NP-MRD: Showing NP-Card for (2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid (NP0252390)

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Record Information

Version

2.0

Created at

2022-09-07 15:53:19 UTC

Updated at

2022-09-07 15:53:20 UTC

NP-MRD ID

NP0252390

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid

Description

Boletocrocin C belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid is found in Crocinoboletus laetissimus. Based on a literature review very few articles have been published on Boletocrocin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217532D          

 32 31  0  0  1  0            999 V2000
   10.0105    4.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250    5.7158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0105    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4395    6.1283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4395    6.9533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1539    7.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8684    6.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1539    8.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8684    8.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8684    9.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5829    9.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5829   10.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2974   11.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2974   11.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0118   12.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0118   13.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7263   13.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7263   14.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0118   14.7908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4408   14.7908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4408   15.6158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.7263   16.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7263   16.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0118   17.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4408   17.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1552   16.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1552   16.8533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8697   15.6158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1539    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8684    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1539    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  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  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
M  END

     RDKit          3D

 60 59  0  0  0  0  0  0  0  0999 V2000
   -9.4143    2.6398    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4007    1.5706    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4176    0.4498   -0.5590 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.8386   -0.0962   -0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5167   -0.6553    0.0047 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2486   -0.2827    0.2291 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1383    0.0710    0.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8960    1.2629    1.1732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878   -0.6048    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6905   -0.1584    0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4570   -0.8187   -0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671   -0.3302    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9732   -1.0071   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1575   -0.5339    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4033   -1.1939   -0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5887   -0.6959   -0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8141   -1.3913   -0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0192   -0.8874   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2407   -1.5188   -0.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1433   -2.7226   -1.3252 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3816   -1.0762   -0.3140 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7472    0.1157    0.4200 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4952    1.3630   -0.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8925    2.5671    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4991    2.5806    1.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5781    3.8055   -0.2116 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1698    0.0163    1.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1099    0.8878    2.6436 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5913   -1.2222    2.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6855   -1.9051   -0.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6614   -2.4747   -1.2813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9028   -2.4812   -1.1018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9554    3.6315    0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3017    2.4755    0.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6987    2.6187   -0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3949    1.9967    0.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6054    1.0886    1.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0970    0.8025   -1.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8822   -0.8795    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0824   -0.5560   -1.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5189    0.7569   -0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0375   -0.9335    0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8989    2.1529    0.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9803   -1.5232   -0.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6394    0.7615    0.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4703   -1.7436   -0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2355    0.5953    0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8969   -1.9255   -0.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1955    0.3897    0.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3806   -2.1135   -0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6408    0.2179    0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7302   -2.3088   -1.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9822    0.0276    0.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7848   -2.6181   -2.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8652    0.0419    0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4475    1.5057   -0.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0690    1.2443   -1.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4205    4.6020    0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9711   -2.0741    1.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9675   -3.5066   -1.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 26  1  0
 24 25  2  0
 22 27  1  0
 27 29  1  0
 27 28  2  0
  5 30  1  0
 30 32  1  0
 30 31  2  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  6
  4 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  1
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 18 53  1  0
 20 54  1  0
 22 55  1  1
 23 56  1  0
 23 57  1  0
 26 58  1  0
 29 59  1  0
 32 60  1  0
M  END


  Mrv1652309072217532D          

 32 31  0  0  1  0            999 V2000
   10.0105    4.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250    5.7158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0105    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4395    6.1283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4395    6.9533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1539    7.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8684    6.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1539    8.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8684    8.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8684    9.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5829    9.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5829   10.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2974   11.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2974   11.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0118   12.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0118   13.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7263   13.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7263   14.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0118   14.7908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4408   14.7908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4408   15.6158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.7263   16.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7263   16.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0118   17.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4408   17.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1552   16.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1552   16.8533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8697   15.6158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1539    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8684    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1539    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  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  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252390

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@H](N=C(O)\C=C\C=C\C=C\C=C\C=C\C(O)=N[C@@H](CC(O)=O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H28N2O8/c1-3-15(2)20(22(31)32)24-18(26)13-11-9-7-5-4-6-8-10-12-17(25)23-16(21(29)30)14-19(27)28/h4-13,15-16,20H,3,14H2,1-2H3,(H,23,25)(H,24,26)(H,27,28)(H,29,30)(H,31,32)/b5-4+,8-6+,9-7+,12-10+,13-11+/t15-,16-,20-/m0/s1

> <INCHI_KEY>
YTWNEOFIUIUJTG-PVVCQKLLSA-N

> <FORMULA>
C22H28N2O8

> <MOLECULAR_WEIGHT>
448.472

> <EXACT_MASS>
448.18456587

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
48.07142102158722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-{[(2E,4E,6E,8E,10E)-11-{[(1S,2S)-1-carboxy-2-methylbutyl]-C-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid

> <JCHEM_LOGP>
3.1439054709849987

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.319915558716341

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5917749303095645

> <JCHEM_PKA_STRONGEST_BASIC>
2.180538830099201

> <JCHEM_POLAR_SURFACE_AREA>
177.07999999999998

> <JCHEM_REFRACTIVITY>
121.15159999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2E,4E,6E,8E,10E)-11-{[(1S,2S)-1-carboxy-2-methylbutyl]-C-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      18.686   8.359   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.020   9.129   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.020  10.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.686  11.439   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.354  11.439   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      21.354  12.979   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      22.687  13.749   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      24.021  12.979   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      22.687  15.289   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.021  16.059   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.021  17.599   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.355  18.369   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.355  19.909   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.688  20.679   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.688  22.219   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.022  22.989   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.022  24.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.356  25.299   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.356  26.839   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      28.022  27.609   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      30.689  27.609   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      30.689  29.149   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      29.356  29.919   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.356  31.459   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      28.022  32.229   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      30.689  32.229   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      32.023  29.919   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      32.023  31.459   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      33.357  29.149   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      22.687  10.669   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      24.021  11.439   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      22.687   9.129   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   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   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    5   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈N₂O₈

Average Mass

448.4720 Da

Monoisotopic Mass

448.18457 Da

IUPAC Name

(2S)-2-{[(2E,4E,6E,8E,10E)-11-{[(1S,2S)-1-carboxy-2-methylbutyl]-C-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid

Traditional Name

(2S)-2-{[(2E,4E,6E,8E,10E)-11-{[(1S,2S)-1-carboxy-2-methylbutyl]-C-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@H](N=C(O)\C=C\C=C\C=C\C=C\C=C\C(O)=N[C@@H](CC(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C22H28N2O8/c1-3-15(2)20(22(31)32)24-18(26)13-11-9-7-5-4-6-8-10-12-17(25)23-16(21(29)30)14-19(27)28/h4-13,15-16,20H,3,14H2,1-2H3,(H,23,25)(H,24,26)(H,27,28)(H,29,30)(H,31,32)/b5-4+,8-6+,9-7+,12-10+,13-11+/t15-,16-,20-/m0/s1

InChI Key

YTWNEOFIUIUJTG-PVVCQKLLSA-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
Crocinoboletus laetissimus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine 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

Isoleucine and derivatives

Alternative Parents

Substituents

Isoleucine or derivatives
Aspartic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Tricarboxylic acid or derivatives
N-acyl-amine
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
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	3.14	ChemAxon
pKa (Strongest Acidic)	3.59	ChemAxon
pKa (Strongest Basic)	2.18	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	177.08 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	121.15 m³·mol⁻¹	ChemAxon
Polarizability	48.07 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

78437420

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100927523

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid (NP0252390)

MOL for NP0252390 ((2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid)

3D MOL for NP0252390 ((2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid)

3D SDF for NP0252390 ((2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid)

3D-SDF for NP0252390 ((2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid)

PDB for NP0252390 ((2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid)

3D PDB for NP0252390 ((2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid)

SMILES for NP0252390 ((2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid)

INCHI for NP0252390 ((2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid)

Structure for NP0252390 ((2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid)

3D Structure for NP0252390 ((2s)-2-{[(2e,4e,6e,8e,10e)-11-{[(1s,2s)-1-carboxy-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-hydroxyundeca-2,4,6,8,10-pentaen-1-ylidene]amino}butanedioic acid)