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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:02 UTC

HMDB ID

HMDB0015586

Secondary Accession Numbers

HMDB15586

Metabolite Identification

Common Name

Cyclandelate

Description

Cyclandelate is only found in individuals that have used or taken this drug. It is a direct-acting smooth muscle relaxant used to dilate blood vessels. It may cause gastrointestinal distress and tachycardia. Cyclandelate is not approved for use in the U.S. or Canada, but is approved in various European countries.Cyclandelate produces peripheral vasodilation by a direct effect on vascular smooth muscle. Pharmacological action may be due to calcium-channel antagonism.

Structure

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

HMDB0015586
     RDKit          3D
Cyclandelate
 44 45  0  0  0  0  0  0  0  0999 V2000
   -4.1749    1.0192    1.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9472    0.2294    1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9612    1.2350    0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8187    0.6586    0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3800    0.5567    0.8880 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.1962    0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5315    1.9339   -0.4239 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8058    1.0881    1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6716    0.2380    2.4658 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301    0.5752    0.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    1.3391    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9340    0.7478   -0.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9616   -0.6271   -0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9547   -1.3952   -0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9720   -0.7881    0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976   -0.6760   -0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449   -0.9049   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6620   -2.3474   -1.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0120   -0.0152   -1.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279   -0.7450    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8480    0.2959    2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8977    1.8726    2.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7497    1.3624    0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5853   -0.2982    2.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5879    1.8003    1.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5379    1.9944    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5866    1.3605   -0.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932    2.0774    1.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9950   -0.4509    2.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9043    2.4049    0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7286    1.3174   -1.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7565   -1.0873   -1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9987   -2.4681   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1989   -1.4303    0.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5301   -0.7724   -1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7192   -1.4719    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6527   -2.5262   -1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775   -3.0088   -0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8678   -2.5238   -2.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8135   -0.5228   -2.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5665    0.9811   -1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1322    0.0684   -1.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5195   -1.7597    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4674   -0.5332    0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20  2  1  0
 15 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
M  END

4838
  Mrv0541 02231217572D          

 20 21  0  0  1  0            999 V2000
    3.5220    0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3634    3.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5384    3.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -2.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -3.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 13  1  0  0  0  0
  2 13  2  0  0  0  0
  3 14  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015586

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC(CC(C)(C)C1)OC(=O)C(O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O3/c1-12-9-14(11-17(2,3)10-12)20-16(19)15(18)13-7-5-4-6-8-13/h4-8,12,14-15,18H,9-11H2,1-3H3

> <INCHI_KEY>
WZHCOOQXZCIUNC-UHFFFAOYSA-N

> <FORMULA>
C17H24O3

> <MOLECULAR_WEIGHT>
276.3707

> <EXACT_MASS>
276.172544634

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.948679403548063

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,3,5-trimethylcyclohexyl 2-hydroxy-2-phenylacetate

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
3.715085545

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.991099938529693

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1148928868871115

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
78.05940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclandelate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015586
     RDKit          3D
Cyclandelate
 44 45  0  0  0  0  0  0  0  0999 V2000
   -4.1749    1.0192    1.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9472    0.2294    1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9612    1.2350    0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8187    0.6586    0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3800    0.5567    0.8880 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.1962    0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5315    1.9339   -0.4239 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8058    1.0881    1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6716    0.2380    2.4658 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301    0.5752    0.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    1.3391    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9340    0.7478   -0.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9616   -0.6271   -0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9547   -1.3952   -0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9720   -0.7881    0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976   -0.6760   -0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449   -0.9049   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6620   -2.3474   -1.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0120   -0.0152   -1.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279   -0.7450    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8480    0.2959    2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8977    1.8726    2.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7497    1.3624    0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5853   -0.2982    2.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5879    1.8003    1.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5379    1.9944    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5866    1.3605   -0.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932    2.0774    1.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9950   -0.4509    2.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9043    2.4049    0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7286    1.3174   -1.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7565   -1.0873   -1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9987   -2.4681   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1989   -1.4303    0.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5301   -0.7724   -1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7192   -1.4719    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6527   -2.5262   -1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775   -3.0088   -0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8678   -2.5238   -2.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8135   -0.5228   -2.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5665    0.9811   -1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1322    0.0684   -1.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5195   -1.7597    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4674   -0.5332    0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20  2  1  0
 15 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4838                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.574   1.258   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.908  -1.052   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907  -0.282   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.242   4.338   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.576   3.568   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.576   2.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.908   3.568   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.908   2.028   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.242   1.258   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.012   5.672   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.472   5.672   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.909   1.258   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -0.282   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.241  -1.052   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.241  -2.592   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.907  -3.362   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.574  -3.362   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.907  -4.902   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.574  -4.902   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.241  -5.672   0.000  0.00  0.00           C+0
CONECT    1    8   13                                                       
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    5    7   10   11                                             
CONECT    5    4    6                                                       
CONECT    6    5    9   12                                                  
CONECT    7    4    8                                                       
CONECT    8    1    7    9                                                  
CONECT    9    6    8                                                       
CONECT   10    4                                                            
CONECT   11    4                                                            
CONECT   12    6                                                            
CONECT   13    1    2   14                                                  
CONECT   14    3   13   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   20                                                       
CONECT   20   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0015586
HETATM    1  C1  UNL     1      -4.175   1.019   1.892  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.947   0.229   1.416  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.961   1.235   0.909  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.819   0.659   0.152  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.380   0.557   0.888  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.549   1.196   0.595  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.532   1.934  -0.424  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.806   1.088   1.369  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.672   0.238   2.466  1.00  0.00           O  
HETATM   10  C7  UNL     1       3.930   0.575   0.556  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.920   1.339   0.020  1.00  0.00           C  
HETATM   12  C9  UNL     1       5.934   0.748  -0.732  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.962  -0.627  -0.955  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.955  -1.395  -0.409  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.972  -0.788   0.326  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.098  -0.676  -0.475  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.545  -0.905  -0.791  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.662  -2.347  -1.295  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.012  -0.015  -1.911  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.428  -0.745   0.411  1.00  0.00           C  
HETATM   21  H1  UNL     1      -4.848   0.296   2.406  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.898   1.873   2.517  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.750   1.362   0.984  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.585  -0.298   2.343  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.588   1.800   1.813  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.538   1.994   0.331  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.587   1.361  -0.694  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.093   2.077   1.763  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.995  -0.451   2.200  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.904   2.405   0.189  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.729   1.317  -1.169  1.00  0.00           H  
HETATM   32  H12 UNL     1       6.756  -1.087  -1.544  1.00  0.00           H  
HETATM   33  H13 UNL     1       4.999  -2.468  -0.597  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.199  -1.430   0.737  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.530  -0.772  -1.422  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.719  -1.472   0.197  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.653  -2.526  -1.749  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.578  -3.009  -0.412  1.00  0.00           H  
HETATM   39  H19 UNL     1      -1.868  -2.524  -2.045  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.814  -0.523  -2.877  1.00  0.00           H  
HETATM   41  H21 UNL     1      -2.566   0.981  -1.844  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.132   0.068  -1.796  1.00  0.00           H  
HETATM   43  H23 UNL     1      -3.520  -1.760   0.891  1.00  0.00           H  
HETATM   44  H24 UNL     1      -4.467  -0.533   0.028  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   20   24
CONECT    3    4   25   26
CONECT    4    5   16   27
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   10   28
CONECT    9   29
CONECT   10   11   11   15
CONECT   11   12   30
CONECT   12   13   13   31
CONECT   13   14   32
CONECT   14   15   15   33
CONECT   15   34
CONECT   16   17   35   36
CONECT   17   18   19   20
CONECT   18   37   38   39
CONECT   19   40   41   42
CONECT   20   43   44
END

HMDB0015586
     RDKit          3D
Cyclandelate
 44 45  0  0  0  0  0  0  0  0999 V2000
   -4.1749    1.0192    1.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9472    0.2294    1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9612    1.2350    0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8187    0.6586    0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3800    0.5567    0.8880 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.1962    0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5315    1.9339   -0.4239 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8058    1.0881    1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6716    0.2380    2.4658 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301    0.5752    0.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    1.3391    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9340    0.7478   -0.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9616   -0.6271   -0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9547   -1.3952   -0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9720   -0.7881    0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976   -0.6760   -0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449   -0.9049   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6620   -2.3474   -1.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0120   -0.0152   -1.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279   -0.7450    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8480    0.2959    2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8977    1.8726    2.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7497    1.3624    0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5853   -0.2982    2.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5879    1.8003    1.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5379    1.9944    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5866    1.3605   -0.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932    2.0774    1.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9950   -0.4509    2.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9043    2.4049    0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7286    1.3174   -1.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7565   -1.0873   -1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9987   -2.4681   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1989   -1.4303    0.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5301   -0.7724   -1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7192   -1.4719    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6527   -2.5262   -1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775   -3.0088   -0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8678   -2.5238   -2.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8135   -0.5228   -2.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5665    0.9811   -1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1322    0.0684   -1.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5195   -1.7597    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4674   -0.5332    0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20  2  1  0
 15 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,3,5-Trimethylcyclohexyl mandelate	ChEBI
3,5,5-Trimethylcyclohexyl amygdalate	ChEBI
Ciclandelato	ChEBI
Cyclandelatum	ChEBI
Cyclospasmol	Kegg
3,3,5-Trimethylcyclohexyl mandelic acid	Generator
3,5,5-Trimethylcyclohexyl amygdalic acid	Generator
Cyclandelic acid	Generator
3,5,5-Trimethylcyclohexyl mandelate	HMDB

Chemical Formula

C₁₇H₂₄O₃

Average Molecular Weight

276.3707

Monoisotopic Molecular Weight

276.172544634

IUPAC Name

3,3,5-trimethylcyclohexyl 2-hydroxy-2-phenylacetate

Traditional Name

cyclandelate

CAS Registry Number

456-59-7

SMILES

CC1CC(CC(C)(C)C1)OC(=O)C(O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H24O3/c1-12-9-14(11-17(2,3)10-12)20-16(19)15(18)13-7-5-4-6-8-13/h4-8,12,14-15,18H,9-11H2,1-3H3

InChI Key

WZHCOOQXZCIUNC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carboxylic ester (CHEBI:3988 )
secondary alcohol (CHEBI:3988 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015586)

Source

Exogenous

Exogenous (HMDB: HMDB0015586)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	56 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.1 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	3.79	ALOGPS
logP	3.72	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.99	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.06 m³·mol⁻¹	ChemAxon
Polarizability	30.95 Å³	ChemAxon
Number of Rings	2	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]+	166.817	31661259
DarkChem	[M-H]-	164.167	31661259
DeepCCS	[M+H]+	168.849	30932474
DeepCCS	[M-H]-	166.491	30932474
DeepCCS	[M-2H]-	199.377	30932474
DeepCCS	[M+Na]+	174.942	30932474
AllCCS	[M+H]+	168.8	32859911
AllCCS	[M+H-H2O]+	165.4	32859911
AllCCS	[M+NH4]+	172.0	32859911
AllCCS	[M+Na]+	172.9	32859911
AllCCS	[M-H]-	171.5	32859911
AllCCS	[M+Na-2H]-	171.7	32859911
AllCCS	[M+HCOO]-	172.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclandelate	CC1CC(CC(C)(C)C1)OC(=O)C(O)C1=CC=CC=C1	2482.8	Standard polar	33892256
Cyclandelate	CC1CC(CC(C)(C)C1)OC(=O)C(O)C1=CC=CC=C1	1854.2	Standard non polar	33892256
Cyclandelate	CC1CC(CC(C)(C)C1)OC(=O)C(O)C1=CC=CC=C1	1978.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclandelate,1TMS,isomer #1	CC1CC(OC(=O)C(O[Si](C)(C)C)C2=CC=CC=C2)CC(C)(C)C1	1944.0	Semi standard non polar	33892256
Cyclandelate,1TBDMS,isomer #1	CC1CC(OC(=O)C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2)CC(C)(C)C1	2169.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclandelate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0900000000-85c7942741dc3b7e0e52	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclandelate GC-MS (1 TMS) - 70eV, Positive	splash10-004i-1900000000-b8c3ab3c4d0f882db58e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclandelate 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 - Cyclandelate 10V, Positive-QTOF	splash10-004i-0950000000-cbd8ed2ef1f62d60ea8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclandelate 20V, Positive-QTOF	splash10-056u-2910000000-6c17a19860e864bd7801	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclandelate 40V, Positive-QTOF	splash10-056s-9600000000-b087aa902df08974369d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclandelate 10V, Negative-QTOF	splash10-002f-0940000000-34f669a689c8a1273bbc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclandelate 20V, Negative-QTOF	splash10-0006-1900000000-8786f54f69e4e1dbbd40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclandelate 40V, Negative-QTOF	splash10-004l-4900000000-b5b000aa05ae5562bbba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclandelate 10V, Positive-QTOF	splash10-004i-0390000000-3ddbca7498541d032cb0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclandelate 20V, Positive-QTOF	splash10-000i-1920000000-fb65e5889cd1041a24dc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclandelate 40V, Positive-QTOF	splash10-004i-9400000000-6d692751d4a04b7a7710	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclandelate 10V, Negative-QTOF	splash10-004i-0590000000-347a226822f353baee19	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclandelate 20V, Negative-QTOF	splash10-0a4i-3900000000-d91be2b6bb6fc89afbbc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclandelate 40V, Negative-QTOF	splash10-056r-5910000000-7f984dc077207098e94a	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04838	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04838	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04838

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2790

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cyclandelate

METLIN ID

Not Available

PubChem Compound

2893

PDB ID

Not Available

ChEBI ID

3988

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

Not Available

Enzymes

Enzyme Details

1. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

References

Heffron F, Middleton B, White DA: Inhibition of acyl coenzyme A: cholesterol acyl transferase by trimethylcyclohexanylmandelate (cyclandelate). Biochem Pharmacol. 1990 Feb 1;39(3):575-80. [PubMed:2306268 ]

Enzyme Details

2. Voltage-dependent calcium channel subunit alpha-2/delta-1

General function:: Involved in metal ion binding
Specific function:: The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Plays an important role in excitation-contraction coupling
Gene Name:: CACNA2D1
Uniprot ID:: P54289
Molecular weight:: 124566.9

References

Pascual J: [New prospects in the treatment of migraine]. Neurologia. 1999 Dec;14 Suppl 6:26-35. [PubMed:10659603 ]

Showing metabocard for Cyclandelate (HMDB0015586)

MOL for HMDB0015586 (Cyclandelate)

3D MOL for HMDB0015586 (Cyclandelate)

3D SDF for HMDB0015586 (Cyclandelate)

3D-SDF for HMDB0015586 (Cyclandelate)

PDB for HMDB0015586 (Cyclandelate)

3D PDB for HMDB0015586 (Cyclandelate)

SMILES for HMDB0015586 (Cyclandelate)

INCHI for HMDB0015586 (Cyclandelate)

Structure for HMDB0015586 (Cyclandelate)

3D Structure for HMDB0015586 (Cyclandelate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References