NP-MRD: Showing NP-Card for (2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1 (NP0150204)

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Record Information

Version

1.0

Created at

2022-09-02 06:14:10 UTC

Updated at

2022-09-02 06:14:10 UTC

NP-MRD ID

NP0150204

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1

Description

Uromycine belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines. (2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1 is found in Streptomyces hygroscopicus. It was first documented in 2006 (PMID: 29999891). Based on a literature review a significant number of articles have been published on Uromycine (PMID: 36049892) (PMID: 36049891) (PMID: 36049888) (PMID: 36049887).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022208142D          

 96102  0  0  1  0            999 V2000
    3.2259    3.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2259    2.8258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5115    2.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7970    2.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5115    1.5883    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2259    1.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2259    0.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5115   -0.0617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5115   -0.8867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7970    0.3508    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0825   -0.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3681    0.3508    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3681    1.1758    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0825    1.5883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0609   -2.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7754   -2.5367    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2451   -3.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6274   -5.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274   -6.0397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9129   -6.4522    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.6274   -7.6897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  5  3  1  6  0  0  0
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  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
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M  END

     RDKit          3D

219225  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309022208142D          

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 94 96  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0150204

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]3O[C@H](CN)CC[C@H]3N)[C@@H]2O)OC[C@]1(C)O.CN[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]3O[C@@H](CC[C@H]3N)C(C)N)[C@@H]2O)OC[C@]1(C)O.CNC(C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C21H43N5O7.C20H41N5O7.C19H39N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20;1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19;1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h9-20,25-29H,5-8,22-24H2,1-4H3;8-19,25-28H,4-7,21-24H2,1-3H3;8-18,24-27H,3-7,20-23H2,1-2H3/t9?,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+;8?,9-,10+,11-,12+,13+,14-,15-,16+,17-,18-,19-,20+;8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-/m110/s1

> <INCHI_KEY>
NPEFREDMMVQEPL-RWPARATISA-N

> <FORMULA>
C60H123N15O21

> <MOLECULAR_WEIGHT>
1390.728

> <EXACT_MASS>
1389.901796041

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
219

> <JCHEM_AVERAGE_POLARIZABILITY>
51.335849406508636

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol

> <ALOGPS_LOGP>
-1.64

> <JCHEM_LOGP>
-3.1371555293333344

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
5

> <JCHEM_PKA>
13.15935180094963

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.54896823324259

> <JCHEM_PKA_STRONGEST_BASIC>
10.117199750062865

> <JCHEM_POLAR_SURFACE_AREA>
199.72999999999996

> <JCHEM_REFRACTIVITY>
118.02069999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.26e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin C1A; gentamycin C1

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.022   6.815   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.022   5.275   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.688   4.505   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.354   5.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.688   2.965   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.022   2.195   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.022   0.655   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.688  -0.115   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.688  -1.655   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.354   0.655   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.021  -0.115   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.687   0.655   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.687   2.195   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.021   2.965   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -0.647   2.965   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.980   2.195   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -3.314   2.965   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -1.980   0.655   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.314  -0.115   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.314  -1.655   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.980  -2.425   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.980  -3.965   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.314  -4.735   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.324  -5.915   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.304  -5.915   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.648  -3.965   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      -5.981  -4.735   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      -7.315  -3.965   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.648  -2.425   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.981  -1.655   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.647  -0.115   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.647  -1.655   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.354   2.195   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.422   7.206   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      10.422   5.666   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0      11.755   4.896   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.755   3.356   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      10.422   2.586   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      13.089   2.586   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      13.089   1.046   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      14.423   0.276   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.423  -1.264   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      13.089  -2.034   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      15.756  -2.034   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      15.756  -3.574   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      17.090  -4.344   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      18.424  -3.574   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      19.758  -4.344   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      21.091  -3.574   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      21.091  -2.034   0.000  0.00  0.00           C+0
HETATM   51  N   UNK     0      22.425  -4.344   0.000  0.00  0.00           N+0
HETATM   52  C   UNK     0      19.758  -5.884   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      18.424  -6.654   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      17.090  -5.884   0.000  0.00  0.00           C+0
HETATM   55  N   UNK     0      15.756  -6.654   0.000  0.00  0.00           N+0
HETATM   56  C   UNK     0      17.090  -1.264   0.000  0.00  0.00           C+0
HETATM   57  N   UNK     0      18.424  -2.034   0.000  0.00  0.00           N+0
HETATM   58  C   UNK     0      17.090   0.276   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      15.756   1.046   0.000  0.00  0.00           C+0
HETATM   60  N   UNK     0      15.756   2.586   0.000  0.00  0.00           N+0
HETATM   61  O   UNK     0      14.423   3.356   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      14.423   4.896   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      13.089   5.666   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      13.812   7.026   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      12.366   7.026   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      -4.904  -9.734   0.000  0.00  0.00           C+0
HETATM   67  N   UNK     0      -4.904 -11.274   0.000  0.00  0.00           N+0
HETATM   68  C   UNK     0      -3.571 -12.044   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      -3.571 -13.584   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      -4.904 -14.354   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0      -2.237 -14.354   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0      -2.237 -15.894   0.000  0.00  0.00           O+0
HETATM   73  C   UNK     0      -0.903 -16.664   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      -0.903 -18.204   0.000  0.00  0.00           C+0
HETATM   75  O   UNK     0      -2.237 -18.974   0.000  0.00  0.00           O+0
HETATM   76  C   UNK     0       0.430 -18.974   0.000  0.00  0.00           C+0
HETATM   77  O   UNK     0       0.430 -20.514   0.000  0.00  0.00           O+0
HETATM   78  C   UNK     0       1.764 -21.284   0.000  0.00  0.00           C+0
HETATM   79  O   UNK     0       3.098 -20.514   0.000  0.00  0.00           O+0
HETATM   80  C   UNK     0       4.431 -21.284   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0       5.765 -20.514   0.000  0.00  0.00           C+0
HETATM   82  N   UNK     0       5.765 -18.974   0.000  0.00  0.00           N+0
HETATM   83  C   UNK     0       4.431 -22.824   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0       3.098 -23.594   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0       1.764 -22.824   0.000  0.00  0.00           C+0
HETATM   86  N   UNK     0       0.430 -23.594   0.000  0.00  0.00           N+0
HETATM   87  C   UNK     0       1.764 -18.204   0.000  0.00  0.00           C+0
HETATM   88  N   UNK     0       3.098 -18.974   0.000  0.00  0.00           N+0
HETATM   89  C   UNK     0       1.764 -16.664   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0       0.430 -15.894   0.000  0.00  0.00           C+0
HETATM   91  N   UNK     0       0.430 -14.354   0.000  0.00  0.00           N+0
HETATM   92  O   UNK     0      -0.903 -13.584   0.000  0.00  0.00           O+0
HETATM   93  C   UNK     0      -0.903 -12.044   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      -2.237 -11.274   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      -1.514  -9.914   0.000  0.00  0.00           C+0
HETATM   96  O   UNK     0      -2.960  -9.914   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   20   30                                                  
CONECT   30   29                                                            
CONECT   31   18   12   32                                                  
CONECT   32   31                                                            
CONECT   33   10    5                                                       
CONECT   34   35                                                            
CONECT   35   34   36                                                       
CONECT   36   35   37   63                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   61                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   59                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   56                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   54                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   52                                                  
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   48   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   46   55                                                  
CONECT   55   54                                                            
CONECT   56   44   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58   41   60                                                  
CONECT   60   59                                                            
CONECT   61   39   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   36   64   65                                             
CONECT   64   63                                                            
CONECT   65   63                                                            
CONECT   66   67                                                            
CONECT   67   66   68                                                       
CONECT   68   67   69   94                                                  
CONECT   69   68   70   71                                                  
CONECT   70   69                                                            
CONECT   71   69   72   92                                                  
CONECT   72   71   73                                                       
CONECT   73   72   74   90                                                  
CONECT   74   73   75   76                                                  
CONECT   75   74                                                            
CONECT   76   74   77   87                                                  
CONECT   77   76   78                                                       
CONECT   78   77   79   85                                                  
CONECT   79   78   80                                                       
CONECT   80   79   81   83                                                  
CONECT   81   80   82                                                       
CONECT   82   81                                                            
CONECT   83   80   84                                                       
CONECT   84   83   85                                                       
CONECT   85   84   78   86                                                  
CONECT   86   85                                                            
CONECT   87   76   88   89                                                  
CONECT   88   87                                                            
CONECT   89   87   90                                                       
CONECT   90   89   73   91                                                  
CONECT   91   90                                                            
CONECT   92   71   93                                                       
CONECT   93   92   94                                                       
CONECT   94   93   68   95   96                                             
CONECT   95   94                                                            
CONECT   96   94                                                            
MASTER        0    0    0    0    0    0    0    0   96    0  204    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₆₀H₁₂₃N₁₅O₂₁

Average Mass

1390.7280 Da

Monoisotopic Mass

1389.90180 Da

IUPAC Name

(2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol

Traditional Name

(2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin C1A; gentamycin C1

CAS Registry Number

Not Available

SMILES

CN[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]3O[C@H](CN)CC[C@H]3N)[C@@H]2O)OC[C@]1(C)O.CN[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]3O[C@@H](CC[C@H]3N)C(C)N)[C@@H]2O)OC[C@]1(C)O.CNC(C)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1

InChI Identifier

InChI=1S/C21H43N5O7.C20H41N5O7.C19H39N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20;1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19;1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h9-20,25-29H,5-8,22-24H2,1-4H3;8-19,25-28H,4-7,21-24H2,1-3H3;8-18,24-27H,3-7,20-23H2,1-2H3/t9?,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+;8?,9-,10+,11-,12+,13+,14-,15-,16+,17-,18-,19-,20+;8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-/m110/s1

InChI Key

NPEFREDMMVQEPL-RWPARATISA-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 hygroscopicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminocyclitol glycosides

Alternative Parents

Substituents

Amino cyclitol glycoside
2-deoxystreptamine aminoglycoside
Glycosyl compound
O-glycosyl compound
Aminocyclitol or derivatives
Cyclohexanol
Cyclohexylamine
Cyclitol or derivatives
Monosaccharide
Oxane
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
1,2-aminoalcohol
Secondary amine
Acetal
Organoheterocyclic compound
Secondary aliphatic amine
Oxacycle
Alcohol
Hydrocarbon derivative
Primary aliphatic amine
Organopnictogen compound
Organic nitrogen compound
Amine
Primary amine
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Not Available

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	-1.6	ALOGPS
logP	-3.1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.55	ChemAxon
pKa (Strongest Basic)	10.12	ChemAxon
Physiological Charge	5	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	199.73 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	118.02 m³·mol⁻¹	ChemAxon
Polarizability	51.34 Å³	ChemAxon
Number of Rings	9	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

8074297

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9898639

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xiang R, Li M, Gu Z, Liu H, Zeng H, Peng J: Chronic endometritis positively correlates with the aggravation of intrauterine adhesions but has limited effects on reproductive prognosis with antibiotic application. Int J Gynaecol Obstet. 2022 Sep 1. doi: 10.1002/ijgo.14434. [PubMed:36049892 ]
Li M, Yue C: Abnormal uterine artery Doppler ultrasound during gestational 21-23 weeks associated with preeclampsia. Int J Gynaecol Obstet. 2022 Sep 1. doi: 10.1002/ijgo.14435. [PubMed:36049891 ]
Meyer R, Weisz B, Eilenberg R, Tsadok MA, Uziel M, Sivan E, Mazaki-Tovi S, Tsur A: Utilizing Machine Learning to Predict Unplanned Cesarean Delivery. Int J Gynaecol Obstet. 2022 Sep 1. doi: 10.1002/ijgo.14433. [PubMed:36049888 ]
Crockett C, Lorimer C: OncoFlash - Research Updates in a Flash! (September Edition). Clin Oncol (R Coll Radiol). 2022 Sep;34(9):551-553. doi: 10.1016/j.clon.2022.07.009. [PubMed:36049887 ]
Authors unspecified: Gentamicin.. 2006. [PubMed:29999891 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1 (NP0150204)

MOL for NP0150204 ((2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1)

3D MOL for NP0150204 ((2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1)

3D SDF for NP0150204 ((2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1)

3D-SDF for NP0150204 ((2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1)

PDB for NP0150204 ((2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1)

3D PDB for NP0150204 ((2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1)

SMILES for NP0150204 ((2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1)

INCHI for NP0150204 ((2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1)

Structure for NP0150204 ((2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1)

3D Structure for NP0150204 ((2r,3r,4r,5r)-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; gentamicin c1a; gentamycin c1)