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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:23:26 UTC

Update Date

2022-03-07 03:17:45 UTC

HMDB ID

HMDB0060474

Secondary Accession Numbers

HMDB60474

Metabolite Identification

Common Name

Diphthine

Description

Diphthine belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Diphthine is a very strong basic compound (based on its pKa). These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0060474
     RDKit          3D
Diphthine
 44 44  0  0  0  0  0  0  0  0999 V2000
   -3.2889    0.9561   -1.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7337    0.0086   -0.4317 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.1545    0.1957   -0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5274   -1.3600   -0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9750    0.3125    0.7779 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5413    0.0162    0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022    0.2780    1.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7870   -0.0653    1.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3177   -1.2882    1.3037 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5536   -1.1710    0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7669    0.1015    0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9054    0.7434   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0821   -0.1448   -0.5633 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6504   -0.7156    0.6081 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1006    0.6390   -1.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7709    1.2167   -2.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4130    0.7685   -0.8985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6243    0.7797    0.5982 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5366   -0.3472    1.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0814   -0.1805    3.1101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6246   -1.2076    1.8453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    1.8046   -0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6456    0.4838   -2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1628    1.4318   -1.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5490    0.7811   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3547    0.8098    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6856   -0.7852   -0.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4328   -1.6974   -1.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6304   -1.4731   -1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3580   -1.9730    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0738    1.4258    0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4890   -1.0721    0.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402    0.5638   -0.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6478    1.3306    1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658   -0.3537    2.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2560   -1.9717    0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2094    1.6230    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5728    1.1831   -1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7592   -0.9667   -1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3448   -0.0671    1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1703   -1.5965    0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6811    1.3961   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068    1.7843    0.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5591   -2.1971    2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 11 18  1  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 18  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  1
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  6
 14 40  1  0
 14 41  1  0
 17 42  1  0
 18 43  1  0
 21 44  1  0
M  CHG  1   2   1
M  END


  Mrv0541 05161318232D          

 21 21  0  0  0  0            999 V2000
    2.6309    2.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5040    3.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3290    1.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0676    2.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346    3.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2471    2.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4032    1.9153    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2020    2.0652    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9414    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236    1.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020    1.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    1.2478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0277    3.2981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6951    2.1421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165    2.4777    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -4.5592    1.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7086    2.4965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165    0.8277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875    0.8277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  9  1  0  0  0  0
 10 13  1  1  0  0  0
  9 14  1  6  0  0  0
 15  7  1  0  0  0  0
 15 11  2  0  0  0  0
 16  8  1  0  0  0  0
 16 11  1  0  0  0  0
 17  1  1  0  0  0  0
 17  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17 10  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 20 13  2  0  0  0  0
 21 13  1  0  0  0  0
M  CHG  1  17   1
M  END
> <DATABASE_ID>
HMDB0060474

> <DATABASE_NAME>
hmdb

> <SMILES>
C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H22N4O4/c1-17(2,3)10(13(20)21)4-5-11-15-7-8(16-11)6-9(14)12(18)19/h7,9-10H,4-6,14H2,1-3H3,(H2-,15,16,18,19,20,21)/p+1/t9-,10+/m0/s1

> <INCHI_KEY>
CBQVLMCHMFGPMX-VHSXEESVSA-O

> <FORMULA>
C13H23N4O4

> <MOLECULAR_WEIGHT>
299.3461

> <EXACT_MASS>
299.171930244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.50320218655586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R)-3-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}-1-carboxypropyl]trimethylazanium

> <ALOGPS_LOGP>
-1.25

> <JCHEM_LOGP>
-7.825253913878314

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.2209355534314703

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4045473593461577

> <JCHEM_PKA_STRONGEST_BASIC>
9.432964087463924

> <JCHEM_POLAR_SURFACE_AREA>
129.29999999999998

> <JCHEM_REFRACTIVITY>
87.1266

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R)-3-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}-1-carboxypropyl]trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060474
     RDKit          3D
Diphthine
 44 44  0  0  0  0  0  0  0  0999 V2000
   -3.2889    0.9561   -1.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7337    0.0086   -0.4317 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.1545    0.1957   -0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5274   -1.3600   -0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9750    0.3125    0.7779 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5413    0.0162    0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022    0.2780    1.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7870   -0.0653    1.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3177   -1.2882    1.3037 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5536   -1.1710    0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7669    0.1015    0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9054    0.7434   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0821   -0.1448   -0.5633 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6504   -0.7156    0.6081 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1006    0.6390   -1.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7709    1.2167   -2.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4130    0.7685   -0.8985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6243    0.7797    0.5982 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5366   -0.3472    1.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0814   -0.1805    3.1101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6246   -1.2076    1.8453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    1.8046   -0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6456    0.4838   -2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1628    1.4318   -1.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5490    0.7811   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3547    0.8098    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6856   -0.7852   -0.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4328   -1.6974   -1.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6304   -1.4731   -1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3580   -1.9730    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0738    1.4258    0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4890   -1.0721    0.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402    0.5638   -0.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6478    1.3306    1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658   -0.3537    2.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2560   -1.9717    0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2094    1.6230    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5728    1.1831   -1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7592   -0.9667   -1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3448   -0.0671    1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1703   -1.5965    0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6811    1.3961   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068    1.7843    0.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5591   -2.1971    2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 11 18  1  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 18  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  1
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  6
 14 40  1  0
 14 41  1  0
 17 42  1  0
 18 43  1  0
 21 44  1  0
M  CHG  1   2   1
M  END

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       4.911   5.395   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.807   5.959   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.347   3.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.910   4.625   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.424   3.855   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.726   4.982   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.425   6.477   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.195   5.143   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.353   3.575   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.244   3.855   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.757   4.625   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.884   3.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.244   2.315   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -5.447   2.329   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -1.918   6.156   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -3.164   3.999   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       3.577   4.625   0.000  0.00  0.00           N+1
HETATM   18  O   UNK     0      -8.511   2.007   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -8.789   4.660   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.577   1.545   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.910   1.545   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   17                                                            
CONECT    3   17                                                            
CONECT    4    5   10                                                       
CONECT    5    4   11                                                       
CONECT    6    8    9                                                       
CONECT    7    8   15                                                       
CONECT    8    6    7   16                                                  
CONECT    9    6   12   14                                                  
CONECT   10    4   13   17                                                  
CONECT   11    5   15   16                                                  
CONECT   12    9   18   19                                                  
CONECT   13   10   20   21                                                  
CONECT   14    9                                                            
CONECT   15    7   11                                                       
CONECT   16    8   11                                                       
CONECT   17    1    2    3   10                                             
CONECT   18   12                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   13                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0060474
HETATM    1  C1  UNL     1      -3.289   0.956  -1.428  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.734   0.009  -0.432  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -5.155   0.196  -0.231  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.527  -1.360  -0.854  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.975   0.312   0.778  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.541   0.016   0.499  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.602   0.278   1.654  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.787  -0.065   1.179  1.00  0.00           C  
HETATM    9  N2  UNL     1       1.318  -1.288   1.304  1.00  0.00           N  
HETATM   10  C8  UNL     1       2.554  -1.171   0.763  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.767   0.101   0.319  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.905   0.743  -0.329  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.082  -0.145  -0.563  1.00  0.00           C  
HETATM   14  N3  UNL     1       5.650  -0.716   0.608  1.00  0.00           N  
HETATM   15  C12 UNL     1       6.101   0.639  -1.318  1.00  0.00           C  
HETATM   16  O1  UNL     1       5.771   1.217  -2.387  1.00  0.00           O  
HETATM   17  O2  UNL     1       7.413   0.768  -0.899  1.00  0.00           O  
HETATM   18  N4  UNL     1       1.624   0.780   0.598  1.00  0.00           N  
HETATM   19  C13 UNL     1      -3.537  -0.347   1.956  1.00  0.00           C  
HETATM   20  O3  UNL     1      -3.081  -0.181   3.110  1.00  0.00           O  
HETATM   21  O4  UNL     1      -4.625  -1.208   1.845  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.712   1.805  -0.990  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.646   0.484  -2.198  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.163   1.432  -1.936  1.00  0.00           H  
HETATM   25  H4  UNL     1      -5.549   0.781  -1.085  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.355   0.810   0.681  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.686  -0.785  -0.187  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.433  -1.697  -1.369  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.630  -1.473  -1.495  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.358  -1.973   0.039  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.074   1.426   0.910  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.489  -1.072   0.201  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.140   0.564  -0.363  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.648   1.331   1.996  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.866  -0.354   2.533  1.00  0.00           H  
HETATM   36  H15 UNL     1       3.256  -1.972   0.699  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.209   1.623   0.304  1.00  0.00           H  
HETATM   38  H17 UNL     1       3.573   1.183  -1.291  1.00  0.00           H  
HETATM   39  H18 UNL     1       4.759  -0.967  -1.256  1.00  0.00           H  
HETATM   40  H19 UNL     1       6.345  -0.067   1.045  1.00  0.00           H  
HETATM   41  H20 UNL     1       6.170  -1.597   0.395  1.00  0.00           H  
HETATM   42  H21 UNL     1       7.681   1.396  -0.133  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.407   1.784   0.406  1.00  0.00           H  
HETATM   44  H23 UNL     1      -4.559  -2.197   2.111  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4    5
CONECT    3   25   26   27
CONECT    4   28   29   30
CONECT    5    6   19   31
CONECT    6    7   32   33
CONECT    7    8   34   35
CONECT    8    9    9   18
CONECT    9   10
CONECT   10   11   11   36
CONECT   11   12   18
CONECT   12   13   37   38
CONECT   13   14   15   39
CONECT   14   40   41
CONECT   15   16   16   17
CONECT   17   42
CONECT   18   43
CONECT   19   20   20   21
CONECT   21   44
END

HMDB0060474
     RDKit          3D
Diphthine
 44 44  0  0  0  0  0  0  0  0999 V2000
   -3.2889    0.9561   -1.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7337    0.0086   -0.4317 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.1545    0.1957   -0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5274   -1.3600   -0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9750    0.3125    0.7779 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5413    0.0162    0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022    0.2780    1.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7870   -0.0653    1.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3177   -1.2882    1.3037 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5536   -1.1710    0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7669    0.1015    0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9054    0.7434   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0821   -0.1448   -0.5633 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6504   -0.7156    0.6081 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1006    0.6390   -1.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7709    1.2167   -2.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4130    0.7685   -0.8985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6243    0.7797    0.5982 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5366   -0.3472    1.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0814   -0.1805    3.1101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6246   -1.2076    1.8453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    1.8046   -0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6456    0.4838   -2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1628    1.4318   -1.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5490    0.7811   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3547    0.8098    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6856   -0.7852   -0.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4328   -1.6974   -1.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6304   -1.4731   -1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3580   -1.9730    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0738    1.4258    0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4890   -1.0721    0.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402    0.5638   -0.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6478    1.3306    1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658   -0.3537    2.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2560   -1.9717    0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2094    1.6230    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5728    1.1831   -1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7592   -0.9667   -1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3448   -0.0671    1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1703   -1.5965    0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6811    1.3961   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068    1.7843    0.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5591   -2.1971    2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 11 18  1  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 18  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  1
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  6
 14 40  1  0
 14 41  1  0
 17 42  1  0
 18 43  1  0
 21 44  1  0
M  CHG  1   2   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₂₃N₄O₄

Average Molecular Weight

299.3461

Monoisotopic Molecular Weight

299.171930244

IUPAC Name

[(1R)-3-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}-1-carboxypropyl]trimethylazanium

Traditional Name

[(1R)-3-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}-1-carboxypropyl]trimethylazanium

CAS Registry Number

Not Available

SMILES

C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O

InChI Identifier

InChI=1S/C13H22N4O4/c1-17(2,3)10(13(20)21)4-5-11-15-7-8(16-11)6-9(14)12(18)19/h7,9-10H,4-6,14H2,1-3H3,(H2-,15,16,18,19,20,21)/p+1/t9-,10+/m0/s1

InChI Key

CBQVLMCHMFGPMX-VHSXEESVSA-O

Chemical Taxonomy

Description

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

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
Alpha-amino acid
L-alpha-amino acid
D-alpha-amino acid
Aralkylamine
Dicarboxylic acid or derivatives
Azole
Tetraalkylammonium salt
Imidazole
Heteroaromatic compound
Quaternary ammonium salt
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Amine
Organic salt
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-7.8	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	1.4	ChemAxon
pKa (Strongest Basic)	9.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.3 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	87.13 m³·mol⁻¹	ChemAxon
Polarizability	31.5 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.444	31661259
DarkChem	[M-H]-	169.905	31661259
DeepCCS	[M+H]+	167.357	30932474
DeepCCS	[M-H]-	164.999	30932474
DeepCCS	[M-2H]-	198.541	30932474
DeepCCS	[M+Na]+	173.996	30932474
AllCCS	[M+H]+	168.6	32859911
AllCCS	[M+H-H2O]+	165.9	32859911
AllCCS	[M+NH4]+	171.2	32859911
AllCCS	[M+Na]+	171.9	32859911
AllCCS	[M-H]-	177.0	32859911
AllCCS	[M+Na-2H]-	177.7	32859911
AllCCS	[M+HCOO]-	178.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diphthine	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O	3524.5	Standard polar	33892256
Diphthine	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O	2102.7	Standard non polar	33892256
Diphthine	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O	2737.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diphthine,1TMS,isomer #1	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(=O)O[Si](C)(C)C)[NH]1)C(=O)O	2669.7	Semi standard non polar	33892256
Diphthine,1TMS,isomer #2	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(=O)O)[NH]1)C(=O)O[Si](C)(C)C	2631.6	Semi standard non polar	33892256
Diphthine,1TMS,isomer #3	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O)[NH]1)C(=O)O	2742.0	Semi standard non polar	33892256
Diphthine,1TMS,isomer #4	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(=O)O)N1[Si](C)(C)C)C(=O)O	2733.3	Semi standard non polar	33892256
Diphthine,2TMS,isomer #1	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(=O)O[Si](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C	2558.5	Semi standard non polar	33892256
Diphthine,2TMS,isomer #2	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[NH]1)C(=O)O	2686.9	Semi standard non polar	33892256
Diphthine,2TMS,isomer #3	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O	2686.1	Semi standard non polar	33892256
Diphthine,2TMS,isomer #4	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O)[NH]1)C(=O)O[Si](C)(C)C	2664.2	Semi standard non polar	33892256
Diphthine,2TMS,isomer #5	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(=O)O)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2654.5	Semi standard non polar	33892256
Diphthine,2TMS,isomer #6	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[NH]1)C(=O)O	2836.3	Semi standard non polar	33892256
Diphthine,2TMS,isomer #7	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O)N1[Si](C)(C)C)C(=O)O	2738.4	Semi standard non polar	33892256
Diphthine,3TMS,isomer #1	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C	2616.3	Semi standard non polar	33892256
Diphthine,3TMS,isomer #1	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C	2550.8	Standard non polar	33892256
Diphthine,3TMS,isomer #1	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C	3129.4	Standard polar	33892256
Diphthine,3TMS,isomer #2	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2622.3	Semi standard non polar	33892256
Diphthine,3TMS,isomer #2	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2554.6	Standard non polar	33892256
Diphthine,3TMS,isomer #2	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N)C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	3388.2	Standard polar	33892256
Diphthine,3TMS,isomer #3	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[NH]1)C(=O)O	2803.7	Semi standard non polar	33892256
Diphthine,3TMS,isomer #3	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[NH]1)C(=O)O	2659.2	Standard non polar	33892256
Diphthine,3TMS,isomer #3	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[NH]1)C(=O)O	3320.3	Standard polar	33892256
Diphthine,3TMS,isomer #4	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O	2703.7	Semi standard non polar	33892256
Diphthine,3TMS,isomer #4	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O	2611.6	Standard non polar	33892256
Diphthine,3TMS,isomer #4	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O	3253.3	Standard polar	33892256
Diphthine,3TMS,isomer #5	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C	2763.1	Semi standard non polar	33892256
Diphthine,3TMS,isomer #5	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C	2650.1	Standard non polar	33892256
Diphthine,3TMS,isomer #5	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C	3274.0	Standard polar	33892256
Diphthine,3TMS,isomer #6	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2689.9	Semi standard non polar	33892256
Diphthine,3TMS,isomer #6	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2590.8	Standard non polar	33892256
Diphthine,3TMS,isomer #6	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	3234.7	Standard polar	33892256
Diphthine,3TMS,isomer #7	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O	2883.1	Semi standard non polar	33892256
Diphthine,3TMS,isomer #7	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O	2692.0	Standard non polar	33892256
Diphthine,3TMS,isomer #7	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O	3390.2	Standard polar	33892256
Diphthine,4TMS,isomer #1	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C	2766.0	Semi standard non polar	33892256
Diphthine,4TMS,isomer #1	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C	2670.7	Standard non polar	33892256
Diphthine,4TMS,isomer #1	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C	2967.6	Standard polar	33892256
Diphthine,4TMS,isomer #2	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2679.4	Semi standard non polar	33892256
Diphthine,4TMS,isomer #2	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2626.2	Standard non polar	33892256
Diphthine,4TMS,isomer #2	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2938.4	Standard polar	33892256
Diphthine,4TMS,isomer #3	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O	2851.3	Semi standard non polar	33892256
Diphthine,4TMS,isomer #3	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O	2734.4	Standard non polar	33892256
Diphthine,4TMS,isomer #3	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O	3117.0	Standard polar	33892256
Diphthine,4TMS,isomer #4	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2833.2	Semi standard non polar	33892256
Diphthine,4TMS,isomer #4	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2720.6	Standard non polar	33892256
Diphthine,4TMS,isomer #4	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	3076.0	Standard polar	33892256
Diphthine,5TMS,isomer #1	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2856.2	Semi standard non polar	33892256
Diphthine,5TMS,isomer #1	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2743.2	Standard non polar	33892256
Diphthine,5TMS,isomer #1	C[N+](C)(C)[C@H](CCC1=NC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2843.2	Standard polar	33892256
Diphthine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)[NH]1	2933.6	Semi standard non polar	33892256
Diphthine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC1=NC=C(C[C@H](N)C(=O)O)[NH]1)[N+](C)(C)C	2887.0	Semi standard non polar	33892256
Diphthine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)[NH]1)C(=O)O	2974.5	Semi standard non polar	33892256
Diphthine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C(C[C@H](N)C(=O)O)=CN=C1CC[C@H](C(=O)O)[N+](C)(C)C	2937.7	Semi standard non polar	33892256
Diphthine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)[NH]1	3061.3	Semi standard non polar	33892256
Diphthine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C(C)(C)C	3167.4	Semi standard non polar	33892256
Diphthine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C	3142.5	Semi standard non polar	33892256
Diphthine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)[NH]1)C(=O)O	3125.8	Semi standard non polar	33892256
Diphthine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC1=NC=C(C[C@H](N)C(=O)O)N1[Si](C)(C)C(C)(C)C)[N+](C)(C)C	3110.6	Semi standard non polar	33892256
Diphthine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)[NH]1)C(=O)O)[Si](C)(C)C(C)(C)C	3251.7	Semi standard non polar	33892256
Diphthine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)O	3189.4	Semi standard non polar	33892256
Diphthine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C(C)(C)C	3290.0	Semi standard non polar	33892256
Diphthine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C(C)(C)C	3175.8	Standard non polar	33892256
Diphthine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)[NH]1)C(=O)O[Si](C)(C)C(C)(C)C	3236.9	Standard polar	33892256
Diphthine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C	3294.6	Semi standard non polar	33892256
Diphthine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C	3153.7	Standard non polar	33892256
Diphthine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C	3498.2	Standard polar	33892256
Diphthine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)[NH]1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3468.8	Semi standard non polar	33892256
Diphthine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)[NH]1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3264.9	Standard non polar	33892256
Diphthine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)[NH]1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3355.9	Standard polar	33892256
Diphthine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3356.3	Semi standard non polar	33892256
Diphthine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3207.0	Standard non polar	33892256
Diphthine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3343.5	Standard polar	33892256
Diphthine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]1)[N+](C)(C)C	3403.0	Semi standard non polar	33892256
Diphthine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]1)[N+](C)(C)C	3245.8	Standard non polar	33892256
Diphthine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]1)[N+](C)(C)C	3319.3	Standard polar	33892256
Diphthine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)O	3350.0	Semi standard non polar	33892256
Diphthine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)O	3184.7	Standard non polar	33892256
Diphthine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)O	3329.4	Standard polar	33892256
Diphthine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3532.8	Semi standard non polar	33892256
Diphthine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3266.1	Standard non polar	33892256
Diphthine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3422.6	Standard polar	33892256
Diphthine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)[NH]1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3632.4	Semi standard non polar	33892256
Diphthine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)[NH]1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3408.3	Standard non polar	33892256
Diphthine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)[NH]1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3149.0	Standard polar	33892256
Diphthine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3504.6	Semi standard non polar	33892256
Diphthine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3343.1	Standard non polar	33892256
Diphthine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3153.8	Standard polar	33892256
Diphthine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3701.3	Semi standard non polar	33892256
Diphthine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3447.0	Standard non polar	33892256
Diphthine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN=C(CC[C@H](C(=O)O)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3247.9	Standard polar	33892256
Diphthine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[N+](C)(C)C	3681.0	Semi standard non polar	33892256
Diphthine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[N+](C)(C)C	3416.5	Standard non polar	33892256
Diphthine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC1=NC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[N+](C)(C)C	3223.2	Standard polar	33892256
Diphthine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3898.1	Semi standard non polar	33892256
Diphthine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3577.6	Standard non polar	33892256
Diphthine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN=C(CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[N+](C)(C)C)N1[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3179.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Diphthine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2390000000-2195e129730e6191a1c8	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diphthine GC-MS (2 TMS) - 70eV, Positive	splash10-0a70-9175100000-74eec40c8d4fd59623f5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diphthine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphthine 10V, Positive-QTOF	splash10-0udj-0090000000-d7a1654f66c6769cf4d4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphthine 20V, Positive-QTOF	splash10-0zg0-0090000000-a62f20efe42486ea47dc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphthine 40V, Positive-QTOF	splash10-053i-2930000000-f0124d8f3c1a52c7c04e	2017-10-06	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

23657814

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Diphthine--ammonia ligase

General function:: Not Available
Specific function:: Amidase that catalyzes the last step of diphthamide biosynthesis using ammonium and ATP. Diphthamide biosynthesis consists in the conversion of an L-histidine residue in the translation elongation factor eEF-2 (EEF2) to diphthamide (Probable).
Gene Name:: ATPBD4
Uniprot ID:: Q7L8W6
Molecular weight:: 18657.27

Reactions

Adenosine triphosphate + Diphthine + Ammonia → ADP + Phosphate + Diphthamide	details

Showing metabocard for Diphthine (HMDB0060474)

MOL for HMDB0060474 (Diphthine)

3D MOL for HMDB0060474 (Diphthine)

3D SDF for HMDB0060474 (Diphthine)

3D-SDF for HMDB0060474 (Diphthine)

PDB for HMDB0060474 (Diphthine)

3D PDB for HMDB0060474 (Diphthine)

SMILES for HMDB0060474 (Diphthine)

INCHI for HMDB0060474 (Diphthine)

Structure for HMDB0060474 (Diphthine)

3D Structure for HMDB0060474 (Diphthine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions