NP-MRD: Showing NP-Card for N-Acetyldaunomycin (NP0021681)

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Record Information

Version

2.0

Created at

2021-01-06 06:57:30 UTC

Updated at

2021-07-15 17:36:59 UTC

NP-MRD ID

NP0021681

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyldaunomycin

Provided By

NPAtlas

Description

N-Acetyldaunomycin is also known as N-acetyldaunorubicin. N-Acetyldaunomycin is found in Streptomyces. Based on a literature review very few articles have been published on N-Acetyldaunomycin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306242105173D          

 72 76  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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 31 61  1  0
 32 62  1  1
 33 63  1  0
 35 64  1  0
 35 65  1  0
 35 66  1  0
 37 67  1  6
 38 68  1  0
 39 69  1  1
 40 70  1  0
 40 71  1  0
 40 72  1  0
M  END

  Mrv1652306242105173D          

 72 76  0  0  0  0            999 V2000
    5.9554   -0.8165    4.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2126   -0.7004    3.6577 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8319   -1.0491    2.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1315   -1.5024    2.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6892   -1.8340    1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9597   -1.7202   -0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669   -1.2688    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1073   -0.9377    1.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379   -0.4609    1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2439   -0.1631    2.4769 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096   -0.3168    0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5781    0.1502    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797    0.4363    1.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8404    0.2722   -0.8669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4437   -0.0742   -2.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7165   -0.5203   -2.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5416    0.1346   -3.2858 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1175    1.6054   -3.1697 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3046    2.3168   -2.9740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5480    2.0680   -4.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8281    1.4604   -4.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0617    2.9491   -5.0565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7692    1.7676   -1.9889 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5531    0.7221   -0.8988 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.1502    0.2753    0.6940 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2983    1.2241    0.9226 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.7208   -1.6012    3.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6893   -2.1865    1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3488   -1.9643   -0.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    0.7670    1.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3280   -0.5269   -3.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0386    0.0023   -4.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0303    3.1974   -2.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
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  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
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 19 20  2  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
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 39 41  1  0  0  0  0
  8  3  1  0  0  0  0
 18 11  1  0  0  0  0
 41 30  1  0  0  0  0
 19  7  1  0  0  0  0
 28 14  1  0  0  0  0
  1 42  1  0  0  0  0
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  1 44  1  0  0  0  0
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  6 47  1  0  0  0  0
 13 48  1  0  0  0  0
 17 49  1  0  0  0  0
 21 50  1  0  0  0  0
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 28 58  1  6  0  0  0
 30 59  1  6  0  0  0
 31 60  1  0  0  0  0
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 39 69  1  1  0  0  0
 40 70  1  0  0  0  0
 40 71  1  0  0  0  0
 40 72  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021681

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C3=C(C(=O)C2=C(O[H])C2=C1C([H])([H])[C@@](O[H])(C(=O)C([H])([H])[H])C([H])([H])[C@]2([H])O[C@@]1([H])O[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(N([H])C(=O)C([H])([H])[H])C1([H])[H])C(OC([H])([H])[H])=C([H])C([H])=C3[H]

> <INCHI_IDENTIFIER>
InChI=1S/C29H31NO11/c1-11-24(33)16(30-13(3)32)8-19(40-11)41-18-10-29(38,12(2)31)9-15-21(18)28(37)23-22(26(15)35)25(34)14-6-5-7-17(39-4)20(14)27(23)36/h5-7,11,16,18-19,24,33,35,37-38H,8-10H2,1-4H3,(H,30,32)/t11-,16-,18+,19-,24-,29+/m1/s1

> <INCHI_KEY>
UCEMIGLIQIYVAH-JEEWRSNPSA-N

> <FORMULA>
C29H31NO11

> <MOLECULAR_WEIGHT>
569.563

> <EXACT_MASS>
569.189710822

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
58.699112462710424

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2R,3S,4R,6S)-6-{[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]acetamide

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
2.140267942

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.822813852583105

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.020812563163895

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2822769603370032

> <JCHEM_POLAR_SURFACE_AREA>
188.92

> <JCHEM_REFRACTIVITY>
142.3353

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2R,3S,4R,6S)-6-{[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
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    5.8319   -1.0491    2.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1315   -1.5024    2.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6892   -1.8340    1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1073   -0.9377    1.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379   -0.4609    1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1175    1.6054   -3.1697 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.9569   -0.4793    1.8132 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3379   -0.4260   -0.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9179    1.9856    1.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5362    1.7546   -0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5561    0.7428    2.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7449    0.7623   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6077    1.0611    0.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7094    2.3000   -0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4762    2.8066    1.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4210   -1.3085    0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9225   -2.0969    1.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0636   -1.7654    2.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345   -2.8736    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8183   -2.4495    0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1018   -3.5583    1.4309 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 15 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 24 26  2  0
 22 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 32 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  1  0
  8  3  1  0
 18 11  1  0
 41 30  1  0
 19  7  1  0
 28 14  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  4 45  1  0
  5 46  1  0
  6 47  1  0
 13 48  1  0
 17 49  1  0
 21 50  1  0
 21 51  1  0
 23 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  6
 30 59  1  6
 31 60  1  0
 31 61  1  0
 32 62  1  1
 33 63  1  0
 35 64  1  0
 35 65  1  0
 35 66  1  0
 37 67  1  6
 38 68  1  0
 39 69  1  1
 40 70  1  0
 40 71  1  0
 40 72  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       5.955  -0.817   4.856  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.213  -0.700   3.658  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.832  -1.049   2.470  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.131  -1.502   2.396  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.689  -1.834   1.174  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.960  -1.720  -0.004  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.667  -1.269   0.074  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.107  -0.938   1.286  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.738  -0.461   1.358  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.244  -0.163   2.477  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.910  -0.317   0.149  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.578   0.150   0.253  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.180   0.436   1.522  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.840   0.272  -0.867  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.444  -0.074  -2.102  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.716  -0.520  -2.197  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.323  -0.864  -3.379  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.498  -0.655  -1.039  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.878  -1.139  -1.142  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.347  -1.430  -2.272  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.542   0.135  -3.286  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.118   1.605  -3.170  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.305   2.317  -2.974  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.548   2.068  -4.386  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.828   1.460  -4.812  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.062   2.949  -5.056  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.769   1.768  -1.989  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.553   0.722  -0.899  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.053   1.041   0.312  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.150   0.275   0.694  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.298   1.224   0.923  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.454   0.488   1.498  0.00  0.00           C+0
HETATM   33  N   UNK     0      -5.679   0.928   0.865  0.00  0.00           N+0
HETATM   34  C   UNK     0      -6.740   1.544   1.541  0.00  0.00           C+0
HETATM   35  C   UNK     0      -7.952   1.955   0.794  0.00  0.00           C+0
HETATM   36  O   UNK     0      -6.726   1.775   2.776  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.266  -1.005   1.386  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.261  -1.609   2.154  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.938  -1.454   1.940  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.502  -2.661   1.137  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.957  -0.479   1.813  0.00  0.00           O+0
HETATM   42  H   UNK     0       6.807  -0.084   4.895  0.00  0.00           H+0
HETATM   43  H   UNK     0       6.427  -1.821   4.954  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.335  -0.592   5.745  0.00  0.00           H+0
HETATM   45  H   UNK     0       7.721  -1.601   3.290  0.00  0.00           H+0
HETATM   46  H   UNK     0       8.689  -2.187   1.085  0.00  0.00           H+0
HETATM   47  H   UNK     0       7.349  -1.964  -0.967  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.404   0.767   1.970  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.847  -0.802  -4.244  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.328  -0.527  -3.136  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.039   0.002  -4.237  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.030   3.197  -2.604  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.084   0.558  -4.228  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.695   2.172  -4.741  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.799   1.169  -5.899  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.826   1.729  -2.316  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.601   2.770  -1.549  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.145  -0.174  -1.301  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.338  -0.426  -0.146  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.918   1.986   1.666  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.536   1.755  -0.025  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.556   0.743   2.582  0.00  0.00           H+0
HETATM   63  H   UNK     0      -5.745   0.762  -0.150  0.00  0.00           H+0
HETATM   64  H   UNK     0      -8.608   1.061   0.687  0.00  0.00           H+0
HETATM   65  H   UNK     0      -7.709   2.300  -0.238  0.00  0.00           H+0
HETATM   66  H   UNK     0      -8.476   2.807   1.276  0.00  0.00           H+0
HETATM   67  H   UNK     0      -4.421  -1.309   0.332  0.00  0.00           H+0
HETATM   68  H   UNK     0      -5.923  -2.097   1.640  0.00  0.00           H+0
HETATM   69  H   UNK     0      -3.064  -1.765   2.993  0.00  0.00           H+0
HETATM   70  H   UNK     0      -1.435  -2.874   1.228  0.00  0.00           H+0
HETATM   71  H   UNK     0      -2.818  -2.450   0.076  0.00  0.00           H+0
HETATM   72  H   UNK     0      -3.102  -3.558   1.431  0.00  0.00           H+0
CONECT    1    2   42   43   44                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   45                                                  
CONECT    5    4    6   46                                                  
CONECT    6    5    7   47                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9    3                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   48                                                       
CONECT   14   12   15   28                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   49                                                       
CONECT   18   16   19   11                                                  
CONECT   19   18   20    7                                                  
CONECT   20   19                                                            
CONECT   21   15   22   50   51                                             
CONECT   22   21   23   24   27                                             
CONECT   23   22   52                                                       
CONECT   24   22   25   26                                                  
CONECT   25   24   53   54   55                                             
CONECT   26   24                                                            
CONECT   27   22   28   56   57                                             
CONECT   28   27   29   14   58                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   41   59                                             
CONECT   31   30   32   60   61                                             
CONECT   32   31   33   37   62                                             
CONECT   33   32   34   63                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   64   65   66                                             
CONECT   36   34                                                            
CONECT   37   32   38   39   67                                             
CONECT   38   37   68                                                       
CONECT   39   37   40   41   69                                             
CONECT   40   39   70   71   72                                             
CONECT   41   39   30                                                       
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    4                                                            
CONECT   46    5                                                            
CONECT   47    6                                                            
CONECT   48   13                                                            
CONECT   49   17                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
CONECT   52   23                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
CONECT   59   30                                                            
CONECT   60   31                                                            
CONECT   61   31                                                            
CONECT   62   32                                                            
CONECT   63   33                                                            
CONECT   64   35                                                            
CONECT   65   35                                                            
CONECT   66   35                                                            
CONECT   67   37                                                            
CONECT   68   38                                                            
CONECT   69   39                                                            
CONECT   70   40                                                            
CONECT   71   40                                                            
CONECT   72   40                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  152    0
END

RDKit          3D

72 76  0  0  0  0  0  0  0  0999 V2000
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    7.1315   -1.5024    2.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6892   -1.8340    1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6669   -1.2688    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1073   -0.9377    1.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379   -0.4609    1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2439   -0.1631    2.4769 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096   -0.3168    0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5781    0.1502    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797    0.4363    1.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8404    0.2722   -0.8669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4437   -0.0742   -2.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7165   -0.5203   -2.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4539    0.4882    1.4981 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -6.7260    1.7753    2.7758 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2605   -1.6091    2.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9378   -1.4538    1.9400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5017   -2.6614    1.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9569   -0.4793    1.8132 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8067   -0.0835    4.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4269   -1.8214    4.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3352   -0.5918    5.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7208   -1.6012    3.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6893   -2.1865    1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3488   -1.9643   -0.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    0.7670    1.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8472   -0.8019   -4.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3280   -0.5269   -3.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0386    0.0023   -4.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0303    3.1974   -2.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837    0.5575   -4.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8257    1.7286   -2.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6012    2.7698   -1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1451   -0.1735   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3379   -0.4260   -0.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5362    1.7546   -0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.6077    1.0611    0.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7094    2.3000   -0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4762    2.8066    1.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4210   -1.3085    0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9225   -2.0969    1.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0636   -1.7654    2.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345   -2.8736    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8183   -2.4495    0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1018   -3.5583    1.4309 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
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 15 16  1  0
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 19 20  2  0
 15 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 24 26  2  0
 22 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 32 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  1  0
  8  3  1  0
 18 11  1  0
 41 30  1  0
 19  7  1  0
 28 14  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  4 45  1  0
  5 46  1  0
  6 47  1  0
 13 48  1  0
 17 49  1  0
 21 50  1  0
 21 51  1  0
 23 52  1  0
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 30 59  1  6
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 31 61  1  0
 32 62  1  1
 33 63  1  0
 35 64  1  0
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 37 67  1  6
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 39 69  1  1
 40 70  1  0
 40 71  1  0
 40 72  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
N-Acetyldaunorubicin	MeSH
N-Acetyldaunomycin, hydrochloride, (8S-cis)-isomer	MeSH

Chemical Formula

C₂₉H₃₁NO₁₁

Average Mass

569.5630 Da

Monoisotopic Mass

569.18971 Da

IUPAC Name

N-[(2R,3S,4R,6S)-6-{[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]acetamide

Traditional Name

N-[(2R,3S,4R,6S)-6-{[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]acetamide

CAS Registry Number

Not Available

SMILES

COC1=CC=CC2=C1C(=O)C1=C(C(O)=C3C[C@](O)(C[C@H](OC4CC(NC(C)=O)C(O)C(C)O4)C3=C1O)C(C)=O)C2=O

InChI Identifier

InChI=1S/C29H31NO11/c1-11-24(33)16(30-13(3)32)8-19(40-11)41-18-10-29(38,12(2)31)9-15-21(18)28(37)23-22(26(15)35)25(34)14-6-5-7-17(39-4)20(14)27(23)36/h5-7,11,16,18-19,24,33,35,37-38H,8-10H2,1-4H3,(H,30,32)/t11?,16?,18-,19?,24?,29-/m0/s1

InChI Key

UCEMIGLIQIYVAH-JEEWRSNPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces	NPAtlas	561047

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	1.82	ALOGPS
logP	2.14	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.02	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	188.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	142.34 m³·mol⁻¹	ChemAxon
Polarizability	58.7 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

External Links

NPAtlas ID

NPA019453

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23142141

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24191042

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for N-Acetyldaunomycin (NP0021681)

MOL for NP0021681 (N-Acetyldaunomycin)

3D MOL for NP0021681 (N-Acetyldaunomycin)

3D SDF for NP0021681 (N-Acetyldaunomycin)

3D-SDF for NP0021681 (N-Acetyldaunomycin)

PDB for NP0021681 (N-Acetyldaunomycin)

3D PDB for NP0021681 (N-Acetyldaunomycin)

SMILES for NP0021681 (N-Acetyldaunomycin)

INCHI for NP0021681 (N-Acetyldaunomycin)

Structure for NP0021681 (N-Acetyldaunomycin)

3D Structure for NP0021681 (N-Acetyldaunomycin)