NP-MRD: Showing NP-Card for Lactonamycin (NP0001660)

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Record Information

Version

2.0

Created at

2020-09-23 02:00:33 UTC

Updated at

2021-08-10 02:56:06 UTC

NP-MRD ID

NP0001660

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lactonamycin

Provided By

NPAtlas

Description

Lactonamycin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Lactonamycin is found in Streptomyces and Streptomyces rishiriensis. Lactonamycin was first documented in 1996 (PMID: 8931735). Based on a literature review a significant number of articles have been published on lactonamycin (PMID: 10348043) (PMID: 15606108) (PMID: 28445072) (PMID: 23303690) (PMID: 22580446) (PMID: 20704431).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117443D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242117443D          

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M  END
> <DATABASE_ID>
NP0001660

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C([H])C3=C(C(O[H])=C2C2=C1C(=O)N(C([H])([H])[H])C2([H])[H])C(=O)[C@@]12OC(=O)C([H])([H])[C@]1(OC([H])([H])[H])OC([H])([H])[C@@]2(O[C@]1([H])O[C@@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C1([H])[H])C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H27NO12/c1-11-15(30)4-5-18(39-11)41-26-10-38-27(37-3)8-17(32)40-28(26,27)24(35)21-13(23(26)34)6-12-7-16(31)20-14(19(12)22(21)33)9-29(2)25(20)36/h6-7,11,15,18,30-31,33H,4-5,8-10H2,1-3H3/t11-,15-,18-,26+,27-,28-/m0/s1

> <INCHI_KEY>
XFQJOLWXLJXJSV-VUAGTGNDSA-N

> <FORMULA>
C28H27NO12

> <MOLECULAR_WEIGHT>
569.519

> <EXACT_MASS>
569.153325313

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
56.166421988189185

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(15S,18S,22R)-2,9-dihydroxy-15-{[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy}-18-methoxy-6-methyl-17,21-dioxa-6-azahexacyclo[11.10.0.0^{3,11}.0^{4,8}.0^{15,22}.0^{18,22}]tricosa-1(13),2,4(8),9,11-pentaene-7,14,20,23-tetrone

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
2.1494554949999998

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.8458074057305796

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.1850366901119

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9583260803446643

> <JCHEM_POLAR_SURFACE_AREA>
178.35999999999996

> <JCHEM_REFRACTIVITY>
136.3774

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(15S,18S,22R)-2,9-dihydroxy-15-{[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy}-18-methoxy-6-methyl-17,21-dioxa-6-azahexacyclo[11.10.0.0^{3,11}.0^{4,8}.0^{15,22}.0^{18,22}]tricosa-1(13),2,4(8),9,11-pentaene-7,14,20,23-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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   -1.1294    1.6549   -2.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  8  7  1  1
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 19 23  1  0
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 30 31  1  1
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  1  0
 30 40  1  0
 40 41  1  0
  8  3  1  0
 21 11  1  0
 39 32  1  0
 41  3  1  0
 30  8  1  0
 20 14  1  0
 26 18  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  4 45  1  0
  4 46  1  0
 13 47  1  0
 15 48  1  0
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 32 56  1  1
 33 57  1  0
 33 58  1  0
 34 59  1  0
 34 60  1  0
 35 61  1  6
 36 62  1  0
 37 63  1  6
 38 64  1  0
 38 65  1  0
 38 66  1  0
 40 67  1  0
 40 68  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      -1.639   4.487  -1.861  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.927   3.434  -1.295  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.847   2.649  -0.583  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.435   3.349   0.590  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.112   2.488   1.735  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.303   2.796   2.961  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.582   1.323   1.260  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.164   1.385  -0.052  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.287   1.640  -0.095  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.691   2.814   0.100  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.285   0.627  -0.350  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.822  -0.480  -1.083  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.709  -1.489  -1.371  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.011  -1.379  -0.933  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.871  -2.413  -1.242  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.193  -2.394  -0.848  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.055  -3.427  -1.155  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.609  -1.292  -0.131  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.773  -0.250   0.190  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.444  -0.287  -0.217  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.575   0.751   0.092  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.053   1.809   0.805  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.505   0.772   0.953  0.00  0.00           C+0
HETATM   24  N   UNK     0       6.844   0.240   1.058  0.00  0.00           N+0
HETATM   25  C   UNK     0       7.951   0.895   1.736  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.941  -1.019   0.404  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.970  -1.769   0.299  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.566  -0.533  -1.518  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.878  -1.368  -2.392  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.647   0.344  -0.992  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.783  -0.320  -0.676  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.857  -1.055   0.465  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.883  -0.410   1.372  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.138  -1.246   1.537  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.394  -1.837   0.170  0.00  0.00           C+0
HETATM   36  O   UNK     0      -6.632  -2.425   0.050  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.285  -2.816  -0.092  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.607  -4.085   0.675  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.047  -2.400   0.284  0.00  0.00           O+0
HETATM   40  C   UNK     0      -2.021   1.236  -2.201  0.00  0.00           C+0
HETATM   41  O   UNK     0      -2.782   2.210  -1.515  0.00  0.00           O+0
HETATM   42  H   UNK     0      -2.148   5.121  -1.105  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.467   4.084  -2.516  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.991   5.147  -2.473  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.841   4.300   0.734  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.514   3.579   0.483  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.348  -2.349  -1.942  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.517  -3.260  -1.803  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.734  -4.218  -1.677  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.636   2.636   1.141  0.00  0.00           H+0
HETATM   51  H   UNK     0       5.120   0.902   1.986  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.567   1.744   0.395  0.00  0.00           H+0
HETATM   53  H   UNK     0       8.460   1.563   1.028  0.00  0.00           H+0
HETATM   54  H   UNK     0       8.667   0.138   2.089  0.00  0.00           H+0
HETATM   55  H   UNK     0       7.581   1.446   2.640  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.887  -0.968   1.002  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.508  -0.243   2.402  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.208   0.578   0.987  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.968  -0.567   1.777  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.999  -2.041   2.300  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.327  -1.036  -0.587  0.00  0.00           H+0
HETATM   62  H   UNK     0      -6.658  -3.191  -0.561  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.338  -3.086  -1.171  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.332  -4.995   0.133  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.999  -4.099   1.628  0.00  0.00           H+0
HETATM   66  H   UNK     0      -5.674  -4.096   1.019  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.702   0.698  -2.873  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.129   1.655  -2.669  0.00  0.00           H+0
CONECT    1    2   42   43   44                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    8   41                                             
CONECT    4    3    5   45   46                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9    3   30                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   21                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12   14   47                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16   48                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   49                                                       
CONECT   18   16   19   26                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21   14                                                  
CONECT   21   20   22   11                                                  
CONECT   22   21   50                                                       
CONECT   23   19   24   51   52                                             
CONECT   24   23   25   26                                                  
CONECT   25   24   53   54   55                                             
CONECT   26   24   27   18                                                  
CONECT   27   26                                                            
CONECT   28   12   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   40    8                                             
CONECT   31   30   32                                                       
CONECT   32   31   33   39   56                                             
CONECT   33   32   34   57   58                                             
CONECT   34   33   35   59   60                                             
CONECT   35   34   36   37   61                                             
CONECT   36   35   62                                                       
CONECT   37   35   38   39   63                                             
CONECT   38   37   64   65   66                                             
CONECT   39   37   32                                                       
CONECT   40   30   41   67   68                                             
CONECT   41   40    3                                                       
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    4                                                            
CONECT   46    4                                                            
CONECT   47   13                                                            
CONECT   48   15                                                            
CONECT   49   17                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   23                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   32                                                            
CONECT   57   33                                                            
CONECT   58   33                                                            
CONECT   59   34                                                            
CONECT   60   34                                                            
CONECT   61   35                                                            
CONECT   62   36                                                            
CONECT   63   37                                                            
CONECT   64   38                                                            
CONECT   65   38                                                            
CONECT   66   38                                                            
CONECT   67   40                                                            
CONECT   68   40                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  148    0
END

RDKit          3D

68 74  0  0  0  0  0  0  0  0999 V2000
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   -0.9270    3.4338   -1.2945 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8223   -0.4798   -1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7089   -1.4888   -1.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0110   -1.3786   -0.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8712   -2.4129   -1.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4436   -0.2874   -0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0531    1.8087    0.8052 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5050    0.7717    0.9530 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8442    0.2401    1.0576 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6317   -2.4253    0.0500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2847   -2.8158   -0.0923 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6074   -4.0852    0.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0471   -2.4003    0.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0210    1.2358   -2.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7817    2.2103   -1.5145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1476    5.1214   -1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4670    4.0844   -2.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3319   -4.9955    0.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9991   -4.0995    1.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6738   -4.0960    1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7020    0.6984   -2.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1294    1.6549   -2.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  8  7  1  1
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
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  8  3  1  0
 21 11  1  0
 39 32  1  0
 41  3  1  0
 30  8  1  0
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 37 63  1  6
 38 64  1  0
 38 65  1  0
 38 66  1  0
 40 67  1  0
 40 68  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₈H₂₇NO₁₂

Average Mass

569.5190 Da

Monoisotopic Mass

569.15333 Da

IUPAC Name

(15S,18S,22R)-2,9-dihydroxy-15-{[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy}-18-methoxy-6-methyl-17,21-dioxa-6-azahexacyclo[11.10.0.0^{3,11}.0^{4,8}.0^{15,22}.0^{18,22}]tricosa-1(13),2,4(8),9,11-pentaene-7,14,20,23-tetrone

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C([H])C3=C(C(O[H])=C2C2=C1C(=O)N(C([H])([H])[H])C2([H])[H])C(=O)[C@@]12OC(=O)C([H])([H])[C@]1(OC([H])([H])[H])OC([H])([H])[C@@]2(O[C@]1([H])O[C@@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C1([H])[H])C3=O

InChI Identifier

InChI=1S/C28H27NO12/c1-11-15(30)4-5-18(39-11)41-26-10-38-27(37-3)8-17(32)40-28(26,27)24(35)21-13(23(26)34)6-12-7-16(31)20-14(19(12)22(21)33)9-29(2)25(20)36/h6-7,11,15,18,30-31,33H,4-5,8-10H2,1-3H3/t11-,15-,18-,26+,27-,28-/m0/s1

InChI Key

XFQJOLWXLJXJSV-VUAGTGNDSA-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	NPAtlas	10348043
Streptomyces rishiriensis	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Streptomyces rishiriensis MJ773-88K4 MJ773-88K4	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	1.35	ALOGPS
logP	2.15	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.19	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	178.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	136.38 m³·mol⁻¹	ChemAxon
Polarizability	56.17 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA011917

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00015353

Chemspider ID

28540457

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

66553

Good Scents ID

Not Available

References

General References

Matsumoto N, Tsuchida T, Nakamura H, Sawa R, Takahashi Y, Naganawa H, Iinuma H, Sawa T, Takeuchi T, Shiro M: Lactonamycin, a new antimicrobial antibiotic produced by Streptomyces rishiriensis MJ773-88K4. II. Structure determination. J Antibiot (Tokyo). 1999 Mar;52(3):276-80. doi: 10.7164/antibiotics.52.276. [PubMed:10348043 ]
Kelly TR, Cai X, Tu B, Elliott EL, Grossmann G, Laurent P: Asymmetric synthesis of the AB ring system of lactonamycin. Org Lett. 2004 Dec 23;6(26):4953-6. doi: 10.1021/ol047922h. [PubMed:15606108 ]
Matsumoto N, Tsuchida T, Maruyama M, Sawa R, Kinoshita N, Homma Y, Takahashi Y, Iinuma H, Naganawa H, Sawa T, Hamada M, Takeuchi T: Lactonamycin, a new antimicrobial antibiotic produced by Streptomyces rishiriensis. J Antibiot (Tokyo). 1996 Sep;49(9):953-4. doi: 10.7164/antibiotics.49.953. [PubMed:8931735 ]
Parsons PJ, Jones DR, Walsh LJ, Allen LAT, Onwubiko A, Preece L, Board J, White AJP: An Approach to the Core of Lactonamycin. Org Lett. 2017 May 19;19(10):2533-2535. doi: 10.1021/acs.orglett.7b00902. Epub 2017 Apr 26. [PubMed:28445072 ]
Adachi S, Watanabe K, Iwata Y, Kameda S, Miyaoka Y, Onozuka M, Mitsui R, Saikawa Y, Nakata M: Total syntheses of lactonamycin and lactonamycin Z with late-stage A-ring formation and glycosylation. Angew Chem Int Ed Engl. 2013 Feb 11;52(7):2087-91. doi: 10.1002/anie.201209205. Epub 2013 Jan 9. [PubMed:23303690 ]
Dubois S, Rodier F, Blanc R, Rahmani R, Heran V, Thibonnet J, Commeiras L, Parrain JL: Dramatic influence of the substitution of alkylidene-5H-furan-2-ones in Diels-Alder cycloadditions with o-quinonedimethide as diene partner: en route to the CDEF polycyclic ring system of lactonamycin. Org Biomol Chem. 2012 Jun 28;10(24):4712-9. doi: 10.1039/c2ob25299f. Epub 2012 May 14. [PubMed:22580446 ]
Watanabe K, Iwata Y, Adachi S, Nishikawa T, Yoshida Y, Kameda S, Ide M, Saikawa Y, Nakata M: Synthetic studies on lactonamycins: synthesis of the model BCDEF aglycon. J Org Chem. 2010 Aug 20;75(16):5573-9. doi: 10.1021/jo100913s. [PubMed:20704431 ]
Zhang X, Alemany LB, Fiedler HP, Goodfellow M, Parry RJ: Biosynthetic investigations of lactonamycin and lactonamycin z: cloning of the biosynthetic gene clusters and discovery of an unusual starter unit. Antimicrob Agents Chemother. 2008 Feb;52(2):574-85. doi: 10.1128/AAC.00717-07. Epub 2007 Dec 10. [PubMed:18070976 ]
Parsons PJ, Waters AJ, Walter DS, Board J: A new route to highly functionalized heterocyclic rings. J Org Chem. 2007 Feb 16;72(4):1395-8. doi: 10.1021/jo062305n. [PubMed:17288385 ]

Showing NP-Card for Lactonamycin (NP0001660)

MOL for NP0001660 (Lactonamycin)

3D MOL for NP0001660 (Lactonamycin)

3D SDF for NP0001660 (Lactonamycin)

3D-SDF for NP0001660 (Lactonamycin)

PDB for NP0001660 (Lactonamycin)

3D PDB for NP0001660 (Lactonamycin)

SMILES for NP0001660 (Lactonamycin)

INCHI for NP0001660 (Lactonamycin)

Structure for NP0001660 (Lactonamycin)

3D Structure for NP0001660 (Lactonamycin)