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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 22:52:01 UTC

Update Date

2021-09-23 22:52:01 UTC

HMDB ID

HMDB0303044

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Verbenalol

Description

Verbenalol belongs to iridoids and derivatives class of compounds. Those are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. Verbenalol is soluble (in water) and a very weakly acidic compound (based on its pKa). Verbenalol can be found in common verbena, which makes verbenalol a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303044
     RDKit          3D
Verbenalol
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.6457    1.8452    0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5407    0.9467    0.1209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    0.3099   -0.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5522    0.5417   -2.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014   -0.5884   -0.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4030   -1.2004   -1.9071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6664   -2.0509   -1.7197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4555   -2.1221   -0.5707 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1254   -3.3237    0.0837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2077   -1.0108    0.3978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6409    0.3356   -0.0962 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9779    0.7541    0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056    1.3471    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3275    0.4965    1.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9527    0.7641    2.2005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137   -0.8264    0.4873 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4983    1.4511    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9630    1.9510   -1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362    2.8452    0.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431   -1.0176   -2.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -2.2136   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7699   -3.1732    0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5798   -1.2717    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6918    0.3746   -1.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3484    1.5920   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6538   -0.1137    0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578    1.0952    1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0612    2.1458    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293    1.7284   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947   -1.6119    1.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16  5  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  8 21  1  6
  9 22  1  0
 10 23  1  1
 11 24  1  6
 12 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 16 30  1  1
M  END

  Mrv0541 02241221392D          

 18 19  0  0  1  0            999 V2000
   -0.3984   -3.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -2.2419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6284   -1.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -0.1224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1620    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -1.9870    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556   -2.3995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0701   -1.9870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -0.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    0.4880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    0.4880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -3.2245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.3370    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.8120    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  0  0  0  0
  7  6  1  0  0  0  0
  7  2  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  1  0  0  0
  6 17  1  1  0  0  0
  7 18  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0303044

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12[C@@H](C)CC(=O)[C@]1([H])C(=CO[C@H]2O)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O5/c1-5-3-7(12)9-6(10(13)15-2)4-16-11(14)8(5)9/h4-5,8-9,11,14H,3H2,1-2H3/t5-,8+,9-,11+/m0/s1

> <INCHI_KEY>
ICLHTGIHDLYEDX-PPZZJSARSA-N

> <FORMULA>
C11H14O5

> <MOLECULAR_WEIGHT>
226.2259

> <EXACT_MASS>
226.084123558

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
22.403456825274418

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,4aS,7S,7aR)-1-hydroxy-7-methyl-5-oxo-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <ALOGPS_LOGP>
-0.00

> <JCHEM_LOGP>
0.3192044350000003

> <ALOGPS_LOGS>
-0.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.406084036192475

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.272496086225559

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0771630800532614

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
54.1359

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.50e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,4aS,7S,7aR)-1-hydroxy-7-methyl-5-oxo-1H,4aH,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303044
     RDKit          3D
Verbenalol
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.6457    1.8452    0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5407    0.9467    0.1209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    0.3099   -0.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5522    0.5417   -2.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014   -0.5884   -0.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4030   -1.2004   -1.9071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6664   -2.0509   -1.7197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4555   -2.1221   -0.5707 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1254   -3.3237    0.0837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2077   -1.0108    0.3978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6409    0.3356   -0.0962 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9779    0.7541    0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056    1.3471    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3275    0.4965    1.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9527    0.7641    2.2005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137   -0.8264    0.4873 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4983    1.4511    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9630    1.9510   -1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362    2.8452    0.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431   -1.0176   -2.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -2.2136   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7699   -3.1732    0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5798   -1.2717    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6918    0.3746   -1.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3484    1.5920   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6538   -0.1137    0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578    1.0952    1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0612    2.1458    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293    1.7284   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947   -1.6119    1.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16  5  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  8 21  1  6
  9 22  1  0
 10 23  1  1
 11 24  1  6
 12 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 16 30  1  1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.744  -5.649   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.268  -4.185   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.173  -2.939   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.268  -1.693   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.744  -0.228   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.197  -2.169   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.197  -3.709   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.530  -4.479   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.864  -3.709   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.864  -2.169   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530  -1.399   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530   0.141   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.197   0.911   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.864   0.911   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.864   2.451   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.530  -6.019   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       1.197  -0.629   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.197  -5.249   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11   17                                             
CONECT    7    6    2    8   18                                             
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16    8                                                            
CONECT   17    6                                                            
CONECT   18    7                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0303044
HETATM    1  C1  UNL     1       3.646   1.845   0.036  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.541   0.947   0.121  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.019   0.310  -0.987  1.00  0.00           C  
HETATM    4  O2  UNL     1       2.552   0.542  -2.113  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.901  -0.588  -0.841  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.403  -1.200  -1.907  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.666  -2.051  -1.720  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.456  -2.122  -0.571  1.00  0.00           C  
HETATM    9  O4  UNL     1      -1.125  -3.324   0.084  1.00  0.00           O  
HETATM   10  C6  UNL     1      -1.208  -1.011   0.398  1.00  0.00           C  
HETATM   11  C7  UNL     1      -1.641   0.336  -0.096  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.978   0.754   0.507  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.606   1.347   0.413  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.327   0.497   1.215  1.00  0.00           C  
HETATM   15  O5  UNL     1       0.953   0.764   2.200  1.00  0.00           O  
HETATM   16  C11 UNL     1       0.314  -0.826   0.487  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.498   1.451   0.626  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.963   1.951  -1.014  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.336   2.845   0.409  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.843  -1.018  -2.878  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.520  -2.214  -0.880  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.770  -3.173   0.988  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.580  -1.272   1.395  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.692   0.375  -1.200  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.348   1.592  -0.118  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.654  -0.114   0.513  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.758   1.095   1.540  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.061   2.146   1.002  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.029   1.728  -0.453  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.795  -1.612   1.062  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   16
CONECT    6    7   20
CONECT    7    8
CONECT    8    9   10   21
CONECT    9   22
CONECT   10   11   16   23
CONECT   11   12   13   24
CONECT   12   25   26   27
CONECT   13   14   28   29
CONECT   14   15   15   16
CONECT   16   30
END

HMDB0303044
     RDKit          3D
Verbenalol
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.6457    1.8452    0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5407    0.9467    0.1209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    0.3099   -0.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5522    0.5417   -2.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014   -0.5884   -0.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4030   -1.2004   -1.9071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6664   -2.0509   -1.7197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4555   -2.1221   -0.5707 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1254   -3.3237    0.0837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2077   -1.0108    0.3978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6409    0.3356   -0.0962 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9779    0.7541    0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056    1.3471    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3275    0.4965    1.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9527    0.7641    2.2005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137   -0.8264    0.4873 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4983    1.4511    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9630    1.9510   -1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362    2.8452    0.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431   -1.0176   -2.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -2.2136   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7699   -3.1732    0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5798   -1.2717    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6918    0.3746   -1.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3484    1.5920   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6538   -0.1137    0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578    1.0952    1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0612    2.1458    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293    1.7284   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947   -1.6119    1.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16  5  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  8 21  1  6
  9 22  1  0
 10 23  1  1
 11 24  1  6
 12 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 16 30  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl (1R,4as,7S,7ar)-1-hydroxy-7-methyl-5-oxo-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-4-carboxylic acid	Generator

Chemical Formula

C₁₁H₁₄O₅

Average Molecular Weight

226.2259

Monoisotopic Molecular Weight

226.084123558

IUPAC Name

methyl (1R,4aS,7S,7aR)-1-hydroxy-7-methyl-5-oxo-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

methyl (1R,4aS,7S,7aR)-1-hydroxy-7-methyl-5-oxo-1H,4aH,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@]12[C@@H](C)CC(=O)[C@]1([H])C(=CO[C@H]2O)C(=O)OC

InChI Identifier

InChI=1S/C11H14O5/c1-5-3-7(12)9-6(10(13)15-2)4-16-11(14)8(5)9/h4-5,8-9,11,14H,3H2,1-2H3/t5-,8+,9-,11+/m0/s1

InChI Key

ICLHTGIHDLYEDX-PPZZJSARSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Iridoid-skeleton
Bicyclic monoterpenoid
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Carboxylic acid ester
Hemiacetal
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0303044)

Food

Herb and spice

Herb

Common verbena (FooDB: FOOD00196)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0	ALOGPS
logP	0.32	ChemAxon
logS	-0.7	ALOGPS
pKa (Strongest Acidic)	9.27	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.14 m³·mol⁻¹	ChemAxon
Polarizability	22.4 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
AllCCS	[M+H]+	149.092	32859911
AllCCS	[M+H-H2O]+	145.241	32859911
AllCCS	[M+Na]+	153.702	32859911
AllCCS	[M+NH4]+	152.671	32859911
AllCCS	[M-H]-	151.034	32859911
AllCCS	[M+Na-2H]-	151.197	32859911
AllCCS	[M+HCOO]-	151.472	32859911
DeepCCS	[M-2H]-	193.571	30932474
DeepCCS	[M+Na]+	168.8	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Verbenalol,2TMS,isomer #1	COC(=O)C1=CO[C@@H](O[Si](C)(C)C)[C@H]2C1=C(O[Si](C)(C)C)C[C@@H]2C	1996.9	Semi standard non polar	33892256
Verbenalol,2TMS,isomer #1	COC(=O)C1=CO[C@@H](O[Si](C)(C)C)[C@H]2C1=C(O[Si](C)(C)C)C[C@@H]2C	1902.2	Standard non polar	33892256
Verbenalol,2TMS,isomer #1	COC(=O)C1=CO[C@@H](O[Si](C)(C)C)[C@H]2C1=C(O[Si](C)(C)C)C[C@@H]2C	2341.1	Standard polar	33892256
Verbenalol,2TMS,isomer #2	COC(=O)C1=CO[C@@H](O[Si](C)(C)C)[C@@H]2[C@@H](C)C=C(O[Si](C)(C)C)[C@H]12	1977.1	Semi standard non polar	33892256
Verbenalol,2TMS,isomer #2	COC(=O)C1=CO[C@@H](O[Si](C)(C)C)[C@@H]2[C@@H](C)C=C(O[Si](C)(C)C)[C@H]12	1867.6	Standard non polar	33892256
Verbenalol,2TMS,isomer #2	COC(=O)C1=CO[C@@H](O[Si](C)(C)C)[C@@H]2[C@@H](C)C=C(O[Si](C)(C)C)[C@H]12	2345.3	Standard polar	33892256
Verbenalol,2TBDMS,isomer #1	COC(=O)C1=CO[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2C1=C(O[Si](C)(C)C(C)(C)C)C[C@@H]2C	2381.5	Semi standard non polar	33892256
Verbenalol,2TBDMS,isomer #1	COC(=O)C1=CO[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2C1=C(O[Si](C)(C)C(C)(C)C)C[C@@H]2C	2281.8	Standard non polar	33892256
Verbenalol,2TBDMS,isomer #1	COC(=O)C1=CO[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2C1=C(O[Si](C)(C)C(C)(C)C)C[C@@H]2C	2549.5	Standard polar	33892256
Verbenalol,2TBDMS,isomer #2	COC(=O)C1=CO[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2[C@@H](C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]12	2372.3	Semi standard non polar	33892256
Verbenalol,2TBDMS,isomer #2	COC(=O)C1=CO[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2[C@@H](C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]12	2202.0	Standard non polar	33892256
Verbenalol,2TBDMS,isomer #2	COC(=O)C1=CO[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2[C@@H](C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]12	2543.9	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenalol 10V, Positive-QTOF	splash10-004i-0690000000-4b29effdce093fa20316	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenalol 20V, Positive-QTOF	splash10-004j-1930000000-b66235615d98ef42e6c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenalol 40V, Positive-QTOF	splash10-0f92-8900000000-c2976c34c0e9120a56fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenalol 10V, Negative-QTOF	splash10-004i-1490000000-ee3a9a1b627db842d864	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenalol 20V, Negative-QTOF	splash10-00os-2930000000-edad0069c90a8b5c21a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenalol 40V, Negative-QTOF	splash10-0f7n-9300000000-b050c0e748bcfacd8cc0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenalol 10V, Positive-QTOF	splash10-056r-0290000000-e221784187afe34a76f5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenalol 20V, Positive-QTOF	splash10-004j-0940000000-53d37dea244bd3737ece	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenalol 40V, Positive-QTOF	splash10-0udi-7900000000-67a1b9f9ca9205bf83bc	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenalol 10V, Negative-QTOF	splash10-004i-0090000000-f086b4b745f3fb72d2ac	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenalol 20V, Negative-QTOF	splash10-004i-0690000000-b082e66f96f698a026e9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenalol 40V, Negative-QTOF	splash10-0002-9410000000-bf2e62aecbf30b1bf98d	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB007476

KNApSAcK ID

Not Available

Chemspider ID

34546627

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12444745

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

Not Available

Showing metabocard for Verbenalol (HMDB0303044)

MOL for HMDB0303044 (Verbenalol)

3D MOL for HMDB0303044 (Verbenalol)

3D SDF for HMDB0303044 (Verbenalol)

3D-SDF for HMDB0303044 (Verbenalol)

PDB for HMDB0303044 (Verbenalol)

3D PDB for HMDB0303044 (Verbenalol)

SMILES for HMDB0303044 (Verbenalol)

INCHI for HMDB0303044 (Verbenalol)

Structure for HMDB0303044 (Verbenalol)

3D Structure for HMDB0303044 (Verbenalol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra