NP-MRD: Showing NP-Card for (1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate (NP0147398)

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Record Information

Version

2.0

Created at

2022-09-02 02:59:41 UTC

Updated at

2022-09-02 02:59:41 UTC

NP-MRD ID

NP0147398

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate

Description

Meilingmycin belongs to the class of organic compounds known as milbemycins. These are a group of macrolides with a structure containing a 16-membered lactone ring fused to a 1,7-dioxaspiroundecane ring system and to either a benzofuran (or hydrogenated derivative thereof). In some cases (e.G. Milbemycin E), the tetrahydrofuranyl ring is missing. Milbemycins can be o-glycosylated at C13 to form Avermectins. Milbemycins are produced by Streptomyces species. (1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate is found in Streptomyces nanchangensis. (1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate was first documented in 2003 (PMID: 12811466). Based on a literature review a significant number of articles have been published on Meilingmycin (PMID: 30227225) (PMID: 34549358) (PMID: 30623120) (PMID: 20348291) (PMID: 15989236).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022204592D          

 44 48  0  0  1  0            999 V2000
   -0.5353    3.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1928    3.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8928    3.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2209    2.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9490    1.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6490    2.2788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9771    1.0176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052    0.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334   -0.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4615   -0.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1405   -1.0078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
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  9 10  2  0  0  0  0
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 15 44  1  0  0  0  0
M  END

     RDKit          3D

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 19 62  1  0
 21 63  1  0
 21 64  1  0
 21 65  1  0
 22 66  1  0
 22 67  1  0
 23 68  1  6
 24 69  1  0
 24 70  1  0
 24 71  1  0
 25 72  1  0
 26 73  1  0
 27 74  1  0
 27 75  1  0
 28 76  1  1
 29 77  1  0
 29 78  1  0
 31 79  1  6
 32 80  1  6
 11 55  1  1
 10 54  1  0
  8 52  1  0
  8 53  1  0
  4 51  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  3 48  1  0
  3 49  1  0
  3 50  1  0
 33 81  1  6
 34 82  1  0
 41 91  1  1
 42 92  1  0
 42 93  1  0
 42 94  1  0
M  END


  Mrv1652309022204592D          

 44 48  0  0  1  0            999 V2000
   -0.5353    3.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1928    3.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8928    3.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2209    2.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9490    1.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6490    2.2788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9771    1.0176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052    0.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334   -0.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4615   -0.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896   -1.4072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3155   -1.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1317   -0.1993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1405   -1.0078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9011   -1.3275    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6391   -1.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6888   -2.5197    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7889   -3.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4692   -4.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8829   -4.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3377   -5.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1190   -5.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2941   -5.1510    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1289   -5.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5335   -4.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9532   -4.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6414   -3.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457   -2.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8286   -2.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4676   -2.0286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615   -1.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7896   -1.8438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0334   -0.6314    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3052   -0.2435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0005   -2.9745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2624   -2.6058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3121   -3.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6238   -3.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8858   -3.5153    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1975   -3.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361   -2.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0981   -2.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5244   -2.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2128   -1.7823    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 31  1  6  0  0  0
 28 32  1  0  0  0  0
 11 32  1  0  0  0  0
 31 33  1  0  0  0  0
  9 33  1  0  0  0  0
 33 34  1  6  0  0  0
 17 35  1  0  0  0  0
 36 35  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 36 43  1  0  0  0  0
 36 44  1  0  0  0  0
 15 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147398

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@]2(C[C@@H]3C[C@@H](C\C=C(C)/C[C@@H](C)\C=C/CC4COC5[C@@H]4[C@@H](C=C(COC(=O)C=C(C)C)[C@H]5O)C(=O)O3)O2)OC1C

> <INCHI_IDENTIFIER>
InChI=1S/C36H52O8/c1-21(2)14-31(37)40-20-27-16-30-32-26(19-41-34(32)33(27)38)9-7-8-22(3)15-23(4)10-11-28-17-29(42-35(30)39)18-36(44-28)13-12-24(5)25(6)43-36/h7-8,10,14,16,22,24-26,28-30,32-34,38H,9,11-13,15,17-20H2,1-6H3/b8-7-,23-10-/t22-,24-,25?,26?,28+,29-,30+,32-,33+,34?,36-/m0/s1

> <INCHI_KEY>
QSHJCXWGTCXGAX-ZCVXJSSDSA-N

> <FORMULA>
C36H52O8

> <MOLECULAR_WEIGHT>
612.804

> <EXACT_MASS>
612.366218634

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
69.250014314426

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1'R,2R,4'S,5S,8'R,10'Z,13'R,14'Z,21'R,24'S)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',22'-trien-22'-yl]methyl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
5.16

> <JCHEM_LOGP>
5.883995057666665

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.536965041393682

> <JCHEM_PKA_STRONGEST_BASIC>
-3.438731490894404

> <JCHEM_POLAR_SURFACE_AREA>
100.52000000000002

> <JCHEM_REFRACTIVITY>
170.68560000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,4'S,5S,8'R,10'Z,13'R,14'Z,21'R,24'S)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.999   6.426   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.360   5.702   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.666   6.517   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.412   4.163   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.771   3.439   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.078   4.254   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.824   1.900   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.183   1.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.236  -0.364   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.595  -1.088   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.647  -2.627   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.189  -1.873   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.846  -0.372   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       7.729  -1.881   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.149  -2.478   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.526  -3.166   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.619  -4.703   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.806  -6.538   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.209  -7.958   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.115  -9.041   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.964 -10.326   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.689  -9.623   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.149  -9.615   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.841 -11.124   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.729  -9.019   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.646  -7.924   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.064  -6.498   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.072  -4.958   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.547  -5.171   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.873  -3.787   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.981  -2.718   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.341  -3.442   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.929  -1.179   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.570  -0.455   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.334  -5.552   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.957  -4.864   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.049  -6.401   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.764  -7.250   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.387  -6.562   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.102  -7.411   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.294  -5.025   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.916  -4.336   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       6.579  -4.176   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       7.864  -3.327   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   32                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   44                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   35                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31   28   11                                                  
CONECT   33   31    9   34                                                  
CONECT   34   33                                                            
CONECT   35   17   36                                                       
CONECT   36   35   37   43   44                                             
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   36                                                       
CONECT   44   36   15                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₅₂O₈

Average Mass

612.8040 Da

Monoisotopic Mass

612.36622 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@]2(C[C@@H]3C[C@@H](C\C=C(C)/C[C@@H](C)\C=C/CC4COC5[C@@H]4[C@@H](C=C(COC(=O)C=C(C)C)[C@H]5O)C(=O)O3)O2)OC1C

InChI Identifier

InChI=1S/C36H52O8/c1-21(2)14-31(37)40-20-27-16-30-32-26(19-41-34(32)33(27)38)9-7-8-22(3)15-23(4)10-11-28-17-29(42-35(30)39)18-36(44-28)13-12-24(5)25(6)43-36/h7-8,10,14,16,22,24-26,28-30,32-34,38H,9,11-13,15,17-20H2,1-6H3/b8-7-,23-10-/t22-,24-,25?,26?,28+,29-,30+,32-,33+,34?,36-/m0/s1

InChI Key

QSHJCXWGTCXGAX-ZCVXJSSDSA-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 nanchangensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as milbemycins. These are a group of macrolides with a structure containing a 16-membered lactone ring fused to a 1,7-dioxaspiroundecane ring system and to either a benzofuran (or hydrogenated derivative thereof). In some cases (e.G. Milbemycin E), the tetrahydrofuranyl ring is missing. Milbemycins can be o-glycosylated at C13 to form Avermectins. Milbemycins are produced by Streptomyces species.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Milbemycins

Direct Parent

Milbemycins

Alternative Parents

Substituents

Milbemycin
Ketal
Fatty acid ester
Fatty acyl
Oxane
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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

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

101260926

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tiwari V, Meena K, Tiwari M: Differential anti-microbial secondary metabolites in different ESKAPE pathogens explain their adaptation in the hospital setup. Infect Genet Evol. 2018 Dec;66:57-65. doi: 10.1016/j.meegid.2018.09.010. Epub 2018 Sep 15. [PubMed:30227225 ]
Frikha-Dammak D, Ayadi H, Hakim-Rekik I, Belbahri L, Maalej S: Genome analysis of the salt-resistant Paludifilum halophilum DSM 102817(T) reveals genes involved in flux-tuning of ectoines and unexplored bioactive secondary metabolites. World J Microbiol Biotechnol. 2021 Sep 22;37(10):178. doi: 10.1007/s11274-021-03147-7. [PubMed:34549358 ]
Deng Q, Xiao L, Liu Y, Zhang L, Deng Z, Zhao C: Streptomyces avermitilis industrial strain as cell factory for Ivermectin B1a production. Synth Syst Biotechnol. 2018 Dec 27;4(1):34-39. doi: 10.1016/j.synbio.2018.12.003. eCollection 2019 Mar. [PubMed:30623120 ]
He Y, Sun Y, Liu T, Zhou X, Bai L, Deng Z: Cloning of separate meilingmycin biosynthesis gene clusters by use of acyltransferase-ketoreductase didomain PCR amplification. Appl Environ Microbiol. 2010 May;76(10):3283-92. doi: 10.1128/AEM.02262-09. Epub 2010 Mar 26. [PubMed:20348291 ]
Wang P, Zhuang YP, Chu J, Zhang SL: [Regulatory effects of ammonium ions on the biosynthesis of meilingmycin]. Wei Sheng Wu Xue Bao. 2005 Jun;45(3):405-9. [PubMed:15989236 ]
Sun Y, Zhou X, Tu G, Deng Z: Identification of a gene cluster encoding meilingmycin biosynthesis among multiple polyketide synthase contigs isolated from Streptomyces nanchangensis NS3226. Arch Microbiol. 2003 Aug;180(2):101-7. doi: 10.1007/s00203-003-0564-1. Epub 2003 Jun 14. [PubMed:12811466 ]
LOTUS database [Link]

Showing NP-Card for (1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate (NP0147398)

MOL for NP0147398 ((1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate)

3D MOL for NP0147398 ((1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate)

3D SDF for NP0147398 ((1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate)

3D-SDF for NP0147398 ((1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate)

PDB for NP0147398 ((1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate)

3D PDB for NP0147398 ((1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate)

SMILES for NP0147398 ((1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate)

INCHI for NP0147398 ((1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate)

Structure for NP0147398 ((1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate)

3D Structure for NP0147398 ((1'r,2r,4's,5s,8'r,10'z,13'r,14'z,21'r,24's)-21'-hydroxy-5,6,11',13'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',22'-trien-22'-ylmethyl 3-methylbut-2-enoate)