NP-MRD: Showing NP-Card for 3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate (NP0245215)

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Record Information

Version

1.0

Created at

2022-09-07 06:12:38 UTC

Updated at

2022-09-07 06:12:38 UTC

NP-MRD ID

NP0245215

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate

Description

{3,21',24'-Trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]Pentacosane]-10',14',16',22'-tetraen-22'-yl}methyl 1H-pyrrole-2-carboxylate 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. 3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate is found in Streptomyces bingchenggensis. Based on a literature review very few articles have been published on {3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]Pentacosane]-10',14',16',22'-tetraen-22'-yl}methyl 1H-pyrrole-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072208122D          

 54 59  0  0  0  0            999 V2000
   11.8233    5.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7101    4.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9458    4.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2947    4.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8327    3.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4838    2.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0684    3.1033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9553    2.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6064    1.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3707    2.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4933    0.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1444    0.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7290    0.6516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0778    1.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4267    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6624    1.3542    0.0000 C   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
  3  4  1  0  0  0  0
  3  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
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  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
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 26 24  1  4  0  0  0
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 29 30  1  0  0  0  0
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 31 32  1  0  0  0  0
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 18 52  1  0  0  0  0
 14 52  1  0  0  0  0
 14 53  1  0  0  0  0
  8 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END

     RDKit          3D

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   10.9271    4.2497   -0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3549    3.1103   -2.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8802    2.3402   -2.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7890    1.8483   -0.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4216   -0.4725   -0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5794   -2.6787    2.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3134    3.1824   -2.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6720    1.6593   -3.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1286    0.7935   -1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7788    2.4896   -2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0854    3.6886    0.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6244    4.8899   -1.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9998    4.9872    0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0216    3.9738   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8 53  1  0
 53 54  1  0
 53 51  1  0
 51 52  1  0
 51 50  1  0
 11 50  1  6
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
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 17 18  2  0
 18 19  1  0
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 21 22  1  0
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 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 32 42  2  0
 42 43  1  0
 43 44  1  0
 44 45  2  0
 44 46  1  0
 43 47  1  0
 47 48  1  1
 15 49  1  0
 11  9  1  0
  9 10  1  0
  9  8  1  0
 49 11  1  0
 46 13  1  0
 47 26  1  0
 47 29  1  0
 41 37  1  0
  1 55  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  0
  2 59  1  0
  3 60  1  6
  4 61  1  0
  4 62  1  0
  4 63  1  0
  8 64  1  1
 53106  1  1
 54107  1  0
 54108  1  0
 54109  1  0
 51102  1  6
 52103  1  0
 52104  1  0
 52105  1  0
 12 67  1  0
 12 68  1  0
 13 69  1  6
 14 70  1  0
 14 71  1  0
 15 72  1  6
 16 73  1  0
 16 74  1  0
 17 75  1  0
 19 76  1  0
 19 77  1  0
 19 78  1  0
 20 79  1  0
 20 80  1  0
 21 81  1  1
 22 82  1  0
 22 83  1  0
 22 84  1  0
 23 85  1  0
 24 86  1  0
 25 87  1  0
 27 88  1  0
 27 89  1  0
 29 90  1  6
 30 91  1  1
 31 92  1  0
 33 93  1  0
 33 94  1  0
 38 95  1  0
 39 96  1  0
 40 97  1  0
 41 98  1  0
 42 99  1  0
 43100  1  6
 48101  1  0
  9 65  1  1
 10 66  1  0
M  END


  Mrv1652309072208122D          

 54 59  0  0  0  0            999 V2000
   11.8233    5.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7101    4.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9458    4.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2947    4.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8327    3.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4838    2.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0684    3.1033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9553    2.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6064    1.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3707    2.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4933    0.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1444    0.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7290    0.6516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0778    1.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4267    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6624    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5492    0.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2004    0.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0873   -0.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3230   -1.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2098   -1.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8610   -2.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4455   -2.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7944   -1.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0301   -2.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9075   -0.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2564   -0.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3695    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7184    0.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8955    0.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5849    1.6340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2158    2.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2429    2.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5423    3.4259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705    3.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9976    4.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7252    4.5923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7523    5.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4800    5.8057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0518    5.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2875    5.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7559    6.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917    6.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9926    6.6755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6710    2.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5958    2.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2469    1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1338    0.7330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0112    1.8608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8315    1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188    2.5665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9647    0.3410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1910    1.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5398    2.4820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  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  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  4  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 24  1  4  0  0  0
 26 27  2  0  0  0  0
 28 27  1  4  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 40 44  1  0  0  0  0
 35 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
 16 49  1  0  0  0  0
 46 50  1  0  0  0  0
 29 50  1  0  0  0  0
 32 50  1  0  0  0  0
 50 51  1  0  0  0  0
 18 52  1  0  0  0  0
 14 52  1  0  0  0  0
 14 53  1  0  0  0  0
  8 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245215

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)OC1C(C)C(C)OC2(CC3CC(CC=C(C)CC(C)C=CC=C4COC5C(O)C(COC(=O)C6=CC=CN6)=CC(C(=O)O3)C45O)O2)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C41H55NO12/c1-7-24(4)37(45)52-34-25(5)26(6)53-40(35(34)44)19-30-18-29(54-40)14-13-23(3)16-22(2)10-8-11-28-21-49-36-33(43)27(17-31(38(46)51-30)41(28,36)48)20-50-39(47)32-12-9-15-42-32/h8-13,15,17,22,24-26,29-31,33-36,42-44,48H,7,14,16,18-21H2,1-6H3

> <INCHI_KEY>
LFQNVDAPCWUUFS-UHFFFAOYSA-N

> <FORMULA>
C41H55NO12

> <MOLECULAR_WEIGHT>
753.886

> <EXACT_MASS>
753.372426215

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
80.94177877501245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-22'-yl}methyl 1H-pyrrole-2-carboxylate

> <JCHEM_LOGP>
4.470942438999997

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.48302064184838

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.985368736563407

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4809360221802166

> <JCHEM_POLAR_SURFACE_AREA>
183.06999999999996

> <JCHEM_REFRACTIVITY>
198.77300000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1H-pyrrole-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      22.070  10.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.859   8.478   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.432   7.898   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.217   8.844   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.221   6.373   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      21.436   5.427   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      18.794   5.793   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      18.583   4.267   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.799   3.322   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.225   3.902   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.587   1.796   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.803   0.851   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      18.161   1.216   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      16.945   2.162   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.730   3.108   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.303   2.528   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.092   1.002   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.307   0.057   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.096  -1.469   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.670  -2.049   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.458  -3.574   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.674  -4.520   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.032  -4.154   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.816  -3.208   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.390  -3.788   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.027  -1.683   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.812  -0.737   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.023   0.788   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.808   1.734   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.272   1.623   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.692   3.050   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.869   4.042   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.920   5.582   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.612   6.395   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.278   6.307   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.329   7.846   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      10.687   8.572   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.738  10.111   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      12.096  10.837   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       9.430  10.925   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.003  10.345   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.011  11.523   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       7.824  12.830   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0       9.319  12.461   0.000  0.00  0.00           N+0
HETATM   45  C   UNK     0      10.586   5.494   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      10.445   3.839   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      11.661   2.894   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      11.450   1.368   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      13.088   3.473   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       9.019   3.259   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       9.182   4.791   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      16.734   0.637   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      17.156   3.687   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      15.941   4.633   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   53                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   52   53                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   49                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   52                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   50                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   50                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   45                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   44                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   40                                                       
CONECT   45   35   46                                                       
CONECT   46   45   47   50                                                  
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   16                                                       
CONECT   50   46   29   32   51                                             
CONECT   51   50                                                            
CONECT   52   18   14                                                       
CONECT   53   14    8   54                                                  
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  118    0
END

View in JSmol

Synonyms

Value	Source
{3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1,.0,]pentacosane]-10',14',16',22'-tetraen-22'-yl}methyl 1H-pyrrole-2-carboxylic acid	Generator

Chemical Formula

C₄₁H₅₅NO₁₂

Average Mass

753.8860 Da

Monoisotopic Mass

753.37243 Da

IUPAC Name

{3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-22'-yl}methyl 1H-pyrrole-2-carboxylate

Traditional Name

3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1H-pyrrole-2-carboxylate

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)OC1C(C)C(C)OC2(CC3CC(CC=C(C)CC(C)C=CC=C4COC5C(O)C(COC(=O)C6=CC=CN6)=CC(C(=O)O3)C45O)O2)C1O

InChI Identifier

InChI=1S/C41H55NO12/c1-7-24(4)37(45)52-34-25(5)26(6)53-40(35(34)44)19-30-18-29(54-40)14-13-23(3)16-22(2)10-8-11-28-21-49-36-33(43)27(17-31(38(46)51-30)41(28,36)48)20-50-39(47)32-12-9-15-42-32/h8-13,15,17,22,24-26,29-31,33-36,42-44,48H,7,14,16,18-21H2,1-6H3

InChI Key

LFQNVDAPCWUUFS-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 bingchenggensis	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
Tricarboxylic acid or derivatives
Pyrrole-2-carboxylic acid or derivatives
Ketal
Fatty acid ester
Fatty acyl
Substituted pyrrole
Oxane
Monosaccharide
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Pyrrole
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.47	ChemAxon
pKa (Strongest Acidic)	11.99	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	183.07 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	198.77 m³·mol⁻¹	ChemAxon
Polarizability	80.94 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74075998

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate (NP0245215)

MOL for NP0245215 (3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate)

3D MOL for NP0245215 (3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate)

3D SDF for NP0245215 (3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate)

3D-SDF for NP0245215 (3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate)

PDB for NP0245215 (3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate)

3D PDB for NP0245215 (3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate)

SMILES for NP0245215 (3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate)

INCHI for NP0245215 (3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate)

Structure for NP0245215 (3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate)

3D Structure for NP0245215 (3,21',24'-trihydroxy-5,6,11',13'-tetramethyl-4-[(2-methylbutanoyl)oxy]-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-22'-ylmethyl 1h-pyrrole-2-carboxylate)