NP-MRD: Showing NP-Card for (2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid (NP0233510)

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Record Information

Version

2.0

Created at

2022-09-06 15:08:23 UTC

Updated at

2022-09-06 15:08:23 UTC

NP-MRD ID

NP0233510

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid

Description

Monensin belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain. (2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid is found in Streptomyces cinnamonensis and Streptomyces glaucescens. Monensin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306031607302D          

 60 64  0  0  1  0            999 V2000
   -1.4587   -1.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6418   -0.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949   -1.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8043    2.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1715    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262   -0.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725    1.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262    1.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2230    1.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1345   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7897    2.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5556    0.7577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3499   -0.4716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1368    2.0631    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9195    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9195    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1570    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1345    0.6083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8205    0.7388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8019    1.0932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7445    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5070    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8650    0.1958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9820    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0400    0.1958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3831    2.3986    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9966    2.7443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3945    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3945    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8445    3.0826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1570    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3499    0.8633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2330    0.0243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7157    1.9137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8882    0.2728    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5350   -0.6007    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0506    2.8836    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3320   -0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3320    2.5559    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695    3.2704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0945   -1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0054    1.4232    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3712    0.0469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4694    1.5782    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3320    1.1270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4904    0.9309    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 12 11  1  0  0  0  0
 14 13  1  0  0  0  0
 19  2  1  1  0  0  0
 19 15  1  0  0  0  0
 20  3  1  6  0  0  0
 20 16  1  0  0  0  0
 21  4  1  1  0  0  0
 21 15  1  0  0  0  0
 22  5  1  6  0  0  0
 23  6  1  6  0  0  0
 24  7  1  1  0  0  0
 25 17  1  0  0  0  0
 25 22  1  0  0  0  0
 26 16  1  0  0  0  0
 27 11  1  0  0  0  0
 28 19  1  0  0  0  0
 26 28  1  1  0  0  0
 29 23  1  0  0  0  0
 29 24  1  0  0  0  0
 30 22  1  0  0  0  0
 30 23  1  6  0  0  0
 31 20  1  0  0  0  0
 32 24  1  0  0  0  0
 33  8  1  1  0  0  0
 33 13  1  0  0  0  0
 27 33  1  6  0  0  0
 34 10  1  1  0  0  0
 34 12  1  0  0  0  0
 31 34  1  6  0  0  0
 35 14  1  0  0  0  0
 35 17  1  0  0  0  0
 36 18  1  6  0  0  0
 36 21  1  0  0  0  0
 37 18  1  0  0  0  0
 25 38  1  1  0  0  0
 39 32  2  0  0  0  0
 40 32  1  0  0  0  0
 36 41  1  1  0  0  0
 42  9  1  0  0  0  0
 29 42  1  1  0  0  0
 43 26  1  0  0  0  0
 43 31  1  0  0  0  0
 44 27  1  0  0  0  0
 34 44  1  6  0  0  0
 45 30  1  0  0  0  0
 45 35  1  0  0  0  0
 28 46  1  6  0  0  0
 46 36  1  0  0  0  0
 33 47  1  6  0  0  0
 35 47  1  1  0  0  0
 19 48  1  6  0  0  0
 20 49  1  1  0  0  0
 21 50  1  6  0  0  0
 22 51  1  1  0  0  0
 23 52  1  1  0  0  0
 24 53  1  6  0  0  0
 25 54  1  6  0  0  0
 26 55  1  6  0  0  0
 27 56  1  1  0  0  0
 28 57  1  1  0  0  0
 29 58  1  6  0  0  0
 30 59  1  1  0  0  0
 31 60  1  1  0  0  0
M  END

     RDKit          3D

109113  0  0  0  0  0  0  0  0999 V2000
    1.8805    3.7388   -2.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635    2.8386   -1.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3730    2.0378   -0.2924 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5424    1.1990   -0.7111 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1543    0.5417    0.3305 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6653   -0.6475   -0.0952 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0980   -0.9134    0.2759 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4026   -2.1791   -0.2643 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792   -2.6424    0.2947 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5604   -2.5792    1.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7551   -4.0863   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8152   -4.2444   -1.4408 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7079   -1.7925   -0.2668 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0270   -2.2580    0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4689   -0.3567    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3943   -0.7949   -1.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0067   -0.7252   -1.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3081   -1.4206   -1.8239 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6488   -1.0657   -1.9163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1354   -0.9581   -3.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1737   -2.7673   -1.2209 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7536   -2.9280    0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1761   -4.4940   -2.8565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2276   -3.9718   -2.0694 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0233510

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](C)(C(O)=O)[C@@]([H])(OC)[C@@]([H])(C)[C@@]1([H])O[C@@]2(CC[C@@](C)(O2)[C@@]2([H])CC[C@](CC)(O2)[C@@]2([H])O[C@@]([H])(C[C@@]2([H])C)[C@@]2([H])O[C@@](O)(CO)[C@]([H])(C)C[C@]2([H])C)C[C@]([H])(O)[C@@]1([H])C

> <INCHI_IDENTIFIER>
InChI=1S/C36H62O11/c1-10-34(31-20(3)16-26(43-31)28-19(2)15-21(4)36(41,18-37)46-28)12-11-27(44-34)33(8)13-14-35(47-33)17-25(38)22(5)30(45-35)23(6)29(42-9)24(7)32(39)40/h19-31,37-38,41H,10-18H2,1-9H3,(H,39,40)/t19-,20+,21+,22+,23+,24+,25-,26-,27+,28-,29-,30-,31-,33+,34-,35+,36-/m0/s1

> <INCHI_KEY>
GAOZTHIDHYLHMS-GDMSFIFLSA-N

> <FORMULA>
C36H62O11

> <MOLECULAR_WEIGHT>
670.881

> <EXACT_MASS>
670.429212816

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
73.78382606976072

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R)-4-[(2R,5R,7S,8R,9S)-2-[(2S,2'S,3'R,5R,5'S)-2-ethyl-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolane]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
4.816267208666666

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.107248313315344

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.23615976355167

> <JCHEM_PKA_STRONGEST_BASIC>
-2.928957471028724

> <JCHEM_POLAR_SURFACE_AREA>
153.37

> <JCHEM_REFRACTIVITY>
172.37980000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R)-4-[(2R,5R,7S,8R,9S)-2-[(2S,2'S,3'R,5R,5'S)-2-ethyl-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolane]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      -2.723  -2.071   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.531  -0.117   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.777  -2.345   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.701   4.756   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.990   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.680   4.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.990   6.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.320   3.046   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.300   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.969  -1.166   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.562   2.523   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.969   1.897   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -11.616   2.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.718  -0.404   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.140  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.941   5.547   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -10.370   1.414   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.253  -0.880   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -11.455   3.851   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.450   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.450   3.437   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.760   4.771   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.718   1.136   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.532   1.379   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.964   2.041   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.990   3.437   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.680   2.104   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.348   0.366   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.300   4.771   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.808   0.366   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -10.049   4.477   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -7.460   5.123   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       5.450  -1.897   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      10.070   6.105   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      10.070   3.437   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0     -10.910   5.754   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       7.760   2.104   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -6.253   1.611   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -2.302   0.045   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       3.140   2.104   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -8.803   3.572   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       1.465   2.016   0.000  0.00  0.00           O+0
HETATM   48  H   UNK     0      -9.125   0.509   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.732  -1.121   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0     -11.294   5.383   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.220  -0.564   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0       6.220   4.771   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0       8.530   6.105   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.910  -1.897   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0      -7.477   2.657   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.693   0.087   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0     -10.209   2.946   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       8.530   3.437   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0       6.220   2.104   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.649   1.738   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5   22                                                            
CONECT    6   23                                                            
CONECT    7   24                                                            
CONECT    8   33                                                            
CONECT    9   42                                                            
CONECT   10    1   34                                                       
CONECT   11   12   27                                                       
CONECT   12   11   34                                                       
CONECT   13   14   33                                                       
CONECT   14   13   35                                                       
CONECT   15   19   21                                                       
CONECT   16   20   26                                                       
CONECT   17   25   35                                                       
CONECT   18   36   37                                                       
CONECT   19    2   15   28   48                                             
CONECT   20    3   16   31   49                                             
CONECT   21    4   15   36   50                                             
CONECT   22    5   25   30   51                                             
CONECT   23    6   29   30   52                                             
CONECT   24    7   29   32   53                                             
CONECT   25   17   22   38   54                                             
CONECT   26   16   28   43   55                                             
CONECT   27   11   33   44   56                                             
CONECT   28   19   26   46   57                                             
CONECT   29   23   24   42   58                                             
CONECT   30   22   23   45   59                                             
CONECT   31   20   34   43   60                                             
CONECT   32   24   39   40                                                  
CONECT   33    8   13   27   47                                             
CONECT   34   10   12   31   44                                             
CONECT   35   14   17   45   47                                             
CONECT   36   18   21   41   46                                             
CONECT   37   18                                                            
CONECT   38   25                                                            
CONECT   39   32                                                            
CONECT   40   32                                                            
CONECT   41   36                                                            
CONECT   42    9   29                                                       
CONECT   43   26   31                                                       
CONECT   44   27   34                                                       
CONECT   45   30   35                                                       
CONECT   46   28   36                                                       
CONECT   47   33   35                                                       
CONECT   48   19                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   23                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   28                                                            
CONECT   58   29                                                            
CONECT   59   30                                                            
CONECT   60   31                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  128    0
END

View in JSmol

Synonyms

Value	Source
Monensin-a-sodium complex	MeSH
Rumensin	MeSH
Monensin a sodium complex	MeSH
Monensin monosodium salt	MeSH
Monensin	MeSH
Monensin sodium	MeSH

Chemical Formula

C₃₆H₆₂O₁₁

Average Mass

670.8810 Da

Monoisotopic Mass

670.42921 Da

IUPAC Name

(2R,3S,4R)-4-[(2R,5R,7S,8R,9S)-2-[(2S,2'S,3'R,5R,5'S)-2-ethyl-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolane]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@](C)(C(O)=O)[C@@]([H])(OC)[C@@]([H])(C)[C@@]1([H])O[C@@]2(CC[C@@](C)(O2)[C@@]2([H])CC[C@](CC)(O2)[C@@]2([H])O[C@@]([H])(C[C@@]2([H])C)[C@@]2([H])O[C@@](O)(CO)[C@]([H])(C)C[C@]2([H])C)C[C@]([H])(O)[C@@]1([H])C

InChI Identifier

InChI=1S/C36H62O11/c1-10-34(31-20(3)16-26(43-31)28-19(2)15-21(4)36(41,18-37)46-28)12-11-27(44-34)33(8)13-14-35(47-33)17-25(38)22(5)30(45-35)23(6)29(42-9)24(7)32(39)40/h19-31,37-38,41H,10-18H2,1-9H3,(H,39,40)/t19-,20+,21+,22+,23+,24+,25-,26-,27+,28-,29-,30-,31-,33+,34-,35+,36-/m0/s1

InChI Key

GAOZTHIDHYLHMS-GDMSFIFLSA-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 cinnamonensis	LOTUS Database	35616633
Streptomyces glaucescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Heterocyclic fatty acids

Alternative Parents

Substituents

Branched fatty acid
Ketal
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Oxane
Tetrahydrofuran
Hemiacetal
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
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	2.7	ALOGPS
logP	4.82	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.24	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	153.37 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	172.38 m³·mol⁻¹	ChemAxon
Polarizability	73.78 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

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

Monensin

METLIN ID

Not Available

PubChem Compound

28263

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid (NP0233510)

MOL for NP0233510 ((2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid)

3D MOL for NP0233510 ((2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid)

3D SDF for NP0233510 ((2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid)

3D-SDF for NP0233510 ((2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid)

PDB for NP0233510 ((2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid)

3D PDB for NP0233510 ((2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid)

SMILES for NP0233510 ((2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid)

INCHI for NP0233510 ((2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid)

Structure for NP0233510 ((2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid)

3D Structure for NP0233510 ((2r,3s,4r)-4-[(2r,5r,7s,8r,9s)-2-[(2s,2's,3'r,5r,5's)-2-ethyl-5'-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolan]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid)