NP-MRD: Showing NP-Card for Lincomycin S (NP0062289)

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Record Information

Version

2.0

Created at

2022-04-28 06:58:53 UTC

Updated at

2022-04-28 06:58:53 UTC

NP-MRD ID

NP0062289

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lincomycin S

Description

(2S,4R)-1-ethyl-N-[(1R,2R)-1-[(2S,3R,4R,5S,6R)-6-(ethylsulfanyl)-3,4,5-trihydroxyoxan-2-yl]-2-hydroxypropyl]-4-propylpyrrolidine-2-carboximidic acid belongs to the class of organic compounds known as thioglycosides. These are glycoside in which a sugar group is bonded through one carbon to another group via a S-glycosidic bond. Lincomycin S is found in Streptomyces lincolnensis. Based on a literature review very few articles have been published on (2S,4R)-1-ethyl-N-[(1R,2R)-1-[(2S,3R,4R,5S,6R)-6-(ethylsulfanyl)-3,4,5-trihydroxyoxan-2-yl]-2-hydroxypropyl]-4-propylpyrrolidine-2-carboximidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208582D          

 29 30  0  0  1  0            999 V2000
   -0.1787    0.5795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6282    0.4080    0.0000 C   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
   -0.0392   -0.7481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912   -0.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2107   -1.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9954   -1.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5143    1.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0294    2.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3649    2.7543    0.0000 C   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
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  8  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  1  0  0  0
 15 11  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 24  1  6  0  0  0
 17 25  1  1  0  0  0
 16 26  1  6  0  0  0
  1 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 67 68  0  0  0  0  0  0  0  0999 V2000
   -4.7450    3.9531   -2.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1779    2.5889   -1.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0965    2.0676   -0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3676    0.7139   -0.1918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1675    0.3602    0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4433   -0.5969   -0.2703 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2702   -1.2384    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2102   -2.4924    0.3212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1742   -0.5231    0.8420 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9507   -1.2191    1.3896 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2385   -0.9518    0.6710 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6029    0.4102    0.6823 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9958    0.3910    0.3803 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8071    1.8578    0.9841 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5807    1.7751    0.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0146    1.8366   -0.7156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0704    0.2224   -1.1044 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2538   -0.4174   -1.5229 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8622   -0.4792   -1.7014 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9062    0.4279   -2.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663   -1.4901   -0.7452 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9702   -2.6946   -0.8231 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1700   -0.8816    2.8604 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3961   -1.6273    3.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983    0.4685    3.0135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5130   -1.4321   -0.7030 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1411   -2.2306    0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2630   -3.0878   -0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4411   -0.3894   -1.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1324    4.1497   -3.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6405    3.9256   -2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0177    4.7628   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1151    2.7619   -1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3481    1.9748   -2.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0168    2.7760    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1251    2.1234   -1.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2946    0.7643    0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5434    1.2605    0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4308   -0.0889    1.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1495    0.0212   -1.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2225    0.5182    0.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7800   -2.3257    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0496   -1.4761    1.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4224   -0.4923    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0220    0.8226    1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0310    2.6042    1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8247    2.6361   -0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2486    2.1356   -1.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5676    0.9193   -1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0793    1.2281   -1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2147   -0.4316   -2.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2247   -1.0427   -2.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3750    1.2849   -2.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337   -1.6985   -1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6535   -3.3272   -0.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3185   -1.2419    3.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2904   -0.9809    3.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707   -1.8405    4.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4796   -2.6081    2.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880    1.0527    2.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6173   -1.6361    1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4036   -2.9316    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2348   -2.5507   -0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4037   -3.9254    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9920   -3.5585   -1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4647   -0.7544   -1.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0946   -0.1323   -2.1964 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 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 23  1  0
 23 24  1  0
 23 25  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 29  4  1  0
 21 11  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  1
  5 38  1  0
  5 39  1  0
  6 40  1  6
 27 61  1  0
 27 62  1  0
 28 63  1  0
 28 64  1  0
 28 65  1  0
 29 66  1  0
 29 67  1  0
  9 41  1  0
 10 42  1  1
 23 56  1  1
 24 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  0
 11 43  1  1
 13 44  1  1
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  6
 18 51  1  0
 19 52  1  6
 20 53  1  0
 21 54  1  6
 22 55  1  0
M  END


  Mrv1652304282208582D          

 29 30  0  0  1  0            999 V2000
   -0.1787    0.5795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6282    0.4080    0.0000 C   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
   -0.0392   -0.7481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912   -0.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2107   -1.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9954   -1.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5143    1.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0294    2.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3649    2.7543    0.0000 C   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
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  8  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  1  0  0  0
 15 11  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 24  1  6  0  0  0
 17 25  1  1  0  0  0
 16 26  1  6  0  0  0
  1 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062289

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@@H]1C[C@H](N(CC)C1)C(=O)N[C@H]([C@@H](C)O)[C@@H]1O[C@H](SCC)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H38N2O6S/c1-5-8-12-9-13(22(6-2)10-12)19(27)21-14(11(4)23)18-16(25)15(24)17(26)20(28-18)29-7-3/h11-18,20,23-26H,5-10H2,1-4H3,(H,21,27)/t11-,12-,13+,14-,15-,16-,17+,18+,20-/m1/s1

> <INCHI_KEY>
BIOYUGIILYQHST-AVVCBRPDSA-N

> <FORMULA>
C20H38N2O6S

> <MOLECULAR_WEIGHT>
434.59

> <EXACT_MASS>
434.245058126

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.50437224148733

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4R)-1-ethyl-N-[(1R,2R)-1-[(2S,3R,4R,5S,6R)-6-(ethylsulfanyl)-3,4,5-trihydroxyoxan-2-yl]-2-hydroxypropyl]-4-propylpyrrolidine-2-carboxamide

> <ALOGPS_LOGP>
1.56

> <JCHEM_LOGP>
0.2929837293333326

> <ALOGPS_LOGS>
-1.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.005157728935806

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.380984934778336

> <JCHEM_PKA_STRONGEST_BASIC>
8.1976142937303

> <JCHEM_POLAR_SURFACE_AREA>
122.49000000000002

> <JCHEM_REFRACTIVITY>
112.21269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R)-1-ethyl-N-[(1R,2R)-1-[(2S,3R,4R,5S,6R)-6-(ethylsulfanyl)-3,4,5-trihydroxyoxan-2-yl]-2-hydroxypropyl]-4-propylpyrrolidine-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.334   1.082   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.173   0.762   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -0.073  -1.396   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -1.104  -0.252   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.393  -2.903   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.858  -3.379   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
HETATM   21  S   UNK     0       1.334  -8.470   0.000  0.00  0.00           S+0
HETATM   22  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.668  -8.470   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.960   2.489   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.055   3.734   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.681   5.141   0.000  0.00  0.00           C+0
CONECT    1    2    5   27                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6                                                            
CONECT    8    3    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16   20                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18   25                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   15                                                       
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   18                                                            
CONECT   25   17                                                            
CONECT   26   16                                                            
CONECT   27    1   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Value	Source
(2S,4R)-1-Ethyl-N-[(1R,2R)-1-[(2S,3R,4R,5S,6R)-6-(ethylsulfanyl)-3,4,5-trihydroxyoxan-2-yl]-2-hydroxypropyl]-4-propylpyrrolidine-2-carboximidate	Generator
(2S,4R)-1-Ethyl-N-[(1R,2R)-1-[(2S,3R,4R,5S,6R)-6-(ethylsulphanyl)-3,4,5-trihydroxyoxan-2-yl]-2-hydroxypropyl]-4-propylpyrrolidine-2-carboximidate	Generator
(2S,4R)-1-Ethyl-N-[(1R,2R)-1-[(2S,3R,4R,5S,6R)-6-(ethylsulphanyl)-3,4,5-trihydroxyoxan-2-yl]-2-hydroxypropyl]-4-propylpyrrolidine-2-carboximidic acid	Generator

Chemical Formula

C₂₀H₃₈N₂O₆S

Average Mass

434.5900 Da

Monoisotopic Mass

434.24506 Da

IUPAC Name

(2S,4R)-1-ethyl-N-[(1R,2R)-1-[(2S,3R,4R,5S,6R)-6-(ethylsulfanyl)-3,4,5-trihydroxyoxan-2-yl]-2-hydroxypropyl]-4-propylpyrrolidine-2-carboxamide

Traditional Name

(2S,4R)-1-ethyl-N-[(1R,2R)-1-[(2S,3R,4R,5S,6R)-6-(ethylsulfanyl)-3,4,5-trihydroxyoxan-2-yl]-2-hydroxypropyl]-4-propylpyrrolidine-2-carboxamide

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H38N2O6S/c1-5-8-12-9-13(22(6-2)10-12)19(27)21-14(11(4)23)18-16(25)15(24)17(26)20(28-18)29-7-3/h11-18,20,23-26H,5-10H2,1-4H3,(H,21,27)/t11-,12-,13+,14-,15-,16-,17+,18+,20-/m1/s1

InChI Key

BIOYUGIILYQHST-AVVCBRPDSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces lincolnensis	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thioglycosides. These are glycoside in which a sugar group is bonded through one carbon to another group via a S-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Thioglycosides

Alternative Parents

Substituents

S-glycosyl compound
N-alkylpyrrolidine
Oxane
Monosaccharide
Pyrrolidine
Monothioacetal
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Polyol
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.56	ALOGPS
logP	0.29	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.38	ChemAxon
pKa (Strongest Basic)	8.2	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	9	ChemAxon
Refractivity	112.21 m³·mol⁻¹	ChemAxon
Polarizability	47.5 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

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

Not Available

METLIN ID

Not Available

PubChem Compound

163043868

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

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MOL for NP0062289 (Lincomycin S)

3D MOL for NP0062289 (Lincomycin S)

3D SDF for NP0062289 (Lincomycin S)

3D-SDF for NP0062289 (Lincomycin S)

PDB for NP0062289 (Lincomycin S)

3D PDB for NP0062289 (Lincomycin S)

SMILES for NP0062289 (Lincomycin S)

INCHI for NP0062289 (Lincomycin S)

Structure for NP0062289 (Lincomycin S)

3D Structure for NP0062289 (Lincomycin S)