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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:33:22 UTC

Update Date

2022-03-07 02:54:11 UTC

HMDB ID

HMDB0034658

Secondary Accession Numbers

HMDB34658

Metabolite Identification

Common Name

9-Acetoxyfukinanolide

Description

9-Acetoxyfukinanolide belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on 9-Acetoxyfukinanolide.

Structure

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

HMDB0034658
     RDKit          3D
9-Acetoxyfukinanolide
 45 47  0  0  0  0  0  0  0  0999 V2000
   -1.7282   -2.1298   -1.9194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5699   -2.0975   -0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0939   -3.1646    0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595   -2.5523    1.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6880   -1.2177    1.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0097   -0.3726    2.3845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8952   -1.0970    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5538   -1.3647    0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991   -0.2619   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855   -0.5923   -1.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140   -0.1031    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4528    0.7739   -0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8597    0.5389    1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0900    1.8630    1.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6190    1.4331    1.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4176    0.9167   -0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9729    0.3080   -0.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357    1.0382    0.5168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0283    1.6174   -0.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617    2.3908    0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1107    1.4562   -1.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566   -2.9569   -2.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179   -1.3184   -2.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1399   -3.3530   -0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5039   -4.0893    0.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991   -1.4880    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -2.3199   -0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476    0.0629   -2.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1316   -1.6675   -1.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4175   -0.4934   -2.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924   -1.0997    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1822    0.1830   -1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017    1.5353   -0.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7514    1.3653   -1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4905   -0.0545    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9182    0.8196    1.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095    2.4645    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1865    2.3517    2.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376    2.2724    1.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5179    0.6263    2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5514    1.7362   -0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327    0.2913   -1.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9717    2.3997   -0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3286    1.9040    1.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7453    3.4458    0.7503 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
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 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
 19 20  1  0
 19 21  2  0
  7  2  1  0
 16  9  1  0
 17  7  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
M  END


  Mrv0541 05061307592D          

 21 23  0  0  0  0            999 V2000
    4.7432    4.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9425    3.9715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576    2.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576    3.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432    1.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4896    2.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441    3.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432    3.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742    2.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287    2.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441    2.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742    3.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287    3.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7592    2.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    4.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4896    3.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4877    1.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4576    1.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1721    0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8866    1.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1721    0.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 11 10  1  0  0  0  0
 13  2  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14  7  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 12  2  0  0  0  0
 16  6  1  0  0  0  0
 16 12  1  0  0  0  0
  9 17  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034658

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCCC2C(OC(C)=O)C3(CC12C)C(=C)COC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O4/c1-10-6-5-7-13-14(21-12(3)18)17(9-16(10,13)4)11(2)8-20-15(17)19/h10,13-14H,2,5-9H2,1,3-4H3

> <INCHI_KEY>
ZZZDGYZKGIPSPD-UHFFFAOYSA-N

> <FORMULA>
C17H24O4

> <MOLECULAR_WEIGHT>
292.3701

> <EXACT_MASS>
292.167459256

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.49289531951589

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3a,4-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-1-yl acetate

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
2.644027968333333

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.792377466308519

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
77.0662

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034658
     RDKit          3D
9-Acetoxyfukinanolide
 45 47  0  0  0  0  0  0  0  0999 V2000
   -1.7282   -2.1298   -1.9194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5699   -2.0975   -0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0939   -3.1646    0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595   -2.5523    1.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6880   -1.2177    1.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0097   -0.3726    2.3845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8952   -1.0970    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5538   -1.3647    0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991   -0.2619   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855   -0.5923   -1.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140   -0.1031    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4528    0.7739   -0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8597    0.5389    1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0900    1.8630    1.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6190    1.4331    1.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4176    0.9167   -0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9729    0.3080   -0.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357    1.0382    0.5168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0283    1.6174   -0.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617    2.3908    0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1107    1.4562   -1.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566   -2.9569   -2.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179   -1.3184   -2.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1399   -3.3530   -0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5039   -4.0893    0.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991   -1.4880    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -2.3199   -0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476    0.0629   -2.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1316   -1.6675   -1.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4175   -0.4934   -2.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924   -1.0997    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1822    0.1830   -1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017    1.5353   -0.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7514    1.3653   -1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4905   -0.0545    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9182    0.8196    1.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095    2.4645    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1865    2.3517    2.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376    2.2724    1.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5179    0.6263    2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5514    1.7362   -0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327    0.2913   -1.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9717    2.3997   -0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3286    1.9040    1.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7453    3.4458    0.7503 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
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 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
 19 20  1  0
 19 21  2  0
  7  2  1  0
 16  9  1  0
 17  7  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  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       8.854   8.192   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.359   7.413   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.188   4.342   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.188   5.882   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.854   3.572   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.781   4.342   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.056   6.358   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.854   6.652   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.245   3.866   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.520   4.342   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.056   3.866   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.245   6.358   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.520   5.882   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.151   5.112   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.721   7.822   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.781   5.882   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.644   2.378   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.454   2.378   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.788   1.608   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.122   2.378   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.788   0.068   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   13                                                            
CONECT    3    4    5                                                       
CONECT    4    3    8                                                       
CONECT    5    3   10                                                       
CONECT    6    9   16                                                       
CONECT    7   13   14                                                       
CONECT    8    1    4   13                                                  
CONECT    9    6   14   17                                                  
CONECT   10    5   11   13                                                  
CONECT   11   10   14   18                                                  
CONECT   12   14   15   16                                                  
CONECT   13    2    7    8   10                                             
CONECT   14    7    9   11   12                                             
CONECT   15   12                                                            
CONECT   16    6   12                                                       
CONECT   17    9                                                            
CONECT   18   11   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0034658
HETATM    1  C1  UNL     1      -1.728  -2.130  -1.919  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.570  -2.097  -0.607  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.094  -3.165   0.308  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.060  -2.552   1.573  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.688  -1.218   1.514  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.010  -0.373   2.384  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.895  -1.097   0.272  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.554  -1.365   0.431  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.299  -0.262  -0.305  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.386  -0.592  -1.798  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.714  -0.103   0.172  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.453   0.774  -0.830  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.860   0.539   1.512  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.090   1.863   1.440  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.619   1.433   1.333  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.418   0.917  -0.052  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.973   0.308  -0.224  1.00  0.00           C  
HETATM   18  O3  UNL     1      -1.936   1.038   0.517  1.00  0.00           O  
HETATM   19  C16 UNL     1      -3.028   1.617  -0.109  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.062   2.391   0.626  1.00  0.00           C  
HETATM   21  O4  UNL     1      -3.111   1.456  -1.360  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.257  -2.957  -2.360  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.318  -1.318  -2.500  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.140  -3.353  -0.010  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.504  -4.089   0.251  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.899  -1.488   1.463  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.799  -2.320  -0.105  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.748   0.063  -2.401  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.132  -1.668  -1.896  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.417  -0.493  -2.192  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.192  -1.100   0.142  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.182   0.183  -1.437  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.102   1.535  -0.303  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.751   1.365  -1.432  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.490  -0.054   2.351  1.00  0.00           H  
HETATM   36  H15 UNL     1       3.918   0.820   1.645  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.410   2.464   0.592  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.187   2.352   2.422  1.00  0.00           H  
HETATM   39  H18 UNL     1      -0.038   2.272   1.599  1.00  0.00           H  
HETATM   40  H19 UNL     1       0.518   0.626   2.090  1.00  0.00           H  
HETATM   41  H20 UNL     1       0.551   1.736  -0.782  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.233   0.291  -1.280  1.00  0.00           H  
HETATM   43  H22 UNL     1      -4.972   2.400  -0.009  1.00  0.00           H  
HETATM   44  H23 UNL     1      -4.329   1.904   1.583  1.00  0.00           H  
HETATM   45  H24 UNL     1      -3.745   3.446   0.750  1.00  0.00           H  
CONECT    1    2    2   22   23
CONECT    2    3    7
CONECT    3    4   24   25
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8   17
CONECT    8    9   26   27
CONECT    9   10   11   16
CONECT   10   28   29   30
CONECT   11   12   13   31
CONECT   12   32   33   34
CONECT   13   14   35   36
CONECT   14   15   37   38
CONECT   15   16   39   40
CONECT   16   17   41
CONECT   17   18   42
CONECT   18   19
CONECT   19   20   21   21
CONECT   20   43   44   45
END

HMDB0034658
     RDKit          3D
9-Acetoxyfukinanolide
 45 47  0  0  0  0  0  0  0  0999 V2000
   -1.7282   -2.1298   -1.9194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5699   -2.0975   -0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0939   -3.1646    0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595   -2.5523    1.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6880   -1.2177    1.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0097   -0.3726    2.3845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8952   -1.0970    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5538   -1.3647    0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991   -0.2619   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855   -0.5923   -1.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140   -0.1031    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4528    0.7739   -0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8597    0.5389    1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0900    1.8630    1.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6190    1.4331    1.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4176    0.9167   -0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9729    0.3080   -0.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357    1.0382    0.5168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0283    1.6174   -0.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617    2.3908    0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1107    1.4562   -1.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566   -2.9569   -2.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179   -1.3184   -2.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1399   -3.3530   -0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5039   -4.0893    0.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991   -1.4880    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -2.3199   -0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476    0.0629   -2.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1316   -1.6675   -1.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4175   -0.4934   -2.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924   -1.0997    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1822    0.1830   -1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017    1.5353   -0.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7514    1.3653   -1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4905   -0.0545    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9182    0.8196    1.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095    2.4645    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1865    2.3517    2.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376    2.2724    1.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5179    0.6263    2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5514    1.7362   -0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327    0.2913   -1.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9717    2.3997   -0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3286    1.9040    1.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7453    3.4458    0.7503 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
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 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
 19 20  1  0
 19 21  2  0
  7  2  1  0
 16  9  1  0
 17  7  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7,7a-Dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-3-yl acetic acid	HMDB

Chemical Formula

C₁₇H₂₄O₄

Average Molecular Weight

292.3701

Monoisotopic Molecular Weight

292.167459256

IUPAC Name

3a,4-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-1-yl acetate

Traditional Name

7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-3-yl acetate

CAS Registry Number

35945-70-1

SMILES

CC1CCCC2C(OC(C)=O)C3(CC12C)C(=C)COC3=O

InChI Identifier

InChI=1S/C17H24O4/c1-10-6-5-7-13-14(21-12(3)18)17(9-16(10,13)4)11(2)8-20-15(17)19/h10,13-14H,2,5-9H2,1,3-4H3

InChI Key

ZZZDGYZKGIPSPD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
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: HMDB0034658)

Source

Endogenous

Endogenous (HMDB: HMDB0034658)

Plant

Plant (HMDB: HMDB0034658)

Animal

Animal (HMDB: HMDB0034658)

Exogenous

Food

Food (HMDB: HMDB0034658)

Vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0034658)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034658)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034658)

Lipid metabolism pathway (HMDB: HMDB0034658)

Cellular process

Cell signaling (HMDB: HMDB0034658)

Biochemical process

Lipid transport (HMDB: HMDB0034658)

Role

Biological role

Energy source (HMDB: HMDB0034658)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034658)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	96 - 97 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	12.71 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	0.029 g/L	ALOGPS
logP	3.42	ALOGPS
logP	2.64	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-6.8	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	2	ChemAxon
Refractivity	77.07 m³·mol⁻¹	ChemAxon
Polarizability	31.49 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]+	168.677	31661259
DarkChem	[M-H]-	163.902	31661259
DeepCCS	[M-2H]-	200.553	30932474
DeepCCS	[M+Na]+	176.119	30932474
AllCCS	[M+H]+	168.0	32859911
AllCCS	[M+H-H2O]+	164.7	32859911
AllCCS	[M+NH4]+	171.0	32859911
AllCCS	[M+Na]+	171.9	32859911
AllCCS	[M-H]-	174.4	32859911
AllCCS	[M+Na-2H]-	174.4	32859911
AllCCS	[M+HCOO]-	174.6	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.	7.76 minutes	32390414
Predicted by Siyang on May 30, 2022	18.099 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.69 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2667.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	511.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	215.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	246.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	461.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	691.6 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	846.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1549.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	534.4 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	1742.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	510.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	482.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	469.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	453.3 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	12.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9-Acetoxyfukinanolide	CC1CCCC2C(OC(C)=O)C3(CC12C)C(=C)COC3=O	2921.5	Standard polar	33892256
9-Acetoxyfukinanolide	CC1CCCC2C(OC(C)=O)C3(CC12C)C(=C)COC3=O	2089.3	Standard non polar	33892256
9-Acetoxyfukinanolide	CC1CCCC2C(OC(C)=O)C3(CC12C)C(=C)COC3=O	2041.9	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 - 9-Acetoxyfukinanolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00e9-1970000000-bf1f8f230fba1f450b2d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Acetoxyfukinanolide 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 - 9-Acetoxyfukinanolide 10V, Positive-QTOF	splash10-0006-0090000000-145d384a60070abe183f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Acetoxyfukinanolide 20V, Positive-QTOF	splash10-0fhc-2590000000-7e91f410f49e1e0a4049	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Acetoxyfukinanolide 40V, Positive-QTOF	splash10-0q29-9510000000-8869bc2d8862c0cab9bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Acetoxyfukinanolide 10V, Negative-QTOF	splash10-0007-0090000000-2ab050abfc4f9a785bc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Acetoxyfukinanolide 20V, Negative-QTOF	splash10-052e-2090000000-68bbddf3df9efe978616	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Acetoxyfukinanolide 40V, Negative-QTOF	splash10-0aor-5190000000-624f8f568fe4ba2b3251	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Acetoxyfukinanolide 10V, Negative-QTOF	splash10-000x-1090000000-d2c76967ae9a04e7fc93	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Acetoxyfukinanolide 20V, Negative-QTOF	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Acetoxyfukinanolide 40V, Negative-QTOF	splash10-052f-9010000000-48edbf79e170ae2df040	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Acetoxyfukinanolide 10V, Positive-QTOF	splash10-0006-0090000000-316e1efc10c90770d792	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Acetoxyfukinanolide 20V, Positive-QTOF	splash10-05fu-1930000000-f092cb734be49dc2943b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Acetoxyfukinanolide 40V, Positive-QTOF	splash10-03di-4910000000-c445999a5db0a6e2c17e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB013182

KNApSAcK ID

C00021352

Chemspider ID

35013761

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78385431

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1844921

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 9-Acetoxyfukinanolide (HMDB0034658)

MOL for HMDB0034658 (9-Acetoxyfukinanolide)

3D MOL for HMDB0034658 (9-Acetoxyfukinanolide)

3D SDF for HMDB0034658 (9-Acetoxyfukinanolide)

3D-SDF for HMDB0034658 (9-Acetoxyfukinanolide)

PDB for HMDB0034658 (9-Acetoxyfukinanolide)

3D PDB for HMDB0034658 (9-Acetoxyfukinanolide)

SMILES for HMDB0034658 (9-Acetoxyfukinanolide)

INCHI for HMDB0034658 (9-Acetoxyfukinanolide)

Structure for HMDB0034658 (9-Acetoxyfukinanolide)

3D Structure for HMDB0034658 (9-Acetoxyfukinanolide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra