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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:32:24 UTC

Update Date

2022-03-07 02:54:32 UTC

HMDB ID

HMDB0035529

Secondary Accession Numbers

HMDB35529

Metabolite Identification

Common Name

Chlorosesamone

Description

Chlorosesamone 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 significant number of articles have been published on Chlorosesamone.

Structure

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

HMDB0035529
     RDKit          3D
Chlorosesamone
 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.8253   -0.2126    1.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611    0.1276    0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106   -0.2412   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6705    0.7600    0.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5676    1.1369   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.4863    0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456   -0.4839    0.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4906   -1.1068    1.8956 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1991   -1.0812    1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3013   -1.9983    1.9615 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3590   -0.6381    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6232   -1.1961    0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7340   -2.2236    1.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7153   -0.7507   -0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5913    0.2705   -1.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377    0.8135   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2003    1.8406   -2.1458 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2279    0.3817   -0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9127    0.9510   -0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7789    1.8890   -1.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082    0.0783    2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7738    0.3290    1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9939   -1.3163    1.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0020   -0.7763   -1.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8254   -0.8473   -1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0248    0.6682   -1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6288    1.0342    1.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145    0.9285   -1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3986    2.2375   -0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133   -2.6687    1.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6958   -1.1928    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4641    0.6028   -1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9592    2.1982   -2.6881 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
 13 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
M  END


  Mrv0541 05061308322D          

 20 21  0  0  0  0            999 V2000
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    3.5724    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    2.4750    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    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  2  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 13  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 14  2  0  0  0  0
 20 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035529

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H13ClO4/c1-7(2)3-4-8-13(16)15(20)12-10(18)6-5-9(17)11(12)14(8)19/h3,5-6,17-18H,4H2,1-2H3

> <INCHI_KEY>
CRNOJRLIVCGQAY-UHFFFAOYSA-N

> <FORMULA>
C15H13ClO4

> <MOLECULAR_WEIGHT>
292.714

> <EXACT_MASS>
292.050236611

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.99800705485149

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
4.186835723333333

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.399859920200717

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.609262055345727

> <JCHEM_PKA_STRONGEST_BASIC>
-4.36932361572615

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
78.49499999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035529
     RDKit          3D
Chlorosesamone
 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.8253   -0.2126    1.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611    0.1276    0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106   -0.2412   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6705    0.7600    0.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5676    1.1369   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.4863    0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456   -0.4839    0.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4906   -1.1068    1.8956 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1991   -1.0812    1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3013   -1.9983    1.9615 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3590   -0.6381    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6232   -1.1961    0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7340   -2.2236    1.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7153   -0.7507   -0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5913    0.2705   -1.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377    0.8135   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2003    1.8406   -2.1458 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2279    0.3817   -0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9127    0.9510   -0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7789    1.8890   -1.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082    0.0783    2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7738    0.3290    1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9939   -1.3163    1.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0020   -0.7763   -1.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8254   -0.8473   -1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0248    0.6682   -1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6288    1.0342    1.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145    0.9285   -1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3986    2.2375   -0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133   -2.6687    1.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6958   -1.1928    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4641    0.6028   -1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9592    2.1982   -2.6881 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
 13 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  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   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       8.002   4.620   0.000  0.00  0.00          Cl+0
HETATM   17  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   6.160   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   17                                                  
CONECT   10    6   12   18                                                  
CONECT   11    9   12   14                                                  
CONECT   12   10   11   15                                                  
CONECT   13    8   15   16                                                  
CONECT   14    8   11   19                                                  
CONECT   15   12   13   20                                                  
CONECT   16   13                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0035529
HETATM    1  C1  UNL     1      -4.825  -0.213   1.272  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.761   0.128   0.310  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.911  -0.241  -1.114  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.671   0.760   0.703  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.568   1.137  -0.175  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.272   0.486   0.073  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.146  -0.484   0.944  1.00  0.00           C  
HETATM    8 CL1  UNL     1      -1.491  -1.107   1.896  1.00  0.00          CL  
HETATM    9  C8  UNL     1       1.199  -1.081   1.133  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.301  -1.998   1.961  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.359  -0.638   0.400  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.623  -1.196   0.575  1.00  0.00           C  
HETATM   13  O2  UNL     1       3.734  -2.224   1.504  1.00  0.00           O  
HETATM   14  C11 UNL     1       4.715  -0.751  -0.141  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.591   0.270  -1.061  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.338   0.813  -1.224  1.00  0.00           C  
HETATM   17  O3  UNL     1       3.200   1.841  -2.146  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.228   0.382  -0.516  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.913   0.951  -0.687  1.00  0.00           C  
HETATM   20  O4  UNL     1       0.779   1.889  -1.526  1.00  0.00           O  
HETATM   21  H1  UNL     1      -4.508   0.078   2.298  1.00  0.00           H  
HETATM   22  H2  UNL     1      -5.774   0.329   1.082  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.994  -1.316   1.215  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.002  -0.776  -1.505  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.825  -0.847  -1.284  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.025   0.668  -1.744  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.629   1.034   1.781  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.914   0.928  -1.234  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.399   2.237  -0.172  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.613  -2.669   1.679  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.696  -1.193   0.003  1.00  0.00           H  
HETATM   32  H12 UNL     1       5.464   0.603  -1.611  1.00  0.00           H  
HETATM   33  H13 UNL     1       3.959   2.198  -2.688  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    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   30
CONECT   14   15   15   31
CONECT   15   16   32
CONECT   16   17   18   18
CONECT   17   33
CONECT   18   19
CONECT   19   20   20
END

HMDB0035529
     RDKit          3D
Chlorosesamone
 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.8253   -0.2126    1.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611    0.1276    0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106   -0.2412   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6705    0.7600    0.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5676    1.1369   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.4863    0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456   -0.4839    0.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4906   -1.1068    1.8956 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1991   -1.0812    1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3013   -1.9983    1.9615 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3590   -0.6381    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6232   -1.1961    0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7340   -2.2236    1.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7153   -0.7507   -0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5913    0.2705   -1.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377    0.8135   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2003    1.8406   -2.1458 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2279    0.3817   -0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9127    0.9510   -0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7789    1.8890   -1.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082    0.0783    2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7738    0.3290    1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9939   -1.3163    1.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0020   -0.7763   -1.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8254   -0.8473   -1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0248    0.6682   -1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6288    1.0342    1.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145    0.9285   -1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3986    2.2375   -0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133   -2.6687    1.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6958   -1.1928    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4641    0.6028   -1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9592    2.1982   -2.6881 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
 13 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-chloro-5,8-Dihydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione, 9ci	HMDB

Chemical Formula

C₁₅H₁₃ClO₄

Average Molecular Weight

292.714

Monoisotopic Molecular Weight

292.050236611

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H13ClO4/c1-7(2)3-4-8-13(16)15(20)12-10(18)6-5-9(17)11(12)14(8)19/h3,5-6,17-18H,4H2,1-2H3

InChI Key

CRNOJRLIVCGQAY-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
Alpha-haloketone
Alpha-chloroketone
Vinylogous acid
Vinylogous halide
Ketone
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Organic oxygen compound
Organooxygen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0035529)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035529)

Source

Endogenous

Endogenous (HMDB: HMDB0035529)

Animal

Animal (HMDB: HMDB0035529)

Exogenous

Food

Food (HMDB: HMDB0035529)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035529)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035529)

Cellular process

Cell signaling (HMDB: HMDB0035529)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035529)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035529)

Nutrient

Nutrient (HMDB: HMDB0035529)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	129 - 130 °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	0.11 g/L	ALOGPS
logP	3.32	ALOGPS
logP	4.19	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.61	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.5 m³·mol⁻¹	ChemAxon
Polarizability	29 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]+	165.46	30932474
DeepCCS	[M-H]-	163.102	30932474
DeepCCS	[M-2H]-	195.988	30932474
DeepCCS	[M+Na]+	171.553	30932474
AllCCS	[M+H]+	163.7	32859911
AllCCS	[M+H-H2O]+	160.1	32859911
AllCCS	[M+NH4]+	166.9	32859911
AllCCS	[M+Na]+	167.9	32859911
AllCCS	[M-H]-	164.2	32859911
AllCCS	[M+Na-2H]-	163.9	32859911
AllCCS	[M+HCOO]-	163.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlorosesamone	CC(C)=CCC1=C(Cl)C(=O)C2=C(O)C=CC(O)=C2C1=O	3638.6	Standard polar	33892256
Chlorosesamone	CC(C)=CCC1=C(Cl)C(=O)C2=C(O)C=CC(O)=C2C1=O	2141.9	Standard non polar	33892256
Chlorosesamone	CC(C)=CCC1=C(Cl)C(=O)C2=C(O)C=CC(O)=C2C1=O	2373.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chlorosesamone,1TMS,isomer #1	CC(C)=CCC1=C(Cl)C(=O)C2=C(O[Si](C)(C)C)C=CC(O)=C2C1=O	2366.7	Semi standard non polar	33892256
Chlorosesamone,1TMS,isomer #2	CC(C)=CCC1=C(Cl)C(=O)C2=C(O)C=CC(O[Si](C)(C)C)=C2C1=O	2362.3	Semi standard non polar	33892256
Chlorosesamone,2TMS,isomer #1	CC(C)=CCC1=C(Cl)C(=O)C2=C(O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C2C1=O	2421.4	Semi standard non polar	33892256
Chlorosesamone,1TBDMS,isomer #1	CC(C)=CCC1=C(Cl)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O)=C2C1=O	2612.2	Semi standard non polar	33892256
Chlorosesamone,1TBDMS,isomer #2	CC(C)=CCC1=C(Cl)C(=O)C2=C(O)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	2604.1	Semi standard non polar	33892256
Chlorosesamone,2TBDMS,isomer #1	CC(C)=CCC1=C(Cl)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	2868.8	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 - Chlorosesamone GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fu-4190000000-acc49115751dca2c3eed	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorosesamone GC-MS (2 TMS) - 70eV, Positive	splash10-024i-9817800000-2c95fdb0de493a2ab3eb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorosesamone 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 - Chlorosesamone 10V, Negative-QTOF	splash10-0006-0090000000-ec9289d40dcee58227d5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorosesamone 20V, Negative-QTOF	splash10-0006-0090000000-617cb756983aa6fe93bc	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorosesamone 40V, Negative-QTOF	splash10-0abi-3980000000-408bc4c0608ac97006d9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorosesamone 10V, Negative-QTOF	splash10-0006-0090000000-076f976bfd49bdf67d35	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorosesamone 20V, Negative-QTOF	splash10-0006-1090000000-8a4e2404236056fb0b08	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorosesamone 40V, Negative-QTOF	splash10-001i-9240000000-a075c4f8de89c3dec096	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorosesamone 10V, Positive-QTOF	splash10-0006-0090000000-a5349765f30c72425de7	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorosesamone 20V, Positive-QTOF	splash10-00ku-3490000000-c9b56d61f646f802f4c9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorosesamone 40V, Positive-QTOF	splash10-014i-9230000000-da37ce59a57a1f3f057f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorosesamone 10V, Positive-QTOF	splash10-000f-0090000000-afd0e68195c768c290e0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorosesamone 20V, Positive-QTOF	splash10-0f79-0190000000-b94cded289ebe82c7fba	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorosesamone 40V, Positive-QTOF	splash10-0a4r-3890000000-e5adbe3becdbf9258578	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB014221

KNApSAcK ID

C00036899

Chemspider ID

21377167

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155118724

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

Hasan AF, Begum S, Furumoto T, Fukui H: A new chlorinated red naphthoquinone from roots of Sesamum indicum. Biosci Biotechnol Biochem. 2000 Apr;64(4):873-4. [PubMed:10830510 ]
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 Chlorosesamone (HMDB0035529)

MOL for HMDB0035529 (Chlorosesamone)

3D MOL for HMDB0035529 (Chlorosesamone)

3D SDF for HMDB0035529 (Chlorosesamone)

3D-SDF for HMDB0035529 (Chlorosesamone)

PDB for HMDB0035529 (Chlorosesamone)

3D PDB for HMDB0035529 (Chlorosesamone)

SMILES for HMDB0035529 (Chlorosesamone)

INCHI for HMDB0035529 (Chlorosesamone)

Structure for HMDB0035529 (Chlorosesamone)

3D Structure for HMDB0035529 (Chlorosesamone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra