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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:46:28 UTC

Update Date

2021-09-26 22:58:44 UTC

HMDB ID

HMDB0248448

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Annamycin

Description

Annamycin belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage. Based on a literature review a significant number of articles have been published on Annamycin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Annamycin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Annamycin 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

  Mrv1652309112103462D          

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M  END

HMDB0248448
     RDKit          3D
Annamycin
 63 67  0  0  0  0  0  0  0  0999 V2000
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M  END

  Mrv1652309112103462D          

 38 42  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0248448

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC(OC2CC(O)(CC3=C(O)C4=C(C(O)=C23)C(=O)C2=CC=CC=C2C4=O)C(=O)CO)C(I)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H25IO11/c1-9-19(30)24(35)18(27)25(37-9)38-13-7-26(36,14(29)8-28)6-12-15(13)23(34)17-16(22(12)33)20(31)10-4-2-3-5-11(10)21(17)32/h2-5,9,13,18-19,24-25,28,30,33-36H,6-8H2,1H3

> <INCHI_KEY>
CIDNKDMVSINJCG-UHFFFAOYSA-N

> <FORMULA>
C26H25IO11

> <MOLECULAR_WEIGHT>
640.379

> <EXACT_MASS>
640.04416

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
56.7267323949299

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-[(4,5-dihydroxy-3-iodo-6-methyloxan-2-yl)oxy]-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.647542398999999

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.845566468064563

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.049667963826677

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3298697473633148

> <JCHEM_POLAR_SURFACE_AREA>
191.04999999999995

> <JCHEM_REFRACTIVITY>
139.2415

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-[(4,5-dihydroxy-3-iodo-6-methyloxan-2-yl)oxy]-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7H-tetracene-5,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248448
     RDKit          3D
Annamycin
 63 67  0  0  0  0  0  0  0  0999 V2000
   -6.2062   -0.2516    0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9673   -1.0284    0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8621   -0.4168    0.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6494   -0.9626    0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7158    0.0490    0.2559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6891   -0.0512    1.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9358    1.0893    2.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6499    2.4274    1.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5459    2.6822    0.4951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8789    3.4515    2.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7476    4.2834    2.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0741    3.4640    3.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248    4.5295    4.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7256    2.5235    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    1.2314    0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6035    1.3278   -0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864    2.5604   -0.0995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2324    0.1938   -0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5908   -1.0052   -0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214   -1.0864    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240   -2.3370    0.2159 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582    0.0232    0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2215   -2.2290   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6621   -3.3415   -0.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5735   -2.2135   -1.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1978   -3.3541   -1.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4708   -3.2951   -2.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1439   -2.1014   -2.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5161   -0.9611   -2.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2410   -1.0176   -1.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5643    0.2064   -1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1862    1.2665   -1.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5889   -1.7359   -0.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083   -3.7817   -0.6825 I   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4970   -1.0633   -1.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3761   -1.6691   -3.1986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9177   -1.0889   -1.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6224   -0.0794   -2.0557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0420   -0.9190    0.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5747    0.3382   -0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0152    0.4383    1.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0883   -2.0486    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4163   -1.7022    1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8645   -0.9691    1.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176    1.0563    2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3408    0.9544    3.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3078    3.5757    0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9942    3.6085    3.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097    2.5295    4.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138    5.3288    4.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944    3.2169    0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3951    2.9687    1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    2.8767   -0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1901   -2.4238    0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6701   -4.2926   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8896   -4.2372   -2.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1289   -2.1170   -2.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0379   -0.0170   -2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5530   -1.6633   -1.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1498   -0.0156   -2.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1389   -1.4263   -3.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3646   -2.0524   -1.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1263    0.7538   -2.1769 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 19 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
  4 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37  2  1  0
 22  6  1  0
 30 25  1  0
 22 15  1  0
 31 18  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  0
  4 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  9 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 17 53  1  0
 21 54  1  0
 26 55  1  0
 27 56  1  0
 28 57  1  0
 29 58  1  0
 33 59  1  0
 35 60  1  0
 36 61  1  0
 37 62  1  0
 38 63  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.208   1.594   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.025   0.288   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.931   2.953   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      14.471   3.007   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      11.486   2.846   0.000  0.00  0.00           O+0
HETATM   36  I   UNK     0       9.336  -5.390   0.000  0.00  0.00           I+0
HETATM   37  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   38                                                  
CONECT    4    3    5   37                                                  
CONECT    5    4    6   36                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   31   35                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   30                                                  
CONECT   15   14   16   28                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17    9   13                                                  
CONECT   19   17                                                            
CONECT   20   16   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27   15   29                                                  
CONECT   29   28                                                            
CONECT   30   14                                                            
CONECT   31   11   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   11                                                            
CONECT   36    5                                                            
CONECT   37    4                                                            
CONECT   38    3                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

COMPND    HMDB0248448
HETATM    1  C1  UNL     1      -6.206  -0.252   0.455  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.967  -1.028   0.063  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.862  -0.417   0.623  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.649  -0.963   0.320  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.716   0.049   0.256  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.689  -0.051   1.190  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.936   1.089   2.174  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.650   2.427   1.530  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.546   2.682   0.495  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.879   3.452   2.587  1.00  0.00           C  
HETATM   11  O4  UNL     1      -1.748   4.283   2.391  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.074   3.464   3.847  1.00  0.00           C  
HETATM   13  O5  UNL     1      -0.525   4.529   4.621  1.00  0.00           O  
HETATM   14  C9  UNL     1       0.726   2.523   0.969  1.00  0.00           C  
HETATM   15  C10 UNL     1       1.304   1.231   0.517  1.00  0.00           C  
HETATM   16  C11 UNL     1       2.604   1.328  -0.036  1.00  0.00           C  
HETATM   17  O6  UNL     1       3.186   2.560  -0.100  1.00  0.00           O  
HETATM   18  C12 UNL     1       3.232   0.194  -0.487  1.00  0.00           C  
HETATM   19  C13 UNL     1       2.591  -1.005  -0.393  1.00  0.00           C  
HETATM   20  C14 UNL     1       1.321  -1.086   0.149  1.00  0.00           C  
HETATM   21  O7  UNL     1       0.724  -2.337   0.216  1.00  0.00           O  
HETATM   22  C15 UNL     1       0.658   0.023   0.611  1.00  0.00           C  
HETATM   23  C16 UNL     1       3.222  -2.229  -0.859  1.00  0.00           C  
HETATM   24  O8  UNL     1       2.662  -3.342  -0.788  1.00  0.00           O  
HETATM   25  C17 UNL     1       4.573  -2.213  -1.448  1.00  0.00           C  
HETATM   26  C18 UNL     1       5.198  -3.354  -1.898  1.00  0.00           C  
HETATM   27  C19 UNL     1       6.471  -3.295  -2.445  1.00  0.00           C  
HETATM   28  C20 UNL     1       7.144  -2.101  -2.553  1.00  0.00           C  
HETATM   29  C21 UNL     1       6.516  -0.961  -2.102  1.00  0.00           C  
HETATM   30  C22 UNL     1       5.241  -1.018  -1.554  1.00  0.00           C  
HETATM   31  C23 UNL     1       4.564   0.206  -1.067  1.00  0.00           C  
HETATM   32  O9  UNL     1       5.186   1.267  -1.175  1.00  0.00           O  
HETATM   33  C24 UNL     1      -2.589  -1.736  -0.972  1.00  0.00           C  
HETATM   34  I1  UNL     1      -3.108  -3.782  -0.682  1.00  0.00           I  
HETATM   35  C25 UNL     1      -3.497  -1.063  -1.963  1.00  0.00           C  
HETATM   36  O10 UNL     1      -3.376  -1.669  -3.199  1.00  0.00           O  
HETATM   37  C26 UNL     1      -4.918  -1.089  -1.439  1.00  0.00           C  
HETATM   38  O11 UNL     1      -5.622  -0.079  -2.056  1.00  0.00           O  
HETATM   39  H1  UNL     1      -7.042  -0.919   0.761  1.00  0.00           H  
HETATM   40  H2  UNL     1      -6.575   0.338  -0.404  1.00  0.00           H  
HETATM   41  H3  UNL     1      -6.015   0.438   1.305  1.00  0.00           H  
HETATM   42  H4  UNL     1      -5.088  -2.049   0.460  1.00  0.00           H  
HETATM   43  H5  UNL     1      -2.416  -1.702   1.126  1.00  0.00           H  
HETATM   44  H6  UNL     1      -0.864  -0.969   1.782  1.00  0.00           H  
HETATM   45  H7  UNL     1      -2.018   1.056   2.416  1.00  0.00           H  
HETATM   46  H8  UNL     1      -0.341   0.954   3.081  1.00  0.00           H  
HETATM   47  H9  UNL     1      -1.308   3.576   0.139  1.00  0.00           H  
HETATM   48  H10 UNL     1       0.994   3.608   3.666  1.00  0.00           H  
HETATM   49  H11 UNL     1      -0.310   2.529   4.409  1.00  0.00           H  
HETATM   50  H12 UNL     1      -0.014   5.329   4.338  1.00  0.00           H  
HETATM   51  H13 UNL     1       0.794   3.217   0.101  1.00  0.00           H  
HETATM   52  H14 UNL     1       1.395   2.969   1.758  1.00  0.00           H  
HETATM   53  H15 UNL     1       4.037   2.877  -0.422  1.00  0.00           H  
HETATM   54  H16 UNL     1      -0.190  -2.424   0.601  1.00  0.00           H  
HETATM   55  H17 UNL     1       4.670  -4.293  -1.813  1.00  0.00           H  
HETATM   56  H18 UNL     1       6.890  -4.237  -2.774  1.00  0.00           H  
HETATM   57  H19 UNL     1       8.129  -2.117  -2.986  1.00  0.00           H  
HETATM   58  H20 UNL     1       7.038  -0.017  -2.183  1.00  0.00           H  
HETATM   59  H21 UNL     1      -1.553  -1.663  -1.369  1.00  0.00           H  
HETATM   60  H22 UNL     1      -3.150  -0.016  -2.064  1.00  0.00           H  
HETATM   61  H23 UNL     1      -4.139  -1.426  -3.796  1.00  0.00           H  
HETATM   62  H24 UNL     1      -5.365  -2.052  -1.755  1.00  0.00           H  
HETATM   63  H25 UNL     1      -5.126   0.754  -2.177  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3   37   42
CONECT    3    4
CONECT    4    5   33   43
CONECT    5    6
CONECT    6    7   22   44
CONECT    7    8   45   46
CONECT    8    9   10   14
CONECT    9   47
CONECT   10   11   11   12
CONECT   12   13   48   49
CONECT   13   50
CONECT   14   15   51   52
CONECT   15   16   16   22
CONECT   16   17   18
CONECT   17   53
CONECT   18   19   19   31
CONECT   19   20   23
CONECT   20   21   22   22
CONECT   21   54
CONECT   23   24   24   25
CONECT   25   26   26   30
CONECT   26   27   55
CONECT   27   28   28   56
CONECT   28   29   57
CONECT   29   30   30   58
CONECT   30   31
CONECT   31   32   32
CONECT   33   34   35   59
CONECT   35   36   37   60
CONECT   36   61
CONECT   37   38   62
CONECT   38   63
END

HMDB0248448
     RDKit          3D
Annamycin
 63 67  0  0  0  0  0  0  0  0999 V2000
   -6.2062   -0.2516    0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9673   -1.0284    0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8621   -0.4168    0.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6494   -0.9626    0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7158    0.0490    0.2559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6891   -0.0512    1.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9358    1.0893    2.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6499    2.4274    1.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5459    2.6822    0.4951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8789    3.4515    2.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7476    4.2834    2.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0741    3.4640    3.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248    4.5295    4.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7256    2.5235    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    1.2314    0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6035    1.3278   -0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864    2.5604   -0.0995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2324    0.1938   -0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5908   -1.0052   -0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214   -1.0864    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240   -2.3370    0.2159 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582    0.0232    0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2215   -2.2290   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6621   -3.3415   -0.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5735   -2.2135   -1.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1978   -3.3541   -1.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4708   -3.2951   -2.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1439   -2.1014   -2.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5161   -0.9611   -2.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2410   -1.0176   -1.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5643    0.2064   -1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1862    1.2665   -1.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5889   -1.7359   -0.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083   -3.7817   -0.6825 I   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4970   -1.0633   -1.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3761   -1.6691   -3.1986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9177   -1.0889   -1.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6224   -0.0794   -2.0557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0420   -0.9190    0.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5747    0.3382   -0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0152    0.4383    1.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0883   -2.0486    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4163   -1.7022    1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8645   -0.9691    1.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176    1.0563    2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3408    0.9544    3.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3078    3.5757    0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9942    3.6085    3.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097    2.5295    4.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138    5.3288    4.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944    3.2169    0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3951    2.9687    1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    2.8767   -0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1901   -2.4238    0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6701   -4.2926   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8896   -4.2372   -2.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1289   -2.1170   -2.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0379   -0.0170   -2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5530   -1.6633   -1.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1498   -0.0156   -2.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1389   -1.4263   -3.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3646   -2.0524   -1.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1263    0.7538   -2.1769 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 19 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
  4 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37  2  1  0
 22  6  1  0
 30 25  1  0
 22 15  1  0
 31 18  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  0
  4 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  9 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 17 53  1  0
 21 54  1  0
 26 55  1  0
 27 56  1  0
 28 57  1  0
 29 58  1  0
 33 59  1  0
 35 60  1  0
 36 61  1  0
 37 62  1  0
 38 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₆H₂₅IO₁₁

Average Molecular Weight

640.379

Monoisotopic Molecular Weight

640.04416

IUPAC Name

7-[(4,5-dihydroxy-3-iodo-6-methyloxan-2-yl)oxy]-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

Traditional Name

7-[(4,5-dihydroxy-3-iodo-6-methyloxan-2-yl)oxy]-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7H-tetracene-5,12-dione

CAS Registry Number

Not Available

SMILES

CC1OC(OC2CC(O)(CC3=C(O)C4=C(C(O)=C23)C(=O)C2=CC=CC=C2C4=O)C(=O)CO)C(I)C(O)C1O

InChI Identifier

InChI=1S/C26H25IO11/c1-9-19(30)24(35)18(27)25(37-9)38-13-7-26(36,14(29)8-28)6-12-15(13)23(34)17-16(22(12)33)20(31)10-4-2-3-5-11(10)21(17)32/h2-5,9,13,18-19,24-25,28,30,33-36H,6-8H2,1H3

InChI Key

CIDNKDMVSINJCG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Anthracyclines

Sub Class

Not Available

Direct Parent

Anthracyclines

Alternative Parents

Substituents

Anthracyclinone-skeleton
Anthracycline
Tetracenequinone
1,4-anthraquinone
9,10-anthraquinone
Anthracene
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Tetralin
Aryl ketone
Benzenoid
Oxane
Monosaccharide
Vinylogous acid
Tertiary alcohol
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Iodohydrin
Halohydrin
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organoiodide
Organohalogen compound
Carbonyl group
Alkyl iodide
Alkyl halide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0248448)

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	2.16	ALOGPS
logP	2.65	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.05	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	191.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	139.24 m³·mol⁻¹	ChemAxon
Polarizability	56.73 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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-2H]-	258.163	30932474
DeepCCS	[M+Na]+	232.98	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Annamycin	CC1OC(OC2CC(O)(CC3=C(O)C4=C(C(O)=C23)C(=O)C2=CC=CC=C2C4=O)C(=O)CO)C(I)C(O)C1O	4161.1	Standard polar	33892256
Annamycin	CC1OC(OC2CC(O)(CC3=C(O)C4=C(C(O)=C23)C(=O)C2=CC=CC=C2C4=O)C(=O)CO)C(I)C(O)C1O	4046.3	Standard non polar	33892256
Annamycin	CC1OC(OC2CC(O)(CC3=C(O)C4=C(C(O)=C23)C(=O)C2=CC=CC=C2C4=O)C(=O)CO)C(I)C(O)C1O	4786.9	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 - Annamycin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_17) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annamycin GC-MS (TMS_2_18) - 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 - Annamycin 10V, Positive-QTOF	splash10-014i-0009000000-d6c4f31849bfffc832da	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annamycin 20V, Positive-QTOF	splash10-066s-0009001000-33407d9048431cd23762	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annamycin 40V, Positive-QTOF	splash10-009i-4030091000-c5347a2c2cd99b4c4144	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annamycin 10V, Negative-QTOF	splash10-000i-0000039000-ec9a0389c4674d60684a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annamycin 20V, Negative-QTOF	splash10-001i-3009054000-e5e3c2d072d718958ba1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annamycin 40V, Negative-QTOF	splash10-014i-2019000000-f5c2104c5e48725b66c3	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

10613660

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Annamycin

METLIN ID

Not Available

PubChem Compound

13491278

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 Annamycin (HMDB0248448)

MOL for HMDB0248448 (Annamycin)

3D MOL for HMDB0248448 (Annamycin)

3D SDF for HMDB0248448 (Annamycin)

3D-SDF for HMDB0248448 (Annamycin)

PDB for HMDB0248448 (Annamycin)

3D PDB for HMDB0248448 (Annamycin)

SMILES for HMDB0248448 (Annamycin)

INCHI for HMDB0248448 (Annamycin)

Structure for HMDB0248448 (Annamycin)

3D Structure for HMDB0248448 (Annamycin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra