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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:59:43 UTC

Update Date

2021-09-23 19:59:43 UTC

HMDB ID

HMDB0302711

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Viscidulin C

Description

Viscidulin c belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Viscidulin c is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Viscidulin c can be found in sweet bay, which makes viscidulin c a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302711
     RDKit          3D
Viscidulin C
 39 42  0  0  0  0  0  0  0  0999 V2000
   -0.9692    3.3436   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6054    2.0760    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8227    1.9037    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421    1.2139   -0.8388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037    1.5814   -0.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609   -0.2528   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3003   -0.6836    0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3890   -1.5868   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346   -1.3105    1.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8362   -2.0708    2.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1386   -0.9094    1.1150 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0691   -0.8290   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1609   -0.2033   -0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6135    1.0417   -0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2431    0.6068    1.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9706   -0.6546    0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6068   -0.6547   -0.4855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3283   -1.1461   -0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0791   -2.6297   -0.5595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768    4.1708    0.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0045    3.5439   -0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    2.8641    0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9838    1.2628    1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0363    1.6291   -1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8307    2.5518   -0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7105   -0.7135   -1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8014    0.1886    0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286   -0.9297   -0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330   -1.9876    0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0487   -2.3506   -0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0598   -1.9050   -0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -0.0564   -1.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4402    1.4757   -0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5574    0.4449    1.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0209    1.3838    1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2528   -1.3400    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065   -2.9978   -1.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0573   -3.1238   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4330   -2.9469    0.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  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
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14  2  1  0
 18 16  1  0
 12  6  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END

  Mrv0541 02241223312D          

 19 22  0  0  0  0            999 V2000
   -1.0282   -2.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7816   -1.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3576   -0.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749   -0.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155    0.2876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6862   -0.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2749   -0.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4523   -0.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0410   -1.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6169   -1.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3576   -1.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0155   -1.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749    1.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6169    1.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6169    0.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049    0.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6169    0.7816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049    1.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4523    2.2621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 15  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302711

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C(OC1=O)C1C(CC3OC13C)C(=C)CC2O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-6-4-9(16)11-7(2)14(17)18-13(11)12-8(6)5-10-15(12,3)19-10/h7-13,16H,1,4-5H2,2-3H3

> <INCHI_KEY>
VHMXKQUYGYSNAU-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.678013677521665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-5,14-dimethyl-9-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-4-one

> <ALOGPS_LOGP>
0.82

> <JCHEM_LOGP>
0.6712802613333322

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.769997150995433

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8994032461545975

> <JCHEM_POLAR_SURFACE_AREA>
59.059999999999995

> <JCHEM_REFRACTIVITY>
67.4729

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-5,14-dimethyl-9-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302711
     RDKit          3D
Viscidulin C
 39 42  0  0  0  0  0  0  0  0999 V2000
   -0.9692    3.3436   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6054    2.0760    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8227    1.9037    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421    1.2139   -0.8388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037    1.5814   -0.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609   -0.2528   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3003   -0.6836    0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3890   -1.5868   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346   -1.3105    1.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8362   -2.0708    2.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1386   -0.9094    1.1150 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0691   -0.8290   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1609   -0.2033   -0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6135    1.0417   -0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2431    0.6068    1.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9706   -0.6546    0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6068   -0.6547   -0.4855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3283   -1.1461   -0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0791   -2.6297   -0.5595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768    4.1708    0.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0045    3.5439   -0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    2.8641    0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9838    1.2628    1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0363    1.6291   -1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8307    2.5518   -0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7105   -0.7135   -1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8014    0.1886    0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286   -0.9297   -0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330   -1.9876    0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0487   -2.3506   -0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0598   -1.9050   -0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -0.0564   -1.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4402    1.4757   -0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5574    0.4449    1.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0209    1.3838    1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2528   -1.3400    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065   -2.9978   -1.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0573   -3.1238   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4330   -2.9469    0.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  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
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14  2  1  0
 18 16  1  0
 12  6  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.919  -4.223   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.459  -2.687   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.534  -1.612   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.380  -0.231   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.762   0.537   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.148  -0.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.380  -1.612   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.844  -1.152   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.077  -2.534   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.152  -3.609   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.534  -3.148   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.762  -2.380   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.380   3.148   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.152   2.227   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.152   0.690   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.382   0.229   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.152   1.459   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.382   2.687   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.844   4.223   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    6    8   11   12                                             
CONECT    8    7    9   16                                                  
CONECT    9    2    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11    7   10   12                                                  
CONECT   12    7   11                                                       
CONECT   13   14                                                            
CONECT   14   13   15   18                                                  
CONECT   15    4   14   16                                                  
CONECT   16    8   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   14   17   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0302711
HETATM    1  C1  UNL     1      -0.969   3.344  -0.098  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.605   2.076   0.048  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.823   1.904   0.384  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.442   1.214  -0.839  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.804   1.581  -0.802  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.361  -0.253  -0.705  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.300  -0.684   0.404  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.389  -1.587  -0.108  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.435  -1.310   1.410  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.836  -2.071   2.358  1.00  0.00           O  
HETATM   11  O3  UNL     1       0.139  -0.909   1.115  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.069  -0.829  -0.282  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.161  -0.203  -0.807  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.613   1.042  -0.131  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.243   0.607   1.150  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.971  -0.655   0.744  1.00  0.00           C  
HETATM   17  O4  UNL     1      -3.607  -0.655  -0.486  1.00  0.00           O  
HETATM   18  C14 UNL     1      -2.328  -1.146  -0.529  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.079  -2.630  -0.560  1.00  0.00           C  
HETATM   20  H1  UNL     1      -0.277   4.171   0.019  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.004   3.544  -0.345  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.285   2.864   0.589  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.984   1.263   1.272  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.036   1.629  -1.776  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.831   2.552  -0.629  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.710  -0.713  -1.665  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.801   0.189   0.881  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.129  -0.930  -0.631  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.933  -1.988   0.779  1.00  0.00           H  
HETATM   30  H11 UNL     1       3.049  -2.351  -0.804  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.060  -1.905  -0.640  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.089  -0.056  -1.881  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.440   1.476  -0.767  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.557   0.445   1.981  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.021   1.384   1.409  1.00  0.00           H  
HETATM   36  H17 UNL     1      -3.253  -1.340   1.541  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.706  -2.998  -1.522  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.057  -3.124  -0.382  1.00  0.00           H  
HETATM   39  H20 UNL     1      -1.433  -2.947   0.307  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   14
CONECT    3    4   22   23
CONECT    4    5    6   24
CONECT    5   25
CONECT    6    7   12   26
CONECT    7    8    9   27
CONECT    8   28   29   30
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   31
CONECT   13   14   18   32
CONECT   14   15   33
CONECT   15   16   34   35
CONECT   16   17   18   36
CONECT   17   18
CONECT   18   19
CONECT   19   37   38   39
END

HMDB0302711
     RDKit          3D
Viscidulin C
 39 42  0  0  0  0  0  0  0  0999 V2000
   -0.9692    3.3436   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6054    2.0760    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8227    1.9037    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421    1.2139   -0.8388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037    1.5814   -0.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609   -0.2528   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3003   -0.6836    0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3890   -1.5868   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346   -1.3105    1.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8362   -2.0708    2.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1386   -0.9094    1.1150 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0691   -0.8290   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1609   -0.2033   -0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6135    1.0417   -0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2431    0.6068    1.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9706   -0.6546    0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6068   -0.6547   -0.4855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3283   -1.1461   -0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0791   -2.6297   -0.5595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768    4.1708    0.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0045    3.5439   -0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    2.8641    0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9838    1.2628    1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0363    1.6291   -1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8307    2.5518   -0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7105   -0.7135   -1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8014    0.1886    0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286   -0.9297   -0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330   -1.9876    0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0487   -2.3506   -0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0598   -1.9050   -0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -0.0564   -1.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4402    1.4757   -0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5574    0.4449    1.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0209    1.3838    1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2528   -1.3400    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065   -2.9978   -1.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0573   -3.1238   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4330   -2.9469    0.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  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
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14  2  1  0
 18 16  1  0
 12  6  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

7-hydroxy-5,14-dimethyl-9-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-4-one

Traditional Name

7-hydroxy-5,14-dimethyl-9-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-4-one

CAS Registry Number

Not Available

SMILES

CC1C2C(OC1=O)C1C(CC3OC13C)C(=C)CC2O

InChI Identifier

InChI=1S/C15H20O4/c1-6-4-9(16)11-7(2)14(17)18-13(11)12-8(6)5-10-15(12,3)19-10/h7-13,16H,1,4-5H2,2-3H3

InChI Key

VHMXKQUYGYSNAU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Oxane
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302711)

Food

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)

Process

Not Available

Role

Industrial application

Agriculture

Pesticide

Herbicide (HMDB: HMDB0302711)

Pesticide (HMDB: HMDB0302711)

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	0.82	ALOGPS
logP	0.67	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	14.77	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.47 m³·mol⁻¹	ChemAxon
Polarizability	27.68 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
AllCCS	[M+H]+	162.009	32859911
AllCCS	[M+H-H2O]+	158.511	32859911
AllCCS	[M+Na]+	166.188	32859911
AllCCS	[M+NH4]+	165.255	32859911
AllCCS	[M-H]-	166.778	32859911
AllCCS	[M+Na-2H]-	166.478	32859911
AllCCS	[M+HCOO]-	166.267	32859911
DeepCCS	[M-2H]-	192.467	30932474
DeepCCS	[M+Na]+	168.032	30932474

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 - Viscidulin C 10V, Positive-QTOF	splash10-00kb-0190000000-4a64e526049eb545b28f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Viscidulin C 20V, Positive-QTOF	splash10-00tb-0690000000-fc8854d0d9b76d98da4c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Viscidulin C 40V, Positive-QTOF	splash10-0fk9-5910000000-d93fe5af9f013c7f4510	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Viscidulin C 10V, Negative-QTOF	splash10-03di-0090000000-42e87d5cb01afad84994	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Viscidulin C 20V, Negative-QTOF	splash10-03xs-0090000000-03ca117fc6908bf9587a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Viscidulin C 40V, Negative-QTOF	splash10-008l-9410000000-fb15522265e35658a629	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Viscidulin C 10V, Positive-QTOF	splash10-00kb-0090000000-99db3d1438a3693f2dcb	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Viscidulin C 20V, Positive-QTOF	splash10-0002-2490000000-0de79a12a7907df8229c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Viscidulin C 40V, Positive-QTOF	splash10-0abd-4930000000-8f8742fde0b84167661f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Viscidulin C 10V, Negative-QTOF	splash10-03di-0090000000-16d43704d08f3756e03a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Viscidulin C 20V, Negative-QTOF	splash10-03dj-0090000000-d25c00a855353368cc93	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Viscidulin C 40V, Negative-QTOF	splash10-0007-9430000000-ef83d0aac2f2b6b37a15	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

FDB005903

KNApSAcK ID

Not Available

Chemspider ID

266697

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

301777

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 Viscidulin C (HMDB0302711)

MOL for HMDB0302711 (Viscidulin C)

3D MOL for HMDB0302711 (Viscidulin C)

3D SDF for HMDB0302711 (Viscidulin C)

3D-SDF for HMDB0302711 (Viscidulin C)

PDB for HMDB0302711 (Viscidulin C)

3D PDB for HMDB0302711 (Viscidulin C)

SMILES for HMDB0302711 (Viscidulin C)

INCHI for HMDB0302711 (Viscidulin C)

Structure for HMDB0302711 (Viscidulin C)

3D Structure for HMDB0302711 (Viscidulin C)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra