NP-MRD: Showing NP-Card for 6-Deoxy-8,17-dihydroxyerythronolide B (NP0003350)

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Record Information

Version

1.0

Created at

2020-12-09 00:38:15 UTC

Updated at

2021-07-15 16:46:11 UTC

NP-MRD ID

NP0003350

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Deoxy-8,17-dihydroxyerythronolide B

Provided By

NPAtlas

Description

(3R,4S,5R,6S,7S,11R,12S,13R,14R)-14-ethyl-4,6,9,12-tetrahydroxy-9-(hydroxymethyl)-3,5,7,11,13-pentamethyl-1-oxacyclotetradecane-2,10-dione belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. 6-Deoxy-8,17-dihydroxyerythronolide B is found in Streptomyces lividans. It was first documented in 2000 (PMID: 10908114). Based on a literature review very few articles have been published on (3R,4S,5R,6S,7S,11R,12S,13R,14R)-14-ethyl-4,6,9,12-tetrahydroxy-9-(hydroxymethyl)-3,5,7,11,13-pentamethyl-1-oxacyclotetradecane-2,10-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117473D          

 67 67  0  0  0  0            999 V2000
    3.6039   -2.9776    1.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2783   -1.5447    1.2636 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4132   -1.7243   -0.0033 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3060   -2.4282    0.3919 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3674   -3.2800   -0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902   -4.5785   -0.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0060   -2.8994   -0.5116 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8387   -2.3701   -1.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7701   -2.1196    0.4802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8968   -1.2163    1.0813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484   -1.3333    0.1106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5779   -1.6156   -1.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7376    0.0977    1.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6724    1.9870    0.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7061   -1.1001    2.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6017   -3.8516   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0703    0.6328   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9705    2.6668   -1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6074    1.9923   -1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2913    1.1214   -2.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3928    2.8348   -1.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6368   -0.9179   -2.8393 H   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  1  0  0  0  0
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  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
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 29 66  1  0  0  0  0
 29 67  1  0  0  0  0
M  END

     RDKit          3D

 67 67  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242117473D          

 67 67  0  0  0  0            999 V2000
    3.6039   -2.9776    1.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2783   -1.5447    1.2636 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4132   -1.7243   -0.0033 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3060   -2.4282    0.3919 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4902   -4.5785   -0.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7334    4.4244    2.2689 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
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  1 30  1  0  0  0  0
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  3 35  1  6  0  0  0
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 29 67  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1(O[H])C(=O)[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])[C@@]([H])(C([H])([H])[H])[C@]([H])(OC(=O)[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])[C@@]([H])(C([H])([H])[H])C1([H])[H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H38O8/c1-7-15-11(3)17(24)13(5)19(26)21(28,9-22)8-10(2)16(23)12(4)18(25)14(6)20(27)29-15/h10-18,22-25,28H,7-9H2,1-6H3/t10-,11-,12+,13+,14+,15+,16-,17-,18-,21+/m0/s1

> <INCHI_KEY>
PREIDDIPLSAKJR-CFWJUOAESA-N

> <FORMULA>
C21H38O8

> <MOLECULAR_WEIGHT>
418.527

> <EXACT_MASS>
418.256668184

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
43.812005044552116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4S,5R,6S,7S,9R,11R,12S,13R,14R)-14-ethyl-4,6,9,12-tetrahydroxy-9-(hydroxymethyl)-3,5,7,11,13-pentamethyl-1-oxacyclotetradecane-2,10-dione

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
0.8410028123333337

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.810867964022325

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.249327805192154

> <JCHEM_PKA_STRONGEST_BASIC>
-2.962847164146188

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
106.11719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4S,5R,6S,7S,9R,11R,12S,13R,14R)-14-ethyl-4,6,9,12-tetrahydroxy-9-(hydroxymethyl)-3,5,7,11,13-pentamethyl-1-oxacyclotetradecane-2,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 67 67  0  0  0  0  0  0  0  0999 V2000
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 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 24 58  1  1
 25 59  1  0
 25 60  1  0
 25 61  1  0
 26 62  1  6
 27 63  1  0
 28 64  1  6
 29 65  1  0
 29 66  1  0
 29 67  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       3.604  -2.978   1.742  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.278  -1.545   1.264  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.413  -1.724  -0.003  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.306  -2.428   0.392  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.367  -3.280  -0.023  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.490  -4.579  -0.068  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.006  -2.899  -0.512  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.839  -2.370  -1.890  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.770  -2.120   0.480  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.897  -1.216   1.081  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.948  -1.333   0.111  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.578  -1.616  -1.222  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.972   0.109   0.532  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.738   0.098   1.923  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.032   1.066  -0.054  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.558   1.726  -1.341  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.828   2.212   0.911  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.481   2.857   0.885  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.412   3.843  -0.124  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.416   3.695   2.175  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.733   4.424   2.269  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.672   1.987   0.739  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.893   1.175   1.623  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.630   1.978  -0.385  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.061   1.984  -1.749  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.631   0.815  -0.266  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.166   0.882   1.010  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.120  -0.463  -0.732  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.504  -0.690  -2.208  0.00  0.00           C+0
HETATM   30  H   UNK     0       2.636  -3.524   1.706  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.062  -2.973   2.735  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.248  -3.454   0.960  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.257  -1.117   1.056  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.706  -1.100   2.095  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.149  -2.294  -0.661  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.602  -3.852  -0.669  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.135  -2.699  -2.322  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.579  -2.805  -2.636  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.821  -1.262  -1.974  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.979  -2.866   1.320  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.843  -1.263   2.041  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.786  -1.727   0.801  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.184  -1.093  -2.081  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.684  -1.356  -1.217  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.591  -2.735  -1.321  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.016   0.472   0.420  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.309  -0.538   2.385  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.070   0.633  -0.345  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.970   2.667  -1.437  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.607   1.992  -1.274  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.291   1.121  -2.234  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.580   3.040   0.716  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.104   1.889   1.955  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.173   4.468  -0.053  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.276   4.394   2.227  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.503   3.042   3.066  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.163   4.345   3.166  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.281   2.894  -0.232  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.939   2.144  -2.447  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.586   1.053  -2.027  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.393   2.835  -1.997  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.477   1.127  -0.954  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.615   1.738   1.135  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.991  -0.391  -0.747  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.144   0.116  -2.592  0.00  0.00           H+0
HETATM   66  H   UNK     0       3.155  -1.614  -2.286  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.637  -0.918  -2.839  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3   33   34                                             
CONECT    3    2    4   28   35                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   36                                             
CONECT    8    7   37   38   39                                             
CONECT    9    7   10   11   40                                             
CONECT   10    9   41                                                       
CONECT   11    9   12   13   42                                             
CONECT   12   11   43   44   45                                             
CONECT   13   11   14   15   46                                             
CONECT   14   13   47                                                       
CONECT   15   13   16   17   48                                             
CONECT   16   15   49   50   51                                             
CONECT   17   15   18   52   53                                             
CONECT   18   17   19   20   22                                             
CONECT   19   18   54                                                       
CONECT   20   18   21   55   56                                             
CONECT   21   20   57                                                       
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   58                                             
CONECT   25   24   59   60   61                                             
CONECT   26   24   27   28   62                                             
CONECT   27   26   63                                                       
CONECT   28   26   29    3   64                                             
CONECT   29   28   65   66   67                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   16                                                            
CONECT   51   16                                                            
CONECT   52   17                                                            
CONECT   53   17                                                            
CONECT   54   19                                                            
CONECT   55   20                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   25                                                            
CONECT   61   25                                                            
CONECT   62   26                                                            
CONECT   63   27                                                            
CONECT   64   28                                                            
CONECT   65   29                                                            
CONECT   66   29                                                            
CONECT   67   29                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  134    0
END

RDKit          3D

67 67  0  0  0  0  0  0  0  0999 V2000
    3.6039   -2.9776    1.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2783   -1.5447    1.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4132   -1.7243   -0.0033 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3060   -2.4282    0.3919 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3674   -3.2800   -0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902   -4.5785   -0.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8387   -2.3701   -1.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7701   -2.1196    0.4802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8968   -1.2163    1.0813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484   -1.3333    0.1106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5779   -1.6156   -1.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9717    0.1093    0.5322 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7376    0.0977    1.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318    1.0660   -0.0542 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5580    1.7262   -1.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8281    2.2115    0.9105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4814    2.8573    0.8852 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4116    3.8428   -0.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4156    3.6951    2.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7334    4.4244    2.2689 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6724    1.9870    0.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8928    1.1752    1.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6301    1.9776   -0.3851 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0612    1.9845   -1.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312    0.8150   -0.2658 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1662    0.8824    1.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205   -0.4631   -0.7324 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5040   -0.6904   -2.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6358   -3.5238    1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0618   -2.9733    2.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2483   -3.4545    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1489   -2.2941   -0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -3.8516   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8210   -1.2620   -1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9790   -2.8657    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8434   -1.2634    2.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7863   -1.7272    0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1840   -1.0932   -2.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6841   -1.3560   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0162    0.4716    0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3092   -0.5380    2.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703    0.6328   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9705    2.6668   -1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6074    1.9923   -1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2913    1.1214   -2.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5802    3.0402    0.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1041    1.8893    1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728    4.4680   -0.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    4.3936    2.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5027    3.0415    3.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1632    4.3454    3.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812    2.8937   -0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9392    2.1444   -2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5857    1.0530   -2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3928    2.8348   -1.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4768    1.1273   -0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6147    1.7381    1.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9905   -0.3907   -0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1442    0.1161   -2.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1552   -1.6136   -2.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6368   -0.9179   -2.8393 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  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28  3  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  6
  7 36  1  6
  8 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  1
 10 41  1  0
 11 42  1  1
 12 43  1  0
 12 44  1  0
 12 45  1  0
 13 46  1  1
 14 47  1  0
 15 48  1  6
 16 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 24 58  1  1
 25 59  1  0
 25 60  1  0
 25 61  1  0
 26 62  1  6
 27 63  1  0
 28 64  1  6
 29 65  1  0
 29 66  1  0
 29 67  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₁H₃₈O₈

Average Mass

418.5270 Da

Monoisotopic Mass

418.25667 Da

IUPAC Name

(3R,4S,5R,6S,7S,9R,11R,12S,13R,14R)-14-ethyl-4,6,9,12-tetrahydroxy-9-(hydroxymethyl)-3,5,7,11,13-pentamethyl-1-oxacyclotetradecane-2,10-dione

Traditional Name

(3R,4S,5R,6S,7S,9R,11R,12S,13R,14R)-14-ethyl-4,6,9,12-tetrahydroxy-9-(hydroxymethyl)-3,5,7,11,13-pentamethyl-1-oxacyclotetradecane-2,10-dione

CAS Registry Number

Not Available

SMILES

CC[C@H]1OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@@H](O)[C@@H](C)CC(O)(CO)C(=O)[C@H](C)[C@@H](O)[C@H]1C

InChI Identifier

InChI=1S/C21H38O8/c1-7-15-11(3)17(24)13(5)19(26)21(28,9-22)8-10(2)16(23)12(4)18(25)14(6)20(27)29-15/h10-18,22-25,28H,7-9H2,1-6H3/t10-,11-,12+,13+,14+,15+,16-,17-,18-,21?/m0/s1

InChI Key

PREIDDIPLSAKJR-CFWJUOAESA-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 lividans	NPAtlas	10908114

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Acyloin
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Cyclic ketone
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Primary alcohol
Organooxygen compound
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	0.21	ALOGPS
logP	0.84	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.25	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	106.12 m³·mol⁻¹	ChemAxon
Polarizability	43.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA019345

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78438587

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588485

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shah S, Xue Q, Tang L, Carney JR, Betlach M, McDaniel R: Cloning, characterization and heterologous expression of a polyketide synthase and P-450 oxidase involved in the biosynthesis of the antibiotic oleandomycin. J Antibiot (Tokyo). 2000 May;53(5):502-8. doi: 10.7164/antibiotics.53.502. [PubMed:10908114 ]

Showing NP-Card for 6-Deoxy-8,17-dihydroxyerythronolide B (NP0003350)

MOL for NP0003350 (6-Deoxy-8,17-dihydroxyerythronolide B)

3D MOL for NP0003350 (6-Deoxy-8,17-dihydroxyerythronolide B)

3D SDF for NP0003350 (6-Deoxy-8,17-dihydroxyerythronolide B)

3D-SDF for NP0003350 (6-Deoxy-8,17-dihydroxyerythronolide B)

PDB for NP0003350 (6-Deoxy-8,17-dihydroxyerythronolide B)

3D PDB for NP0003350 (6-Deoxy-8,17-dihydroxyerythronolide B)

SMILES for NP0003350 (6-Deoxy-8,17-dihydroxyerythronolide B)

INCHI for NP0003350 (6-Deoxy-8,17-dihydroxyerythronolide B)

Structure for NP0003350 (6-Deoxy-8,17-dihydroxyerythronolide B)

3D Structure for NP0003350 (6-Deoxy-8,17-dihydroxyerythronolide B)