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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:42:14 UTC

Update Date

2022-03-07 02:54:57 UTC

HMDB ID

HMDB0036550

Secondary Accession Numbers

HMDB36550

Metabolite Identification

Common Name

3-Ketoapotrichothecene

Description

3-Ketoapotrichothecene belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. 3-Ketoapotrichothecene is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0036550
     RDKit          3D
3-Ketoapotrichothecene
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.5187    0.2941    1.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5222    0.2719    0.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6505    1.2376    0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6520    1.2642   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070    1.8224    0.0170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3140    0.7757    0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7412    1.1815    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0774    1.4920   -1.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    0.5317    1.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -0.9424    2.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4551   -1.5767    3.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123   -1.4791    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9021   -0.4620   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0157   -1.0475   -1.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2951   -0.0591   -1.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    0.1532   -2.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3949   -1.0542   -1.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5505   -0.8378   -0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0614    0.5347    2.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342   -0.6805    1.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3409    1.0356    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6591    2.0514    1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015    1.9692   -1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219    2.1346    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4541    0.4539    0.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784    2.0774   -1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0108    0.9041    2.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2474    1.0283    2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -1.7135    0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1399   -2.4489    0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2401   -0.4668   -2.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8852   -1.2066   -0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6618   -2.0494   -1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    0.9412   -2.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230    0.4534   -3.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4641   -0.8381   -2.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952   -1.1861   -2.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9490   -2.0752   -0.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7733   -1.7649    0.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5161   -0.7193   -0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18  2  1  0
 15  4  1  0
 13  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 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
 18 39  1  0
 18 40  1  0
M  END


  Mrv0541 05061309112D          

 18 20  0  0  0  0            999 V2000
    1.0991   -0.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5060   -1.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4064   -1.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -1.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9454   -1.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4666    0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9920   -1.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4295    0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750    0.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9026   -0.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689   -0.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2700    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094   -0.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343   -0.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6046    0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6852    1.0745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4483   -0.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9469    0.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 10  1  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 13  2  1  0  0  0  0
 13  5  1  0  0  0  0
 13 12  1  0  0  0  0
 14  3  1  0  0  0  0
 14  7  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17 11  2  0  0  0  0
 18 12  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036550

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2OC3(CO)CC(=O)CC3(C)C2(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-10-4-5-13(2)12(6-10)18-15(9-16)8-11(17)7-14(13,15)3/h6,12,16H,4-5,7-9H2,1-3H3

> <INCHI_KEY>
JJBMWLFFOIHRLZ-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.390867048852712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
1.659309464666666

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.55098848813364

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.317058821095365

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0915117713747575

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
69.089

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036550
     RDKit          3D
3-Ketoapotrichothecene
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.5187    0.2941    1.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5222    0.2719    0.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6505    1.2376    0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6520    1.2642   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070    1.8224    0.0170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3140    0.7757    0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7412    1.1815    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0774    1.4920   -1.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    0.5317    1.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -0.9424    2.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4551   -1.5767    3.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123   -1.4791    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9021   -0.4620   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0157   -1.0475   -1.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2951   -0.0591   -1.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    0.1532   -2.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3949   -1.0542   -1.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5505   -0.8378   -0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0614    0.5347    2.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342   -0.6805    1.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3409    1.0356    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6591    2.0514    1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015    1.9692   -1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219    2.1346    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4541    0.4539    0.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784    2.0774   -1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0108    0.9041    2.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2474    1.0283    2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -1.7135    0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1399   -2.4489    0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2401   -0.4668   -2.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8852   -1.2066   -0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6618   -2.0494   -1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    0.9412   -2.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230    0.4534   -3.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4641   -0.8381   -2.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952   -1.1861   -2.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9490   -2.0752   -0.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7733   -1.7649    0.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5161   -0.7193   -0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18  2  1  0
 15  4  1  0
 13  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 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
 18 39  1  0
 18 40  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       2.052  -0.115   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.545  -2.748   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.225  -2.734   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.998  -1.938   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.498  -2.288   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.604   0.659   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.318  -2.124   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.135   0.230   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.100   1.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.552  -0.465   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.582  -1.244   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.104   0.309   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.551  -1.164   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.091  -1.194   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.595   0.260   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.612   2.006   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      12.037  -1.748   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.368   1.190   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    5   10                                                       
CONECT    5    4   13                                                       
CONECT    6   10   12                                                       
CONECT    7   11   14                                                       
CONECT    8   11   15                                                       
CONECT    9   15   16                                                       
CONECT   10    1    4    6                                                  
CONECT   11    7    8   17                                                  
CONECT   12    6   13   18                                                  
CONECT   13    2    5   12   14                                             
CONECT   14    3    7   13   15                                             
CONECT   15    8    9   14   18                                             
CONECT   16    9                                                            
CONECT   17   11                                                            
CONECT   18   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0036550
HETATM    1  C1  UNL     1       3.519   0.294   1.770  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.522   0.272   0.662  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.650   1.238   0.551  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.652   1.264  -0.516  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.507   1.822   0.017  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.314   0.776   0.424  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.741   1.182   0.235  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.077   1.492  -1.081  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.143   0.532   1.931  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.126  -0.942   2.076  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.455  -1.577   3.030  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.612  -1.479   0.788  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.902  -0.462  -0.279  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.016  -1.047  -1.141  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.295  -0.059  -1.093  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.175   0.153  -2.521  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.395  -1.054  -1.160  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.550  -0.838  -0.278  1.00  0.00           C  
HETATM   19  H1  UNL     1       3.061   0.535   2.743  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.034  -0.680   1.887  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.341   1.036   1.569  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.659   2.051   1.268  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.001   1.969  -1.301  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.922   2.135   0.812  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.454   0.454   0.683  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.878   2.077  -1.054  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.011   0.904   2.512  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.247   1.028   2.307  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.437  -1.713   0.954  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.140  -2.449   0.624  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.240  -0.467  -2.029  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.885  -1.207  -0.480  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.662  -2.049  -1.462  1.00  0.00           H  
HETATM   34  H16 UNL     1      -0.902   0.941  -2.651  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.723   0.453  -3.141  1.00  0.00           H  
HETATM   36  H18 UNL     1      -0.464  -0.838  -2.949  1.00  0.00           H  
HETATM   37  H19 UNL     1       1.795  -1.186  -2.215  1.00  0.00           H  
HETATM   38  H20 UNL     1       0.949  -2.075  -0.967  1.00  0.00           H  
HETATM   39  H21 UNL     1       2.773  -1.765   0.337  1.00  0.00           H  
HETATM   40  H22 UNL     1       3.516  -0.719  -0.862  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   18
CONECT    3    4   22
CONECT    4    5   15   23
CONECT    5    6
CONECT    6    7    9   13
CONECT    7    8   24   25
CONECT    8   26
CONECT    9   10   27   28
CONECT   10   11   11   12
CONECT   12   13   29   30
CONECT   13   14   15
CONECT   14   31   32   33
CONECT   15   16   17
CONECT   16   34   35   36
CONECT   17   18   37   38
CONECT   18   39   40
END

HMDB0036550
     RDKit          3D
3-Ketoapotrichothecene
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.5187    0.2941    1.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5222    0.2719    0.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6505    1.2376    0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6520    1.2642   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070    1.8224    0.0170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3140    0.7757    0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7412    1.1815    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0774    1.4920   -1.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    0.5317    1.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -0.9424    2.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4551   -1.5767    3.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123   -1.4791    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9021   -0.4620   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0157   -1.0475   -1.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2951   -0.0591   -1.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    0.1532   -2.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3949   -1.0542   -1.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5505   -0.8378   -0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0614    0.5347    2.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342   -0.6805    1.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3409    1.0356    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6591    2.0514    1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015    1.9692   -1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219    2.1346    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4541    0.4539    0.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784    2.0774   -1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0108    0.9041    2.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2474    1.0283    2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -1.7135    0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1399   -2.4489    0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2401   -0.4668   -2.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8852   -1.2066   -0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6618   -2.0494   -1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    0.9412   -2.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230    0.4534   -3.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4641   -0.8381   -2.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952   -1.1861   -2.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9490   -2.0752   -0.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7733   -1.7649    0.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5161   -0.7193   -0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18  2  1  0
 15  4  1  0
 13  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 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
 18 39  1  0
 18 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₃

Average Molecular Weight

250.3334

Monoisotopic Molecular Weight

250.15689457

IUPAC Name

6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one

Traditional Name

6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one

CAS Registry Number

Not Available

SMILES

CC1=CC2OC3(CO)CC(=O)CC3(C)C2(C)CC1

InChI Identifier

InChI=1S/C15H22O3/c1-10-4-5-13(2)12(6-10)18-15(9-16)8-11(17)7-14(13,15)3/h6,12,16H,4-5,7-9H2,1-3H3

InChI Key

JJBMWLFFOIHRLZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036550)

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0036550)

Exogenous

Food

Food (HMDB: HMDB0036550)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036550)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036550)

Nutrient

Nutrient (HMDB: HMDB0036550)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036550)

Emulsifier (HMDB: HMDB0036550)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.64 g/L	ALOGPS
logP	1.35	ALOGPS
logP	1.66	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	14.32	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.09 m³·mol⁻¹	ChemAxon
Polarizability	27.39 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]+	156.197	31661259
DarkChem	[M-H]-	156.368	31661259
DeepCCS	[M+H]+	163.402	30932474
DeepCCS	[M-H]-	161.044	30932474
DeepCCS	[M-2H]-	193.936	30932474
DeepCCS	[M+Na]+	169.495	30932474
AllCCS	[M+H]+	159.5	32859911
AllCCS	[M+H-H2O]+	155.9	32859911
AllCCS	[M+NH4]+	162.9	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	166.1	32859911
AllCCS	[M+Na-2H]-	166.2	32859911
AllCCS	[M+HCOO]-	166.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Ketoapotrichothecene	CC1=CC2OC3(CO)CC(=O)CC3(C)C2(C)CC1	2762.6	Standard polar	33892256
3-Ketoapotrichothecene	CC1=CC2OC3(CO)CC(=O)CC3(C)C2(C)CC1	1864.6	Standard non polar	33892256
3-Ketoapotrichothecene	CC1=CC2OC3(CO)CC(=O)CC3(C)C2(C)CC1	1969.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Ketoapotrichothecene,1TMS,isomer #1	CC1=CC2OC3(CO[Si](C)(C)C)CC(=O)CC3(C)C2(C)CC1	2031.1	Semi standard non polar	33892256
3-Ketoapotrichothecene,1TMS,isomer #2	CC1=CC2OC3(CO)CC(O[Si](C)(C)C)=CC3(C)C2(C)CC1	2013.4	Semi standard non polar	33892256
3-Ketoapotrichothecene,1TMS,isomer #3	CC1=CC2OC3(CO)C=C(O[Si](C)(C)C)CC3(C)C2(C)CC1	2014.0	Semi standard non polar	33892256
3-Ketoapotrichothecene,2TMS,isomer #1	CC1=CC2OC3(CO[Si](C)(C)C)CC(O[Si](C)(C)C)=CC3(C)C2(C)CC1	2055.9	Semi standard non polar	33892256
3-Ketoapotrichothecene,2TMS,isomer #1	CC1=CC2OC3(CO[Si](C)(C)C)CC(O[Si](C)(C)C)=CC3(C)C2(C)CC1	1992.4	Standard non polar	33892256
3-Ketoapotrichothecene,2TMS,isomer #2	CC1=CC2OC3(CO[Si](C)(C)C)C=C(O[Si](C)(C)C)CC3(C)C2(C)CC1	2040.9	Semi standard non polar	33892256
3-Ketoapotrichothecene,2TMS,isomer #2	CC1=CC2OC3(CO[Si](C)(C)C)C=C(O[Si](C)(C)C)CC3(C)C2(C)CC1	1986.5	Standard non polar	33892256
3-Ketoapotrichothecene,1TBDMS,isomer #1	CC1=CC2OC3(CO[Si](C)(C)C(C)(C)C)CC(=O)CC3(C)C2(C)CC1	2250.5	Semi standard non polar	33892256
3-Ketoapotrichothecene,1TBDMS,isomer #2	CC1=CC2OC3(CO)CC(O[Si](C)(C)C(C)(C)C)=CC3(C)C2(C)CC1	2239.1	Semi standard non polar	33892256
3-Ketoapotrichothecene,1TBDMS,isomer #3	CC1=CC2OC3(CO)C=C(O[Si](C)(C)C(C)(C)C)CC3(C)C2(C)CC1	2245.7	Semi standard non polar	33892256
3-Ketoapotrichothecene,2TBDMS,isomer #1	CC1=CC2OC3(CO[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)=CC3(C)C2(C)CC1	2555.6	Semi standard non polar	33892256
3-Ketoapotrichothecene,2TBDMS,isomer #1	CC1=CC2OC3(CO[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)=CC3(C)C2(C)CC1	2423.5	Standard non polar	33892256
3-Ketoapotrichothecene,2TBDMS,isomer #2	CC1=CC2OC3(CO[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)CC3(C)C2(C)CC1	2547.0	Semi standard non polar	33892256
3-Ketoapotrichothecene,2TBDMS,isomer #2	CC1=CC2OC3(CO[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)CC3(C)C2(C)CC1	2408.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Ketoapotrichothecene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2960000000-9aa9c8af7d474ccd61a4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Ketoapotrichothecene GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-4962000000-d5d8f83dd6149a6cc90a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Ketoapotrichothecene 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 - 3-Ketoapotrichothecene 10V, Positive-QTOF	splash10-0udi-0190000000-3d23a39ec5a536efa7e2	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ketoapotrichothecene 20V, Positive-QTOF	splash10-0f9x-3980000000-59531da85d9985e84e63	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ketoapotrichothecene 40V, Positive-QTOF	splash10-0pvi-9600000000-30928a2978aa20e90873	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ketoapotrichothecene 10V, Negative-QTOF	splash10-0002-0090000000-9617f46f281ed4789b7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ketoapotrichothecene 20V, Negative-QTOF	splash10-0002-0090000000-38c9be910efd6f656c21	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ketoapotrichothecene 40V, Negative-QTOF	splash10-0abc-3920000000-aa473c4a2259bbdea80f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ketoapotrichothecene 10V, Negative-QTOF	splash10-0002-0090000000-0dd1e5565d33dd37f20a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ketoapotrichothecene 20V, Negative-QTOF	splash10-0002-0190000000-9e24ea7c59434cbc49f2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ketoapotrichothecene 40V, Negative-QTOF	splash10-016r-0490000000-2b24cf08d518e0f93041	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ketoapotrichothecene 10V, Positive-QTOF	splash10-0f89-0190000000-cc2876c3721e1973c45d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ketoapotrichothecene 20V, Positive-QTOF	splash10-0pb9-0490000000-549fd59ef4e0c8782cf3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ketoapotrichothecene 40V, Positive-QTOF	splash10-0a4l-9520000000-871523579f1698ada40c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB015453

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14408092

PDB ID

Not Available

ChEBI ID

143041

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 3-Ketoapotrichothecene (HMDB0036550)

MOL for HMDB0036550 (3-Ketoapotrichothecene)

3D MOL for HMDB0036550 (3-Ketoapotrichothecene)

3D SDF for HMDB0036550 (3-Ketoapotrichothecene)

3D-SDF for HMDB0036550 (3-Ketoapotrichothecene)

PDB for HMDB0036550 (3-Ketoapotrichothecene)

3D PDB for HMDB0036550 (3-Ketoapotrichothecene)

SMILES for HMDB0036550 (3-Ketoapotrichothecene)

INCHI for HMDB0036550 (3-Ketoapotrichothecene)

Structure for HMDB0036550 (3-Ketoapotrichothecene)

3D Structure for HMDB0036550 (3-Ketoapotrichothecene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra