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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 17:00:18 UTC

Update Date

2021-09-23 17:00:19 UTC

HMDB ID

HMDB0302336

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Psilostachyin C

Description

Psilostachyin c is a member of the class of compounds known as ambrosanolides and secoambrosanolides. Ambrosanolides and secoambrosanolides are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides). Psilostachyin c is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Psilostachyin c can be found in mugwort, which makes psilostachyin c a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302336
     RDKit          3D
Psilostachyin C
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.0223   -0.2469    0.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9191   -0.8198    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418   -2.1802    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0424   -3.0817    1.0318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118   -2.3143   -0.3158 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6493   -1.0055   -0.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8754   -0.1962   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    1.2529   -0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3447    1.5222   -1.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    1.6422   -0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8977    2.2651   -0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.4646    0.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5739    0.1166    0.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9947   -0.6259   -0.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2247   -1.9019   -0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5610   -2.8549   -1.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1777   -1.9243    0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -0.7892    0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4490   -1.1212    1.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7154   -0.8256    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    0.7776    0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0961   -1.1430   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294   -0.2685   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379    1.5018    0.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4589    1.8278   -0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665    2.5419   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1513    0.8384   -1.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3867    2.4993    0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8577    1.9887   -2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049    3.3944   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8975    2.0646   -0.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9393    0.7919    1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6325   -0.6576    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2004    0.9231    1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7404   -0.1602   -1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0853   -0.8028   -0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5901   -2.1930    1.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2904   -0.8180    2.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3121   -0.4824    1.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  7  2  1  0
 18 12  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END

  Mrv0541 02241223372D          

 19 21  0  0  0  0            999 V2000
    1.9384   -1.5668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1131   -1.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6180   -2.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1243   -2.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5358   -1.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3611   -1.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083   -2.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009   -0.9074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0414   -0.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6180   -0.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9384   -0.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8555   -0.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1960    0.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4537    0.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407    0.8245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8555    1.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1960    1.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4537    1.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2065    2.2270    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  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302336

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2C(OC(=O)C2=C)C2(C)OC(=O)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-4-5-10-9(2)14(17)18-13(10)15(3)11(8)6-7-12(16)19-15/h8,10-11,13H,2,4-7H2,1,3H3

> <INCHI_KEY>
FZYIWDQVFMUXPW-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.818011471457226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,9-dimethyl-5-methylidene-3,14-dioxatricyclo[8.4.0.0²,⁶]tetradecane-4,13-dione

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
2.654705635333333

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.652545607537194

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
67.89529999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,9-dimethyl-5-methylidene-3,14-dioxatricyclo[8.4.0.0²,⁶]tetradecane-4,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302336
     RDKit          3D
Psilostachyin C
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.0223   -0.2469    0.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9191   -0.8198    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418   -2.1802    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0424   -3.0817    1.0318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118   -2.3143   -0.3158 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6493   -1.0055   -0.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8754   -0.1962   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    1.2529   -0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3447    1.5222   -1.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    1.6422   -0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8977    2.2651   -0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.4646    0.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5739    0.1166    0.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9947   -0.6259   -0.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2247   -1.9019   -0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5610   -2.8549   -1.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1777   -1.9243    0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -0.7892    0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4490   -1.1212    1.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7154   -0.8256    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    0.7776    0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0961   -1.1430   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294   -0.2685   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379    1.5018    0.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4589    1.8278   -0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665    2.5419   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1513    0.8384   -1.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3867    2.4993    0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8577    1.9887   -2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049    3.3944   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8975    2.0646   -0.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9393    0.7919    1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6325   -0.6576    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2004    0.9231    1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7404   -0.1602   -1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0853   -0.8028   -0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5901   -2.1930    1.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2904   -0.8180    2.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3121   -0.4824    1.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  7  2  1  0
 18 12  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 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  O   UNK     0       3.618  -2.925   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.078  -2.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.154  -4.157   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.232  -3.849   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.000  -2.463   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.541  -2.617   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.002  -4.157   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.308  -1.694   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.077  -1.078   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.154  -0.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.618  -1.694   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.464  -0.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.233   0.615   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.847   0.307   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.076   1.539   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.464   3.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.233   2.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.847   2.771   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.385   4.157   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6                                                            
CONECT    8    2    9                                                       
CONECT    9    5    8   10   14                                             
CONECT   10    9                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14    9   13   15                                                  
CONECT   15   14   18                                                       
CONECT   16   17                                                            
CONECT   17   13   16   18                                                  
CONECT   18   15   17   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0302336
HETATM    1  C1  UNL     1       4.022  -0.247   0.579  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.919  -0.820   0.155  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.442  -2.180   0.359  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.042  -3.082   1.032  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.212  -2.314  -0.316  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.649  -1.006  -0.557  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.875  -0.196  -0.652  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.620   1.253  -0.411  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.345   1.522  -1.188  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.766   1.642  -0.167  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.898   2.265  -0.952  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.072   0.465   0.645  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.574   0.117   0.693  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.995  -0.626  -0.543  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.225  -1.902  -0.475  1.00  0.00           C  
HETATM   16  O3  UNL     1      -2.561  -2.855  -1.216  1.00  0.00           O  
HETATM   17  O4  UNL     1      -1.178  -1.924   0.423  1.00  0.00           O  
HETATM   18  C14 UNL     1      -0.318  -0.789   0.530  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.449  -1.121   1.837  1.00  0.00           C  
HETATM   20  H1  UNL     1       4.715  -0.826   1.173  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.288   0.778   0.373  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.096  -1.143  -1.527  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.229  -0.269  -1.727  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.538   1.502   0.656  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.459   1.828  -0.851  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.466   2.542  -1.628  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.151   0.838  -1.997  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.387   2.499   0.480  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.858   1.989  -2.049  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.805   3.394  -0.996  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.898   2.065  -0.618  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.939   0.792   1.737  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.633  -0.658   1.523  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.200   0.923   1.021  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.740  -0.160  -1.491  1.00  0.00           H  
HETATM   36  H17 UNL     1      -4.085  -0.803  -0.449  1.00  0.00           H  
HETATM   37  H18 UNL     1       0.590  -2.193   1.971  1.00  0.00           H  
HETATM   38  H19 UNL     1      -0.290  -0.818   2.639  1.00  0.00           H  
HETATM   39  H20 UNL     1       1.312  -0.482   1.982  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   18   22
CONECT    7    8   23
CONECT    8    9   24   25
CONECT    9   10   26   27
CONECT   10   11   12   28
CONECT   11   29   30   31
CONECT   12   13   18   32
CONECT   13   14   33   34
CONECT   14   15   35   36
CONECT   15   16   16   17
CONECT   17   18
CONECT   18   19
CONECT   19   37   38   39
END

HMDB0302336
     RDKit          3D
Psilostachyin C
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.0223   -0.2469    0.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9191   -0.8198    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418   -2.1802    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0424   -3.0817    1.0318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118   -2.3143   -0.3158 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6493   -1.0055   -0.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8754   -0.1962   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    1.2529   -0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3447    1.5222   -1.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    1.6422   -0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8977    2.2651   -0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.4646    0.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5739    0.1166    0.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9947   -0.6259   -0.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2247   -1.9019   -0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5610   -2.8549   -1.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1777   -1.9243    0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -0.7892    0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4490   -1.1212    1.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7154   -0.8256    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    0.7776    0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0961   -1.1430   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294   -0.2685   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379    1.5018    0.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4589    1.8278   -0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665    2.5419   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1513    0.8384   -1.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3867    2.4993    0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8577    1.9887   -2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049    3.3944   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8975    2.0646   -0.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9393    0.7919    1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6325   -0.6576    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2004    0.9231    1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7404   -0.1602   -1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0853   -0.8028   -0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5901   -2.1930    1.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2904   -0.8180    2.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3121   -0.4824    1.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  7  2  1  0
 18 12  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 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

1,9-dimethyl-5-methylidene-3,14-dioxatricyclo[8.4.0.0²,⁶]tetradecane-4,13-dione

Traditional Name

1,9-dimethyl-5-methylidene-3,14-dioxatricyclo[8.4.0.0²,⁶]tetradecane-4,13-dione

CAS Registry Number

Not Available

SMILES

CC1CCC2C(OC(=O)C2=C)C2(C)OC(=O)CCC12

InChI Identifier

InChI=1S/C15H20O4/c1-8-4-5-10-9(2)14(17)18-13(10)15(3)11(8)6-7-12(16)19-15/h8,10-11,13H,2,4-7H2,1,3H3

InChI Key

FZYIWDQVFMUXPW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Ambrosanolides and secoambrosanolides

Alternative Parents

Substituents

Secoambrosanolide
Sesquiterpenoid
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302336)

Food

Herb and spice

Herb

Mugwort (FooDB: FOOD00020)

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	2.81	ALOGPS
logP	2.65	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.9 m³·mol⁻¹	ChemAxon
Polarizability	27.82 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
AllCCS	[M+H]+	161.289	32859911
AllCCS	[M+H-H2O]+	157.602	32859911
AllCCS	[M+Na]+	165.699	32859911
AllCCS	[M+NH4]+	164.713	32859911
AllCCS	[M-H]-	167.773	32859911
AllCCS	[M+Na-2H]-	167.698	32859911
AllCCS	[M+HCOO]-	167.736	32859911
DeepCCS	[M-2H]-	191.198	30932474
DeepCCS	[M+Na]+	166.764	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 - Psilostachyin C 10V, Positive-QTOF	splash10-014i-0190000000-8ea791ae47bb8e1994bf	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin C 20V, Positive-QTOF	splash10-01bl-0690000000-dc315a5f59fba10fa749	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin C 40V, Positive-QTOF	splash10-05mo-9710000000-13e5287b26a6912999c4	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin C 10V, Negative-QTOF	splash10-03xr-0090000000-df3cc11c383da40cf533	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin C 20V, Negative-QTOF	splash10-02t9-0190000000-83a84efad1aeba609c9a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin C 40V, Negative-QTOF	splash10-0006-9810000000-8f7b8437c5e4d6d8ec4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin C 10V, Positive-QTOF	splash10-014i-0090000000-26f58baa9a663e44f5d5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin C 20V, Positive-QTOF	splash10-1000-0490000000-f2e9018872edbff3c74f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin C 40V, Positive-QTOF	splash10-0903-2950000000-ce7f5ac1c09d984cf01f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin C 10V, Negative-QTOF	splash10-03di-0090000000-16d43704d08f3756e03a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin C 20V, Negative-QTOF	splash10-03di-0290000000-9b05ddd2327a902b7d7a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin C 40V, Negative-QTOF	splash10-01ox-2930000000-c8f2596c64381ae71f17	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

FDB004166

KNApSAcK ID

Not Available

Chemspider ID

87742

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

97213

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 Psilostachyin C (HMDB0302336)

MOL for HMDB0302336 (Psilostachyin C)

3D MOL for HMDB0302336 (Psilostachyin C)

3D SDF for HMDB0302336 (Psilostachyin C)

3D-SDF for HMDB0302336 (Psilostachyin C)

PDB for HMDB0302336 (Psilostachyin C)

3D PDB for HMDB0302336 (Psilostachyin C)

SMILES for HMDB0302336 (Psilostachyin C)

INCHI for HMDB0302336 (Psilostachyin C)

Structure for HMDB0302336 (Psilostachyin C)

3D Structure for HMDB0302336 (Psilostachyin C)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra