NP-MRD: Showing NP-Card for (1's,2s,3r,4'r,5s,6s,7's,9's,10'e,12'e,14'r,16'e,19'r)-6-[(2e)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one (NP0220517)

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Record Information

Version

2.0

Created at

2022-09-05 21:51:04 UTC

Updated at

2022-09-05 21:51:04 UTC

NP-MRD ID

NP0220517

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2s,3r,4'r,5s,6s,7's,9's,10'e,12'e,14'r,16'e,19'r)-6-[(2e)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one

Description

VM48640 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. Based on a literature review very few articles have been published on VM48640.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223512D          

 43 46  0  0  1  0            999 V2000
   12.3253   -1.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5793   -1.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5115   -0.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1896    0.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7655    0.0601    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0874   -0.4097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3414   -0.0573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5955    0.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9173   -0.1748    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9851   -0.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7311   -1.3494    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7989   -2.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1208   -2.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1886   -3.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9345   -3.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5104   -3.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7645   -3.5811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0863   -4.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6967   -2.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9507   -2.4065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8829   -1.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1369   -1.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588   -1.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7128   -1.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0691   -0.4097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3910   -0.8795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232   -0.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2553    0.7649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5094    1.1172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8312    0.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9335    1.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8657    2.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6794    0.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7473    0.0601    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4932   -0.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5610   -1.1145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1714    0.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4092   -0.8795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2736    0.7649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5277    1.1172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9518    1.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6977    0.8823    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3759    1.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 34 33  1  1  0  0  0
 25 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  9 37  1  0  0  0  0
 11 38  1  0  0  0  0
  7 38  1  0  0  0  0
  7 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
  5 42  1  0  0  0  0
 42 43  1  6  0  0  0
M  END


  Mrv1652309052223512D          

 43 46  0  0  1  0            999 V2000
   12.3253   -1.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5793   -1.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5115   -0.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1896    0.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7655    0.0601    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0874   -0.4097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3414   -0.0573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5955    0.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9173   -0.1748    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9851   -0.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7311   -1.3494    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7989   -2.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1208   -2.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1886   -3.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9345   -3.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5104   -3.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7645   -3.5811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0863   -4.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6967   -2.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9507   -2.4065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8829   -1.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1369   -1.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588   -1.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7128   -1.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0691   -0.4097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3910   -0.8795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232   -0.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2553    0.7649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5094    1.1172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8312    0.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9335    1.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8657    2.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6794    0.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7473    0.0601    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4932   -0.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5610   -1.1145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1714    0.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4092   -0.8795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2736    0.7649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5277    1.1172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9518    1.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6977    0.8823    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3759    1.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 34 33  1  1  0  0  0
 25 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  9 37  1  0  0  0  0
 11 38  1  0  0  0  0
  7 38  1  0  0  0  0
  7 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
  5 42  1  0  0  0  0
 42 43  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0220517

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@]2(O)[C@@H](C=C1C)C(=O)O[C@H]1C[C@@H](C\C=C(C)\C[C@@H](C)\C=C\C=C2/CO)O[C@@]2(C1)O[C@@H]([C@@H](C)C[C@H]2O)C(\C)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C35H52O8/c1-8-23(4)32-25(6)16-31(37)35(43-32)18-28-17-27(42-35)13-12-22(3)14-21(2)10-9-11-26(20-36)34(39)19-30(40-7)24(5)15-29(34)33(38)41-28/h8-12,15,21,25,27-32,36-37,39H,13-14,16-20H2,1-7H3/b10-9+,22-12+,23-8+,26-11+/t21-,25-,27+,28-,29-,30-,31+,32+,34+,35-/m0/s1

> <INCHI_KEY>
RZZQRUATDNDCKY-BDIOVGCPSA-N

> <FORMULA>
C35H52O8

> <MOLECULAR_WEIGHT>
600.793

> <EXACT_MASS>
600.366218634

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
67.08420981124308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2S,3R,4'R,5S,6S,7'S,9'S,10'E,12'E,14'R,16'E,19'R)-6-[(2E)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0^{4,9}]tricosane]-5',10',12',16'-tetraen-3'-one

> <JCHEM_LOGP>
4.336814937333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.675174989537261

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.040610815870107

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7710049663174017

> <JCHEM_POLAR_SURFACE_AREA>
114.68000000000002

> <JCHEM_REFRACTIVITY>
169.85720000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,3R,4'R,5S,6S,7'S,9'S,10'E,12'E,14'R,16'E,19'R)-6-[(2E)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0^{4,9}]tricosane]-5',10',12',16'-tetraen-3'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      23.007  -2.738   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.615  -2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.488  -0.546   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.754   0.331   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.096   0.112   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      18.830  -0.765   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      17.437  -0.107   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.045   0.551   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.779  -0.326   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.906  -1.861   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.298  -2.519   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.425  -4.054   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.159  -4.931   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.285  -6.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.678  -7.123   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.019  -7.342   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.627  -6.685   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.361  -7.562   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.500  -5.150   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.108  -4.492   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.981  -2.957   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.589  -2.300   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.323  -3.177   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.931  -2.519   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.462  -0.765   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.196  -1.642   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.070  -0.107   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.943   1.428   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.551   2.086   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.285   1.209   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.209   2.305   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.083   3.840   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.602   1.647   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.728   0.112   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.121  -0.546   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.247  -2.080   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      13.387   0.331   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      17.564  -1.642   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      17.311   1.428   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      15.918   2.086   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      18.577   2.305   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.969   1.647   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      21.235   2.524   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   42                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   38   39                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   37                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   38                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27   34                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   25   35                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    9                                                       
CONECT   38   11    7                                                       
CONECT   39    7   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41    5   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₅₂O₈

Average Mass

600.7930 Da

Monoisotopic Mass

600.36622 Da

IUPAC Name

(1'S,2S,3R,4'R,5S,6S,7'S,9'S,10'E,12'E,14'R,16'E,19'R)-6-[(2E)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0^{4,9}]tricosane]-5',10',12',16'-tetraen-3'-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@]2(O)[C@@H](C=C1C)C(=O)O[C@H]1C[C@@H](C\C=C(C)\C[C@@H](C)\C=C\C=C2/CO)O[C@@]2(C1)O[C@@H]([C@@H](C)C[C@H]2O)C(\C)=C\C

InChI Identifier

InChI=1S/C35H52O8/c1-8-23(4)32-25(6)16-31(37)35(43-32)18-28-17-27(42-35)13-12-22(3)14-21(2)10-9-11-26(20-36)34(39)19-30(40-7)24(5)15-29(34)33(38)41-28/h8-12,15,21,25,27-32,36-37,39H,13-14,16-20H2,1-7H3/b10-9+,22-12+,23-8+,26-11+/t21-,25-,27+,28-,29-,30-,31+,32+,34+,35-/m0/s1

InChI Key

RZZQRUATDNDCKY-BDIOVGCPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Oxane
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Acetal
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Primary 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
logP	4.34	ChemAxon
pKa (Strongest Acidic)	13.04	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	169.86 m³·mol⁻¹	ChemAxon
Polarizability	67.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

8874169

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10698827

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1's,2s,3r,4'r,5s,6s,7's,9's,10'e,12'e,14'r,16'e,19'r)-6-[(2e)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one (NP0220517)

MOL for NP0220517 ((1's,2s,3r,4'r,5s,6s,7's,9's,10'e,12'e,14'r,16'e,19'r)-6-[(2e)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

3D MOL for NP0220517 ((1's,2s,3r,4'r,5s,6s,7's,9's,10'e,12'e,14'r,16'e,19'r)-6-[(2e)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

3D SDF for NP0220517 ((1's,2s,3r,4'r,5s,6s,7's,9's,10'e,12'e,14'r,16'e,19'r)-6-[(2e)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

3D-SDF for NP0220517 ((1's,2s,3r,4'r,5s,6s,7's,9's,10'e,12'e,14'r,16'e,19'r)-6-[(2e)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

PDB for NP0220517 ((1's,2s,3r,4'r,5s,6s,7's,9's,10'e,12'e,14'r,16'e,19'r)-6-[(2e)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

3D PDB for NP0220517 ((1's,2s,3r,4'r,5s,6s,7's,9's,10'e,12'e,14'r,16'e,19'r)-6-[(2e)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

SMILES for NP0220517 ((1's,2s,3r,4'r,5s,6s,7's,9's,10'e,12'e,14'r,16'e,19'r)-6-[(2e)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

INCHI for NP0220517 ((1's,2s,3r,4'r,5s,6s,7's,9's,10'e,12'e,14'r,16'e,19'r)-6-[(2e)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

Structure for NP0220517 ((1's,2s,3r,4'r,5s,6s,7's,9's,10'e,12'e,14'r,16'e,19'r)-6-[(2e)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)

3D Structure for NP0220517 ((1's,2s,3r,4'r,5s,6s,7's,9's,10'e,12'e,14'r,16'e,19'r)-6-[(2e)-but-2-en-2-yl]-3,9'-dihydroxy-10'-(hydroxymethyl)-7'-methoxy-5,6',14',16'-tetramethyl-2',20'-dioxaspiro[oxane-2,21'-tricyclo[17.3.1.0⁴,⁹]tricosane]-5',10',12',16'-tetraen-3'-one)