  0  0
 19 13  1  0  0  0  0
 20  8  1  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039814

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1COC(=O)C2OC3(C)OC4CC3(C12)C(O)C(=O)C4C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O6/c1-6-5-19-13(18)11-9(6)15-4-8(20-14(15,3)21-11)7(2)10(16)12(15)17/h6-9,11-12,17H,4-5H2,1-3H3

> <INCHI_KEY>
HQXFOQULVCDQQO-UHFFFAOYSA-N

> <FORMULA>
C15H20O6

> <MOLECULAR_WEIGHT>
296.3157

> <EXACT_MASS>
296.125988372

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.21462790368226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-hydroxy-3,9,12-trimethyl-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadecane-6,13-dione

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
0.698888473666667

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.3519849162877

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.766909120676715

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7724163972576976

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
69.84580000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-3,9,12-trimethyl-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadecane-6,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039814
     RDKit          3D
Cyclocalopin E
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.3943    2.0518    0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3690    0.6038    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7778    0.0664    0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -1.3092    0.3825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8116   -2.1430    0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0626   -3.3722   -0.0296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620   -1.6433   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299   -1.7655    0.9534 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5313   -1.0659    0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769   -2.0152   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2407   -0.6162    1.6716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958    0.6946    1.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056    1.2423    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0356    0.1307   -0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8322    0.5029   -1.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428   -0.3808   -2.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2094    0.8289   -0.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0239    1.0777   -1.8421 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    0.8775    0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8416   -0.0554    0.6964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900   -0.1596   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412    2.3666   -0.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775    2.3761   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4211    2.6439    0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361    0.4115    1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1160    0.3348   -0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4438    0.5849    0.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542   -2.1478   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0358   -2.5463    0.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -2.8671   -0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442   -1.6271   -0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7562    1.2286    2.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6173    2.1908    0.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542    1.3918    1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3887    1.4785   -1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -0.3863   -2.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0906    1.9180    0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1004   -0.5843   -0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7383    0.4511    1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -0.7751    1.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6424    0.0070   -1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 14 21  1  0
 21  2  1  0
 21  7  1  0
 14  9  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  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       3.500   2.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.010  -0.112   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.725  -3.958   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.458  -1.119   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.500   1.037   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.963   0.946   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.477  -0.254   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.798  -1.719   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.273  -0.431   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.555   1.041   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.121  -1.717   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.050   0.776   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.658  -1.625   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.721  -2.418   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.731  -0.763   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.146   2.463   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.663   2.049   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.506  -2.911   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.348  -0.248   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.186  -2.988   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.173  -2.949   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   14                                                            
CONECT    4    8   15                                                       
CONECT    5    6   19                                                       
CONECT    6    1    5    9                                                  
CONECT    7    2    8   10                                                  
CONECT    8    4    7   20                                                  
CONECT    9    6   11   15                                                  
CONECT   10    7   12   16                                                  
CONECT   11    9   13   21                                                  
CONECT   12   10   15   17                                                  
CONECT   13   11   18   19                                                  
CONECT   14    3   15   20   21                                             
CONECT   15    4    9   12   14                                             
CONECT   16   10                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19    5   13                                                       
CONECT   20    8   14                                                       
CONECT   21   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0039814
HETATM    1  C1  UNL     1      -2.394   2.052   0.042  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.369   0.604   0.395  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.778   0.066   0.106  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.865  -1.309   0.382  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.812  -2.143   0.066  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.063  -3.372  -0.030  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.462  -1.643  -0.152  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.630  -1.766   0.953  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.531  -1.066   0.547  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.377  -2.015  -0.192  1.00  0.00           C  
HETATM   11  O4  UNL     1       1.241  -0.616   1.672  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.596   0.695   1.445  1.00  0.00           C  
HETATM   13  C9  UNL     1       0.306   1.242   0.812  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.036   0.131  -0.176  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.832   0.503  -1.401  1.00  0.00           C  
HETATM   16  O5  UNL     1       0.743  -0.381  -2.431  1.00  0.00           O  
HETATM   17  C12 UNL     1       2.209   0.829  -0.968  1.00  0.00           C  
HETATM   18  O6  UNL     1       3.024   1.078  -1.842  1.00  0.00           O  
HETATM   19  C13 UNL     1       2.676   0.877   0.428  1.00  0.00           C  
HETATM   20  C14 UNL     1       3.842  -0.055   0.696  1.00  0.00           C  
HETATM   21  C15 UNL     1      -1.390  -0.160  -0.430  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.341   2.367  -0.490  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.578   2.376  -0.630  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.421   2.644   0.997  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.236   0.412   1.495  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.116   0.335  -0.901  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.444   0.585   0.829  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.054  -2.148  -1.059  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.036  -2.546   0.561  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.813  -2.867  -0.673  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.044  -1.627  -0.948  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.756   1.229   2.382  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.617   2.191   0.318  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.454   1.392   1.561  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.389   1.479  -1.763  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.534  -0.386  -2.991  1.00  0.00           H  
HETATM   37  H16 UNL     1       3.091   1.918   0.585  1.00  0.00           H  
HETATM   38  H17 UNL     1       4.100  -0.584  -0.239  1.00  0.00           H  
HETATM   39  H18 UNL     1       4.738   0.451   1.050  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.518  -0.775   1.489  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.642   0.007  -1.497  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   21   25
CONECT    3    4   26   27
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8   21   28
CONECT    8    9
CONECT    9   10   11   14
CONECT   10   29   30   31
CONECT   11   12
CONECT   12   13   19   32
CONECT   13   14   33   34
CONECT   14   15   21
CONECT   15   16   17   35
CONECT   16   36
CONECT   17   18   18   19
CONECT   19   20   37
CONECT   20   38   39   40
CONECT   21   41
END

HMDB0039814
     RDKit          3D
Cyclocalopin E
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.3943    2.0518    0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3690    0.6038    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7778    0.0664    0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -1.3092    0.3825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8116   -2.1430    0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0626   -3.3722   -0.0296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620   -1.6433   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299   -1.7655    0.9534 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5313   -1.0659    0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769   -2.0152   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2407   -0.6162    1.6716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958    0.6946    1.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056    1.2423    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0356    0.1307   -0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8322    0.5029   -1.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428   -0.3808   -2.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2094    0.8289   -0.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0239    1.0777   -1.8421 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    0.8775    0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8416   -0.0554    0.6964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900   -0.1596   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412    2.3666   -0.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775    2.3761   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4211    2.6439    0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361    0.4115    1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1160    0.3348   -0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4438    0.5849    0.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542   -2.1478   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0358   -2.5463    0.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -2.8671   -0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442   -1.6271   -0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7562    1.2286    2.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6173    2.1908    0.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542    1.3918    1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3887    1.4785   -1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -0.3863   -2.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0906    1.9180    0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1004   -0.5843   -0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7383    0.4511    1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -0.7751    1.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6424    0.0070   -1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 14 21  1  0
 21  2  1  0
 21  7  1  0
 14  9  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₆

Average Molecular Weight

296.3157

Monoisotopic Molecular Weight

296.125988372

IUPAC Name

14-hydroxy-3,9,12-trimethyl-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadecane-6,13-dione

Traditional Name

14-hydroxy-3,9,12-trimethyl-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadecane-6,13-dione

CAS Registry Number

Not Available

SMILES

CC1COC(=O)C2OC3(C)OC4CC3(C12)C(O)C(=O)C4C

InChI Identifier

InChI=1S/C15H20O6/c1-6-5-19-13(18)11-9(6)15-4-8(20-14(15,3)21-11)7(2)10(16)12(15)17/h6-9,11-12,17H,4-5H2,1-3H3

InChI Key

HQXFOQULVCDQQO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Furopyran
Furofuran
Ketal
Delta valerolactone
Delta_valerolactone
Oxepane
Pyran
Oxane
Cyclic alcohol
Furan
Tetrahydrofuran
Carboxylic acid ester
Cyclic ketone
Ketone
Secondary alcohol
Lactone
Oxacycle
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039814)

Source

Endogenous

Endogenous (HMDB: HMDB0039814)

Plant

Plant (HMDB: HMDB0039814)

Exogenous

Food

Food (HMDB: HMDB0039814)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0039814)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0039814)

Role

Biological role

Energy source (HMDB: HMDB0039814)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039814)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183 °C	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	12.2 g/L	ALOGPS
logP	0.52	ALOGPS
logP	0.7	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	12.77	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.85 m³·mol⁻¹	ChemAxon
Polarizability	29.21 Å³	ChemAxon
Number of Rings	4	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]+	166.522	31661259
DarkChem	[M-H]-	163.542	31661259
DeepCCS	[M-2H]-	202.613	30932474
DeepCCS	[M+Na]+	177.84	30932474
AllCCS	[M+H]+	168.4	32859911
AllCCS	[M+H-H2O]+	165.1	32859911
AllCCS	[M+NH4]+	171.5	32859911
AllCCS	[M+Na]+	172.4	32859911
AllCCS	[M-H]-	173.6	32859911
AllCCS	[M+Na-2H]-	173.3	32859911
AllCCS	[M+HCOO]-	173.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclocalopin E	CC1COC(=O)C2OC3(C)OC4CC3(C12)C(O)C(=O)C4C	3168.1	Standard polar	33892256
Cyclocalopin E	CC1COC(=O)C2OC3(C)OC4CC3(C12)C(O)C(=O)C4C	2026.4	Standard non polar	33892256
Cyclocalopin E	CC1COC(=O)C2OC3(C)OC4CC3(C12)C(O)C(=O)C4C	2292.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclocalopin E,1TMS,isomer #1	CC1COC(=O)C2OC3(C)OC4CC3(C(O[Si](C)(C)C)C(=O)C4C)C12	2305.2	Semi standard non polar	33892256
Cyclocalopin E,1TMS,isomer #2	CC1=C(O[Si](C)(C)C)C(O)C23CC1OC2(C)OC1C(=O)OCC(C)C13	2261.7	Semi standard non polar	33892256
Cyclocalopin E,1TMS,isomer #3	CC1COC(=O)C2OC3(C)OC4CC3(C(O)=C(O[Si](C)(C)C)C4C)C12	2232.2	Semi standard non polar	33892256
Cyclocalopin E,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)C23CC1OC2(C)OC1C(=O)OCC(C)C13	2327.4	Semi standard non polar	33892256
Cyclocalopin E,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)C23CC1OC2(C)OC1C(=O)OCC(C)C13	2301.4	Standard non polar	33892256
Cyclocalopin E,2TMS,isomer #2	CC1COC(=O)C2OC3(C)OC4CC3(C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C4C)C12	2323.2	Semi standard non polar	33892256
Cyclocalopin E,2TMS,isomer #2	CC1COC(=O)C2OC3(C)OC4CC3(C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C4C)C12	2236.7	Standard non polar	33892256
Cyclocalopin E,1TBDMS,isomer #1	CC1COC(=O)C2OC3(C)OC4CC3(C(O[Si](C)(C)C(C)(C)C)C(=O)C4C)C12	2523.3	Semi standard non polar	33892256
Cyclocalopin E,1TBDMS,isomer #2	CC1=C(O[Si](C)(C)C(C)(C)C)C(O)C23CC1OC2(C)OC1C(=O)OCC(C)C13	2492.3	Semi standard non polar	33892256
Cyclocalopin E,1TBDMS,isomer #3	CC1COC(=O)C2OC3(C)OC4CC3(C(O)=C(O[Si](C)(C)C(C)(C)C)C4C)C12	2460.7	Semi standard non polar	33892256
Cyclocalopin E,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C23CC1OC2(C)OC1C(=O)OCC(C)C13	2764.3	Semi standard non polar	33892256
Cyclocalopin E,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C23CC1OC2(C)OC1C(=O)OCC(C)C13	2792.8	Standard non polar	33892256
Cyclocalopin E,2TBDMS,isomer #2	CC1COC(=O)C2OC3(C)OC4CC3(C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C4C)C12	2748.3	Semi standard non polar	33892256
Cyclocalopin E,2TBDMS,isomer #2	CC1COC(=O)C2OC3(C)OC4CC3(C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C4C)C12	2716.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclocalopin E GC-MS (Non-derivatized) - 70eV, Positive	splash10-067i-3290000000-09a23b618833436650fb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclocalopin E GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-6159000000-a63752cbad8422cb9760	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclocalopin E GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclocalopin E 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 - Cyclocalopin E 10V, Positive-QTOF	splash10-0002-0190000000-9b46a8107cf0b2c97940	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocalopin E 20V, Positive-QTOF	splash10-0f92-1290000000-8ecf1975451cf92724b5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocalopin E 40V, Positive-QTOF	splash10-0bvl-9840000000-7a1b4180097b1fe37269	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocalopin E 10V, Negative-QTOF	splash10-0f6t-0090000000-787a20a6cb0500a73010	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocalopin E 20V, Negative-QTOF	splash10-0002-0090000000-41cfe58613a7c65f1a6a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocalopin E 40V, Negative-QTOF	splash10-014i-3930000000-7cfcefa45684a4b78619	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocalopin E 10V, Positive-QTOF	splash10-0002-0090000000-48ced8340a75902cccfe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocalopin E 20V, Positive-QTOF	splash10-0002-0090000000-005c9df2277b692175b4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocalopin E 40V, Positive-QTOF	splash10-014i-1890000000-30bc8d5acfdaa639266d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocalopin E 10V, Negative-QTOF	splash10-0002-0090000000-b424237b05a2bd372d62	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocalopin E 20V, Negative-QTOF	splash10-0002-0090000000-d6e71dfb25b0eed30c18	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclocalopin E 40V, Negative-QTOF	splash10-014l-1890000000-6dc7a43ffe407a7679df	2021-09-23	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
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

FDB019464

KNApSAcK ID

Not Available

Chemspider ID

35014882

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85304669

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

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

Showing metabocard for Cyclocalopin E (HMDB0039814)

MOL for HMDB0039814 (Cyclocalopin E)

3D MOL for HMDB0039814 (Cyclocalopin E)

3D SDF for HMDB0039814 (Cyclocalopin E)

3D-SDF for HMDB0039814 (Cyclocalopin E)

PDB for HMDB0039814 (Cyclocalopin E)

3D PDB for HMDB0039814 (Cyclocalopin E)

SMILES for HMDB0039814 (Cyclocalopin E)

INCHI for HMDB0039814 (Cyclocalopin E)

Structure for HMDB0039814 (Cyclocalopin E)

3D Structure for HMDB0039814 (Cyclocalopin E)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra