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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:32:31 UTC

Update Date

2022-03-07 02:55:41 UTC

HMDB ID

HMDB0038256

Secondary Accession Numbers

HMDB38256

Metabolite Identification

Common Name

Geranyl acetoacetate

Description

Geranyl acetoacetate belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Based on a literature review a small amount of articles have been published on Geranyl acetoacetate.

Structure

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

HMDB0038256
     RDKit          3D
Geranyl acetoacetate
 39 38  0  0  0  0  0  0  0  0999 V2000
    6.0768    1.2876   -0.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4308    0.3441    0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8412   -0.8049    0.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3354    0.7577    1.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0022    0.3358    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9325    0.5830    1.2293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154   -0.3422   -0.5824 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -0.7587   -1.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9419   -1.6740   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2535   -1.4862    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760   -2.5408    1.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9844   -0.2484   -0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3189   -0.5356   -0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0134    0.7469   -0.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1966    0.9698   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8739    2.2841   -0.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8540   -0.0617    0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4449    0.7442   -1.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3400    2.0439   -1.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8788    1.8806   -0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3606    1.8728    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4286    0.3635    2.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1254    0.0586   -1.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946   -1.3992   -2.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616   -2.6208   -0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2581   -2.1020    2.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306   -3.2923    1.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6888   -2.9995    0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4915    0.5134   -0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3206    0.1403    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462   -1.1163   -1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9126   -1.1114   -0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088    1.4848   -1.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4817    3.0861   -0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9601    2.1734   -0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7662    2.4886   -1.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9428   -1.0083   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9196    0.2153    0.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2789   -0.2722    1.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  4 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
M  END

  Mrv0541 05061310192D          

 17 16  0  0  0  0            999 V2000
   -3.2704   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  3  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  4  1  0  0  0  0
 13 10  1  0  0  0  0
 14 10  1  0  0  0  0
 15 13  2  0  0  0  0
 16 14  2  0  0  0  0
 17  9  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038256

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CC(=O)OC\C=C(\C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O3/c1-11(2)6-5-7-12(3)8-9-17-14(16)10-13(4)15/h6,8H,5,7,9-10H2,1-4H3/b12-8-

> <INCHI_KEY>
RYILZWKGLGVPOC-WQLSENKSSA-N

> <FORMULA>
C14H22O3

> <MOLECULAR_WEIGHT>
238.3227

> <EXACT_MASS>
238.15689457

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.24669036674354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3,7-dimethylocta-2,6-dien-1-yl 3-oxobutanoate

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
3.165362674999999

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.392428162495866

> <JCHEM_PKA_STRONGEST_BASIC>
-6.967411446340511

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
70.22879999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3,7-dimethylocta-2,6-dien-1-yl 3-oxobutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038256
     RDKit          3D
Geranyl acetoacetate
 39 38  0  0  0  0  0  0  0  0999 V2000
    6.0768    1.2876   -0.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4308    0.3441    0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8412   -0.8049    0.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3354    0.7577    1.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0022    0.3358    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9325    0.5830    1.2293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154   -0.3422   -0.5824 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -0.7587   -1.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9419   -1.6740   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2535   -1.4862    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760   -2.5408    1.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9844   -0.2484   -0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3189   -0.5356   -0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0134    0.7469   -0.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1966    0.9698   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8739    2.2841   -0.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8540   -0.0617    0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4449    0.7442   -1.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3400    2.0439   -1.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8788    1.8806   -0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3606    1.8728    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4286    0.3635    2.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1254    0.0586   -1.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946   -1.3992   -2.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616   -2.6208   -0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2581   -2.1020    2.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306   -3.2923    1.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6888   -2.9995    0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4915    0.5134   -0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3206    0.1403    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462   -1.1163   -1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9126   -1.1114   -0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088    1.4848   -1.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4817    3.0861   -0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9601    2.1734   -0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7662    2.4886   -1.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9428   -1.0083   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9196    0.2153    0.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2789   -0.2722    1.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  4 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -6.105  -7.494   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.438  -5.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.771  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.898  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.771  -3.644   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.771  -5.184   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.437  -2.874   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.231  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.105  -5.954   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.437  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.565  -1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.897  -1.334   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.565  -2.874   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.897  -2.874   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5    6    7                                                       
CONECT    6    5   11                                                       
CONECT    7    5   12                                                       
CONECT    8    9   12                                                       
CONECT    9    8   17                                                       
CONECT   10   13   14                                                       
CONECT   11    1    2    6                                                  
CONECT   12    3    7    8                                                  
CONECT   13    4   10   15                                                  
CONECT   14   10   16   17                                                  
CONECT   15   13                                                            
CONECT   16   14                                                            
CONECT   17    9   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0038256
HETATM    1  C1  UNL     1       6.077   1.288  -0.662  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.431   0.344   0.282  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.841  -0.805   0.289  1.00  0.00           O  
HETATM    4  C3  UNL     1       4.335   0.758   1.183  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.002   0.336   0.625  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.933   0.583   1.229  1.00  0.00           O  
HETATM    7  O3  UNL     1       2.915  -0.342  -0.582  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.667  -0.759  -1.145  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.942  -1.674  -0.267  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.253  -1.486   0.251  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.876  -2.541   1.151  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.984  -0.248  -0.030  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.319  -0.536  -0.739  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.013   0.747  -0.994  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.197   0.970  -0.490  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.874   2.284  -0.769  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.854  -0.062   0.339  1.00  0.00           C  
HETATM   18  H1  UNL     1       6.445   0.744  -1.559  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.340   2.044  -1.055  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.879   1.881  -0.173  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.361   1.873   1.249  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.429   0.363   2.193  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.125   0.059  -1.599  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.995  -1.399  -2.033  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.462  -2.621  -0.018  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.258  -2.102   2.072  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.131  -3.292   1.406  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.689  -3.000   0.544  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.492   0.513  -0.611  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.321   0.140   0.985  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.146  -1.116  -1.666  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.913  -1.111  -0.003  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.509   1.485  -1.607  1.00  0.00           H  
HETATM   34  H17 UNL     1      -4.482   3.086  -0.137  1.00  0.00           H  
HETATM   35  H18 UNL     1      -5.960   2.173  -0.567  1.00  0.00           H  
HETATM   36  H19 UNL     1      -4.766   2.489  -1.842  1.00  0.00           H  
HETATM   37  H20 UNL     1      -4.943  -1.008  -0.266  1.00  0.00           H  
HETATM   38  H21 UNL     1      -5.920   0.215   0.573  1.00  0.00           H  
HETATM   39  H22 UNL     1      -4.279  -0.272   1.254  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3    4
CONECT    4    5   21   22
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   23   24
CONECT    9   10   10   25
CONECT   10   11   12
CONECT   11   26   27   28
CONECT   12   13   29   30
CONECT   13   14   31   32
CONECT   14   15   15   33
CONECT   15   16   17
CONECT   16   34   35   36
CONECT   17   37   38   39
END

HMDB0038256
     RDKit          3D
Geranyl acetoacetate
 39 38  0  0  0  0  0  0  0  0999 V2000
    6.0768    1.2876   -0.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4308    0.3441    0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8412   -0.8049    0.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3354    0.7577    1.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0022    0.3358    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9325    0.5830    1.2293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154   -0.3422   -0.5824 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -0.7587   -1.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9419   -1.6740   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2535   -1.4862    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760   -2.5408    1.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9844   -0.2484   -0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3189   -0.5356   -0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0134    0.7469   -0.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1966    0.9698   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8739    2.2841   -0.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8540   -0.0617    0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4449    0.7442   -1.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3400    2.0439   -1.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8788    1.8806   -0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3606    1.8728    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4286    0.3635    2.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1254    0.0586   -1.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946   -1.3992   -2.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616   -2.6208   -0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2581   -2.1020    2.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306   -3.2923    1.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6888   -2.9995    0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4915    0.5134   -0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3206    0.1403    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462   -1.1163   -1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9126   -1.1114   -0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088    1.4848   -1.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4817    3.0861   -0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9601    2.1734   -0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7662    2.4886   -1.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9428   -1.0083   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9196    0.2153    0.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2789   -0.2722    1.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  4 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Geranyl acetoacetic acid	Generator
(e)-3,7-Dimethyl-2,6-octadienyl 3-oxobutanoate	HMDB
(e)-3,7-Dimethyl-2,6-octadienyl acetoacetate	HMDB
3,7-Dimethyl-2,6-octadienyl ester(e)-acetoacetic acid	HMDB
Acetoacetic acid, 3,7-dimethyl-2,6-octadienyl ester	HMDB
FEMA 2510	HMDB
Geranyl 3-oxobutanoate	HMDB
Geranyl beta-ketobutyrate	HMDB
trans-3,7-Dimethyl-2,6-octadien-1-yl 3-oxobutanoate	HMDB
trans-3,7-Dimethyl-2,6-octadien-1-yl acetoacetate	HMDB

Chemical Formula

C₁₄H₂₂O₃

Average Molecular Weight

238.3227

Monoisotopic Molecular Weight

238.15689457

IUPAC Name

(2Z)-3,7-dimethylocta-2,6-dien-1-yl 3-oxobutanoate

Traditional Name

(2Z)-3,7-dimethylocta-2,6-dien-1-yl 3-oxobutanoate

CAS Registry Number

10032-00-5

SMILES

CC(=O)CC(=O)OC\C=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C14H22O3/c1-11(2)6-5-7-12(3)8-9-17-14(16)10-13(4)15/h6,8H,5,7,9-10H2,1-4H3/b12-8-

InChI Key

RYILZWKGLGVPOC-WQLSENKSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohol esters

Direct Parent

Fatty alcohol esters

Alternative Parents

Substituents

Fatty alcohol ester
Acyclic monoterpenoid
Monoterpenoid
Beta-keto acid
Fatty acid ester
1,3-dicarbonyl compound
Keto acid
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0038256)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038256)

Source

Endogenous

Endogenous (HMDB: HMDB0038256)

Animal

Animal (HMDB: HMDB0038256)

Exogenous

Food

Food (HMDB: HMDB0038256)

Exogenous (HMDB: HMDB0038256)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038256)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038256)

Lipid metabolism pathway (HMDB: HMDB0038256)

Cellular process

Cell signaling (HMDB: HMDB0038256)

Biochemical process

Lipid transport (HMDB: HMDB0038256)

Role

Biological role

Energy source (HMDB: HMDB0038256)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038256)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0038256)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	127.00 to 129.00 °C. @ 22.00 mm Hg	The Good Scents Company Information System
Water Solubility	33.71 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.517 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	3.7	ALOGPS
logP	3.17	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	10.39	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	70.23 m³·mol⁻¹	ChemAxon
Polarizability	27.25 Å³	ChemAxon
Number of Rings	0	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]+	159.409	31661259
DarkChem	[M-H]-	156.797	31661259
DeepCCS	[M+H]+	156.404	30932474
DeepCCS	[M-H]-	154.046	30932474
DeepCCS	[M-2H]-	187.085	30932474
DeepCCS	[M+Na]+	162.497	30932474
AllCCS	[M+H]+	160.7	32859911
AllCCS	[M+H-H2O]+	157.3	32859911
AllCCS	[M+NH4]+	163.8	32859911
AllCCS	[M+Na]+	164.7	32859911
AllCCS	[M-H]-	161.3	32859911
AllCCS	[M+Na-2H]-	162.2	32859911
AllCCS	[M+HCOO]-	163.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Geranyl acetoacetate	CC(=O)CC(=O)OC\C=C(\C)CCC=C(C)C	2206.6	Standard polar	33892256
Geranyl acetoacetate	CC(=O)CC(=O)OC\C=C(\C)CCC=C(C)C	1564.0	Standard non polar	33892256
Geranyl acetoacetate	CC(=O)CC(=O)OC\C=C(\C)CCC=C(C)C	1720.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Geranyl acetoacetate,1TMS,isomer #1	CC(C)=CCC/C(C)=C\COC(=O)C=C(C)O[Si](C)(C)C	1832.2	Semi standard non polar	33892256
Geranyl acetoacetate,1TMS,isomer #1	CC(C)=CCC/C(C)=C\COC(=O)C=C(C)O[Si](C)(C)C	1856.1	Standard non polar	33892256
Geranyl acetoacetate,1TMS,isomer #2	C=C(CC(=O)OC/C=C(/C)CCC=C(C)C)O[Si](C)(C)C	1790.7	Semi standard non polar	33892256
Geranyl acetoacetate,1TMS,isomer #2	C=C(CC(=O)OC/C=C(/C)CCC=C(C)C)O[Si](C)(C)C	1802.3	Standard non polar	33892256
Geranyl acetoacetate,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C\COC(=O)C=C(C)O[Si](C)(C)C(C)(C)C	2068.3	Semi standard non polar	33892256
Geranyl acetoacetate,1TBDMS,isomer #1	CC(C)=CCC/C(C)=C\COC(=O)C=C(C)O[Si](C)(C)C(C)(C)C	2060.5	Standard non polar	33892256
Geranyl acetoacetate,1TBDMS,isomer #2	C=C(CC(=O)OC/C=C(/C)CCC=C(C)C)O[Si](C)(C)C(C)(C)C	2015.3	Semi standard non polar	33892256
Geranyl acetoacetate,1TBDMS,isomer #2	C=C(CC(=O)OC/C=C(/C)CCC=C(C)C)O[Si](C)(C)C(C)(C)C	1994.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Geranyl acetoacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ku-9700000000-464bbd7934d9173adbaf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Geranyl acetoacetate 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 - Geranyl acetoacetate 10V, Positive-QTOF	splash10-000i-4790000000-97db0649e83f5b5bae96	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl acetoacetate 20V, Positive-QTOF	splash10-000i-9500000000-640dd734c70bcee51f77	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl acetoacetate 40V, Positive-QTOF	splash10-0670-9100000000-90966489ab2f1b35805b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl acetoacetate 10V, Negative-QTOF	splash10-0019-8690000000-16ea337a0db3b28e6a31	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl acetoacetate 20V, Negative-QTOF	splash10-0pc0-9700000000-d0f333fc4eb48adf9423	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl acetoacetate 40V, Negative-QTOF	splash10-0a4i-9300000000-bc23db33f8ce067ee6a4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl acetoacetate 10V, Negative-QTOF	splash10-0udi-1920000000-b22cd9cb2907b3277097	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl acetoacetate 20V, Negative-QTOF	splash10-0zfr-9700000000-47320c01017af31ea1e4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl acetoacetate 40V, Negative-QTOF	splash10-0a70-9500000000-de1c444d4d58dee8b261	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl acetoacetate 10V, Positive-QTOF	splash10-001i-9600000000-b004eca92447f1950afe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl acetoacetate 20V, Positive-QTOF	splash10-001i-9400000000-1414a7dc914c2216b61f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Geranyl acetoacetate 40V, Positive-QTOF	splash10-0aou-9300000000-37319bd69b0189d41410	2021-09-22	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

FDB017550

KNApSAcK ID

Not Available

Chemspider ID

30777244

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54611954

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1024841

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 Geranyl acetoacetate (HMDB0038256)

MOL for HMDB0038256 (Geranyl acetoacetate)

3D MOL for HMDB0038256 (Geranyl acetoacetate)

3D SDF for HMDB0038256 (Geranyl acetoacetate)

3D-SDF for HMDB0038256 (Geranyl acetoacetate)

PDB for HMDB0038256 (Geranyl acetoacetate)

3D PDB for HMDB0038256 (Geranyl acetoacetate)

SMILES for HMDB0038256 (Geranyl acetoacetate)

INCHI for HMDB0038256 (Geranyl acetoacetate)

Structure for HMDB0038256 (Geranyl acetoacetate)

3D Structure for HMDB0038256 (Geranyl acetoacetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra