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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:59:50 UTC

Update Date

2021-09-23 16:59:50 UTC

HMDB ID

HMDB0302335

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Psilostachyin

Description

Psilostachyin 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 is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Psilostachyin can be found in mugwort, which makes psilostachyin a potential biomarker for the consumption of this food product. Psilostachyins are bio-active isolates of Ambrosia psilostachya .

Structure

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

HMDB0302335
     RDKit          3D
Psilostachyin
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.3631    0.2034   -0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0841    0.5186   -0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    1.5466   -1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7922    2.2905   -2.2482 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0135    1.5564   -0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440    1.0403    0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0643   -0.1217    0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163   -1.1041   -0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2906   -1.8934    0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0764   -1.3163    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8759   -1.7588   -1.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2036    0.1267    0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5233    0.9601   -0.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0262    0.9426   -1.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4829    0.4567    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6742    0.1801    0.5852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971    0.3538    1.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149    0.7642    1.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0827    0.0130    2.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557    2.0265    1.5586 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0544    0.7067   -1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673   -0.5946   -0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7166    1.8025    1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4797   -0.5771    1.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9935   -0.5552   -1.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152   -1.8189   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -2.8855   -0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851   -2.1782    1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5748   -1.8608    1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5751   -1.2642   -1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9622   -1.7579   -0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6102   -2.8497   -1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415    0.6893   -1.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2613    2.0227   -0.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4444    1.9847   -1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3714    0.3793   -1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0899   -0.3911    2.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6694   -0.8264    2.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1403    0.6234    3.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079    2.5659    1.8393 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
 12 18  1  0
 18 19  1  0
 18 20  1  0
  7  2  1  0
 17 12  1  0
 18  6  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 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
 20 40  1  0
M  END

  Mrv0541 02241221342D          

 20 22  0  0  0  0            999 V2000
    1.8290    0.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5591    0.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2220    0.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0193    0.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3505   -0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9662   -0.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1559   -1.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5296   -0.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3534   -1.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5325   -1.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013   -0.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3953   -0.5534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8176   -0.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3288   -1.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6049   -1.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5418   -1.5711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2818   -1.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0118   -1.5906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1635   -0.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7546    0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 13  1  0  0  0  0
  7 14  1  0  0  0  0
  7 15  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302335

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2C(OC(=O)C2=C)C(C)(O)C11CCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O5/c1-8-4-5-10-9(2)13(17)19-12(10)14(3,18)15(8)7-6-11(16)20-15/h8,10,12,18H,2,4-7H2,1,3H3

> <INCHI_KEY>
IRPFOXRBPHCCTG-UHFFFAOYSA-N

> <FORMULA>
C15H20O5

> <MOLECULAR_WEIGHT>
280.3163

> <EXACT_MASS>
280.13107375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.619150383689117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-6,8-dimethyl-3-methylidene-octahydrospiro[cyclohepta[b]furan-7,2'-oxolane]-2,5'-dione

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
1.6513133303333334

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.886564644435737

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7232166245238085

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
69.2694

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-6,8-dimethyl-3-methylidene-tetrahydro-3aH-spiro[cyclohepta[b]furan-7,2'-oxolane]-2,5'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302335
     RDKit          3D
Psilostachyin
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.3631    0.2034   -0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0841    0.5186   -0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    1.5466   -1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7922    2.2905   -2.2482 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0135    1.5564   -0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440    1.0403    0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0643   -0.1217    0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163   -1.1041   -0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2906   -1.8934    0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0764   -1.3163    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8759   -1.7588   -1.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2036    0.1267    0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5233    0.9601   -0.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0262    0.9426   -1.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4829    0.4567    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6742    0.1801    0.5852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971    0.3538    1.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149    0.7642    1.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0827    0.0130    2.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557    2.0265    1.5586 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0544    0.7067   -1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673   -0.5946   -0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7166    1.8025    1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4797   -0.5771    1.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9935   -0.5552   -1.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152   -1.8189   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -2.8855   -0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851   -2.1782    1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5748   -1.8608    1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5751   -1.2642   -1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9622   -1.7579   -0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6102   -2.8497   -1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415    0.6893   -1.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2613    2.0227   -0.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4444    1.9847   -1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3714    0.3793   -1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0899   -0.3911    2.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6694   -0.8264    2.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1403    0.6234    3.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079    2.5659    1.8393 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
 12 18  1  0
 18 19  1  0
 18 20  1  0
  7  2  1  0
 17 12  1  0
 18  6  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 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
 20 40  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       3.414   1.141   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.777   0.423   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.014   1.340   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.503   0.944   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.121  -0.467   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.404  -1.830   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.891  -2.118   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.722  -1.116   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.393  -2.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.861  -2.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.242  -1.362   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.738  -1.033   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.393  -0.338   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.214  -3.624   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.862  -3.265   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.478  -2.933   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.859  -2.252   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.222  -2.969   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.639  -0.728   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.742   0.347   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8   14   15                                             
CONECT    8    7    2    9   13                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    8                                                       
CONECT   14    7                                                            
CONECT   15    7                                                            
CONECT   16    6   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    5   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0302335
HETATM    1  C1  UNL     1       4.363   0.203  -0.713  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.084   0.519  -0.623  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.328   1.547  -1.332  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.792   2.291  -2.248  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.013   1.556  -0.816  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.144   1.040   0.484  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.064  -0.122   0.255  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.316  -1.104  -0.639  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.291  -1.893   0.059  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.076  -1.316   0.150  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.876  -1.759  -1.071  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.204   0.127   0.359  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.523   0.960  -0.840  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.026   0.943  -1.006  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.483   0.457   0.295  1.00  0.00           C  
HETATM   16  O3  UNL     1      -4.674   0.180   0.585  1.00  0.00           O  
HETATM   17  O4  UNL     1      -2.397   0.354   1.142  1.00  0.00           O  
HETATM   18  C14 UNL     1      -0.115   0.764   1.189  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.083   0.013   2.456  1.00  0.00           C  
HETATM   20  O5  UNL     1      -0.656   2.027   1.559  1.00  0.00           O  
HETATM   21  H1  UNL     1       5.054   0.707  -1.371  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.767  -0.595  -0.110  1.00  0.00           H  
HETATM   23  H3  UNL     1       1.717   1.803   1.066  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.480  -0.577   1.140  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.994  -0.555  -1.526  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.115  -1.819  -1.003  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.192  -2.886  -0.476  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.685  -2.178   1.069  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.575  -1.861   1.011  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.575  -1.264  -1.990  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.962  -1.758  -0.864  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.610  -2.850  -1.203  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.042   0.689  -1.765  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.261   2.023  -0.576  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.444   1.985  -1.130  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.371   0.379  -1.873  1.00  0.00           H  
HETATM   37  H17 UNL     1       1.090  -0.391   2.618  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.669  -0.826   2.516  1.00  0.00           H  
HETATM   39  H19 UNL     1      -0.140   0.623   3.381  1.00  0.00           H  
HETATM   40  H20 UNL     1       0.108   2.566   1.839  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   18   23
CONECT    7    8   24
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   12   29
CONECT   11   30   31   32
CONECT   12   13   17   18
CONECT   13   14   33   34
CONECT   14   15   35   36
CONECT   15   16   16   17
CONECT   18   19   20
CONECT   19   37   38   39
CONECT   20   40
END

HMDB0302335
     RDKit          3D
Psilostachyin
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.3631    0.2034   -0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0841    0.5186   -0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    1.5466   -1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7922    2.2905   -2.2482 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0135    1.5564   -0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440    1.0403    0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0643   -0.1217    0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163   -1.1041   -0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2906   -1.8934    0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0764   -1.3163    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8759   -1.7588   -1.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2036    0.1267    0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5233    0.9601   -0.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0262    0.9426   -1.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4829    0.4567    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6742    0.1801    0.5852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971    0.3538    1.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149    0.7642    1.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0827    0.0130    2.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557    2.0265    1.5586 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0544    0.7067   -1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673   -0.5946   -0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7166    1.8025    1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4797   -0.5771    1.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9935   -0.5552   -1.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152   -1.8189   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -2.8855   -0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851   -2.1782    1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5748   -1.8608    1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5751   -1.2642   -1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9622   -1.7579   -0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6102   -2.8497   -1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415    0.6893   -1.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2613    2.0227   -0.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4444    1.9847   -1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3714    0.3793   -1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0899   -0.3911    2.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6694   -0.8264    2.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1403    0.6234    3.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079    2.5659    1.8393 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
 12 18  1  0
 18 19  1  0
 18 20  1  0
  7  2  1  0
 17 12  1  0
 18  6  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 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
 20 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Psilostachyin a	MeSH

Chemical Formula

C₁₅H₂₀O₅

Average Molecular Weight

280.3163

Monoisotopic Molecular Weight

280.13107375

IUPAC Name

8-hydroxy-6,8-dimethyl-3-methylidene-octahydrospiro[cyclohepta[b]furan-7,2'-oxolane]-2,5'-dione

Traditional Name

8-hydroxy-6,8-dimethyl-3-methylidene-tetrahydro-3aH-spiro[cyclohepta[b]furan-7,2'-oxolane]-2,5'-dione

CAS Registry Number

Not Available

SMILES

CC1CCC2C(OC(=O)C2=C)C(C)(O)C11CCC(=O)O1

InChI Identifier

InChI=1S/C15H20O5/c1-8-4-5-10-9(2)13(17)19-12(10)14(3,18)15(8)7-6-11(16)20-15/h8,10,12,18H,2,4-7H2,1,3H3

InChI Key

IRPFOXRBPHCCTG-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
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302335)

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	0.8	ALOGPS
logP	1.65	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.89	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.27 m³·mol⁻¹	ChemAxon
Polarizability	28.62 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]+	165.254	32859911
AllCCS	[M+H-H2O]+	161.714	32859911
AllCCS	[M+Na]+	169.484	32859911
AllCCS	[M+NH4]+	168.539	32859911
AllCCS	[M-H]-	170.256	32859911
AllCCS	[M+Na-2H]-	170.192	32859911
AllCCS	[M+HCOO]-	170.246	32859911
DeepCCS	[M-2H]-	193.085	30932474
DeepCCS	[M+Na]+	168.65	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 10V, Positive-QTOF	splash10-001i-0090000000-55362f21ef6c34383075	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin 20V, Positive-QTOF	splash10-0540-1190000000-1202768111cc1857f40a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin 40V, Positive-QTOF	splash10-0006-9210000000-a3864ad47d4d953b5c53	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin 10V, Negative-QTOF	splash10-004i-0090000000-94d2e2cb421e8ab4bc9d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin 20V, Negative-QTOF	splash10-002r-0190000000-ee4d8b053525967e7081	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin 40V, Negative-QTOF	splash10-0006-9410000000-e94efddab48e74fb1890	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin 10V, Positive-QTOF	splash10-001i-0090000000-632849b0c86a1b0f8d71	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin 20V, Positive-QTOF	splash10-0ik9-1590000000-620d5c57ac312d3aa52a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin 40V, Positive-QTOF	splash10-0btd-6950000000-4e66d41d63cf48543622	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin 10V, Negative-QTOF	splash10-004i-0090000000-4fbf1b6b59c3fc97c138	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin 20V, Negative-QTOF	splash10-004r-1090000000-74798020b19f2fee7115	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Psilostachyin 40V, Negative-QTOF	splash10-0pdi-2390000000-c2e555f7e67c203b741b	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

FDB004165

KNApSAcK ID

Not Available

Chemspider ID

88794

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

98331

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 (HMDB0302335)

MOL for HMDB0302335 (Psilostachyin)

3D MOL for HMDB0302335 (Psilostachyin)

3D SDF for HMDB0302335 (Psilostachyin)

3D-SDF for HMDB0302335 (Psilostachyin)

PDB for HMDB0302335 (Psilostachyin)

3D PDB for HMDB0302335 (Psilostachyin)

SMILES for HMDB0302335 (Psilostachyin)

INCHI for HMDB0302335 (Psilostachyin)

Structure for HMDB0302335 (Psilostachyin)

3D Structure for HMDB0302335 (Psilostachyin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra