NP-MRD: Showing NP-Card for (2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid (NP0308650)

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Record Information

Version

2.0

Created at

2022-09-11 02:35:33 UTC

Updated at

2022-09-11 02:35:33 UTC

NP-MRD ID

NP0308650

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid

Description

Volicitin belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid is found in Spodoptera frugiperda. (2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid was first documented in 2015 (PMID: 26454474). Based on a literature review a small amount of articles have been published on Volicitin (PMID: 35834769) (PMID: 34618284) (PMID: 34413869) (PMID: 34052696).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112204352D          

 30 29  0  0  1  0            999 V2000
    7.2849    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    3.7934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8559    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8572    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    3.7934    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  1  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 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
 19 20  1  4  0  0  0
 19 21  2  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 68 67  0  0  0  0  0  0  0  0999 V2000
   -6.4244    2.8597    1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7733    2.8212    0.3088 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8344    2.1507    0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2385    2.1455   -1.3022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5596    1.4352    1.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6435   -0.0592    0.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2577   -0.6733    0.7627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4811   -0.1016   -0.3073 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2197   -0.3146   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6437   -1.1081    0.5907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3496    0.2366   -1.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2753    1.1333   -0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3193    0.5426    0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5323   -0.6235   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5759   -1.1943    0.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4804   -0.2790    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1218   -0.7669   -0.7904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4338   -0.7734   -0.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3134    0.1832   -0.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1728   -0.4732    0.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4700   -0.4214    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2091    0.2876   -0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0726   -0.6675   -0.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3739   -0.4890   -0.9305 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0757    0.6054   -0.2602 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1833    0.3529    1.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4021    0.6519   -0.7606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3623   -2.1468    0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8012   -2.6828   -0.3669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0603   -2.9351    1.5095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8407    2.8949   -1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6010    1.8409    1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1092    1.6545    2.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1341   -0.4903    1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2631   -0.2780   -0.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7943   -0.4992    1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1980   -1.9825    0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9892   -0.5480   -2.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0287    0.8805   -2.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486    1.5763   -1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7818    2.0100   -0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5756    1.3495    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8046    0.2786    0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9644   -0.3319   -1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2040   -1.4453   -0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1396   -1.5562    1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913   -2.0777    0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0948    0.5643    1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1248   -0.8697    1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6814    0.7348   -0.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9221    1.1053    0.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5647   -1.5485   -1.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9378   -1.5790   -1.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8623    0.6924   -0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8038    1.0149    0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6277   -1.0159    1.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0575   -0.9439    1.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9425    0.9916    0.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    0.9728   -0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6416   -1.5143   -1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9668   -1.2251   -1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6423    1.6133   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8658    1.2543    1.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2165    0.0528    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.4817   -3.8144    1.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
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 11  9  1  0
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  5  3  1  0
  3  4  1  0
  3  2  2  0
  7 29  1  0
 29 31  1  0
 29 30  2  0
 27 64  1  0
 27 65  1  0
 27 66  1  0
 26 63  1  1
 28 67  1  0
 25 62  1  0
 24 61  1  0
 23 59  1  0
 23 60  1  0
 22 58  1  0
 21 57  1  0
 20 55  1  0
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 16 49  1  0
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 13 44  1  0
 12 41  1  0
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 11 39  1  0
 11 40  1  0
 10 38  1  0
  7 37  1  1
  6 35  1  0
  6 36  1  0
  5 33  1  0
  5 34  1  0
  4 32  1  0
  2  1  1  0
 31 68  1  0
M  END


  Mrv1652309112204352D          

 30 29  0  0  1  0            999 V2000
    7.2849    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    3.7934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8559    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8572    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    3.7934    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  1  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 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
 19 20  1  4  0  0  0
 19 21  2  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308650

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)\C=C/C\C=C/C\C=C/CCCCCCCC(O)=N[C@@H](CCC(O)=N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H38N2O5/c1-19(26)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-22(28)25-20(23(29)30)17-18-21(24)27/h2-3,7,9,13,15,19-20,26H,4-6,8,10-12,14,16-18H2,1H3,(H2,24,27)(H,25,28)(H,29,30)/b3-2-,9-7-,15-13-/t19-,20+/m1/s1

> <INCHI_KEY>
YDUZXFXPORORCL-VJEDGTANSA-N

> <FORMULA>
C23H38N2O5

> <MOLECULAR_WEIGHT>
422.566

> <EXACT_MASS>
422.278072332

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
48.12792767612699

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(9Z,12Z,15Z,17R)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

> <JCHEM_LOGP>
1.9815743256599478

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.960219774017147

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.42831372344633056

> <JCHEM_PKA_STRONGEST_BASIC>
12.9245745582831

> <JCHEM_POLAR_SURFACE_AREA>
134.2

> <JCHEM_REFRACTIVITY>
132.5962

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(9Z,12Z,15Z,17R)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      13.598   6.311   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.265   7.081   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.931   6.311   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.265   8.621   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.931   9.391   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.597   8.621   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.264   9.391   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.930   8.621   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.930   7.081   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.596   6.311   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.266   6.311   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      17.599   4.001   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      18.933   4.771   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.267   4.001   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.600   4.771   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.934   4.001   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      24.268   4.771   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0      22.934   2.461   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      18.933   6.311   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      17.599   7.081   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      20.267   7.081   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END

View in JSmol

Synonyms

Value	Source
N-(17-Hydroxylinolenoyl)glutamine	MeSH

Chemical Formula

C₂₃H₃₈N₂O₅

Average Mass

422.5660 Da

Monoisotopic Mass

422.27807 Da

IUPAC Name

(2S)-2-{[(9Z,12Z,15Z,17R)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

Traditional Name

(2S)-2-{[(9Z,12Z,15Z,17R)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](O)\C=C/C\C=C/C\C=C/CCCCCCCC(O)=N[C@@H](CCC(O)=N)C(O)=O

InChI Identifier

InChI=1S/C23H38N2O5/c1-19(26)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-22(28)25-20(23(29)30)17-18-21(24)27/h2-3,7,9,13,15,19-20,26H,4-6,8,10-12,14,16-18H2,1H3,(H2,24,27)(H,25,28)(H,29,30)/b3-2-,9-7-,15-13-/t19-,20+/m1/s1

InChI Key

YDUZXFXPORORCL-VJEDGTANSA-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
Spodoptera frugiperda	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamine and derivatives

Alternative Parents

Substituents

Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
N-acyl-l-glutamine
Fatty amide
N-acyl-amine
Fatty acyl
Secondary carboxylic acid amide
Secondary alcohol
Primary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	1.98	ChemAxon
pKa (Strongest Acidic)	-0.43	ChemAxon
pKa (Strongest Basic)	12.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	134.2 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	132.6 m³·mol⁻¹	ChemAxon
Polarizability	48.13 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

79536123

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101095716

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tumlinson JH: Complex and Beautiful: Unraveling the Intricate Communication Systems Among Plants and Insects. Annu Rev Entomol. 2023 Jan 23;68:1-12. doi: 10.1146/annurev-ento-021622-111028. Epub 2022 Jul 14. [PubMed:35834769 ]
Jones AC, Felton GW, Tumlinson JH: The dual function of elicitors and effectors from insects: reviewing the 'arms race' against plant defenses. Plant Mol Biol. 2022 Jul;109(4-5):427-445. doi: 10.1007/s11103-021-01203-2. Epub 2021 Oct 7. [PubMed:34618284 ]
Arce CM, Besomi G, Glauser G, Turlings TCJ: Caterpillar-Induced Volatile Emissions in Cotton: The Relative Importance of Damage and Insect-Derived Factors. Front Plant Sci. 2021 Aug 3;12:709858. doi: 10.3389/fpls.2021.709858. eCollection 2021. [PubMed:34413869 ]
Nishidono Y, Niwa K, Kitajima A, Watanabe S, Tezuka Y, Arita M, Takabayashi J, Tanaka K: alpha-Linolenic acid in Papilio machaon larvae regurgitant induces a defensive response in Apiaceae. Phytochemistry. 2021 Aug;188:112796. doi: 10.1016/j.phytochem.2021.112796. Epub 2021 May 27. [PubMed:34052696 ]
LeClair G, Williams M, Silk P, Eveleigh E, Mayo P, Brophy M, Francis B: Spruce Budworm (Lepidoptera: Tortricidae) Oral Secretions II: Chemistry. Environ Entomol. 2015 Dec;44(6):1531-43. doi: 10.1093/ee/nvv149. Epub 2015 Oct 9. [PubMed:26454474 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid (NP0308650)

MOL for NP0308650 ((2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D MOL for NP0308650 ((2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D SDF for NP0308650 ((2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D-SDF for NP0308650 ((2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

PDB for NP0308650 ((2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D PDB for NP0308650 ((2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

SMILES for NP0308650 ((2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

INCHI for NP0308650 ((2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

Structure for NP0308650 ((2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D Structure for NP0308650 ((2s)-2-{[(9z,12z,15z,17r)-1,17-dihydroxyoctadeca-9,12,15-trien-1-ylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)