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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:11:45 UTC

Update Date

2022-03-07 02:54:47 UTC

HMDB ID

HMDB0036130

Secondary Accession Numbers

HMDB36130

Metabolite Identification

Common Name

Vulgarin

Description

Vulgarin belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Based on a literature review a significant number of articles have been published on Vulgarin.

Structure

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

HMDB0036130
     RDKit          3D
Vulgarin
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.9132   -0.4558   -0.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4827   -0.0102   -0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.4718   -0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3019    2.2629   -1.1309 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2937    1.7981    0.0367 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6788    0.6879    0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932   -0.3872    0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1368   -1.7667    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2340   -1.7031    1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1204   -0.9679    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1147   -1.8206   -1.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5279   -0.9248    0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9808   -1.6157    1.5309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4268   -0.0201   -0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9537    1.1764   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735    1.5148   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625    2.1199    1.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1841    2.5848   -0.8815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5825    0.4135   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784   -1.0349    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0934   -1.2010   -1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6328    0.3832   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680   -0.3383   -1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967    0.8231    1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572   -0.3697    1.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7229   -2.4835    1.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -2.1807   -0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520   -1.0889    2.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5829   -2.7152    1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950   -2.8631   -0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0783   -1.7498   -1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3326   -1.5532   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4492   -0.3375   -0.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5961    1.8759   -0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7451    2.6666    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4878    2.8617    1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355    1.3542    2.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5403    3.1811   -0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279    0.4124   -1.2134 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  7  2  1  0
 19 10  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv0541 05061308532D          

 19 21  0  0  0  0            999 V2000
    4.2295    1.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7591    1.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8705   -0.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613   -0.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9359   -1.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  1  1  0  0  0  0
  9  4  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 14  2  1  0  0  0  0
 14  6  1  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  1  0  0  0  0
 16 10  2  0  0  0  0
 17 13  2  0  0  0  0
 18 15  1  0  0  0  0
 19 11  1  0  0  0  0
 19 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036130

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CCC3(C)C(C2OC1=O)C(C)(O)C=CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h5,7-9,11-12,18H,4,6H2,1-3H3

> <INCHI_KEY>
NGPDZEACIWDCKX-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.773741506211408

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,6H,9H,9aH,9bH-naphtho[1,2-b]furan-2,6-dione

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
1.7767635190000004

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.252761655446307

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1256420519077857

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
69.83229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
judaicin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036130
     RDKit          3D
Vulgarin
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.9132   -0.4558   -0.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4827   -0.0102   -0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.4718   -0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3019    2.2629   -1.1309 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2937    1.7981    0.0367 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6788    0.6879    0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932   -0.3872    0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1368   -1.7667    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2340   -1.7031    1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1204   -0.9679    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1147   -1.8206   -1.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5279   -0.9248    0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9808   -1.6157    1.5309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4268   -0.0201   -0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9537    1.1764   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735    1.5148   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625    2.1199    1.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1841    2.5848   -0.8815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5825    0.4135   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784   -1.0349    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0934   -1.2010   -1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6328    0.3832   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680   -0.3383   -1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967    0.8231    1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572   -0.3697    1.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7229   -2.4835    1.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -2.1807   -0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520   -1.0889    2.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5829   -2.7152    1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950   -2.8631   -0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0783   -1.7498   -1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3326   -1.5532   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4492   -0.3375   -0.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5961    1.8759   -0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7451    2.6666    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4878    2.8617    1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355    1.3542    2.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5403    3.1811   -0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279    0.4124   -1.2134 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  7  2  1  0
 19 10  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.895   2.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.417   3.436   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.492  -1.159   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.719   1.616   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.062  -0.587   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.122   3.484   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.141  -0.731   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.747  -2.095   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.406  -0.502   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4    6    9                                                       
CONECT    5    7   10                                                       
CONECT    6    4   14                                                       
CONECT    7    5   15                                                       
CONECT    8    1    9   13                                                  
CONECT    9    4    8   11                                                  
CONECT   10    5   14   16                                                  
CONECT   11    9   12   19                                                  
CONECT   12   11   14   15                                                  
CONECT   13    8   17   19                                                  
CONECT   14    2    6   10   12                                             
CONECT   15    3    7   12   18                                             
CONECT   16   10                                                            
CONECT   17   13                                                            
CONECT   18   15                                                            
CONECT   19   11   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0036130
HETATM    1  C1  UNL     1       3.913  -0.456  -0.698  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.483  -0.010  -0.769  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.430   1.472  -0.656  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.302   2.263  -1.131  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.294   1.798   0.037  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.679   0.688   0.661  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.693  -0.387   0.474  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.137  -1.767   0.447  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.234  -1.703   1.116  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.120  -0.968   0.116  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.115  -1.821  -1.148  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.528  -0.925   0.575  1.00  0.00           C  
HETATM   13  O3  UNL     1      -2.981  -1.616   1.531  1.00  0.00           O  
HETATM   14  C11 UNL     1      -3.427  -0.020  -0.138  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.954   1.176  -0.437  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.573   1.515  -0.036  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.662   2.120   1.347  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.184   2.585  -0.882  1.00  0.00           O  
HETATM   19  C15 UNL     1      -0.582   0.413  -0.138  1.00  0.00           C  
HETATM   20  H1  UNL     1       4.078  -1.035   0.247  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.093  -1.201  -1.526  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.633   0.383  -0.765  1.00  0.00           H  
HETATM   23  H4  UNL     1       1.968  -0.338  -1.700  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.497   0.823   1.732  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.457  -0.370   1.307  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.723  -2.484   1.058  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.104  -2.181  -0.563  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.152  -1.089   2.023  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.583  -2.715   1.304  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.995  -2.863  -0.836  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.078  -1.750  -1.688  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.333  -1.553  -1.854  1.00  0.00           H  
HETATM   33  H14 UNL     1      -4.449  -0.337  -0.401  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.596   1.876  -0.969  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.745   2.667   1.631  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.488   2.862   1.351  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.936   1.354   2.109  1.00  0.00           H  
HETATM   38  H19 UNL     1      -0.540   3.181  -0.435  1.00  0.00           H  
HETATM   39  H20 UNL     1      -0.228   0.412  -1.213  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    7   23
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   19   24
CONECT    7    8   25
CONECT    8    9   26   27
CONECT    9   10   28   29
CONECT   10   11   12   19
CONECT   11   30   31   32
CONECT   12   13   13   14
CONECT   14   15   15   33
CONECT   15   16   34
CONECT   16   17   18   19
CONECT   17   35   36   37
CONECT   18   38
CONECT   19   39
END

HMDB0036130
     RDKit          3D
Vulgarin
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.9132   -0.4558   -0.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4827   -0.0102   -0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.4718   -0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3019    2.2629   -1.1309 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2937    1.7981    0.0367 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6788    0.6879    0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932   -0.3872    0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1368   -1.7667    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2340   -1.7031    1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1204   -0.9679    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1147   -1.8206   -1.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5279   -0.9248    0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9808   -1.6157    1.5309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4268   -0.0201   -0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9537    1.1764   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735    1.5148   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625    2.1199    1.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1841    2.5848   -0.8815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5825    0.4135   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784   -1.0349    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0934   -1.2010   -1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6328    0.3832   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680   -0.3383   -1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967    0.8231    1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572   -0.3697    1.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7229   -2.4835    1.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -2.1807   -0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520   -1.0889    2.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5829   -2.7152    1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950   -2.8631   -0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0783   -1.7498   -1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3326   -1.5532   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4492   -0.3375   -0.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5961    1.8759   -0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7451    2.6666    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4878    2.8617    1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355    1.3542    2.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5403    3.1811   -0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2279    0.4124   -1.2134 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  7  2  1  0
 19 10  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Barrelin	HMDB
Judaicin	HMDB
Judaicin (eudesmane naphthofuran)	HMDB
Judaicin (sesquiterpene)	HMDB
Tauremisin	HMDB
Tauremisin a	HMDB
Tauremizin	HMDB
Tauresmin	HMDB

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

9-hydroxy-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,6H,9H,9aH,9bH-naphtho[1,2-b]furan-2,6-dione

Traditional Name

judaicin

CAS Registry Number

3162-56-9

SMILES

CC1C2CCC3(C)C(C2OC1=O)C(C)(O)C=CC3=O

InChI Identifier

InChI=1S/C15H20O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h5,7-9,11-12,18H,4,6H2,1-3H3

InChI Key

NGPDZEACIWDCKX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Cyclohexenone
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036130)

Source

Endogenous

Endogenous (HMDB: HMDB0036130)

Plant

Plant (HMDB: HMDB0036130)

Animal

Animal (HMDB: HMDB0036130)

Exogenous

Food

Food (HMDB: HMDB0036130)

Herb and spice

Herb

Mugwort (FooDB: FOOD00020)

Exogenous (HMDB: HMDB0036130)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036130)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036130)

Lipid metabolism pathway (HMDB: HMDB0036130)

Cellular process

Cell signaling (HMDB: HMDB0036130)

Biochemical process

Lipid transport (HMDB: HMDB0036130)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174 - 175 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	40490 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.32 g/L	ALOGPS
logP	0.75	ALOGPS
logP	1.78	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.25	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.83 m³·mol⁻¹	ChemAxon
Polarizability	27.77 Å³	ChemAxon
Number of Rings	3	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]+	161.587	31661259
DarkChem	[M-H]-	157.724	31661259
DeepCCS	[M+H]+	166.639	30932474
DeepCCS	[M-H]-	164.281	30932474
DeepCCS	[M-2H]-	197.167	30932474
DeepCCS	[M+Na]+	172.732	30932474
AllCCS	[M+H]+	160.7	32859911
AllCCS	[M+H-H2O]+	157.1	32859911
AllCCS	[M+NH4]+	164.1	32859911
AllCCS	[M+Na]+	165.0	32859911
AllCCS	[M-H]-	167.0	32859911
AllCCS	[M+Na-2H]-	167.0	32859911
AllCCS	[M+HCOO]-	167.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.84 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8847 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.0 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1956.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	227.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	131.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	404.8 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	515.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	84.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	842.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	335.7 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	1139.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	267.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	292.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	295.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	192.5 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	61.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vulgarin	CC1C2CCC3(C)C(C2OC1=O)C(C)(O)C=CC3=O	3333.6	Standard polar	33892256
Vulgarin	CC1C2CCC3(C)C(C2OC1=O)C(C)(O)C=CC3=O	2108.4	Standard non polar	33892256
Vulgarin	CC1C2CCC3(C)C(C2OC1=O)C(C)(O)C=CC3=O	2120.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vulgarin,1TMS,isomer #1	CC1C(=O)OC2C1CCC1(C)C(=O)C=CC(C)(O[Si](C)(C)C)C21	2324.5	Semi standard non polar	33892256
Vulgarin,1TBDMS,isomer #1	CC1C(=O)OC2C1CCC1(C)C(=O)C=CC(C)(O[Si](C)(C)C(C)(C)C)C21	2569.8	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 - Vulgarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ay1-7390000000-f3b7b031e2bd5ce67efb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vulgarin GC-MS (1 TMS) - 70eV, Positive	splash10-00b9-6694000000-29a96556fa9dccd120eb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vulgarin 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 - Vulgarin 10V, Positive-QTOF	splash10-00kb-0190000000-317d449691d81af7d9c0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 20V, Positive-QTOF	splash10-00mk-0690000000-cb4df13a679d9ff6796a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 40V, Positive-QTOF	splash10-0f6x-7920000000-c934a33edd5f8bce2521	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 10V, Positive-QTOF	splash10-00kb-0190000000-317d449691d81af7d9c0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 20V, Positive-QTOF	splash10-00mk-0690000000-cb4df13a679d9ff6796a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 40V, Positive-QTOF	splash10-0f6x-7920000000-c934a33edd5f8bce2521	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 10V, Negative-QTOF	splash10-03di-0090000000-b2d4f4080b70752b2d55	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 20V, Negative-QTOF	splash10-03xs-0190000000-f2796cc7b5eda709c7ce	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 40V, Negative-QTOF	splash10-0udi-9750000000-7ea279dead6bad682e4f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 10V, Negative-QTOF	splash10-03di-0090000000-b2d4f4080b70752b2d55	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 20V, Negative-QTOF	splash10-03xs-0190000000-f2796cc7b5eda709c7ce	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 40V, Negative-QTOF	splash10-0udi-9750000000-7ea279dead6bad682e4f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 10V, Negative-QTOF	splash10-03di-0090000000-3f27ef3c2ceb771717b4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 20V, Negative-QTOF	splash10-02t9-0190000000-44d1e4851c3a25bfc4a2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 40V, Negative-QTOF	splash10-004i-3920000000-4dbf2c15f65cf08df021	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 10V, Positive-QTOF	splash10-014i-0090000000-7e0609ac23949c6e9195	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 20V, Positive-QTOF	splash10-014i-0490000000-64186fc06445ef7edc7f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vulgarin 40V, Positive-QTOF	splash10-05fu-6920000000-32d47e89a79b70f5d2f2	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

619337

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1434961

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Vulgarin (HMDB0036130)

MOL for HMDB0036130 (Vulgarin)

3D MOL for HMDB0036130 (Vulgarin)

3D SDF for HMDB0036130 (Vulgarin)

3D-SDF for HMDB0036130 (Vulgarin)

PDB for HMDB0036130 (Vulgarin)

3D PDB for HMDB0036130 (Vulgarin)

SMILES for HMDB0036130 (Vulgarin)

INCHI for HMDB0036130 (Vulgarin)

Structure for HMDB0036130 (Vulgarin)

3D Structure for HMDB0036130 (Vulgarin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra