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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:59:10 UTC

Update Date

2021-09-26 23:02:32 UTC

HMDB ID

HMDB0250841

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Damnacanthal

Description

damnacanthal belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. damnacanthal is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Damnacanthal is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Damnacanthal is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0250841
     RDKit          3D
Damnacanthal
 31 33  0  0  0  0  0  0  0  0999 V2000
   -2.6559    2.1831   -0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2090    1.5836    0.3847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7335    0.2763    0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5729   -0.8044    0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9711   -0.5045    0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8642   -1.3311    1.1762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -2.0842    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066   -3.1439    1.0925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7253   -2.3136    0.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1046   -1.2536    0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3921    0.0382    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5119    1.1571    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0546    2.3118   -0.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275    0.8673   -0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8085    1.9175   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1406    1.6158   -0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6166    0.3171   -0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7573   -0.7249   -0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4149   -0.4207   -0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5225   -1.5253    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9503   -2.7288    0.2681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1672    1.6436   -1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988    3.2691   -0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7466    2.0525   -0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3030    0.5300    0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8418   -3.2965    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072   -3.3054    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4139    2.9158   -0.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8583    2.4003   -0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6723    0.0895   -0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1478   -1.7318   -0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  4  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  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
 11  3  1  0
 19 14  1  0
 20 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  8 26  1  0
  9 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END


  Mrv1533004261516472D          

 21 23  0  0  0  0            999 V2000
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
    2.8579   -1.6500    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
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  3 21  1  0  0  0  0
 10 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250841

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C=O)C(O)=CC2=C1C(=O)C1=CC=CC=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O5/c1-21-16-11(7-17)12(18)6-10-13(16)15(20)9-5-3-2-4-8(9)14(10)19/h2-7,18H,1H3

> <INCHI_KEY>
IPDMWUNUULAXLU-UHFFFAOYSA-N

> <FORMULA>
C16H10O5

> <MOLECULAR_WEIGHT>
282.251

> <EXACT_MASS>
282.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.542830266686707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-1-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
2.819971832

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.435238454598038

> <JCHEM_PKA_STRONGEST_BASIC>
-4.936592518502855

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
76.17909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
damnacanthal

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250841
     RDKit          3D
Damnacanthal
 31 33  0  0  0  0  0  0  0  0999 V2000
   -2.6559    2.1831   -0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2090    1.5836    0.3847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7335    0.2763    0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5729   -0.8044    0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9711   -0.5045    0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8642   -1.3311    1.1762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -2.0842    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066   -3.1439    1.0925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7253   -2.3136    0.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1046   -1.2536    0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3921    0.0382    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5119    1.1571    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0546    2.3118   -0.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275    0.8673   -0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8085    1.9175   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1406    1.6158   -0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6166    0.3171   -0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7573   -0.7249   -0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4149   -0.4207   -0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5225   -1.5253    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9503   -2.7288    0.2681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1672    1.6436   -1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988    3.2691   -0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7466    2.0525   -0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3030    0.5300    0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8418   -3.2965    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072   -3.3054    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4139    2.9158   -0.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8583    2.4003   -0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6723    0.0895   -0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1478   -1.7318   -0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  4  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  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
 11  3  1  0
 19 14  1  0
 20 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  8 26  1  0
  9 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3   10                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0250841
HETATM    1  C1  UNL     1      -2.656   2.183  -0.793  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.209   1.584   0.385  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.734   0.276   0.474  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.573  -0.804   0.744  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.971  -0.504   0.929  1.00  0.00           C  
HETATM    6  O2  UNL     1      -4.864  -1.331   1.176  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.106  -2.084   0.832  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.907  -3.144   1.092  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.725  -2.314   0.641  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.105  -1.254   0.375  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.392   0.038   0.291  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.512   1.157   0.006  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.055   2.312  -0.067  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.927   0.867  -0.182  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.809   1.918  -0.455  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.141   1.616  -0.628  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.617   0.317  -0.540  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.757  -0.725  -0.272  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.415  -0.421  -0.097  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.522  -1.525   0.184  1.00  0.00           C  
HETATM   21  O5  UNL     1       1.950  -2.729   0.268  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.167   1.644  -1.656  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.399   3.269  -0.857  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.747   2.052  -0.914  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.303   0.530   0.852  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.842  -3.296   1.260  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.307  -3.305   0.700  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.414   2.916  -0.518  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.858   2.400  -0.842  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.672   0.090  -0.679  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.148  -1.732  -0.207  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5    7
CONECT    5    6    6   25
CONECT    7    8    9    9
CONECT    8   26
CONECT    9   10   27
CONECT   10   11   11   20
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   19
CONECT   15   16   28
CONECT   16   17   17   29
CONECT   17   18   30
CONECT   18   19   19   31
CONECT   19   20
CONECT   20   21   21
END

HMDB0250841
     RDKit          3D
Damnacanthal
 31 33  0  0  0  0  0  0  0  0999 V2000
   -2.6559    2.1831   -0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2090    1.5836    0.3847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7335    0.2763    0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5729   -0.8044    0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9711   -0.5045    0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8642   -1.3311    1.1762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -2.0842    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066   -3.1439    1.0925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7253   -2.3136    0.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1046   -1.2536    0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3921    0.0382    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5119    1.1571    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0546    2.3118   -0.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275    0.8673   -0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8085    1.9175   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1406    1.6158   -0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6166    0.3171   -0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7573   -0.7249   -0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4149   -0.4207   -0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5225   -1.5253    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9503   -2.7288    0.2681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1672    1.6436   -1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988    3.2691   -0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7466    2.0525   -0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3030    0.5300    0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8418   -3.2965    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072   -3.3054    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4139    2.9158   -0.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8583    2.4003   -0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6723    0.0895   -0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1478   -1.7318   -0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  4  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  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
 11  3  1  0
 19 14  1  0
 20 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  8 26  1  0
  9 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₀O₅

Average Molecular Weight

282.251

Monoisotopic Molecular Weight

282.052823422

IUPAC Name

3-hydroxy-1-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde

Traditional Name

damnacanthal

CAS Registry Number

Not Available

SMILES

COC1=C(C=O)C(O)=CC2=C1C(=O)C1=CC=CC=C1C2=O

InChI Identifier

InChI=1S/C16H10O5/c1-21-16-11(7-17)12(18)6-10-13(16)15(20)9-5-3-2-4-8(9)14(10)19/h2-7,18H,1H3

InChI Key

IPDMWUNUULAXLU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Aryl ketone
Anisole
1-hydroxy-2-unsubstituted benzenoid
Aryl-aldehyde
Alkyl aryl ether
Vinylogous acid
Ketone
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aldehyde
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.91	ALOGPS
logP	2.82	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.44	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.18 m³·mol⁻¹	ChemAxon
Polarizability	27.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	160.957	30932474
DeepCCS	[M-H]-	158.599	30932474
DeepCCS	[M-2H]-	191.484	30932474
DeepCCS	[M+Na]+	167.05	30932474
AllCCS	[M+H]+	163.9	32859911
AllCCS	[M+H-H2O]+	160.7	32859911
AllCCS	[M+NH4]+	166.9	32859911
AllCCS	[M+Na]+	167.8	32859911
AllCCS	[M-H]-	162.2	32859911
AllCCS	[M+Na-2H]-	161.4	32859911
AllCCS	[M+HCOO]-	160.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Damnacanthal	COC1=C(C=O)C(O)=CC2=C1C(=O)C1=CC=CC=C1C2=O	3628.9	Standard polar	33892256
Damnacanthal	COC1=C(C=O)C(O)=CC2=C1C(=O)C1=CC=CC=C1C2=O	2402.2	Standard non polar	33892256
Damnacanthal	COC1=C(C=O)C(O)=CC2=C1C(=O)C1=CC=CC=C1C2=O	2640.2	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 - Damnacanthal GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ufr-0590000000-c9fdf21109eb3091ba13	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Damnacanthal GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Damnacanthal GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Damnacanthal GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - Damnacanthal 10V, Positive-QTOF	splash10-001i-0090000000-03c912f44b4d54fe7f1b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Damnacanthal 20V, Positive-QTOF	splash10-001i-0090000000-31f48ce4d17704e224c4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Damnacanthal 40V, Positive-QTOF	splash10-0ab9-1980000000-49a01ed5c763452e06c7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Damnacanthal 10V, Negative-QTOF	splash10-001i-0090000000-60166d79143e3c19fb0f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Damnacanthal 20V, Negative-QTOF	splash10-0ue9-0090000000-793ab6efca7df6cbc9d1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Damnacanthal 40V, Negative-QTOF	splash10-0g4i-0090000000-f9eee082e13131346c27	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Damnacanthal

METLIN ID

Not Available

PubChem Compound

2948

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Damnacanthal (HMDB0250841)

MOL for HMDB0250841 (Damnacanthal)

3D MOL for HMDB0250841 (Damnacanthal)

3D SDF for HMDB0250841 (Damnacanthal)

3D-SDF for HMDB0250841 (Damnacanthal)

PDB for HMDB0250841 (Damnacanthal)

3D PDB for HMDB0250841 (Damnacanthal)

SMILES for HMDB0250841 (Damnacanthal)

INCHI for HMDB0250841 (Damnacanthal)

Structure for HMDB0250841 (Damnacanthal)

3D Structure for HMDB0250841 (Damnacanthal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra