NP-MRD: Showing NP-Card for (3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione (NP0305197)

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Record Information

Version

2.0

Created at

2022-09-10 20:48:48 UTC

Updated at

2022-09-10 20:48:48 UTC

NP-MRD ID

NP0305197

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione

Description

Oleandomycin belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. (3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione is found in Streptomyces lividans. (3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione was first documented in 2015 (PMID: 26340418). Based on a literature review a significant number of articles have been published on oleandomycin (PMID: 34254896) (PMID: 33878330) (PMID: 33545126) (PMID: 33463404) (PMID: 33036250) (PMID: 32693204).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102222482D          

 48 51  0  0  1  0            999 V2000
    7.3145    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1806    1.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6020    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4270    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    4.6993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    5.4138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
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 26 27  1  0  0  0  0
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 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 31 30  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 36 40  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  1  0  0  0
 29 42  1  0  0  0  0
  7 42  1  0  0  0  0
 42 43  1  6  0  0  0
  5 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  1  0  0  0
 45 47  1  0  0  0  0
  3 47  1  0  0  0  0
 47 48  1  6  0  0  0
M  END

     RDKit          3D

109112  0  0  0  0  0  0  0  0999 V2000
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  8 57  1  1
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  9 59  1  0
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 45104  1  6
 46105  1  0
 46106  1  0
 46107  1  0
 47108  1  6
 48109  1  0
M  END


  Mrv1652309102222482D          

 48 51  0  0  1  0            999 V2000
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    5.2520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1806    1.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1895    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4270    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    4.6993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    5.4138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    3.9849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 25  1  6  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 31 30  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 36 40  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  1  0  0  0
 29 42  1  0  0  0  0
  7 42  1  0  0  0  0
 42 43  1  6  0  0  0
  5 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  1  0  0  0
 45 47  1  0  0  0  0
  3 47  1  0  0  0  0
 47 48  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0305197

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@@H](OC2[C@@H](C)[C@H](O[C@H]3O[C@@H](C)C[C@H]([C@@H]3O)N(C)C)[C@H](C)C[C@]3(CO3)C(=O)C(C)[C@H](O)[C@H](C)[C@H](C)OC(=O)[C@H]2C)O[C@H](C)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C35H61NO12/c1-16-14-35(15-43-35)32(40)19(4)27(37)18(3)22(7)46-33(41)21(6)31(47-26-13-25(42-11)28(38)23(8)45-26)20(5)30(16)48-34-29(39)24(36(9)10)12-17(2)44-34/h16-31,34,37-39H,12-15H2,1-11H3/t16-,17+,18-,19?,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31?,34-,35+/m1/s1

> <INCHI_KEY>
RZPAKFUAFGMUPI-GAPKVHOQSA-N

> <FORMULA>
C35H61NO12

> <MOLECULAR_WEIGHT>
687.868

> <EXACT_MASS>
687.419376408

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
74.10277448671937

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6R,7S,8S,11S,13S,14R,15R)-14-{[(2R,3S,4R,6S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2S,4R,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione

> <JCHEM_LOGP>
2.975138413666669

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.335033432431384

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.67332835224039

> <JCHEM_PKA_STRONGEST_BASIC>
8.380991580439494

> <JCHEM_POLAR_SURFACE_AREA>
165.98

> <JCHEM_REFRACTIVITY>
173.6925

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6R,7S,8S,11S,13S,14R,15R)-14-{[(2R,3S,4R,6S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2S,4R,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      13.654   6.105   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.114   6.105   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.344   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.804   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.264   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.671   2.730   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.574   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.264  -0.564   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.954   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.724  -3.231   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.644  -3.231   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334  -1.897   0.000  0.00  0.00           O+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  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.644   4.771   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.414   6.105   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.954   6.105   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.724   7.438   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.264   7.438   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.954   8.772   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.414   8.772   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0       3.644  10.106   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0       2.104  10.106   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.414  11.439   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.644   7.438   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.104   7.438   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       6.724   4.771   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       9.804   2.104   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      12.114   3.437   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      13.654   3.437   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   47                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   44                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   42                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   26                                             
CONECT   24   23   25                                                       
CONECT   25   24   23                                                       
CONECT   26   23   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   42                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   40                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   40                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   36   31   41                                                  
CONECT   41   40                                                            
CONECT   42   29    7   43                                                  
CONECT   43   42                                                            
CONECT   44    5   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45    3   48                                                  
CONECT   48   47                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  102    0
END

View in JSmol

Synonyms

Value	Source
Phosphate, oleandomycin	MeSH
Oleandomycin phosphate	MeSH

Chemical Formula

C₃₅H₆₁NO₁₂

Average Mass

687.8680 Da

Monoisotopic Mass

687.41938 Da

IUPAC Name

(3S,6R,7S,8S,11S,13S,14R,15R)-14-{[(2R,3S,4R,6S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2S,4R,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@@H](OC2[C@@H](C)[C@H](O[C@H]3O[C@@H](C)C[C@H]([C@@H]3O)N(C)C)[C@H](C)C[C@]3(CO3)C(=O)C(C)[C@H](O)[C@H](C)[C@H](C)OC(=O)[C@H]2C)O[C@H](C)[C@H]1O

InChI Identifier

InChI=1S/C35H61NO12/c1-16-14-35(15-43-35)32(40)19(4)27(37)18(3)22(7)46-33(41)21(6)31(47-26-13-25(42-11)28(38)23(8)45-26)20(5)30(16)48-34-29(39)24(36(9)10)12-17(2)44-34/h16-31,34,37-39H,12-15H2,1-11H3/t16-,17+,18-,19?,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31?,34-,35+/m1/s1

InChI Key

RZPAKFUAFGMUPI-GAPKVHOQSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Aminoglycoside core
Macrolide
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Amino acid or derivatives
1,2-aminoalcohol
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	2.98	ChemAxon
pKa (Strongest Acidic)	12.67	ChemAxon
pKa (Strongest Basic)	8.38	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	165.98 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	173.69 m³·mol⁻¹	ChemAxon
Polarizability	74.1 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oleandomycin

METLIN ID

Not Available

PubChem Compound

133562742

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pereira BFM, Pereira MU, Ferreira RG, Spisso BF: Dietary exposure assessment to macrolide antimicrobial residues through infant formulas marketed in Brazil. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2021 Jul 13:1-17. doi: 10.1080/19440049.2021.1933204. [PubMed:34254896 ]
Nurhafizah Wan Ibrahim W, Kok Leong L, Abdul Razzak L, Musa N, Danish-Daniel M, Catherine Zainathan S, Musa N: Virulence properties and pathogenicity of multidrug-resistant Vibrio harveyi associated with luminescent vibriosis in pacific white shrimp, Penaeus vannamei. J Invertebr Pathol. 2021 Apr 17:107594. doi: 10.1016/j.jip.2021.107594. [PubMed:33878330 ]
Zeng S, Sun J, Chen Z, Xu Q, Wei W, Wang D, Ni BJ: The impact and fate of clarithromycin in anaerobic digestion of waste activated sludge for biogas production. Environ Res. 2021 Apr;195:110792. doi: 10.1016/j.envres.2021.110792. Epub 2021 Feb 2. [PubMed:33545126 ]
Grutes JV, Ferreira RG, Pereira MU, Candido FS, Spisso BF: Development and validation of an LC-MS/MS screening method for macrolide and quinolone residues in baby food. J Environ Sci Health B. 2021;56(3):197-211. doi: 10.1080/03601234.2021.1872324. Epub 2021 Jan 19. [PubMed:33463404 ]
Parisi G, Freda I, Exertier C, Cecchetti C, Gugole E, Cerutti G, D'Auria L, Macone A, Vallone B, Savino C, Montemiglio LC: Dissecting the Cytochrome P450 OleP Substrate Specificity: Evidence for a Preferential Substrate. Biomolecules. 2020 Oct 6;10(10). pii: biom10101411. doi: 10.3390/biom10101411. [PubMed:33036250 ]
Raysyan A, Galvidis IA, Schneider RJ, Eremin SA, Burkin MA: Development of a latex particles-based lateral flow immunoassay for group determination of macrolide antibiotics in breast milk. J Pharm Biomed Anal. 2020 Sep 10;189:113450. doi: 10.1016/j.jpba.2020.113450. Epub 2020 Jul 13. [PubMed:32693204 ]
Grobe S, Wszolek A, Brundiek H, Fekete M, Bornscheuer UT: Highly selective bile acid hydroxylation by the multifunctional bacterial P450 monooxygenase CYP107D1 (OleP). Biotechnol Lett. 2020 May;42(5):819-824. doi: 10.1007/s10529-020-02813-4. Epub 2020 Jan 23. [PubMed:31974648 ]
Risdian C, Mozef T, Wink J: Biosynthesis of Polyketides in Streptomyces. Microorganisms. 2019 May 6;7(5). pii: microorganisms7050124. doi: 10.3390/microorganisms7050124. [PubMed:31064143 ]
Parisi G, Montemiglio LC, Giuffre A, Macone A, Scaglione A, Cerutti G, Exertier C, Savino C, Vallone B: Substrate-induced conformational change in cytochrome P450 OleP. FASEB J. 2019 Feb;33(2):1787-1800. doi: 10.1096/fj.201800450RR. Epub 2018 Sep 12. [PubMed:30207799 ]
Tay JH, Arguelles AJ, DeMars MD 2nd, Zimmerman PM, Sherman DH, Nagorny P: Regiodivergent Glycosylations of 6-Deoxy-erythronolide B and Oleandomycin-Derived Macrolactones Enabled by Chiral Acid Catalysis. J Am Chem Soc. 2017 Jun 28;139(25):8570-8578. doi: 10.1021/jacs.7b03198. Epub 2017 Jun 19. [PubMed:28627172 ]
Laith AA, Ambak MA, Hassan M, Sheriff SM, Nadirah M, Draman AS, Wahab W, Ibrahim WN, Aznan AS, Jabar A, Najiah M: Molecular identification and histopathological study of natural Streptococcus agalactiae infection in hybrid tilapia (Oreochromis niloticus). Vet World. 2017 Jan;10(1):101-111. doi: 10.14202/vetworld.2017.101-111. Epub 2017 Jan 24. [PubMed:28246454 ]
Porter JD, Watson J, Roberts LR, Gill SK, Groves H, Dhariwal J, Almond MH, Wong E, Walton RP, Jones LH, Tregoning J, Kilty I, Johnston SL, Edwards MR: Identification of novel macrolides with antibacterial, anti-inflammatory and type I and III IFN-augmenting activity in airway epithelium. J Antimicrob Chemother. 2016 Oct;71(10):2767-81. doi: 10.1093/jac/dkw222. Epub 2016 Jul 25. [PubMed:27494903 ]
Bryan MA, Hea SY, Mannering SA, Booker R: Demonstration of non-inferiority of a novel combination intramammary antimicrobial in the treatment of clinical mastitis. N Z Vet J. 2016 Nov;64(6):337-42. doi: 10.1080/00480169.2016.1210044. Epub 2016 Jul 27. [PubMed:27430313 ]
Singh P, Singh H, Kim YJ, Mathiyalagan R, Wang C, Yang DC: Extracellular synthesis of silver and gold nanoparticles by Sporosarcina koreensis DC4 and their biological applications. Enzyme Microb Technol. 2016 May;86:75-83. doi: 10.1016/j.enzmictec.2016.02.005. Epub 2016 Feb 12. [PubMed:26992796 ]
Montemiglio LC, Parisi G, Scaglione A, Sciara G, Savino C, Vallone B: Functional analysis and crystallographic structure of clotrimazole bound OleP, a cytochrome P450 epoxidase from Streptomyces antibioticus involved in oleandomycin biosynthesis. Biochim Biophys Acta. 2016 Mar;1860(3):465-75. doi: 10.1016/j.bbagen.2015.10.009. Epub 2015 Oct 22. [PubMed:26475642 ]
Lawther K, Santos FG, Oyama LB, Rubino F, Morrison S, Creevey CJ, McGrath JW, Huws SA: Resistome Analysis of Global Livestock and Soil Microbiomes. Front Microbiol. 2022 Jul 7;13:897905. doi: 10.3389/fmicb.2022.897905. eCollection 2022. [PubMed:35875563 ]
Zrieq R, Snoussi M, Algahtan FD, Tasleem M, Saeed M, Noumi E, Khalifa NE, Gad-Elkareem MAM, Aouadi K, Kadri A: Repurposing of anisomycin and oleandomycin as a potential anti-(SARS-CoV-2) virus targeting key enzymes using virtual computational approaches. Cell Mol Biol (Noisy-le-grand). 2022 Feb 4;67(5):387-398. doi: 10.14715/cmb/2021.67.5.51. [PubMed:35818229 ]
de Carvalho LP, Groeger-Otero S, Kreidenweiss A, Kremsner PG, Mordmuller B, Held J: Boromycin has Rapid-Onset Antibiotic Activity Against Asexual and Sexual Blood Stages of Plasmodium falciparum. Front Cell Infect Microbiol. 2022 Jan 14;11:802294. doi: 10.3389/fcimb.2021.802294. eCollection 2021. [PubMed:35096650 ]
Nguyen HP, Weisberg AJ, Chang JH, Clarke CR: Streptomyces caniscabiei sp. nov., which causes potato common scab and is distributed across the world. Int J Syst Evol Microbiol. 2022 Jan;72(1). doi: 10.1099/ijsem.0.005225. [PubMed:35085064 ]
da Costa RP, Spisso BF, Pereira MU, Monteiro MA, Ferreira RG, da Nobrega AW: Innovative mixture of salts in the quick, easy, cheap, effective, rugged, and safe method for the extraction of residual macrolides in milk followed by analysis with liquid chromatography and tandem mass spectrometry. J Sep Sci. 2015 Nov;38(21):3743-9. doi: 10.1002/jssc.201500373. [PubMed:26340418 ]
LOTUS database [Link]

Showing NP-Card for (3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione (NP0305197)

MOL for NP0305197 ((3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione)

3D MOL for NP0305197 ((3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione)

3D SDF for NP0305197 ((3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione)

3D-SDF for NP0305197 ((3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione)

PDB for NP0305197 ((3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione)

3D PDB for NP0305197 ((3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione)

SMILES for NP0305197 ((3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione)

INCHI for NP0305197 ((3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione)

Structure for NP0305197 ((3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione)

3D Structure for NP0305197 ((3s,6r,7s,8s,11s,13s,14r,15r)-14-{[(2r,3s,4r,6s)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-6-hydroxy-12-{[(2s,4r,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione)