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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:01:09 UTC

Update Date

2022-03-07 02:55:30 UTC

HMDB ID

HMDB0037760

Secondary Accession Numbers

HMDB37760

Metabolite Identification

Common Name

Hydroxysesamone

Description

Hydroxysesamone belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position. Based on a literature review a small amount of articles have been published on Hydroxysesamone.

Structure

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

HMDB0037760
     RDKit          3D
Hydroxysesamone
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.2058   -1.5811   -0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3828   -0.3247   -0.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491    0.5802   -1.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5466   -0.0681    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177    1.1431    0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2433    0.8485    0.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4296    1.3453    1.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325    2.1076    2.5505 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8738    1.0808    1.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418    1.5829    2.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5730    0.2744    0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318    0.0248    0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6677    0.5144    1.8240 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5740   -0.7525   -0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8428   -1.2491   -1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4844   -1.0013   -1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7284   -1.5092   -2.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486   -0.2452   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244    0.0449   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264   -0.4307   -1.4210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9559   -2.1699    0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2648   -1.2644   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9650   -2.1326   -1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2054    0.1039   -2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5498    0.8487   -2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9519    1.5470   -1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4630   -0.7464    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248    1.7995   -0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    1.7569    1.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9409    1.6562    3.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    1.0502    2.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6352   -0.9140   -0.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3283   -1.8508   -2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1465   -2.0690   -3.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19  6  1  0
 18 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
M  END

  Mrv0541 05061310002D          

 20 21  0  0  0  0            999 V2000
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  1  0  0  0  0
 20 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037760

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C(=O)C2=C(O)C=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-7(2)3-4-8-13(18)11-9(16)5-6-10(17)12(11)15(20)14(8)19/h3,5-6,16-17,19H,4H2,1-2H3

> <INCHI_KEY>
KNOSIOWNDGUGFJ-UHFFFAOYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.75713789818379

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5,8-trihydroxy-3-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
3.2792257253333337

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.025868755824655

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.569892193717443

> <JCHEM_PKA_STRONGEST_BASIC>
-4.384547515530561

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
75.6711

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5,8-trihydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037760
     RDKit          3D
Hydroxysesamone
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.2058   -1.5811   -0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3828   -0.3247   -0.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491    0.5802   -1.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5466   -0.0681    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177    1.1431    0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2433    0.8485    0.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4296    1.3453    1.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325    2.1076    2.5505 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8738    1.0808    1.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418    1.5829    2.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5730    0.2744    0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318    0.0248    0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6677    0.5144    1.8240 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5740   -0.7525   -0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8428   -1.2491   -1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4844   -1.0013   -1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7284   -1.5092   -2.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486   -0.2452   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244    0.0449   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264   -0.4307   -1.4210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9559   -2.1699    0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2648   -1.2644   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9650   -2.1326   -1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2054    0.1039   -2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5498    0.8487   -2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9519    1.5470   -1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4630   -0.7464    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248    1.7995   -0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    1.7569    1.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9409    1.6562    3.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    1.0502    2.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6352   -0.9140   -0.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3283   -1.8508   -2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1465   -2.0690   -3.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19  6  1  0
 18 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  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      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    1    2    3                                                  
CONECT    8    4   13   14                                                  
CONECT    9    5   11   16                                                  
CONECT   10    6   12   17                                                  
CONECT   11    9   12   13                                                  
CONECT   12   10   11   15                                                  
CONECT   13    8   11   18                                                  
CONECT   14    8   15   19                                                  
CONECT   15   12   14   20                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0037760
HETATM    1  C1  UNL     1      -4.206  -1.581  -0.427  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.383  -0.325  -0.484  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.549   0.580  -1.648  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.547  -0.068   0.508  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.718   1.143   0.504  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.243   0.849   0.575  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.430   1.345   1.595  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.233   2.108   2.550  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.874   1.081   1.702  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.442   1.583   2.693  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.573   0.274   0.692  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.932   0.025   0.792  1.00  0.00           C  
HETATM   13  O3  UNL     1       4.668   0.514   1.824  1.00  0.00           O  
HETATM   14  C11 UNL     1       4.574  -0.753  -0.193  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.843  -1.249  -1.234  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.484  -1.001  -1.337  1.00  0.00           C  
HETATM   17  O4  UNL     1       1.728  -1.509  -2.404  1.00  0.00           O  
HETATM   18  C14 UNL     1       1.849  -0.245  -0.382  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.424   0.045  -0.442  1.00  0.00           C  
HETATM   20  O5  UNL     1      -0.226  -0.431  -1.421  1.00  0.00           O  
HETATM   21  H1  UNL     1      -3.956  -2.170   0.473  1.00  0.00           H  
HETATM   22  H2  UNL     1      -5.265  -1.264  -0.412  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.965  -2.133  -1.374  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.205   0.104  -2.375  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.550   0.849  -2.074  1.00  0.00           H  
HETATM   26  H6  UNL     1      -3.952   1.547  -1.267  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.463  -0.746   1.332  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.925   1.799  -0.388  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.026   1.757   1.373  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.941   1.656   3.133  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.421   1.050   2.574  1.00  0.00           H  
HETATM   32  H12 UNL     1       5.635  -0.914  -0.063  1.00  0.00           H  
HETATM   33  H13 UNL     1       4.328  -1.851  -2.001  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.146  -2.069  -3.130  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4    4
CONECT    3   24   25   26
CONECT    4    5   27
CONECT    5    6   28   29
CONECT    6    7    7   19
CONECT    7    8    9
CONECT    8   30
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   31
CONECT   14   15   15   32
CONECT   15   16   33
CONECT   16   17   18   18
CONECT   17   34
CONECT   18   19
CONECT   19   20   20
END

HMDB0037760
     RDKit          3D
Hydroxysesamone
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.2058   -1.5811   -0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3828   -0.3247   -0.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491    0.5802   -1.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5466   -0.0681    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177    1.1431    0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2433    0.8485    0.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4296    1.3453    1.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325    2.1076    2.5505 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8738    1.0808    1.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418    1.5829    2.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5730    0.2744    0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318    0.0248    0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6677    0.5144    1.8240 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5740   -0.7525   -0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8428   -1.2491   -1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4844   -1.0013   -1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7284   -1.5092   -2.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486   -0.2452   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244    0.0449   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264   -0.4307   -1.4210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9559   -2.1699    0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2648   -1.2644   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9650   -2.1326   -1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2054    0.1039   -2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5498    0.8487   -2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9519    1.5470   -1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4630   -0.7464    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248    1.7995   -0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    1.7569    1.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9409    1.6562    3.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    1.0502    2.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6352   -0.9140   -0.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3283   -1.8508   -2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1465   -2.0690   -3.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19  6  1  0
 18 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,5,8-Trihydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione	HMDB

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.2687

Monoisotopic Molecular Weight

274.084123558

IUPAC Name

2,5,8-trihydroxy-3-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione

Traditional Name

2,5,8-trihydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C(=O)C2=C(O)C=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C15H14O5/c1-7(2)3-4-8-13(18)11-9(16)5-6-10(17)12(11)15(20)14(8)19/h3,5-6,16-17,19H,4H2,1-2H3

InChI Key

KNOSIOWNDGUGFJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Vitamin K compounds

Alternative Parents

Substituents

Naphthoquinone
Naphthalene
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Ketone
Polyol
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037760)

Source

Endogenous

Endogenous (HMDB: HMDB0037760)

Animal

Animal (HMDB: HMDB0037760)

Exogenous

Food

Food (HMDB: HMDB0037760)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0037760)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037760)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037760)

Lipid metabolism pathway (HMDB: HMDB0037760)

Cellular process

Cell signaling (HMDB: HMDB0037760)

Biochemical process

Lipid transport (HMDB: HMDB0037760)

Role

Biological role

Energy source (HMDB: HMDB0037760)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	145 - 146 °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	0.32 g/L	ALOGPS
logP	2.11	ALOGPS
logP	3.28	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.57	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.67 m³·mol⁻¹	ChemAxon
Polarizability	27.76 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
DeepCCS	[M+H]+	164.278	30932474
DeepCCS	[M-H]-	161.92	30932474
DeepCCS	[M-2H]-	194.805	30932474
DeepCCS	[M+Na]+	170.371	30932474
AllCCS	[M+H]+	161.9	32859911
AllCCS	[M+H-H2O]+	158.2	32859911
AllCCS	[M+NH4]+	165.3	32859911
AllCCS	[M+Na]+	166.2	32859911
AllCCS	[M-H]-	163.9	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	163.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxysesamone	CC(C)=CCC1=C(O)C(=O)C2=C(O)C=CC(O)=C2C1=O	3823.7	Standard polar	33892256
Hydroxysesamone	CC(C)=CCC1=C(O)C(=O)C2=C(O)C=CC(O)=C2C1=O	2017.1	Standard non polar	33892256
Hydroxysesamone	CC(C)=CCC1=C(O)C(=O)C2=C(O)C=CC(O)=C2C1=O	2320.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxysesamone,1TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C(=O)C2=C(O)C=CC(O)=C2C1=O	2306.0	Semi standard non polar	33892256
Hydroxysesamone,1TMS,isomer #2	CC(C)=CCC1=C(O)C(=O)C2=C(O[Si](C)(C)C)C=CC(O)=C2C1=O	2370.5	Semi standard non polar	33892256
Hydroxysesamone,1TMS,isomer #3	CC(C)=CCC1=C(O)C(=O)C2=C(O)C=CC(O[Si](C)(C)C)=C2C1=O	2373.9	Semi standard non polar	33892256
Hydroxysesamone,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C(=O)C2=C(O[Si](C)(C)C)C=CC(O)=C2C1=O	2384.7	Semi standard non polar	33892256
Hydroxysesamone,2TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C(=O)C2=C(O)C=CC(O[Si](C)(C)C)=C2C1=O	2378.7	Semi standard non polar	33892256
Hydroxysesamone,2TMS,isomer #3	CC(C)=CCC1=C(O)C(=O)C2=C(O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C2C1=O	2405.7	Semi standard non polar	33892256
Hydroxysesamone,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C(=O)C2=C(O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C2C1=O	2443.1	Semi standard non polar	33892256
Hydroxysesamone,1TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C(O)C=CC(O)=C2C1=O	2569.3	Semi standard non polar	33892256
Hydroxysesamone,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O)=C2C1=O	2615.4	Semi standard non polar	33892256
Hydroxysesamone,1TBDMS,isomer #3	CC(C)=CCC1=C(O)C(=O)C2=C(O)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	2623.2	Semi standard non polar	33892256
Hydroxysesamone,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O)=C2C1=O	2862.1	Semi standard non polar	33892256
Hydroxysesamone,2TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C(O)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	2859.0	Semi standard non polar	33892256
Hydroxysesamone,2TBDMS,isomer #3	CC(C)=CCC1=C(O)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	2847.2	Semi standard non polar	33892256
Hydroxysesamone,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3088.8	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 - Hydroxysesamone GC-MS (Non-derivatized) - 70eV, Positive	splash10-052e-3190000000-8c9579e4f15771c64eb0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxysesamone GC-MS (3 TMS) - 70eV, Positive	splash10-004i-6604900000-2fed28feedc0d382c8e1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxysesamone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxysesamone 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 - Hydroxysesamone 10V, Positive-QTOF	splash10-004i-0090000000-d4dab64055eb62c18e0b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysesamone 20V, Positive-QTOF	splash10-014i-4490000000-674781278f6fba894538	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysesamone 40V, Positive-QTOF	splash10-014i-9320000000-40c154f34e19fe12a758	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysesamone 10V, Negative-QTOF	splash10-00di-0090000000-88d21d340145aaaad240	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysesamone 20V, Negative-QTOF	splash10-00di-0190000000-2875740b3c68e5326a5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysesamone 40V, Negative-QTOF	splash10-0a4u-5940000000-4161ebde27a3a1ae1744	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysesamone 10V, Negative-QTOF	splash10-00di-0090000000-7dbb1e549f6404042b70	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysesamone 20V, Negative-QTOF	splash10-00di-0090000000-3d6f550b097ebcba5ad2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysesamone 40V, Negative-QTOF	splash10-00li-2790000000-977a6bff84436bf4032e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysesamone 10V, Positive-QTOF	splash10-014i-0090000000-176c348959be48af80e0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysesamone 20V, Positive-QTOF	splash10-014i-0790000000-570ec4cd023f0eeff2de	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxysesamone 40V, Positive-QTOF	splash10-000i-3920000000-12e4ea1f5d34b5e8373c	2021-09-25	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

FDB016900

KNApSAcK ID

Not Available

Chemspider ID

20056990

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 Hydroxysesamone (HMDB0037760)

MOL for HMDB0037760 (Hydroxysesamone)

3D MOL for HMDB0037760 (Hydroxysesamone)

3D SDF for HMDB0037760 (Hydroxysesamone)

3D-SDF for HMDB0037760 (Hydroxysesamone)

PDB for HMDB0037760 (Hydroxysesamone)

3D PDB for HMDB0037760 (Hydroxysesamone)

SMILES for HMDB0037760 (Hydroxysesamone)

INCHI for HMDB0037760 (Hydroxysesamone)

Structure for HMDB0037760 (Hydroxysesamone)

3D Structure for HMDB0037760 (Hydroxysesamone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra