NP-MRD: Showing NP-Card for 5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone (NP0223967)

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Record Information

Version

2.0

Created at

2022-09-06 02:12:34 UTC

Updated at

2022-09-06 02:12:34 UTC

NP-MRD ID

NP0223967

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone

Description

Valinomycin belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. The twelve carbonyl groups are essential for the binding of metal ions, and also for solvation in polar solvent. Valinomycin is a very weakly acidic compound (based on its pKa). The molecule is "locked" into a conformation with the isopropyl groups on the exterior. Valinomycin is highly selective for potassium ions over sodium ions within the cell membrane. K ions must give up their water of hydration to pass through the pore. Valinomycin is obtained from the cells of several Streptomyces species, S. 5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone is found in Solibacillus silvestris. Fulvissimus being a notable one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231518372D          

 78 78  0  0  0  0            999 V2000
   -0.9355    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205    0.7388    0.0000 O   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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8250   -3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6184   -2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3809    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    3.4914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5395    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3809    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1133    4.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5562    2.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7229   -0.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4030   -4.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8060   -4.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5230   -2.5559    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
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 17 18  1  0  0  0  0
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 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
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 42 43  1  0  0  0  0
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  4 53  1  0  0  0  0
 53 54  2  0  0  0  0
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 55 56  1  0  0  0  0
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 47 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 38 61  1  0  0  0  0
 61 62  1  0  0  0  0
 61 63  1  0  0  0  0
 34 64  1  0  0  0  0
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 17 73  1  0  0  0  0
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 73 75  1  0  0  0  0
 13 76  1  0  0  0  0
 76 77  1  0  0  0  0
 76 78  1  0  0  0  0
M  END

     RDKit          3D

168168  0  0  0  0  0  0  0  0999 V2000
    2.2865   -5.0505    1.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0128   -5.4921    0.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4453   -6.9582    0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2279   -5.3856   -1.2170 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9352   -4.0430   -1.6599 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3441   -2.8224   -1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4412   -2.0545   -0.6588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7165   -2.2370   -1.0902 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7202   -2.9397   -1.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0357   -2.0639    0.2426 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1390   -2.2100    0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -3.1735    1.8357 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3846   -1.3717    0.9599 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5341   -2.3235    1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6471   -3.4503    0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8589   -1.6361    1.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5958   -0.6774   -0.2777 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2015    0.6137   -0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5058    0.7052   -1.7186 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4641    1.8934    0.0354 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7933    1.9007    0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9426    1.6659   -0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0790    3.1931    1.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4414    2.3751    0.8414 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5797    6.6021    1.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384    5.4737    2.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3205    3.6042   -1.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.3924    4.7384    0.7843 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0368   -0.8710   -1.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9826   -1.0805   -2.6833 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3765   -4.0564   -1.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1282   -4.1368   -3.0909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5775   -5.0006   -0.9917 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4834   -6.1548   -0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8847   -6.8181   -2.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7690   -7.2528    0.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004231518372D          

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    3.3809    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1133    4.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5562    2.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7229   -0.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4030   -4.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8060   -4.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4735   -3.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -2.5559    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
  4 53  1  0  0  0  0
 53 54  2  0  0  0  0
 51 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  1  0  0  0  0
 47 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 38 61  1  0  0  0  0
 61 62  1  0  0  0  0
 61 63  1  0  0  0  0
 34 64  1  0  0  0  0
 64 65  1  0  0  0  0
 64 66  1  0  0  0  0
 30 67  1  0  0  0  0
 67 68  1  0  0  0  0
 67 69  1  0  0  0  0
 21 70  1  0  0  0  0
 70 71  1  0  0  0  0
 70 72  1  0  0  0  0
 17 73  1  0  0  0  0
 73 74  1  0  0  0  0
 73 75  1  0  0  0  0
 13 76  1  0  0  0  0
 76 77  1  0  0  0  0
 76 78  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223967

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1NC(=O)C(C)OC(=O)C(NC(=O)C(OC(=O)C(NC(=O)C(C)OC(=O)C(NC(=O)C(OC(=O)C(NC(=O)C(C)OC(=O)C(NC(=O)C(OC1=O)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C54H90N6O18/c1-22(2)34-49(67)73-31(19)43(61)55-38(26(9)10)53(71)77-41(29(15)16)47(65)59-36(24(5)6)51(69)75-33(21)45(63)57-39(27(11)12)54(72)78-42(30(17)18)48(66)60-35(23(3)4)50(68)74-32(20)44(62)56-37(25(7)8)52(70)76-40(28(13)14)46(64)58-34/h22-42H,1-21H3,(H,55,61)(H,56,62)(H,57,63)(H,58,64)(H,59,65)(H,60,66)

> <INCHI_KEY>
FCFNRCROJUBPLU-UHFFFAOYSA-N

> <FORMULA>
C54H90N6O18

> <MOLECULAR_WEIGHT>
1111.338

> <EXACT_MASS>
1110.631160082

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
168

> <JCHEM_AVERAGE_POLARIZABILITY>
115.98429871027926

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,18,30-trimethyl-3,9,12,15,21,24,27,33,36-nonakis(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
5.924192648000002

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.549843893095915

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.189128966162498

> <JCHEM_POLAR_SURFACE_AREA>
332.3999999999999

> <JCHEM_REFRACTIVITY>
276.83040000000017

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
valinomycin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -1.746   4.977   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.976   3.644   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.746   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564   3.644   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.532   1.379   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.564  -2.104   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.976  -2.104   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -3.437   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.874  -3.437   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.874  -4.977   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.540  -5.747   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.207  -5.747   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.541  -4.977   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.311  -6.311   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.541  -7.645   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.851  -6.311   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       8.621  -4.977   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       9.955  -5.747   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.955  -7.287   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.288  -4.977   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.622  -5.747   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.288  -3.437   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.828  -3.437   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.598  -4.771   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      13.598  -2.104   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      12.828  -0.770   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      14.162   0.000   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.496  -0.770   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.162   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.828   2.310   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      13.598   3.644   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      15.138   3.644   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.828   4.977   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0      11.288   4.977   0.000  0.00  0.00           N+0
HETATM   40  C   UNK     0      11.288   6.517   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      12.622   7.287   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       9.955   7.287   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.955   8.827   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       8.621   6.517   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       7.851   7.851   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       8.621   9.185   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       6.311   7.851   0.000  0.00  0.00           C+0
HETATM   48  N   UNK     0       5.541   6.517   0.000  0.00  0.00           N+0
HETATM   49  C   UNK     0       4.207   7.287   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       4.207   8.827   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       2.874   6.517   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       2.874   4.977   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       1.334   4.977   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       0.564   6.311   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       1.540   7.287   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       0.034   6.967   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       1.540   8.827   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       5.541   9.185   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       4.076   9.661   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       6.311  10.518   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      13.598   6.311   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      13.278   7.817   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      15.138   6.311   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      15.496   2.310   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      15.972   3.775   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      16.829   1.540   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      15.138  -2.104   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      16.283  -1.073   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      15.908  -3.437   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0       8.621  -7.645   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      10.086  -8.121   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0       7.851  -8.978   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0       4.207  -7.287   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0       5.238  -8.432   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0       2.874  -8.057   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0       0.564  -4.771   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0       0.884  -6.277   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      -0.976  -4.771   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   53                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   76                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   73                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   70                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   67                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   64                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   61                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   58                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52   55                                                  
CONECT   52   51   53                                                       
CONECT   53   52    4   54                                                  
CONECT   54   53                                                            
CONECT   55   51   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55                                                            
CONECT   58   47   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58                                                            
CONECT   61   38   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61                                                            
CONECT   64   34   65   66                                                  
CONECT   65   64                                                            
CONECT   66   64                                                            
CONECT   67   30   68   69                                                  
CONECT   68   67                                                            
CONECT   69   67                                                            
CONECT   70   21   71   72                                                  
CONECT   71   70                                                            
CONECT   72   70                                                            
CONECT   73   17   74   75                                                  
CONECT   74   73                                                            
CONECT   75   73                                                            
CONECT   76   13   77   78                                                  
CONECT   77   76                                                            
CONECT   78   76                                                            
MASTER        0    0    0    0    0    0    0    0   78    0  156    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₄H₉₀N₆O₁₈

Average Mass

1111.3380 Da

Monoisotopic Mass

1110.63116 Da

IUPAC Name

6,18,30-trimethyl-3,9,12,15,21,24,27,33,36-nonakis(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone

Traditional Name

valinomycin

CAS Registry Number

Not Available

SMILES

CC(C)C1NC(=O)C(C)OC(=O)C(NC(=O)C(OC(=O)C(NC(=O)C(C)OC(=O)C(NC(=O)C(OC(=O)C(NC(=O)C(C)OC(=O)C(NC(=O)C(OC1=O)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C

InChI Identifier

InChI=1S/C54H90N6O18/c1-22(2)34-49(67)73-31(19)43(61)55-38(26(9)10)53(71)77-41(29(15)16)47(65)59-36(24(5)6)51(69)75-33(21)45(63)57-39(27(11)12)54(72)78-42(30(17)18)48(66)60-35(23(3)4)50(68)74-32(20)44(62)56-37(25(7)8)52(70)76-40(28(13)14)46(64)58-34/h22-42H,1-21H3,(H,55,61)(H,56,62)(H,57,63)(H,58,64)(H,59,65)(H,60,66)

InChI Key

FCFNRCROJUBPLU-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, 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
Solibacillus silvestris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Hexacarboxylic acid or derivatives
Alpha-amino acid ester
Macrolactam
Macrolide
Alpha-amino acid or derivatives
Cyclic carboximidic acid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	3.07	ALOGPS
logP	5.92	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	11.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	332.4 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	276.83 m³·mol⁻¹	ChemAxon
Polarizability	115.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

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

Valinomycin

METLIN ID

Not Available

PubChem Compound

5649

PDB ID

Not Available

ChEBI ID

95123

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone (NP0223967)

MOL for NP0223967 (5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone)

3D MOL for NP0223967 (5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone)

3D SDF for NP0223967 (5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone)

3D-SDF for NP0223967 (5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone)

PDB for NP0223967 (5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone)

3D PDB for NP0223967 (5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone)

SMILES for NP0223967 (5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone)

INCHI for NP0223967 (5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone)

Structure for NP0223967 (5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone)

3D Structure for NP0223967 (5,11,17,23,29,35-hexahydroxy-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone)