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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:55 UTC

Update Date

2022-03-07 02:52:29 UTC

HMDB ID

HMDB0030287

Secondary Accession Numbers

HMDB30287

Metabolite Identification

Common Name

10-Acetoxytoxol

Description

10-Acetoxytoxol belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure. Based on a literature review very few articles have been published on 10-Acetoxytoxol.

Structure

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

HMDB0030287
     RDKit          3D
10-Acetoxytoxol
 36 37  0  0  0  0  0  0  0  0999 V2000
   -2.6393   -1.5939    0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445   -0.3899    0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9756    0.8309    0.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3424    0.6400    0.7407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9317    0.0634   -0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4096   -0.1409   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2184   -0.3082   -1.3202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6843   -0.1856    1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0465   -1.3947    0.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609   -1.0006    0.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6210   -1.5693    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7845   -0.9739    0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7521    0.2280   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9743    0.9136   -0.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2697    0.2386   -0.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9287    2.0166   -1.2056 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    0.8044   -0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3351    0.2100    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0905    0.5973   -0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2656    1.9755    0.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9719   -2.4603    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917   -1.8361    0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7218    1.4161    1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5416    1.4510    0.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8695    0.7910   -0.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7422   -1.0217    0.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7359   -0.1919   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919    0.3058    1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6124   -2.5401    1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194   -1.4539    0.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2659   -0.1064    0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3010   -0.6627   -1.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1191    0.9187   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5232    1.7632   -0.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844    0.2677   -1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611    2.3981   -0.8399 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  1  0
  5  7  2  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19  8  1  0
 18 10  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
M  END


  Mrv0541 05061305082D          

 20 21  0  0  0  0            999 V2000
    3.2215    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2737   -2.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763   -2.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013   -2.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763   -0.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2215    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612   -1.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0362   -1.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013   -0.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6138   -1.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534    0.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2737   -0.5795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5818    0.8406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208   -1.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  1  2  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11  6  2  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 13  5  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  2  0  0  0  0
 17 10  2  0  0  0  0
 18 14  1  0  0  0  0
 19  7  1  0  0  0  0
 19 10  1  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030287

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCC(=C)C1OC2=C(C=C(C=C2)C(C)=O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O5/c1-8(7-19-10(3)17)15-14(18)12-6-11(9(2)16)4-5-13(12)20-15/h4-6,14-15,18H,1,7H2,2-3H3

> <INCHI_KEY>
JWOFLZQIQQWHRY-UHFFFAOYSA-N

> <FORMULA>
C15H16O5

> <MOLECULAR_WEIGHT>
276.2845

> <EXACT_MASS>
276.099773622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.662610556990774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(5-acetyl-3-hydroxy-2,3-dihydro-1-benzofuran-2-yl)prop-2-en-1-yl acetate

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
0.6888468470000002

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.247450750587273

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.027263022251471

> <JCHEM_PKA_STRONGEST_BASIC>
-3.661550750891684

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
71.4822

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(5-acetyl-3-hydroxy-2,3-dihydro-1-benzofuran-2-yl)prop-2-en-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030287
     RDKit          3D
10-Acetoxytoxol
 36 37  0  0  0  0  0  0  0  0999 V2000
   -2.6393   -1.5939    0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445   -0.3899    0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9756    0.8309    0.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3424    0.6400    0.7407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9317    0.0634   -0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4096   -0.1409   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2184   -0.3082   -1.3202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6843   -0.1856    1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0465   -1.3947    0.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609   -1.0006    0.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6210   -1.5693    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7845   -0.9739    0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7521    0.2280   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9743    0.9136   -0.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2697    0.2386   -0.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9287    2.0166   -1.2056 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    0.8044   -0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3351    0.2100    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0905    0.5973   -0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2656    1.9755    0.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9719   -2.4603    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917   -1.8361    0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7218    1.4161    1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5416    1.4510    0.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8695    0.7910   -0.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7422   -1.0217    0.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7359   -0.1919   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919    0.3058    1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6124   -2.5401    1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194   -1.4539    0.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2659   -0.1064    0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3010   -0.6627   -1.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1191    0.9187   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5232    1.7632   -0.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844    0.2677   -1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611    2.3981   -0.8399 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  1  0
  5  7  2  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19  8  1  0
 18 10  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  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       6.013   1.746   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.378  -3.749   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.348   0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.702  -3.749   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.242  -3.749   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.702  -1.082   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.347  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.013   0.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.608  -2.415   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.014  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.068  -2.415   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.242  -1.082   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.012  -2.415   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.273   0.063   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.378  -1.082   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.014  -2.104   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.953   1.569   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.681   0.206   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.519  -2.095   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5   11                                                       
CONECT    5    4   13                                                       
CONECT    6   11   12                                                       
CONECT    7    8   19                                                       
CONECT    8    1    7   15                                                  
CONECT    9    2   11   16                                                  
CONECT   10    3   17   19                                                  
CONECT   11    4    6    9                                                  
CONECT   12    6   13   14                                                  
CONECT   13    5   12   20                                                  
CONECT   14   12   15   18                                                  
CONECT   15    8   14   20                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   14                                                            
CONECT   19    7   10                                                       
CONECT   20   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0030287
HETATM    1  C1  UNL     1      -2.639  -1.594   0.871  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.145  -0.390   0.928  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.976   0.831   0.871  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.342   0.640   0.741  1.00  0.00           O  
HETATM    5  C4  UNL     1      -4.932   0.063  -0.366  1.00  0.00           C  
HETATM    6  C5  UNL     1      -6.410  -0.141  -0.477  1.00  0.00           C  
HETATM    7  O2  UNL     1      -4.218  -0.308  -1.320  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.684  -0.186   1.056  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.047  -1.395   0.975  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.361  -1.001   0.671  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.621  -1.569   0.888  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.785  -0.974   0.485  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.752   0.228  -0.160  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.974   0.914  -0.615  1.00  0.00           C  
HETATM   15  C12 UNL     1       6.270   0.239  -0.343  1.00  0.00           C  
HETATM   16  O4  UNL     1       4.929   2.017  -1.206  1.00  0.00           O  
HETATM   17  C13 UNL     1       2.500   0.804  -0.382  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.335   0.210   0.021  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.091   0.597  -0.087  1.00  0.00           C  
HETATM   20  O5  UNL     1      -0.266   1.976   0.061  1.00  0.00           O  
HETATM   21  H1  UNL     1      -1.972  -2.460   0.917  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.692  -1.836   0.793  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.722   1.416   1.802  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.542   1.451   0.034  1.00  0.00           H  
HETATM   25  H5  UNL     1      -6.869   0.791  -0.043  1.00  0.00           H  
HETATM   26  H6  UNL     1      -6.742  -1.022   0.077  1.00  0.00           H  
HETATM   27  H7  UNL     1      -6.736  -0.192  -1.522  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.392   0.306   1.995  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.612  -2.540   1.410  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.719  -1.454   0.678  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.266  -0.106   0.714  1.00  0.00           H  
HETATM   32  H12 UNL     1       6.301  -0.663  -1.005  1.00  0.00           H  
HETATM   33  H13 UNL     1       7.119   0.919  -0.548  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.523   1.763  -0.899  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.484   0.268  -1.073  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.261   2.398  -0.840  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3    8
CONECT    3    4   23   24
CONECT    4    5
CONECT    5    6    7    7
CONECT    6   25   26   27
CONECT    8    9   19   28
CONECT    9   10
CONECT   10   11   11   18
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14   17
CONECT   14   15   16   16
CONECT   15   31   32   33
CONECT   17   18   18   34
CONECT   18   19
CONECT   19   20   35
CONECT   20   36
END

HMDB0030287
     RDKit          3D
10-Acetoxytoxol
 36 37  0  0  0  0  0  0  0  0999 V2000
   -2.6393   -1.5939    0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445   -0.3899    0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9756    0.8309    0.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3424    0.6400    0.7407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9317    0.0634   -0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4096   -0.1409   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2184   -0.3082   -1.3202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6843   -0.1856    1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0465   -1.3947    0.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609   -1.0006    0.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6210   -1.5693    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7845   -0.9739    0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7521    0.2280   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9743    0.9136   -0.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2697    0.2386   -0.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9287    2.0166   -1.2056 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    0.8044   -0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3351    0.2100    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0905    0.5973   -0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2656    1.9755    0.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9719   -2.4603    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917   -1.8361    0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7218    1.4161    1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5416    1.4510    0.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8695    0.7910   -0.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7422   -1.0217    0.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7359   -0.1919   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919    0.3058    1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6124   -2.5401    1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194   -1.4539    0.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2659   -0.1064    0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3010   -0.6627   -1.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1191    0.9187   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5232    1.7632   -0.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844    0.2677   -1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611    2.3981   -0.8399 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  1  0
  5  7  2  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19  8  1  0
 18 10  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(5-Acetyl-3-hydroxy-2,3-dihydro-1-benzofuran-2-yl)prop-2-en-1-yl acetic acid	HMDB

Chemical Formula

C₁₅H₁₆O₅

Average Molecular Weight

276.2845

Monoisotopic Molecular Weight

276.099773622

IUPAC Name

2-(5-acetyl-3-hydroxy-2,3-dihydro-1-benzofuran-2-yl)prop-2-en-1-yl acetate

Traditional Name

2-(5-acetyl-3-hydroxy-2,3-dihydro-1-benzofuran-2-yl)prop-2-en-1-yl acetate

CAS Registry Number

75680-15-8

SMILES

CC(=O)OCC(=C)C1OC2=C(C=C(C=C2)C(C)=O)C1O

InChI Identifier

InChI=1S/C15H16O5/c1-8(7-19-10(3)17)15-14(18)12-6-11(9(2)16)4-5-13(12)20-15/h4-6,14-15,18H,1,7H2,2-3H3

InChI Key

JWOFLZQIQQWHRY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Acetophenones

Direct Parent

Acetophenones

Alternative Parents

Substituents

Acetophenone
Coumaran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Carboxylic acid ester
Ketone
Secondary alcohol
Carboxylic acid derivative
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organic oxide
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030287)
Cytoplasm (HMDB: HMDB0030287)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030287)

Source

Endogenous

Endogenous (HMDB: HMDB0030287)

Plant

Plant (HMDB: HMDB0030287)

Exogenous

Food

Food (HMDB: HMDB0030287)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	110 °C	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
Water Solubility	1.57 g/L	ALOGPS
logP	1	ALOGPS
logP	0.69	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.03	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.48 m³·mol⁻¹	ChemAxon
Polarizability	28.66 Å³	ChemAxon
Number of Rings	2	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]+	167.206	31661259
DarkChem	[M-H]-	164.07	31661259
DeepCCS	[M+H]+	163.794	30932474
DeepCCS	[M-H]-	161.436	30932474
DeepCCS	[M-2H]-	194.818	30932474
DeepCCS	[M+Na]+	170.045	30932474
AllCCS	[M+H]+	164.2	32859911
AllCCS	[M+H-H2O]+	160.7	32859911
AllCCS	[M+NH4]+	167.5	32859911
AllCCS	[M+Na]+	168.4	32859911
AllCCS	[M-H]-	166.8	32859911
AllCCS	[M+Na-2H]-	166.8	32859911
AllCCS	[M+HCOO]-	166.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
10-Acetoxytoxol	CC(=O)OCC(=C)C1OC2=C(C=C(C=C2)C(C)=O)C1O	3235.9	Standard polar	33892256
10-Acetoxytoxol	CC(=O)OCC(=C)C1OC2=C(C=C(C=C2)C(C)=O)C1O	2044.2	Standard non polar	33892256
10-Acetoxytoxol	CC(=O)OCC(=C)C1OC2=C(C=C(C=C2)C(C)=O)C1O	2291.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
10-Acetoxytoxol,1TMS,isomer #1	C=C(COC(C)=O)C1OC2=CC=C(C(C)=O)C=C2C1O[Si](C)(C)C	2243.4	Semi standard non polar	33892256
10-Acetoxytoxol,1TBDMS,isomer #1	C=C(COC(C)=O)C1OC2=CC=C(C(C)=O)C=C2C1O[Si](C)(C)C(C)(C)C	2466.1	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 - 10-Acetoxytoxol GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9550000000-331a3e2c9c03d09ccdee	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10-Acetoxytoxol GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9031000000-2554bcd84b9f14e0d086	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10-Acetoxytoxol 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 - 10-Acetoxytoxol 10V, Negative-QTOF	splash10-004i-3090000000-62d5a3cfa4848e365d81	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Acetoxytoxol 20V, Negative-QTOF	splash10-0a6r-9160000000-f08a79a5051a0064b43b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Acetoxytoxol 40V, Negative-QTOF	splash10-0a4l-9210000000-7114efa48d31534ff5a6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Acetoxytoxol 10V, Negative-QTOF	splash10-0a4i-9450000000-f8ccd1e97021eb9c0815	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Acetoxytoxol 20V, Negative-QTOF	splash10-0a4i-7910000000-a10f8e86ed12ad40ea9f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Acetoxytoxol 40V, Negative-QTOF	splash10-0aou-2900000000-663b396f599e593fc763	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Acetoxytoxol 10V, Positive-QTOF	splash10-00or-0190000000-0d58a6146e966bf102f8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Acetoxytoxol 20V, Positive-QTOF	splash10-014i-2490000000-897477a3f255b988dfcf	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Acetoxytoxol 40V, Positive-QTOF	splash10-0fr7-5920000000-8c0409a31d25c5e60857	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Acetoxytoxol 10V, Positive-QTOF	splash10-016r-0390000000-29e24dc95ea8d3f17755	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Acetoxytoxol 20V, Positive-QTOF	splash10-014s-0960000000-2601e0e38a4a481c9176	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Acetoxytoxol 40V, Positive-QTOF	splash10-00sd-6920000000-71da5ef8850a19e336ec	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB002123

KNApSAcK ID

C00054539

Chemspider ID

35013172

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750993

PDB ID

Not Available

ChEBI ID

174636

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 10-Acetoxytoxol (HMDB0030287)

MOL for HMDB0030287 (10-Acetoxytoxol)

3D MOL for HMDB0030287 (10-Acetoxytoxol)

3D SDF for HMDB0030287 (10-Acetoxytoxol)

3D-SDF for HMDB0030287 (10-Acetoxytoxol)

PDB for HMDB0030287 (10-Acetoxytoxol)

3D PDB for HMDB0030287 (10-Acetoxytoxol)

SMILES for HMDB0030287 (10-Acetoxytoxol)

INCHI for HMDB0030287 (10-Acetoxytoxol)

Structure for HMDB0030287 (10-Acetoxytoxol)

3D Structure for HMDB0030287 (10-Acetoxytoxol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra