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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015607

Secondary Accession Numbers

HMDB15607

Metabolite Identification

Common Name

Lucanthone

Description

Lucanthone is only found in individuals that have used or taken this drug. It is one of the schistosomicides, it has been replaced largely by hycanthone and more recently praziquantel. (From Martindale The Extrapharmacopoeia, 30th ed., p46). It is currently being tested as a radiation sensitizer.Recent data suggests that lucanthone inhibits post-radiation DNA repair in tumor cells. The ability of lucanthone to inhibit AP endonuclease and topoisomerase II probably account for the specific DNA repair inhibition in irradiated cells.

Structure

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

HMDB0015607
     RDKit          3D
Lucanthone
 48 50  0  0  0  0  0  0  0  0999 V2000
    4.3686    0.3564   -1.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4626    0.6787   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9700   -0.3521    0.4560 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301   -1.5163    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833   -1.2456    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6105   -0.7597    0.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520    0.3543    0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2744   -0.0780    0.1851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8119    0.7902    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4522    2.0819    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795    3.0685    1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6998    2.7456    0.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8095    3.7166    1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0532    1.4741    0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6951    1.0405    0.2322 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9183   -0.5572   -0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1575   -1.1415   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2689   -2.4479   -0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1317   -3.2004   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073   -2.6311   -0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7702   -1.2905   -0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5106   -0.7917   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5902   -1.6595   -0.3995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345    0.4479    0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230    0.5289   -2.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061   -0.7045   -2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6256    1.0564   -2.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5608    0.7983   -0.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0009    1.6655   -0.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0024   -1.8746   -0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3547   -2.3346    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6521   -2.2006    1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1311   -0.5677    1.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8964   -0.8168    0.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4841   -1.1297   -0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3668   -1.6135    0.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7464    0.5672    1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042    1.2059   -0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647   -1.0244   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769    2.3515    0.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1029    4.0618    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2386    3.6082    2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5037    4.7619    0.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6255    3.4835    0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0074   -0.4842   -0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2360   -2.8815   -1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927   -4.2594   -1.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0507   -3.2805   -0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24  9  1  0
 24 14  2  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
 10 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
M  END

  Mrv0541 02231218032D          

 24 26  0  0  0  0            999 V2000
    3.7709   -2.2345    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7709    0.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5649    1.8504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1839    0.2180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8698    1.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8791    0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1932   -0.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -1.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2694    1.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5556    2.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -1.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1932   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7709   -0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9255   -1.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0710   -1.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9255   -1.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0710   -1.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9647    1.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2508    3.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1839   -3.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3486   -0.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3486   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6164   -1.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6164   -1.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 17  1  0  0  0  0
  2 13  2  0  0  0  0
  3  5  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  7 14  1  0  0  0  0
  8 11  1  0  0  0  0
  8 13  1  0  0  0  0
  9 18  1  0  0  0  0
 10 19  1  0  0  0  0
 11 12  2  0  0  0  0
 12 16  1  0  0  0  0
 12 20  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 21  2  0  0  0  0
 17 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015607

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CCNC1=C2C(=O)C3=CC=CC=C3SC2=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2OS/c1-4-22(5-2)13-12-21-16-11-10-14(3)20-18(16)19(23)15-8-6-7-9-17(15)24-20/h6-11,21H,4-5,12-13H2,1-3H3

> <INCHI_KEY>
FBQPGGIHOFZRGH-UHFFFAOYSA-N

> <FORMULA>
C20H24N2OS

> <MOLECULAR_WEIGHT>
340.482

> <EXACT_MASS>
340.16093409

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
39.600377716600136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{[2-(diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-one

> <ALOGPS_LOGP>
4.72

> <JCHEM_LOGP>
5.0165624493333345

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.841315559332447

> <JCHEM_PKA_STRONGEST_BASIC>
8.69395226253895

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
106.01090000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lucanthone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015607
     RDKit          3D
Lucanthone
 48 50  0  0  0  0  0  0  0  0999 V2000
    4.3686    0.3564   -1.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4626    0.6787   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9700   -0.3521    0.4560 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301   -1.5163    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833   -1.2456    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6105   -0.7597    0.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520    0.3543    0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2744   -0.0780    0.1851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8119    0.7902    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4522    2.0819    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795    3.0685    1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6998    2.7456    0.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8095    3.7166    1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0532    1.4741    0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6951    1.0405    0.2322 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9183   -0.5572   -0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1575   -1.1415   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2689   -2.4479   -0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1317   -3.2004   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073   -2.6311   -0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7702   -1.2905   -0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5106   -0.7917   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5902   -1.6595   -0.3995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345    0.4479    0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230    0.5289   -2.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061   -0.7045   -2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6256    1.0564   -2.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5608    0.7983   -0.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0009    1.6655   -0.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0024   -1.8746   -0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3547   -2.3346    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6521   -2.2006    1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1311   -0.5677    1.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8964   -0.8168    0.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4841   -1.1297   -0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3668   -1.6135    0.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7464    0.5672    1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042    1.2059   -0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647   -1.0244   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769    2.3515    0.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1029    4.0618    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2386    3.6082    2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5037    4.7619    0.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6255    3.4835    0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0074   -0.4842   -0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2360   -2.8815   -1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927   -4.2594   -1.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0507   -3.2805   -0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24  9  1  0
 24 14  2  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
 10 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       7.039  -4.171   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       7.039   0.355   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      12.254   3.454   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.677   0.407   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      10.957   2.685   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.974   1.176   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.694  -1.102   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.346  -1.908   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.570   2.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.237   4.962   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.346  -3.417   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.694  -4.223   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.039  -1.154   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.061  -1.877   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.733  -1.908   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.061  -3.448   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.733  -3.417   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.867   3.484   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.535   5.732   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.677  -5.732   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.384  -1.102   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.384  -4.223   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.017  -1.877   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.017  -3.448   0.000  0.00  0.00           C+0
CONECT    1   11   17                                                       
CONECT    2   13                                                            
CONECT    3    5    9   10                                                  
CONECT    4    6    7                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    4    8   14                                                  
CONECT    8    7   11   13                                                  
CONECT    9    3   18                                                       
CONECT   10    3   19                                                       
CONECT   11    1    8   12                                                  
CONECT   12   11   16   20                                                  
CONECT   13    2    8   15                                                  
CONECT   14    7   16                                                       
CONECT   15   13   17   21                                                  
CONECT   16   12   14                                                       
CONECT   17    1   15   22                                                  
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   12                                                            
CONECT   21   15   23                                                       
CONECT   22   17   24                                                       
CONECT   23   21   24                                                       
CONECT   24   22   23                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0015607
HETATM    1  C1  UNL     1       4.369   0.356  -1.875  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.463   0.679  -0.406  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.970  -0.352   0.456  1.00  0.00           N  
HETATM    4  C3  UNL     1       4.830  -1.516   0.401  1.00  0.00           C  
HETATM    5  C4  UNL     1       6.183  -1.246   1.020  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.610  -0.760   0.159  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.652   0.354   0.484  1.00  0.00           C  
HETATM    8  N2  UNL     1       0.274  -0.078   0.185  1.00  0.00           N  
HETATM    9  C7  UNL     1      -0.812   0.790   0.401  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.452   2.082   0.823  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.379   3.068   1.068  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.700   2.746   0.882  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.810   3.717   1.109  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.053   1.474   0.466  1.00  0.00           C  
HETATM   15  S1  UNL     1      -4.695   1.041   0.232  1.00  0.00           S  
HETATM   16  C13 UNL     1      -4.918  -0.557  -0.269  1.00  0.00           C  
HETATM   17  C14 UNL     1      -6.158  -1.142  -0.525  1.00  0.00           C  
HETATM   18  C15 UNL     1      -6.269  -2.448  -0.931  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.132  -3.200  -1.090  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.907  -2.631  -0.840  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.770  -1.291  -0.423  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.511  -0.792  -0.192  1.00  0.00           C  
HETATM   23  O1  UNL     1      -1.590  -1.659  -0.400  1.00  0.00           O  
HETATM   24  C20 UNL     1      -2.135   0.448   0.210  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.323   0.529  -2.421  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.106  -0.705  -2.048  1.00  0.00           H  
HETATM   27  H3  UNL     1       3.626   1.056  -2.325  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.561   0.798  -0.179  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.001   1.666  -0.148  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.002  -1.875  -0.639  1.00  0.00           H  
HETATM   31  H7  UNL     1       4.355  -2.335   0.965  1.00  0.00           H  
HETATM   32  H8  UNL     1       6.652  -2.201   1.380  1.00  0.00           H  
HETATM   33  H9  UNL     1       6.131  -0.568   1.897  1.00  0.00           H  
HETATM   34  H10 UNL     1       6.896  -0.817   0.286  1.00  0.00           H  
HETATM   35  H11 UNL     1       2.484  -1.130  -0.880  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.367  -1.613   0.835  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.746   0.567   1.560  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.904   1.206  -0.174  1.00  0.00           H  
HETATM   39  H15 UNL     1       0.165  -1.024  -0.189  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.577   2.351   0.973  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.103   4.062   1.392  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.239   3.608   2.131  1.00  0.00           H  
HETATM   43  H19 UNL     1      -3.504   4.762   0.936  1.00  0.00           H  
HETATM   44  H20 UNL     1      -4.626   3.483   0.395  1.00  0.00           H  
HETATM   45  H21 UNL     1      -7.007  -0.484  -0.376  1.00  0.00           H  
HETATM   46  H22 UNL     1      -7.236  -2.881  -1.124  1.00  0.00           H  
HETATM   47  H23 UNL     1      -5.193  -4.259  -1.415  1.00  0.00           H  
HETATM   48  H24 UNL     1      -3.051  -3.281  -0.986  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4    6
CONECT    4    5   30   31
CONECT    5   32   33   34
CONECT    6    7   35   36
CONECT    7    8   37   38
CONECT    8    9   39
CONECT    9   10   10   24
CONECT   10   11   40
CONECT   11   12   12   41
CONECT   12   13   14
CONECT   13   42   43   44
CONECT   14   15   24   24
CONECT   15   16
CONECT   16   17   17   21
CONECT   17   18   45
CONECT   18   19   19   46
CONECT   19   20   47
CONECT   20   21   21   48
CONECT   21   22
CONECT   22   23   23   24
END

HMDB0015607
     RDKit          3D
Lucanthone
 48 50  0  0  0  0  0  0  0  0999 V2000
    4.3686    0.3564   -1.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4626    0.6787   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9700   -0.3521    0.4560 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301   -1.5163    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833   -1.2456    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6105   -0.7597    0.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520    0.3543    0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2744   -0.0780    0.1851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8119    0.7902    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4522    2.0819    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795    3.0685    1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6998    2.7456    0.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8095    3.7166    1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0532    1.4741    0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6951    1.0405    0.2322 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9183   -0.5572   -0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1575   -1.1415   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2689   -2.4479   -0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1317   -3.2004   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073   -2.6311   -0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7702   -1.2905   -0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5106   -0.7917   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5902   -1.6595   -0.3995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345    0.4479    0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230    0.5289   -2.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061   -0.7045   -2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6256    1.0564   -2.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5608    0.7983   -0.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0009    1.6655   -0.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0024   -1.8746   -0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3547   -2.3346    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6521   -2.2006    1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1311   -0.5677    1.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8964   -0.8168    0.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4841   -1.1297   -0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3668   -1.6135    0.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7464    0.5672    1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042    1.2059   -0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647   -1.0244   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769    2.3515    0.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1029    4.0618    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2386    3.6082    2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5037    4.7619    0.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6255    3.4835    0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0074   -0.4842   -0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2360   -2.8815   -1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927   -4.2594   -1.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0507   -3.2805   -0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24  9  1  0
 24 14  2  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
 10 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-((2-(Diethylamino)ethyl)amino)-4-methylthioxanthen-9-one	ChEBI
1-Diethylaminoethylethylamino-4-methyl-thioxanthenone	ChEBI
1-{[2-(diethylamino)ethyl]amino}-4-methylthioxanthen-9-one	ChEBI
Lucanthonum	ChEBI
Lucantona	ChEBI
1-[[2-(Diethylamino)ethyl]amino]-4-methylthioxanthone	HMDB
Lucanthon	HMDB
Lucanthone monohydrochloride	HMDB
Lucanthone hydrochloride	HMDB
Tixantone	HMDB
Miracil D	HMDB

Chemical Formula

C₂₀H₂₄N₂OS

Average Molecular Weight

340.482

Monoisotopic Molecular Weight

340.16093409

IUPAC Name

1-{[2-(diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-one

Traditional Name

lucanthone

CAS Registry Number

479-50-5

SMILES

CCN(CC)CCNC1=C2C(=O)C3=CC=CC=C3SC2=C(C)C=C1

InChI Identifier

InChI=1S/C20H24N2OS/c1-4-22(5-2)13-12-21-16-11-10-14(3)20-18(16)19(23)15-8-6-7-9-17(15)24-20/h6-11,21H,4-5,12-13H2,1-3H3

InChI Key

FBQPGGIHOFZRGH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiochromenes. These are organosulfur compounds that are analogues to chromene, with the difference that are sulfur atom replaces the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thiochromenes

Sub Class

Not Available

Direct Parent

Thiochromenes

Alternative Parents

Substituents

Thiochromene
Benzothiopyran
1-benzothiopyran
Secondary aliphatic/aromatic amine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Tertiary aliphatic amine
Tertiary amine
Secondary amine
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

thioxanthenes (CHEBI:51052 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015607)

Source

Exogenous

Exogenous (HMDB: HMDB0015607)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0032 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0032 g/L	ALOGPS
logP	4.72	ALOGPS
logP	5.02	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	18.84	ChemAxon
pKa (Strongest Basic)	8.69	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.34 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.01 m³·mol⁻¹	ChemAxon
Polarizability	39.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	180.388	31661259
DarkChem	[M-H]-	177.785	31661259
DeepCCS	[M+H]+	184.842	30932474
DeepCCS	[M-H]-	182.484	30932474
DeepCCS	[M-2H]-	215.584	30932474
DeepCCS	[M+Na]+	190.936	30932474
AllCCS	[M+H]+	180.5	32859911
AllCCS	[M+H-H2O]+	177.4	32859911
AllCCS	[M+NH4]+	183.3	32859911
AllCCS	[M+Na]+	184.1	32859911
AllCCS	[M-H]-	186.0	32859911
AllCCS	[M+Na-2H]-	185.7	32859911
AllCCS	[M+HCOO]-	185.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lucanthone	CCN(CC)CCNC1=C2C(=O)C3=CC=CC=C3SC2=C(C)C=C1	4156.5	Standard polar	33892256
Lucanthone	CCN(CC)CCNC1=C2C(=O)C3=CC=CC=C3SC2=C(C)C=C1	3098.7	Standard non polar	33892256
Lucanthone	CCN(CC)CCNC1=C2C(=O)C3=CC=CC=C3SC2=C(C)C=C1	3239.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lucanthone,1TMS,isomer #1	CCN(CC)CCN(C1=CC=C(C)C2=C1C(=O)C1=CC=CC=C1S2)[Si](C)(C)C	2946.7	Semi standard non polar	33892256
Lucanthone,1TMS,isomer #1	CCN(CC)CCN(C1=CC=C(C)C2=C1C(=O)C1=CC=CC=C1S2)[Si](C)(C)C	2958.3	Standard non polar	33892256
Lucanthone,1TMS,isomer #1	CCN(CC)CCN(C1=CC=C(C)C2=C1C(=O)C1=CC=CC=C1S2)[Si](C)(C)C	3453.9	Standard polar	33892256
Lucanthone,1TBDMS,isomer #1	CCN(CC)CCN(C1=CC=C(C)C2=C1C(=O)C1=CC=CC=C1S2)[Si](C)(C)C(C)(C)C	3141.9	Semi standard non polar	33892256
Lucanthone,1TBDMS,isomer #1	CCN(CC)CCN(C1=CC=C(C)C2=C1C(=O)C1=CC=CC=C1S2)[Si](C)(C)C(C)(C)C	3117.0	Standard non polar	33892256
Lucanthone,1TBDMS,isomer #1	CCN(CC)CCN(C1=CC=C(C)C2=C1C(=O)C1=CC=CC=C1S2)[Si](C)(C)C(C)(C)C	3543.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lucanthone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zi9-9052000000-539114a80db1e32eb9a2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lucanthone 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 - Lucanthone 10V, Positive-QTOF	splash10-0006-1219000000-50d0c1ff5c50d70b4431	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucanthone 20V, Positive-QTOF	splash10-0uxr-4892000000-0bb96e502a524f51b203	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucanthone 40V, Positive-QTOF	splash10-0fmi-9240000000-ca20c5fb0c954a7a972b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucanthone 10V, Negative-QTOF	splash10-000i-0019000000-ba002b772294de47ce3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucanthone 20V, Negative-QTOF	splash10-000i-3049000000-a845a36b91098f229d50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucanthone 40V, Negative-QTOF	splash10-006x-9250000000-a6c9d2e8f2de1502d55c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucanthone 10V, Positive-QTOF	splash10-0006-0009000000-0e4a03265785e2302ee0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucanthone 20V, Positive-QTOF	splash10-0006-0219000000-c11e2a98f430732b9205	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucanthone 40V, Positive-QTOF	splash10-0fk9-9450000000-47cea156c4178a4990ee	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucanthone 10V, Negative-QTOF	splash10-000i-0009000000-301993047e54373ba45d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucanthone 20V, Negative-QTOF	splash10-000i-0069000000-dab0fdc698464727ec21	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucanthone 40V, Negative-QTOF	splash10-0fb9-0190000000-f557d9b5c78b2d05b543	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04967	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04967	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04967

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9772

KEGG Compound ID

C11715

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lucanthone

METLIN ID

Not Available

PubChem Compound

10180

PDB ID

Not Available

ChEBI ID

51052

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

Luo M, Kelley MR: Inhibition of the human apurinic/apyrimidinic endonuclease (APE1) repair activity and sensitization of breast cancer cells to DNA alkylating agents with lucanthone. Anticancer Res. 2004 Jul-Aug;24(4):2127-34. [PubMed:15330152 ]
Del Rowe JD, Bello J, Mitnick R, Sood B, Filippi C, Moran J, Freeman K, Mendez F, Bases R: Accelerated regression of brain metastases in patients receiving whole brain radiation and the topoisomerase II inhibitor, lucanthone. Int J Radiat Oncol Biol Phys. 1999 Jan 1;43(1):89-93. [PubMed:9989518 ]

Enzymes

Enzyme Details

1. DNA-(apurinic or apyrimidinic site) lyase

General function:: Involved in DNA binding
Specific function:: Repairs oxidative DNA damages in vitro. May have a role in protection against cell lethality and suppression of mutations. Removes the blocking groups from the 3'-termini of the DNA strand breaks generated by ionizing radiations and bleomycin
Gene Name:: APEX1
Uniprot ID:: P27695
Molecular weight:: 35554.2

References

Luo M, Kelley MR: Inhibition of the human apurinic/apyrimidinic endonuclease (APE1) repair activity and sensitization of breast cancer cells to DNA alkylating agents with lucanthone. Anticancer Res. 2004 Jul-Aug;24(4):2127-34. [PubMed:15330152 ]

Enzyme Details

2. DNA topoisomerase 2-alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:: TOP2A
Uniprot ID:: P11388
Molecular weight:: 174383.9

References

Bases RE, Mendez F: Topoisomerase inhibition by lucanthone, an adjuvant in radiation therapy. Int J Radiat Oncol Biol Phys. 1997 Mar 15;37(5):1133-7. [PubMed:9169823 ]
Dassonneville L, Bailly C: Stimulation of topoisomerase II-mediated DNA cleavage by an indazole analogue of lucanthone. Biochem Pharmacol. 1999 Oct 15;58(8):1307-12. [PubMed:10487533 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Lucanthone (HMDB0015607)

MOL for HMDB0015607 (Lucanthone)

3D MOL for HMDB0015607 (Lucanthone)

3D SDF for HMDB0015607 (Lucanthone)

3D-SDF for HMDB0015607 (Lucanthone)

PDB for HMDB0015607 (Lucanthone)

3D PDB for HMDB0015607 (Lucanthone)

SMILES for HMDB0015607 (Lucanthone)

INCHI for HMDB0015607 (Lucanthone)

Structure for HMDB0015607 (Lucanthone)

3D Structure for HMDB0015607 (Lucanthone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References