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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:15:27 UTC

Update Date

2021-09-23 16:15:27 UTC

HMDB ID

HMDB0302242

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Neocnidolide

Description

Neocnidolide, also known as neocnidilide, cis-(-)-isomer or sedanolide, is a member of the class of compounds known as isobenzofurans. Isobenzofurans are organic aromatic compounds containing an isobenzofuran moiety. Neocnidolide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Neocnidolide can be found in dill, which makes neocnidolide a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302242
     RDKit          3D
Neocnidolide
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.8920    0.4008    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6978    0.0686   -0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    0.1352    0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -0.1910   -0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0559   -0.0976    0.4776 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2114   -1.0301    1.5617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0919   -1.1676    2.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3496   -1.7555    3.1961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410   -0.5539    1.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2621   -0.1149    1.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316    0.4952    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980    0.1205   -1.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076    0.4858   -1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -0.4887   -0.0937 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6918    0.9085   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3028   -0.4934    0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6266    1.1302    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6208    0.7941   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236   -0.9575   -0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5903   -0.6490    1.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849    1.0938    0.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111   -1.1598   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0963    0.6217   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0138    0.9144    0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7573   -0.2049    2.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0171    1.6152    0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0943    0.1785    0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4252   -1.0077   -1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8600    0.5811   -1.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4953    0.3160   -2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7783    1.5257   -0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2385   -1.5141   -0.4881 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  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14  5  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  1
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  6
M  END


  Mrv1533007131513282D          

 16 17  0  0  1  0            999 V2000
   -0.9851   -1.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    1.5229    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3239    0.7264    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  6  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  2  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
  9 15  1  6  0  0  0
 11 16  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0302242

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CCCC)OC(=O)C2=CCCC[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h7,9,11H,2-6,8H2,1H3/t9-,11+/m1/s1

> <INCHI_KEY>
UPJFTVFLSIQQAV-KOLCDFICSA-N

> <FORMULA>
C12H18O2

> <MOLECULAR_WEIGHT>
194.274

> <EXACT_MASS>
194.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
22.69720589944824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aR)-3-butyl-1,3,3a,4,5,6-hexahydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
3.3948776213333325

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.875980152871816

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
55.7747

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR)-3-butyl-3a,4,5,6-tetrahydro-3H-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302242
     RDKit          3D
Neocnidolide
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.8920    0.4008    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6978    0.0686   -0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    0.1352    0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -0.1910   -0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0559   -0.0976    0.4776 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2114   -1.0301    1.5617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0919   -1.1676    2.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3496   -1.7555    3.1961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410   -0.5539    1.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2621   -0.1149    1.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316    0.4952    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980    0.1205   -1.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076    0.4858   -1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -0.4887   -0.0937 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6918    0.9085   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3028   -0.4934    0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6266    1.1302    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6208    0.7941   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236   -0.9575   -0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5903   -0.6490    1.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849    1.0938    0.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111   -1.1598   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0963    0.6217   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0138    0.9144    0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7573   -0.2049    2.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0171    1.6152    0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0943    0.1785    0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4252   -1.0077   -1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8600    0.5811   -1.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4953    0.3160   -2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7783    1.5257   -0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2385   -1.5141   -0.4881 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  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14  5  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  1
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  6
M  END

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      -1.839  -1.973   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.333  -1.652   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.220   2.843   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0       4.924   2.843   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.605   1.356   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    8                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5   10                                                       
CONECT    8    3   11                                                       
CONECT    9    6   10   11   15                                             
CONECT   10    7    9   12                                                  
CONECT   11    8    9   14   16                                             
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   11   12                                                       
CONECT   15    9                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0302242
HETATM    1  C1  UNL     1       4.892   0.401   0.293  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.698   0.069  -0.568  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.472   0.135   0.315  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.209  -0.191  -0.486  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.056  -0.098   0.478  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.211  -1.030   1.562  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.092  -1.168   2.090  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.350  -1.756   3.196  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.041  -0.554   1.200  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.262  -0.115   1.300  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.032   0.495   0.188  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.398   0.120  -1.118  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.908   0.486  -1.030  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.252  -0.489  -0.094  1.00  0.00           C  
HETATM   15  H1  UNL     1       5.692   0.909  -0.296  1.00  0.00           H  
HETATM   16  H2  UNL     1       5.303  -0.493   0.807  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.627   1.130   1.103  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.621   0.794  -1.415  1.00  0.00           H  
HETATM   19  H5  UNL     1       3.824  -0.957  -0.946  1.00  0.00           H  
HETATM   20  H6  UNL     1       2.590  -0.649   1.087  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.385   1.094   0.822  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.311  -1.160  -0.975  1.00  0.00           H  
HETATM   23  H9  UNL     1       1.096   0.622  -1.216  1.00  0.00           H  
HETATM   24  H10 UNL     1       0.014   0.914   0.881  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.757  -0.205   2.284  1.00  0.00           H  
HETATM   26  H12 UNL     1      -4.017   1.615   0.251  1.00  0.00           H  
HETATM   27  H13 UNL     1      -5.094   0.179   0.256  1.00  0.00           H  
HETATM   28  H14 UNL     1      -3.425  -1.008  -1.170  1.00  0.00           H  
HETATM   29  H15 UNL     1      -3.860   0.581  -1.990  1.00  0.00           H  
HETATM   30  H16 UNL     1      -1.495   0.316  -2.044  1.00  0.00           H  
HETATM   31  H17 UNL     1      -1.778   1.526  -0.756  1.00  0.00           H  
HETATM   32  H18 UNL     1      -1.238  -1.514  -0.488  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   18   19
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6   14   24
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   14
CONECT   10   11   25
CONECT   11   12   26   27
CONECT   12   13   28   29
CONECT   13   14   30   31
CONECT   14   32
END

HMDB0302242
     RDKit          3D
Neocnidolide
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.8920    0.4008    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6978    0.0686   -0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    0.1352    0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -0.1910   -0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0559   -0.0976    0.4776 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2114   -1.0301    1.5617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0919   -1.1676    2.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3496   -1.7555    3.1961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410   -0.5539    1.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2621   -0.1149    1.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316    0.4952    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980    0.1205   -1.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076    0.4858   -1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -0.4887   -0.0937 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6918    0.9085   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3028   -0.4934    0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6266    1.1302    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6208    0.7941   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236   -0.9575   -0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5903   -0.6490    1.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849    1.0938    0.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111   -1.1598   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0963    0.6217   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0138    0.9144    0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7573   -0.2049    2.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0171    1.6152    0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0943    0.1785    0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4252   -1.0077   -1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8600    0.5811   -1.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4953    0.3160   -2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7783    1.5257   -0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2385   -1.5141   -0.4881 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  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14  5  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  1
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Neocnidilide, (cis)-isomer	MeSH
Neocnidilide, (trans)-isomer	MeSH
Sedanolide	MeSH
Neocnidilide, cis-(-)-isomer	MeSH

Chemical Formula

C₁₂H₁₈O₂

Average Molecular Weight

194.274

Monoisotopic Molecular Weight

194.13067982

IUPAC Name

(3S,3aR)-3-butyl-1,3,3a,4,5,6-hexahydro-2-benzofuran-1-one

Traditional Name

(3S,3aR)-3-butyl-3a,4,5,6-tetrahydro-3H-2-benzofuran-1-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CCCC)OC(=O)C2=CCCC[C@@]12[H]

InChI Identifier

InChI=1S/C12H18O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h7,9,11H,2-6,8H2,1H3/t9-,11+/m1/s1

InChI Key

UPJFTVFLSIQQAV-KOLCDFICSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isobenzofurans

Sub Class

Not Available

Direct Parent

Isobenzofurans

Alternative Parents

Substituents

Isobenzofuran
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Carbonyl group
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

gamma-lactone (CHEBI:80853 )

Ontology

Not Available

Exogenous (HMDB: HMDB0302242)

Food

Herb and spice

Herb

Dill (FooDB: FOOD00013)

Process

Not Available

Role

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0302242)

Pesticide (HMDB: HMDB0302242)

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	3.28	ALOGPS
logP	3.39	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	55.77 m³·mol⁻¹	ChemAxon
Polarizability	22.7 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	146.471	32859911
AllCCS	[M+H-H2O]+	142.405	32859911
AllCCS	[M+Na]+	151.345	32859911
AllCCS	[M+NH4]+	150.255	32859911
AllCCS	[M-H]-	151.37	32859911
AllCCS	[M+Na-2H]-	151.908	32859911
AllCCS	[M+HCOO]-	152.598	32859911
DeepCCS	[M-2H]-	186.09	30932474
DeepCCS	[M+Na]+	160.448	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	18.6823 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.14 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2111.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	546.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	205.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	327.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	712.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	763.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	126.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1428.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	446.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1447.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	466.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	353.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	572.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	548.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	62.3 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neocnidolide 10V, Positive-QTOF	splash10-0002-3900000000-d39a7ef515fc66b140c4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neocnidolide 20V, Positive-QTOF	splash10-000b-7900000000-eacd70bed5997c596974	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neocnidolide 40V, Positive-QTOF	splash10-0ufu-9100000000-830232c52182598f582c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neocnidolide 10V, Negative-QTOF	splash10-0006-0900000000-cb068c432eb0727709e5	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neocnidolide 20V, Negative-QTOF	splash10-0007-1900000000-93b3dde9e3e983c129d2	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neocnidolide 40V, Negative-QTOF	splash10-002e-9600000000-d8f8b9313f8bdb98b622	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neocnidolide 10V, Positive-QTOF	splash10-0002-1900000000-49b367cb0fc7718e4e78	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neocnidolide 20V, Positive-QTOF	splash10-00nb-9500000000-0134a38e6be28331b888	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neocnidolide 40V, Positive-QTOF	splash10-001i-9000000000-a0e31e4c37e2ab6ad44f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neocnidolide 10V, Negative-QTOF	splash10-0006-0900000000-c3ede4c1eb6b090e0d1d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neocnidolide 20V, Negative-QTOF	splash10-0006-0900000000-f7600350916de5d6cd4d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neocnidolide 40V, Negative-QTOF	splash10-0089-5900000000-9c268746fcfb8a224c53	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

FDB003860

KNApSAcK ID

Not Available

Chemspider ID

2341004

KEGG Compound ID

C17002

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1117681

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Neocnidolide (HMDB0302242)

MOL for HMDB0302242 (Neocnidolide)

3D MOL for HMDB0302242 (Neocnidolide)

3D SDF for HMDB0302242 (Neocnidolide)

3D-SDF for HMDB0302242 (Neocnidolide)

PDB for HMDB0302242 (Neocnidolide)

3D PDB for HMDB0302242 (Neocnidolide)

SMILES for HMDB0302242 (Neocnidolide)

INCHI for HMDB0302242 (Neocnidolide)

Structure for HMDB0302242 (Neocnidolide)

3D Structure for HMDB0302242 (Neocnidolide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra