NP-MRD: Showing NP-Card for n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid (NP0194651)

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Record Information

Version

2.0

Created at

2022-09-04 12:21:11 UTC

Updated at

2022-09-04 12:21:12 UTC

NP-MRD ID

NP0194651

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid

Description

Virginiamycin, also known as staphylomycin S or cebin V, belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. Virginiamycin is a moderately basic compound (based on its pKa). Virginiamycin is used in the fuel ethanol industry to prevent microbial contamination. n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid is found in Streptomyces virginiae. n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid was first documented in 2001 (PMID: 11443899). Antibacterial food additive.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305182D          

 60 65  0  0  0  0            999 V2000
    5.4978  -16.0357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5105  -16.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2184  -15.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7921  -15.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2266  -17.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8003  -17.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2126  -14.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0170  -15.8217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784  -16.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9403  -16.8540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2255  -18.0960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0773  -16.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4966  -14.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6127  -14.0734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6563  -17.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3635  -17.2842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6035  -13.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6656  -18.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3623  -16.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2010  -13.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7678  -13.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8419  -13.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8519  -14.7778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9554  -18.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3810  -18.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6668  -13.3457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6742  -16.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4688  -11.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0803  -14.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9162  -12.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2416  -12.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6807  -19.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4478  -16.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3101  -15.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9018  -14.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6698  -14.7686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1158  -15.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1650  -16.8975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3231  -14.7570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7301  -14.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3115  -15.3752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8767  -16.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1344  -13.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5939  -16.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8711  -15.6552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3056  -16.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5995  -17.7128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0228  -16.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3000  -15.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3168  -18.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0284  -17.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  0  0  0  0
 10 15  1  0  0  0  0
 12 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  1  0  0  0  0
 15 21  1  0  0  0  0
 17 22  2  0  0  0  0
 17 23  1  0  0  0  0
 18 24  1  0  0  0  0
 18 25  2  0  0  0  0
 20 26  2  0  0  0  0
 20 27  1  0  0  0  0
 21 28  1  0  0  0  0
 21 29  2  0  0  0  0
 22 30  1  0  0  0  0
 23 31  2  0  0  0  0
 24 32  1  0  0  0  0
 24 33  1  0  0  0  0
 26 34  1  0  0  0  0
 27 35  2  0  0  0  0
 28 36  1  0  0  0  0
 30 37  2  0  0  0  0
 32 38  1  0  0  0  0
 32 39  1  0  0  0  0
 33 40  1  0  0  0  0
 34 41  2  0  0  0  0
 36 42  1  0  0  0  0
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 42 46  1  0  0  0  0
 44 48  1  0  0  0  0
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 47 51  1  0  0  0  0
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 53 55  1  0  0  0  0
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 55 57  2  0  0  0  0
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 56 59  1  0  0  0  0
 57 60  1  0  0  0  0
  9 12  1  0  0  0  0
 31 37  1  0  0  0  0
 35 41  1  0  0  0  0
 39 40  1  0  0  0  0
 46 48  1  0  0  0  0
 59 60  2  0  0  0  0
 47 42  1  0  0  0  0
M  END

     RDKit          3D

109114  0  0  0  0  0  0  0  0999 V2000
    1.9915   -4.5053   -0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -3.0694   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8985   -2.4363    0.2689 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0225   -1.0724    0.6913 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1115   -0.2822    1.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2745   -0.0064    2.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1715    0.3406    0.2206 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4312   -0.3494    0.2410 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6371    0.2643    0.7520 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6115    1.4277    1.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8864   -0.4729    0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2339   -1.9228    0.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2403   -0.6273    1.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0440    0.0960    1.2354 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0706    1.3726    1.7357 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128    0.6975   -1.2032 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0217    1.1189   -1.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    1.7530   -1.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0170    3.2424   -0.8426 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8467    4.4724   -0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8028    0.3186    0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3611   -0.3605   -0.8137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175   -0.2269    1.4928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5824   -0.3435    1.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3768   -1.2021    0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5887   -2.5317    1.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3471   -2.0111   -1.9134 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9432   -4.8145   -0.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2634   -4.6507   -1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8516   -3.0822    0.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285   -3.0800    1.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0642   -0.5918    0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206    1.3799    0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9868   -3.4424   -0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1290   -2.5418    0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061305182D          

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M  END
> <DATABASE_ID>
NP0194651

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1NC(=O)C(NC(=O)C2=NC=CC=C2O)C(C)OC(=O)C(NC(=O)C2CC(=O)CCN2C(=O)C(CC2=CC=CC=C2)N(C)C(=O)C2CCCN2C1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C43H49N7O10/c1-4-29-40(56)49-21-12-17-30(49)41(57)48(3)32(23-26-13-7-5-8-14-26)42(58)50-22-19-28(51)24-31(50)37(53)47-35(27-15-9-6-10-16-27)43(59)60-25(2)34(38(54)45-29)46-39(55)36-33(52)18-11-20-44-36/h5-11,13-16,18,20,25,29-32,34-35,52H,4,12,17,19,21-24H2,1-3H3,(H,45,54)(H,46,55)(H,47,53)

> <INCHI_KEY>
FEPMHVLSLDOMQC-UHFFFAOYSA-N

> <FORMULA>
C43H49N7O10

> <MOLECULAR_WEIGHT>
823.8901

> <EXACT_MASS>
823.354090823

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
82.2694385092926

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosan-15-yl}-3-hydroxypyridine-2-carboxamide

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
1.8531505056666662

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.453010859469142

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.529841701905064

> <JCHEM_PKA_STRONGEST_BASIC>
1.5727269020165608

> <JCHEM_POLAR_SURFACE_AREA>
224.72

> <JCHEM_REFRACTIVITY>
213.23720000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
virginiamycin factor S1

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  N   UNK     0      10.263 -29.933   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      10.286 -31.479   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.608 -29.140   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.945 -29.172   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.623 -32.233   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.961 -32.252   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.597 -27.607   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.098 -29.534   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.613 -29.952   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      12.955 -31.461   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      11.621 -33.779   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.611 -31.498   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.260 -26.860   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      12.344 -26.270   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      14.292 -32.208   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.279 -32.264   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.249 -25.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.884 -26.260   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.327 -24.731   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.309 -33.754   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.610 -31.421   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.575 -24.527   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.900 -24.566   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.638 -24.923   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.657 -27.585   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.983 -34.533   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.645 -34.507   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.946 -32.182   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      15.592 -29.889   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.551 -22.988   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.883 -23.019   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      16.178 -24.912   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      14.151 -23.465   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.994 -36.072   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.662 -36.047   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      18.059 -31.066   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.208 -22.234   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      16.950 -26.231   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.644 -23.447   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      15.384 -22.556   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      14.337 -36.840   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.503 -30.671   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      17.379 -29.684   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      18.483 -26.221   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      16.184 -27.568   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      18.883 -29.043   0.000  0.00  0.00           C+0
HETATM   47  N   UNK     0      20.841 -31.542   0.000  0.00  0.00           N+0
HETATM   48  N   UNK     0      19.270 -27.546   0.000  0.00  0.00           N+0
HETATM   49  C   UNK     0      20.030 -26.210   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      17.381 -28.700   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      22.170 -30.763   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      20.784 -24.867   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      23.509 -31.524   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      22.159 -29.223   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      24.837 -30.745   0.000  0.00  0.00           C+0
HETATM   56  N   UNK     0      23.519 -33.064   0.000  0.00  0.00           N+0
HETATM   57  C   UNK     0      26.176 -31.506   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      24.827 -29.205   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      24.858 -33.825   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      26.186 -33.046   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13   14                                                  
CONECT    8    3                                                            
CONECT    9    4   12                                                       
CONECT   10    5   15                                                       
CONECT   11    5                                                            
CONECT   12    6   16    9                                                  
CONECT   13    7   17                                                       
CONECT   14    7   18   19                                                  
CONECT   15   10   20   21                                                  
CONECT   16   12                                                            
CONECT   17   13   22   23                                                  
CONECT   18   14   24   25                                                  
CONECT   19   14                                                            
CONECT   20   15   26   27                                                  
CONECT   21   15   28   29                                                  
CONECT   22   17   30                                                       
CONECT   23   17   31                                                       
CONECT   24   18   32   33                                                  
CONECT   25   18                                                            
CONECT   26   20   34                                                       
CONECT   27   20   35                                                       
CONECT   28   21   36                                                       
CONECT   29   21                                                            
CONECT   30   22   37                                                       
CONECT   31   23   37                                                       
CONECT   32   24   38   39                                                  
CONECT   33   24   40                                                       
CONECT   34   26   41                                                       
CONECT   35   27   41                                                       
CONECT   36   28   42   43                                                  
CONECT   37   30   31                                                       
CONECT   38   32   44   45                                                  
CONECT   39   32   40                                                       
CONECT   40   33   39                                                       
CONECT   41   34   35                                                       
CONECT   42   36   46   47                                                  
CONECT   43   36                                                            
CONECT   44   38   48   49                                                  
CONECT   45   38                                                            
CONECT   46   42   50   48                                                  
CONECT   47   51   42                                                       
CONECT   48   44   46                                                       
CONECT   49   44   52                                                       
CONECT   50   46                                                            
CONECT   51   47   53   54                                                  
CONECT   52   49                                                            
CONECT   53   51   55   56                                                  
CONECT   54   51                                                            
CONECT   55   53   57   58                                                  
CONECT   56   53   59                                                       
CONECT   57   55   60                                                       
CONECT   58   55                                                            
CONECT   59   56   60                                                       
CONECT   60   57   59                                                       
MASTER        0    0    0    0    0    0    0    0   60    0  130    0
END

View in JSmol

Synonyms

Value	Source
Virginiamycin factor S	Kegg
Antibiotic 1754Z3b	HMDB
Cebin V	HMDB
Eskalin V	HMDB
Eskamicin	HMDB
Mikamycin	HMDB
Ostreogrycin	HMDB
Patricin	HMDB
Pristinamycin	HMDB
Stafac	HMDB
Staphylomycin S	HMDB
Staphylomycin S1	HMDB
Stephylomycin	HMDB
Streptogramin	HMDB
Vernamycin	HMDB
Virginiamycin factor S1	HMDB
Virginiamycin S1	HMDB
Virginiamycin, ban, inn, usan	HMDB
VirginiamycinVirginiamycin S1	HMDB
Dihydrovirginiamycin S1	MeSH

Chemical Formula

C₄₃H₄₉N₇O₁₀

Average Mass

823.8901 Da

Monoisotopic Mass

823.35409 Da

IUPAC Name

N-{3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosan-15-yl}-3-hydroxypyridine-2-carboxamide

Traditional Name

virginiamycin factor S1

CAS Registry Number

Not Available

SMILES

CCC1NC(=O)C(NC(=O)C2=NC=CC=C2O)C(C)OC(=O)C(NC(=O)C2CC(=O)CCN2C(=O)C(CC2=CC=CC=C2)N(C)C(=O)C2CCCN2C1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C43H49N7O10/c1-4-29-40(56)49-21-12-17-30(49)41(57)48(3)32(23-26-13-7-5-8-14-26)42(58)50-22-19-28(51)24-31(50)37(53)47-35(27-15-9-6-10-16-27)43(59)60-25(2)34(38(54)45-29)46-39(55)36-33(52)18-11-20-44-36/h5-11,13-16,18,20,25,29-32,34-35,52H,4,12,17,19,21-24H2,1-3H3,(H,45,54)(H,46,55)(H,47,53)

InChI Key

FEPMHVLSLDOMQC-UHFFFAOYSA-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 virginiae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizidines

Sub Class

Not Available

Direct Parent

Pyrrolizidines

Alternative Parents

Substituents

Pyrrolizidine
Fatty acid ester
N-alkylpyrrolidine
Fatty acyl
1,3-aminoalcohol
Pyrrolidine
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Primary alcohol
Alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.25	ALOGPS
logP	1.85	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.53	ChemAxon
pKa (Strongest Basic)	1.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	224.72 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	213.24 m³·mol⁻¹	ChemAxon
Polarizability	82.27 Å³	ChemAxon
Number of Rings	6	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

HMDB0030520

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002392

KNApSAcK ID

Not Available

Chemspider ID

109411

KEGG Compound ID

C11269

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Virginiamycin

METLIN ID

Not Available

PubChem Compound

122731

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zvenigorodskii VI, Tiaglov BV, Voeikova TA: [Isolation of peptide antibiotic virginiamycin components and selection of their producer Streptomyces virginiae]. Prikl Biokhim Mikrobiol. 2001 May-Jun;37(3):301-8. [PubMed:11443899 ]
LOTUS database [Link]

Showing NP-Card for n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid (NP0194651)

MOL for NP0194651 (n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid)

3D MOL for NP0194651 (n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid)

3D SDF for NP0194651 (n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid)

3D-SDF for NP0194651 (n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid)

PDB for NP0194651 (n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid)

3D PDB for NP0194651 (n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid)

SMILES for NP0194651 (n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid)

INCHI for NP0194651 (n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid)

Structure for NP0194651 (n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid)

3D Structure for NP0194651 (n-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid)