NP-MRD: Showing NP-Card for N-(5-hydroxyselaginelloyl)-L-phenylalanine (NP0034517)

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Record Information

Version

2.0

Created at

2021-06-20 18:13:29 UTC

Updated at

2021-06-30 00:04:57 UTC

NP-MRD ID

NP0034517

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-(5-hydroxyselaginelloyl)-L-phenylalanine

Provided By

JEOL Database JEOL Logo

Description

(3AS,8aR)-3a-[(2E)-3-{[(1S)-1-carboxylato-2-phenylethyl]-C-hydroxycarbonimidoyl}-3-methylprop-2-en-1-yl]-5-hydroxy-1,8,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-8-ium belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-(5-hydroxyselaginelloyl)-L-phenylalanine is found in Selaginella moellendorfii. N-(5-hydroxyselaginelloyl)-L-phenylalanine was first documented in 2009 (Wang, Y. -H., et al.). Based on a literature review very few articles have been published on (3aS,8aR)-3a-[(2E)-3-{[(1S)-1-carboxylato-2-phenylethyl]-C-hydroxycarbonimidoyl}-3-methylprop-2-en-1-yl]-5-hydroxy-1,8,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-8-ium.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120133D          

 67 70  0  0  0  0            999 V2000
    0.0552   -1.4032   -2.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0632    3.6583   -2.0727 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1503    3.7541   -1.2596 N   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3498    3.5950   -2.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6418    2.3758    1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8231    3.1418    3.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 37  1  0  0  0  0
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 30 66  1  0  0  0  0
 31 67  1  0  0  0  0
 18 57  1  0  0  0  0
M  CHG  2  11   1  34  -1
M  END

     RDKit          3D

 67 70  0  0  0  0  0  0  0  0999 V2000
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 31 67  1  0
 18 57  1  0
M  CHG  2  11   1  34  -1
M  END


  Mrv1652306202120133D          

 67 70  0  0  0  0            999 V2000
    0.0552   -1.4032   -2.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1484   -1.1980   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8884   -0.2555   -0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6735    0.8382   -0.7066 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4272    2.2727   -0.1626 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1298    3.3094   -1.0509 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0632    3.6583   -2.0727 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1503    3.7541   -1.2596 N   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3498    3.5950   -2.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0738    2.7031   -0.2326 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4678    3.2076    1.1908 N   0  3  2  0  0  4  0  0  0  0  0  0
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    0.7175    2.9327    2.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8231    3.1418    3.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0361    2.8528    4.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3091    2.0854    3.8503 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7855    2.4407    1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1464   -2.8344    1.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8583   -1.5412   -0.5884 C   0  0  1  0  0  0  0  0  0  0  0  0
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  8  7  1  0  0  0  0
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  5  4  1  6  0  0  0
 32 33  2  0  0  0  0
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  4  3  1  0  0  0  0
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 20 14  1  0  0  0  0
 28 29  2  0  0  0  0
  3  2  2  0  0  0  0
 29 30  1  0  0  0  0
 14 11  1  0  0  0  0
 30 31  2  0  0  0  0
 31 26  1  0  0  0  0
  2 21  1  0  0  0  0
 24 60  1  6  0  0  0
 11 10  1  0  0  0  0
 17 18  1  0  0  0  0
  7 43  1  0  0  0  0
  7 44  1  0  0  0  0
  6 41  1  0  0  0  0
  6 42  1  0  0  0  0
 16 56  1  0  0  0  0
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  4 39  1  0  0  0  0
  4 40  1  0  0  0  0
  3 38  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  9 45  1  0  0  0  0
  9 46  1  0  0  0  0
  9 47  1  0  0  0  0
 12 49  1  0  0  0  0
 12 50  1  0  0  0  0
 12 51  1  0  0  0  0
 13 52  1  0  0  0  0
 13 53  1  0  0  0  0
 13 54  1  0  0  0  0
 23 59  1  0  0  0  0
 25 61  1  0  0  0  0
 25 62  1  0  0  0  0
 27 63  1  0  0  0  0
 28 64  1  0  0  0  0
 29 65  1  0  0  0  0
 30 66  1  0  0  0  0
 31 67  1  0  0  0  0
 18 57  1  0  0  0  0
M  CHG  2  11   1  34  -1
M  END
> <DATABASE_ID>
NP0034517

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C2C(=C1[H])[C@]1(C([H])([H])C(\[H])=C(\C(=O)N([H])[C@]([H])(C([O-])=O)C([H])([H])C3=C([H])C([H])=C([H])C([H])=C3[H])C([H])([H])[H])C([H])([H])C([H])([H])N(C([H])([H])[H])[C@]1([H])[N+]2(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H33N3O4/c1-18(24(32)28-22(25(33)34)16-19-8-6-5-7-9-19)12-13-27-14-15-29(2)26(27)30(3,4)23-11-10-20(31)17-21(23)27/h5-12,17,22,26H,13-16H2,1-4H3,(H2-,28,31,32,33,34)/b18-12+/t22-,26+,27-/m0/s1

> <INCHI_KEY>
YTWGHAVFFCUVLQ-PJJXWCSSSA-N

> <FORMULA>
C27H33N3O4

> <MOLECULAR_WEIGHT>
463.578

> <EXACT_MASS>
463.247106555

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.993271361947315

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aS,8aR)-3a-[(2E)-3-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}-3-methylprop-2-en-1-yl]-5-hydroxy-1,8,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-8-ium

> <ALOGPS_LOGP>
0.32

> <JCHEM_LOGP>
0.10877578454244138

> <ALOGPS_LOGS>
-5.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.95940051248831

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1222381775242822

> <JCHEM_PKA_STRONGEST_BASIC>
4.396360564498774

> <JCHEM_POLAR_SURFACE_AREA>
92.7

> <JCHEM_REFRACTIVITY>
154.5369

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.88e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,8aR)-3a-[(2E)-3-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}-3-methylprop-2-en-1-yl]-5-hydroxy-1,8,8-trimethyl-2H,3H,8aH-pyrrolo[2,3-b]indol-8-ium

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 67 70  0  0  0  0  0  0  0  0999 V2000
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 20 19  2  0
 25 26  1  0
 19 17  1  0
 24 32  1  0
 32 34  1  0
  5  4  1  6
 32 33  2  0
  5 10  1  0
 26 27  2  0
  4  3  1  0
 27 28  1  0
 20 14  1  0
 28 29  2  0
  3  2  2  0
 29 30  1  0
 14 11  1  0
 30 31  2  0
 31 26  1  0
  2 21  1  0
 24 60  1  6
 11 10  1  0
 17 18  1  0
  7 43  1  0
  7 44  1  0
  6 41  1  0
  6 42  1  0
 16 56  1  0
 15 55  1  0
 19 58  1  0
  4 39  1  0
  4 40  1  0
  3 38  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  9 45  1  0
  9 46  1  0
  9 47  1  0
 12 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 13 54  1  0
 23 59  1  0
 25 61  1  0
 25 62  1  0
 27 63  1  0
 28 64  1  0
 29 65  1  0
 30 66  1  0
 31 67  1  0
 18 57  1  0
M  CHG  2  11   1  34  -1
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.055  -1.403  -2.124  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.148  -1.198  -0.648  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.888  -0.256  -0.028  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.674   0.838  -0.707  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.427   2.273  -0.163  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.130   3.309  -1.051  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.063   3.658  -2.073  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.150   3.754  -1.260  0.00  0.00           N+0
HETATM    9  C   UNK     0      -1.350   3.595  -2.086  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.074   2.703  -0.233  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.468   3.208   1.191  0.00  0.00           N+1
HETATM   12  C   UNK     0      -1.642   2.376   1.684  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.803   4.673   1.234  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.718   2.933   2.017  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.823   3.142   3.388  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.036   2.853   4.020  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.111   2.371   3.269  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.309   2.085   3.850  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.000   2.163   1.897  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.786   2.441   1.280  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.518  -2.186   0.247  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.146  -2.834   1.053  0.00  0.00           O+0
HETATM   23  N   UNK     0      -1.868  -2.329   0.182  0.00  0.00           N+0
HETATM   24  C   UNK     0      -2.858  -1.541  -0.588  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.249  -2.201  -0.676  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.723  -2.984   0.530  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.283  -2.332   1.635  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.712  -3.060   2.746  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.586  -4.447   2.765  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.029  -5.108   1.673  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.600  -4.381   0.561  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.014  -0.067  -0.138  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.717   0.805  -1.010  0.00  0.00           O+0
HETATM   34  O   UNK     0      -3.336   0.147   1.065  0.00  0.00           O-1
HETATM   35  H   UNK     0      -0.353  -2.390  -2.368  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.581  -0.641  -2.585  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.046  -1.352  -2.589  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.940  -0.286   1.061  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.738   0.589  -0.601  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.470   0.828  -1.783  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.409   4.209  -0.485  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.040   2.924  -1.523  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.285   4.605  -2.576  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.994   2.870  -2.833  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.363   2.641  -2.626  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.255   3.661  -1.473  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.407   4.404  -2.823  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.696   1.842  -0.472  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.475   2.547   0.999  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.325   1.331   1.726  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.926   2.720   2.684  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.061   5.259   0.903  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.062   4.951   2.262  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.672   4.860   0.597  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.010   3.516   3.973  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.129   3.009   5.091  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.228   2.168   4.815  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.848   1.780   1.336  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.237  -2.913   0.924  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.487  -1.500  -1.618  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.235  -2.894  -1.530  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.014  -1.458  -0.937  0.00  0.00           H+0
HETATM   63  H   UNK     0      -5.376  -1.247   1.641  0.00  0.00           H+0
HETATM   64  H   UNK     0      -6.136  -2.537   3.599  0.00  0.00           H+0
HETATM   65  H   UNK     0      -5.916  -5.011   3.633  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.925  -6.189   1.687  0.00  0.00           H+0
HETATM   67  H   UNK     0      -4.161  -4.911  -0.281  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    1    3   21                                                  
CONECT    3    4    2   38                                                  
CONECT    4    5    3   39   40                                             
CONECT    5   20    6    4   10                                             
CONECT    6    5    7   41   42                                             
CONECT    7    8    6   43   44                                             
CONECT    8   10    9    7                                                  
CONECT    9    8   45   46   47                                             
CONECT   10   48    8    5   11                                             
CONECT   11   12   13   14   10                                             
CONECT   12   11   49   50   51                                             
CONECT   13   11   52   53   54                                             
CONECT   14   15   20   11                                                  
CONECT   15   16   14   55                                                  
CONECT   16   17   15   56                                                  
CONECT   17   16   19   18                                                  
CONECT   18   17   57                                                       
CONECT   19   20   17   58                                                  
CONECT   20    5   19   14                                                  
CONECT   21   22   23    2                                                  
CONECT   22   21                                                            
CONECT   23   21   24   59                                                  
CONECT   24   23   25   32   60                                             
CONECT   25   24   26   61   62                                             
CONECT   26   25   27   31                                                  
CONECT   27   26   28   63                                                  
CONECT   28   27   29   64                                                  
CONECT   29   28   30   65                                                  
CONECT   30   29   31   66                                                  
CONECT   31   30   26   67                                                  
CONECT   32   24   34   33                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    3                                                            
CONECT   39    4                                                            
CONECT   40    4                                                            
CONECT   41    6                                                            
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44    7                                                            
CONECT   45    9                                                            
CONECT   46    9                                                            
CONECT   47    9                                                            
CONECT   48   10                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   13                                                            
CONECT   54   13                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   18                                                            
CONECT   58   19                                                            
CONECT   59   23                                                            
CONECT   60   24                                                            
CONECT   61   25                                                            
CONECT   62   25                                                            
CONECT   63   27                                                            
CONECT   64   28                                                            
CONECT   65   29                                                            
CONECT   66   30                                                            
CONECT   67   31                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  140    0
END

RDKit          3D

67 70  0  0  0  0  0  0  0  0999 V2000
    0.0552   -1.4032   -2.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1484   -1.1980   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8884   -0.2555   -0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6735    0.8382   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272    2.2727   -0.1626 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1298    3.3094   -1.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0632    3.6583   -2.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3498    3.5950   -2.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0738    2.7031   -0.2326 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4678    3.2076    1.1908 N   0  0  2  0  0  4  0  0  0  0  0  0
   -1.6418    2.3758    1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8030    4.6729    1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7175    2.9327    2.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8231    3.1418    3.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0361    2.8528    4.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1108    2.3707    3.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091    2.0854    3.8503 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9998    2.1627    1.8967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7855    2.4407    1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5179   -2.1857    0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1464   -2.8344    1.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8682   -2.3292    0.1822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8583   -1.5412   -0.5884 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2486   -2.2014   -0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7233   -2.9839    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2832   -2.3322    1.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7115   -3.0596    2.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5856   -4.4470    2.7655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290   -5.1081    1.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6000   -4.3812    0.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -0.0673   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    0.8050   -1.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3358    0.1469    1.0651 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.3525   -2.3900   -2.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5809   -0.6414   -2.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458   -1.3518   -2.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9401   -0.2859    1.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7376    0.5894   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4696    0.8276   -1.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4090    4.2089   -0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0399    2.9239   -1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846    4.6048   -2.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9942    2.8702   -2.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3626    2.6414   -2.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2549    3.6608   -1.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4066    4.4040   -2.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6958    1.8419   -0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4751    2.5466    0.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3246    1.3313    1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9255    2.7205    2.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0610    5.2588    0.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0621    4.9512    2.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6720    4.8603    0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0100    3.5164    3.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1294    3.0087    5.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2283    2.1679    4.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483    1.7802    1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367   -2.9133    0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871   -1.4997   -1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2346   -2.8941   -1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0143   -1.4582   -0.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3762   -1.2474    1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1364   -2.5371    3.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9162   -5.0107    3.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9247   -6.1894    1.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1608   -4.9111   -0.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 48  1  6
  5 20  1  0
  2  1  1  0
 10  8  1  0
  8  9  1  0
  8  7  1  0
 11 12  1  1
 17 16  2  0
 11 13  1  0
  6  5  1  0
 21 22  2  0
 16 15  1  0
 21 23  1  0
 15 14  2  0
 24 23  1  0
  7  6  1  0
 24 25  1  0
 20 19  2  0
 25 26  1  0
 19 17  1  0
 24 32  1  0
 32 34  1  0
  5  4  1  6
 32 33  2  0
  5 10  1  0
 26 27  2  0
  4  3  1  0
 27 28  1  0
 20 14  1  0
 28 29  2  0
  3  2  2  0
 29 30  1  0
 14 11  1  0
 30 31  2  0
 31 26  1  0
  2 21  1  0
 24 60  1  6
 11 10  1  0
 17 18  1  0
  7 43  1  0
  7 44  1  0
  6 41  1  0
  6 42  1  0
 16 56  1  0
 15 55  1  0
 19 58  1  0
  4 39  1  0
  4 40  1  0
  3 38  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  9 45  1  0
  9 46  1  0
  9 47  1  0
 12 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 13 54  1  0
 23 59  1  0
 25 61  1  0
 25 62  1  0
 27 63  1  0
 28 64  1  0
 29 65  1  0
 30 66  1  0
 31 67  1  0
 18 57  1  0
M  CHG  2  11   1  34  -1
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₃N₃O₄

Average Mass

463.5780 Da

Monoisotopic Mass

463.24711 Da

IUPAC Name

(3aS,8aR)-3a-[(2E)-3-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}-3-methylprop-2-en-1-yl]-5-hydroxy-1,8,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-8-ium

Traditional Name

(3aS,8aR)-3a-[(2E)-3-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}-3-methylprop-2-en-1-yl]-5-hydroxy-1,8,8-trimethyl-2H,3H,8aH-pyrrolo[2,3-b]indol-8-ium

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C2C(=C1[H])[C@]1(C([H])([H])C(\[H])=C(\C(=O)N([H])[C@]([H])(C([O-])=O)C([H])([H])C3=C([H])C([H])=C([H])C([H])=C3[H])C([H])([H])[H])C([H])([H])C([H])([H])N(C([H])([H])[H])[C@]1([H])[N+]2(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C27H33N3O4/c1-18(24(32)28-22(25(33)34)16-19-8-6-5-7-9-19)12-13-27-14-15-29(2)26(27)30(3,4)23-11-10-20(31)17-21(23)27/h5-12,17,22,26H,13-16H2,1-4H3,(H2-,28,31,32,33,34)/b18-12+/t22-,26+,27-/m0/s1

InChI Key

YTWGHAVFFCUVLQ-PJJXWCSSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Selaginella moellendorffii	JEOL database	Wang, Y. -H., et al, J. Nat. Prod. 72, 1151 (2009)

Chemical Taxonomy

Description

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

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Pyrroloindole
3-phenylpropanoic-acid
Amphetamine or derivatives
Indole
Indole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
N-acyl-amine
Benzenoid
N-alkylpyrrolidine
Pyrrole
Pyrrolidine
Secondary carboxylic acid amide
Tertiary amine
Carboxamide group
Carboxylic acid salt
Amino acid
Aminal
Carboxylic acid
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Amine
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic salt
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organic zwitterion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.32	ALOGPS
logP	0.11	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	3.12	ChemAxon
pKa (Strongest Basic)	4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.7 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	154.54 m³·mol⁻¹	ChemAxon
Polarizability	49.99 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44179509

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang, Y. -H., et al. (2009). Wang, Y. -H., et al, J. Nat. Prod. 72, 1151 (2009). J. Nat. Prod..

Showing NP-Card for N-(5-hydroxyselaginelloyl)-L-phenylalanine (NP0034517)

MOL for NP0034517 (N-(5-hydroxyselaginelloyl)-L-phenylalanine)

3D MOL for NP0034517 (N-(5-hydroxyselaginelloyl)-L-phenylalanine)

3D SDF for NP0034517 (N-(5-hydroxyselaginelloyl)-L-phenylalanine)

3D-SDF for NP0034517 (N-(5-hydroxyselaginelloyl)-L-phenylalanine)

PDB for NP0034517 (N-(5-hydroxyselaginelloyl)-L-phenylalanine)

3D PDB for NP0034517 (N-(5-hydroxyselaginelloyl)-L-phenylalanine)

SMILES for NP0034517 (N-(5-hydroxyselaginelloyl)-L-phenylalanine)

INCHI for NP0034517 (N-(5-hydroxyselaginelloyl)-L-phenylalanine)

Structure for NP0034517 (N-(5-hydroxyselaginelloyl)-L-phenylalanine)

3D Structure for NP0034517 (N-(5-hydroxyselaginelloyl)-L-phenylalanine)