NP-MRD: Showing NP-Card for Lincomycin (NP0004837)

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Record Information

Version

2.0

Created at

2020-12-09 02:14:58 UTC

Updated at

2021-07-15 16:50:18 UTC

NP-MRD ID

NP0004837

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lincomycin

Provided By

NPAtlas

Description

Lincomycin, also known as cillimycin or LCM, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. In humans, lincomycin is involved in the lincomycin action pathway. Lincomycin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Lincomycin is found in Apis cerana, Kitasatospora aureofaciens, Streptomyces, Streptomyces caelestis, Streptomyces coelicolor, Streptomyces espinosus, Streptomyces lincolnensis and Streptomyces roseolus. Lincomycin was first documented in 1964 (PMID: 14217764). Based on a literature review very few articles have been published on Lincomycin (PMID: 24324587).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118093D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242118093D          

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   -1.8352   -1.3538    0.6915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6986   -2.7368    0.4875 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3743   -1.0479    0.1545 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9774   -1.9249   -0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1298   -0.0096    0.7390 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9180    1.1640    2.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6106    1.8560    0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7926    2.6902    2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0375    3.6527    0.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7457    3.5545    2.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7761    3.0889    1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1816    1.6958    2.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799    1.6666   -0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2485    1.3945   -0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5277    0.8950    1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4686   -1.2419    0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2486   -1.2328   -2.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409   -1.7861   -2.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3429    1.1939   -2.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125    0.2090   -5.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698   -1.2835   -4.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0214    0.1800   -4.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4069    1.1219   -3.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0601    0.4819   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9800   -1.3965    0.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7214    0.2372    1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6961   -0.0632    2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8492    1.8093    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2472   -0.5617    2.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3136   -2.2929    2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384   -0.9710    1.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5339   -3.1345    0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4856   -1.3881   -1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3433   -2.7958   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348   -2.4479   -0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2011    0.0272    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375   -0.0870    1.8638 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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27  4  1  0  0  0  0
 23 14  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  2 31  1  0  0  0  0
  2 32  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4 35  1  6  0  0  0
  5 36  1  0  0  0  0
  5 37  1  0  0  0  0
  6 38  1  1  0  0  0
  9 39  1  0  0  0  0
 10 40  1  6  0  0  0
 11 41  1  1  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
 12 44  1  0  0  0  0
 13 45  1  0  0  0  0
 14 46  1  1  0  0  0
 16 47  1  1  0  0  0
 18 48  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 19 51  1  1  0  0  0
 20 52  1  0  0  0  0
 21 53  1  1  0  0  0
 22 54  1  0  0  0  0
 23 55  1  1  0  0  0
 24 56  1  0  0  0  0
 26 57  1  0  0  0  0
 26 58  1  0  0  0  0
 26 59  1  0  0  0  0
 27 60  1  0  0  0  0
 27 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004837

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1

> <INCHI_KEY>
OJMMVQQUTAEWLP-KIDUDLJLSA-N

> <FORMULA>
C18H34N2O6S

> <MOLECULAR_WEIGHT>
406.54

> <EXACT_MASS>
406.213757997

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
44.11723864144504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
-0.3168542156666674

> <ALOGPS_LOGS>
-1.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.974957082319083

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.365502680731499

> <JCHEM_PKA_STRONGEST_BASIC>
7.970140139750563

> <JCHEM_POLAR_SURFACE_AREA>
122.49000000000001

> <JCHEM_REFRACTIVITY>
102.6663

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lincomycin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 62  0  0  0  0  0  0  0  0999 V2000
    6.0364    2.0644    1.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9774   -1.9249   -0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1298   -0.0096    0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9180    1.1640    2.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6106    1.8560    0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7457    3.5545    2.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1816    1.6958    2.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799    1.6666   -0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2485    1.3945   -0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5277    0.8950    1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4686   -1.2419    0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6961   -0.0632    2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8492    1.8093    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2472   -0.5617    2.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3136   -2.2929    2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384   -0.9710    1.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4856   -1.3881   -1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3433   -2.7958   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348   -2.4479   -0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2011    0.0272    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375   -0.0870    1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
  6 25  1  0
 25 26  1  0
 25 27  1  0
 27  4  1  0
 23 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  6
  5 36  1  0
  5 37  1  0
  6 38  1  1
  9 39  1  0
 10 40  1  6
 11 41  1  1
 12 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  1
 16 47  1  1
 18 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  1
 20 52  1  0
 21 53  1  1
 22 54  1  0
 23 55  1  1
 24 56  1  0
 26 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  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       6.036   2.064   1.874  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.841   2.902   1.685  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.520   2.254   1.535  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.371   1.269   0.402  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.912   0.775   0.438  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.019  -0.662   0.044  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.402  -0.907  -1.260  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.264  -1.188  -2.203  0.00  0.00           O+0
HETATM    9  N   UNK     0       0.068  -0.865  -1.493  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.280  -0.824  -1.731  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.689   0.223  -2.814  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.077  -0.152  -4.140  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.087   0.239  -2.915  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.205  -0.627  -0.546  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.531  -0.704  -0.924  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.412  -0.447   0.075  0.00  0.00           C+0
HETATM   17  S   UNK     0      -5.713   0.759  -0.386  0.00  0.00           S+0
HETATM   18  C   UNK     0      -6.676   1.127   1.092  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.826  -0.033   1.395  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.398   1.293   1.425  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.792  -1.013   1.812  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.418  -2.157   2.346  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.835  -1.354   0.692  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.699  -2.737   0.488  0.00  0.00           O+0
HETATM   25  N   UNK     0       3.374  -1.048   0.155  0.00  0.00           N+0
HETATM   26  C   UNK     0       3.977  -1.925  -0.736  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.130  -0.010   0.739  0.00  0.00           C+0
HETATM   28  H   UNK     0       5.918   1.164   2.468  0.00  0.00           H+0
HETATM   29  H   UNK     0       6.611   1.856   0.905  0.00  0.00           H+0
HETATM   30  H   UNK     0       6.793   2.690   2.457  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.037   3.653   0.881  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.746   3.555   2.626  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.776   3.089   1.383  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.182   1.696   2.443  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.580   1.667  -0.580  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.248   1.395  -0.200  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.528   0.895   1.484  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.469  -1.242   0.868  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.249  -1.233  -2.816  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.641  -1.786  -2.235  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.343   1.194  -2.498  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.712   0.209  -5.007  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.070  -1.284  -4.188  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.021   0.180  -4.248  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.407   1.122  -3.263  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.060   0.482  -0.302  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.980  -1.397   0.308  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.173   1.911   1.728  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.721   0.237   1.783  0.00  0.00           H+0
HETATM   50  H   UNK     0      -7.707   1.394   0.854  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.696  -0.063   2.115  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.849   1.809   0.700  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.247  -0.562   2.682  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.314  -2.293   2.012  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.838  -0.971   1.036  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.534  -3.135   0.104  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.486  -1.388  -1.577  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.343  -2.796  -1.055  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.835  -2.448  -0.203  0.00  0.00           H+0
HETATM   60  H   UNK     0       5.201   0.027   0.423  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.037  -0.087   1.864  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    1    3   31   32                                             
CONECT    3    2    4   33   34                                             
CONECT    4    3    5   27   35                                             
CONECT    5    4    6   36   37                                             
CONECT    6    5    7   25   38                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   39                                                  
CONECT   10    9   11   14   40                                             
CONECT   11   10   12   13   41                                             
CONECT   12   11   42   43   44                                             
CONECT   13   11   45                                                       
CONECT   14   10   15   23   46                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   19   47                                             
CONECT   17   16   18                                                       
CONECT   18   17   48   49   50                                             
CONECT   19   16   20   21   51                                             
CONECT   20   19   52                                                       
CONECT   21   19   22   23   53                                             
CONECT   22   21   54                                                       
CONECT   23   21   24   14   55                                             
CONECT   24   23   56                                                       
CONECT   25    6   26   27                                                  
CONECT   26   25   57   58   59                                             
CONECT   27   25    4   60   61                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    2                                                            
CONECT   32    2                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   16                                                            
CONECT   48   18                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
CONECT   60   27                                                            
CONECT   61   27                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  124    0
END

RDKit          3D

61 62  0  0  0  0  0  0  0  0999 V2000
    6.0364    2.0644    1.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8411    2.9019    1.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5200    2.2542    1.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3714    1.2689    0.4018 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9122    0.7749    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0188   -0.6621    0.0437 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4022   -0.9066   -1.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2637   -1.1876   -2.2027 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684   -0.8651   -1.4930 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799   -0.8239   -1.7312 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6893    0.2229   -2.8142 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0773   -0.1516   -4.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0867    0.2391   -2.9151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2046   -0.6271   -0.5462 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5305   -0.7042   -0.9235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4125   -0.4467    0.0749 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7132    0.7592   -0.3864 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6760    1.1270    1.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8261   -0.0330    1.3945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3985    1.2929    1.4254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924   -1.0129    1.8120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4183   -2.1571    2.3459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8352   -1.3538    0.6915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6986   -2.7368    0.4875 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3743   -1.0479    0.1545 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9774   -1.9249   -0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1298   -0.0096    0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9180    1.1640    2.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6106    1.8560    0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7926    2.6902    2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0375    3.6527    0.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7457    3.5545    2.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7761    3.0889    1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1816    1.6958    2.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799    1.6666   -0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2485    1.3945   -0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5277    0.8950    1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4686   -1.2419    0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2486   -1.2328   -2.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409   -1.7861   -2.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3429    1.1939   -2.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125    0.2090   -5.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698   -1.2835   -4.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0214    0.1800   -4.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4069    1.1219   -3.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0601    0.4819   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9800   -1.3965    0.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1727    1.9111    1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7214    0.2372    1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7074    1.3939    0.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6961   -0.0632    2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8492    1.8093    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2472   -0.5617    2.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3136   -2.2929    2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384   -0.9710    1.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5339   -3.1345    0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4856   -1.3881   -1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3433   -2.7958   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348   -2.4479   -0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2011    0.0272    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375   -0.0870    1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
  6 25  1  0
 25 26  1  0
 25 27  1  0
 27  4  1  0
 23 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  6
  5 36  1  0
  5 37  1  0
  6 38  1  1
  9 39  1  0
 10 40  1  6
 11 41  1  1
 12 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  1
 16 47  1  1
 18 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  1
 20 52  1  0
 21 53  1  1
 22 54  1  0
 23 55  1  1
 24 56  1  0
 26 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Cillimycin	ChEBI
Lincomicina	ChEBI
Lincomycine	ChEBI
Lincomycinum	ChEBI
Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-alpha-D-galacto-octopyranoside	ChEBI
LCM	Kegg
Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-a-D-galacto-octopyranoside	Generator
Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-α-D-galacto-octopyranoside	Generator
(2S,4R)-N-[(1R,2R)-2-Hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulphanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide	Generator
Lincomycin	MeSH
Lincomycin hydrochloride	MeSH
Lincocin	MeSH
Lincolnensin	MeSH
Lincomycin monohydrochloride	MeSH
Lincomycin monohydrochloride, (2S-cis)-isomer	MeSH
Lincomycin, (L-threo)-isomer	MeSH
Epilincomycin	MeSH
Lincomycin, (2S-cis)-isomer	MeSH
Lincomycin a	MeSH
Hemihydrate lincomycin monohydrochloride	MeSH
Lincomycin monohydrochloride, (L-threo)-isomer	MeSH
Lincomycin monohydrochloride, hemihydrate	MeSH

Chemical Formula

C₁₈H₃₄N₂O₆S

Average Mass

406.5400 Da

Monoisotopic Mass

406.21376 Da

IUPAC Name

(2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide

Traditional Name

lincomycin

CAS Registry Number

Not Available

SMILES

CCC[C@@H]1C[C@H](N(C)C1)C(=O)N[C@H]([C@@H](C)O)[C@H]1O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1

InChI Key

OJMMVQQUTAEWLP-KIDUDLJLSA-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
Apis cerana	LOTUS Database	35616633
Kitasatospora aureofaciens	LOTUS Database	35616633
Streptomyces	NPAtlas	14217764
Streptomyces caelestis	LOTUS Database	35616633
Streptomyces coelicolor	LOTUS Database	35616633
Streptomyces espinosus	LOTUS Database	35616633
Streptomyces lincolnensis	LOTUS Database	35616633
Streptomyces roseolus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Streptomyces lincolnensis var. lincolnensis	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Alpha-amino acid amide
Glycosyl compound
S-glycosyl compound
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Monosaccharide
Oxane
N-alkylpyrrolidine
Monothioacetal
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Azacycle
Organoheterocyclic compound
Oxacycle
Sulfenyl compound
Polyol
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organopnictogen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Amine
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:6472 )
pyrrolidinecarboxamide (CHEBI:6472 )
L-proline derivative (CHEBI:6472 )
carbohydrate-containing antibiotic (CHEBI:6472 )
S-glycosyl compound (CHEBI:6472 )

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	0.5	ALOGPS
logP	-0.32	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	7.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	122.49 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	102.67 m³·mol⁻¹	ChemAxon
Polarizability	44.12 Å³	ChemAxon
Number of Rings	2	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

NPA024602

HMDB ID

Not Available

DrugBank ID

DB01627

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00017955

Chemspider ID

2272112

KEGG Compound ID

C06812

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lincomycin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

6472

Good Scents ID

Not Available

References

General References

MACLEOD AJ, ROSS HB, OZERE RL, DIGOUT G, VAN ROOYENC: LINCOMYCIN: A NEW ANTIBIOTIC ACTIVE AGAINST STAPHYLOCOCCI AND OTHER GRAM-POSITIVE COCCI: CLINICAL AND LABORATORY STUDIES. Can Med Assoc J. 1964 Nov 14;91:1056-60. [PubMed:14217764 ]
Novotna J, Olsovska J, Novak P, Mojzes P, Chaloupkova R, Kamenik Z, Spizek J, Kutejova E, Mareckova M, Tichy P, Damborsky J, Janata J: Lincomycin biosynthesis involves a tyrosine hydroxylating heme protein of an unusual enzyme family. PLoS One. 2013 Dec 4;8(12):e79974. doi: 10.1371/journal.pone.0079974. eCollection 2013. [PubMed:24324587 ]

Showing NP-Card for Lincomycin (NP0004837)

MOL for NP0004837 (Lincomycin)

3D MOL for NP0004837 (Lincomycin)

3D SDF for NP0004837 (Lincomycin)

3D-SDF for NP0004837 (Lincomycin)

PDB for NP0004837 (Lincomycin)

3D PDB for NP0004837 (Lincomycin)

SMILES for NP0004837 (Lincomycin)

INCHI for NP0004837 (Lincomycin)

Structure for NP0004837 (Lincomycin)

3D Structure for NP0004837 (Lincomycin)