NP-MRD: Showing NP-Card for Aspartylphenylalanine (NP0000870)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:19:00 UTC

NP-MRD ID

NP0000870

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aspartylphenylalanine

Description

This is a metabolic byproduct of aspartame (Nutrasweet). Aspartame is the methyl ester of aspartylphenylalanine. After hydrolysis of the ester bond in the intestinal lumen, the dipeptide is apparently absorbed and digested in the same manner as dipeptides derived from protein digestion. There are several Asp-Phe dipeptidases that degrade this peptide. It has been suggested that individuals with aspartame allergies may be defficient in this peptidase. (PMID 3743970 ). It has been observed that the N-beta-L-aspartyl-L-phenylalanine (a breakdown product of Asn-Phe) is a naturally occurring peptide found in both blood and urine.(PMID: 2723819 ).

Structure

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

HMDB0000706
     RDKit          3D
Aspartylphenylalanine
 36 36  0  0  0  0  0  0  0  0999 V2000
   -2.9711   -1.9902    1.4280 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2262   -1.4344    0.1339 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2189   -0.2997    0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7387    0.8069    1.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6453    0.7920    1.6303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5497    1.9266    1.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9633   -0.9920   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0146   -0.4792   -1.6506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7468   -1.1560    0.1813 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4976   -0.7332   -0.4197 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0572    0.3589    0.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.9102   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5715    0.3870    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252    0.9575   -0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7296    2.0213   -0.9711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5140    2.5337   -1.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374    1.9809   -0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4221   -1.8435   -0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1435   -3.0227   -0.3346 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6524   -1.6020   -1.2397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160   -2.9231    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3064   -1.3791    2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544   -2.2375   -0.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3275    0.0965   -0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2125   -0.6538    0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5402    1.8661    1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7052   -1.5804    1.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2524   -0.3078   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961   -0.1045    1.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315    1.1790    0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5688   -0.4477    1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6866    0.5538    0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6587    2.4556   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    3.3710   -2.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3696    2.3610   -1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3713   -2.2295 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
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 18 20  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  6 26  1  0
  9 27  1  0
 10 28  1  6
 11 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 20 36  1  0
M  END


  Mrv1652305271900032D          

 20 20  0  0  0  0            999 V2000
 2499.9958 2501.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7107 2500.6135    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2500.7107 2499.7880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4339 2499.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1488 2499.8002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4339 2498.5629    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2500.7190 2498.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0041 2498.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2892 2498.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0041 2499.3884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1488 2498.1491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4256 2501.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1406 2500.6135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4256 2501.8508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2812 2500.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5667 2501.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8522 2500.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8522 2499.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5666 2499.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2812 2499.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  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  2  0  0  0  0
 20 15  1  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000870

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O5/c14-9(7-11(16)17)12(18)15-10(13(19)20)6-8-4-2-1-3-5-8/h1-5,9-10H,6-7,14H2,(H,15,18)(H,16,17)(H,19,20)/t9-,10-/m0/s1

> <INCHI_KEY>
YZQCXOFQZKCETR-UWVGGRQHSA-N

> <FORMULA>
C13H16N2O5

> <MOLECULAR_WEIGHT>
280.2765

> <EXACT_MASS>
280.105921632

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.38327503100304

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-amino-3-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}propanoic acid

> <ALOGPS_LOGP>
-2.43

> <JCHEM_LOGP>
-2.7545904565625334

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.859550014641755

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1651475800604603

> <JCHEM_PKA_STRONGEST_BASIC>
8.526464863794741

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
68.4491

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-aspartyl-L-phenylalanine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000706
     RDKit          3D
Aspartylphenylalanine
 36 36  0  0  0  0  0  0  0  0999 V2000
   -2.9711   -1.9902    1.4280 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2262   -1.4344    0.1339 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2189   -0.2997    0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7387    0.8069    1.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6453    0.7920    1.6303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5497    1.9266    1.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9633   -0.9920   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0146   -0.4792   -1.6506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7468   -1.1560    0.1813 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4976   -0.7332   -0.4197 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0572    0.3589    0.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.9102   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5715    0.3870    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252    0.9575   -0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7296    2.0213   -0.9711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5140    2.5337   -1.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374    1.9809   -0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4221   -1.8435   -0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1435   -3.0227   -0.3346 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6524   -1.6020   -1.2397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160   -2.9231    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3064   -1.3791    2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544   -2.2375   -0.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3275    0.0965   -0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2125   -0.6538    0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5402    1.8661    1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7052   -1.5804    1.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2524   -0.3078   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961   -0.1045    1.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315    1.1790    0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5688   -0.4477    1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6866    0.5538    0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6587    2.4556   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    3.3710   -2.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3696    2.3610   -1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3713   -2.2295 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
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 18 20  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  6 26  1  0
  9 27  1  0
 10 28  1  6
 11 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    4666.6594668.581   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4667.9934667.812   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    4667.9934666.271   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    4669.3434665.525   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    4670.6784666.294   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    4669.3434663.984   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4668.0094663.212   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4666.6744663.984   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    4665.3404663.212   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    4666.6744665.525   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    4670.6784663.212   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0    4669.3284668.581   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    4670.6624667.812   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    4669.3284670.121   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    4665.3254667.811   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4663.9914668.581   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4662.6574667.811   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4662.6574666.271   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    4663.9914665.501   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    4665.3254666.271   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6                                                            
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   16   20    1                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0000706
HETATM    1  N1  UNL     1      -2.971  -1.990   1.428  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.226  -1.434   0.134  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.219  -0.300   0.170  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.739   0.807   1.022  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.645   0.792   1.630  1.00  0.00           O  
HETATM    6  O2  UNL     1      -4.550   1.927   1.153  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.963  -0.992  -0.505  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.015  -0.479  -1.651  1.00  0.00           O  
HETATM    9  N2  UNL     1      -0.747  -1.156   0.181  1.00  0.00           N  
HETATM   10  C5  UNL     1       0.498  -0.733  -0.420  1.00  0.00           C  
HETATM   11  C6  UNL     1       1.057   0.359   0.465  1.00  0.00           C  
HETATM   12  C7  UNL     1       2.346   0.910  -0.013  1.00  0.00           C  
HETATM   13  C8  UNL     1       3.571   0.387   0.400  1.00  0.00           C  
HETATM   14  C9  UNL     1       4.725   0.957  -0.091  1.00  0.00           C  
HETATM   15  C10 UNL     1       4.730   2.021  -0.971  1.00  0.00           C  
HETATM   16  C11 UNL     1       3.514   2.534  -1.375  1.00  0.00           C  
HETATM   17  C12 UNL     1       2.337   1.981  -0.898  1.00  0.00           C  
HETATM   18  C13 UNL     1       1.422  -1.843  -0.651  1.00  0.00           C  
HETATM   19  O4  UNL     1       1.143  -3.023  -0.335  1.00  0.00           O  
HETATM   20  O5  UNL     1       2.652  -1.602  -1.240  1.00  0.00           O  
HETATM   21  H1  UNL     1      -3.416  -2.923   1.573  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.306  -1.379   2.201  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.654  -2.238  -0.509  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.328   0.096  -0.865  1.00  0.00           H  
HETATM   25  H5  UNL     1      -5.213  -0.654   0.491  1.00  0.00           H  
HETATM   26  H6  UNL     1      -5.540   1.866   1.354  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.705  -1.580   1.129  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.252  -0.308  -1.423  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.196  -0.105   1.485  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.332   1.179   0.605  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.569  -0.448   1.090  1.00  0.00           H  
HETATM   32  H12 UNL     1       5.687   0.554   0.227  1.00  0.00           H  
HETATM   33  H13 UNL     1       5.659   2.456  -1.346  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.426   3.371  -2.066  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.370   2.361  -1.197  1.00  0.00           H  
HETATM   36  H16 UNL     1       2.751  -1.371  -2.230  1.00  0.00           H  
CONECT    1    2   21   22
CONECT    2    3    7   23
CONECT    3    4   24   25
CONECT    4    5    5    6
CONECT    6   26
CONECT    7    8    8    9
CONECT    9   10   27
CONECT   10   11   18   28
CONECT   11   12   29   30
CONECT   12   13   13   17
CONECT   13   14   31
CONECT   14   15   15   32
CONECT   15   16   33
CONECT   16   17   17   34
CONECT   17   35
CONECT   18   19   19   20
CONECT   20   36
END

HMDB0000706
     RDKit          3D
Aspartylphenylalanine
 36 36  0  0  0  0  0  0  0  0999 V2000
   -2.9711   -1.9902    1.4280 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2262   -1.4344    0.1339 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2189   -0.2997    0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7387    0.8069    1.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6453    0.7920    1.6303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5497    1.9266    1.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9633   -0.9920   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0146   -0.4792   -1.6506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7468   -1.1560    0.1813 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4976   -0.7332   -0.4197 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0572    0.3589    0.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.9102   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5715    0.3870    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252    0.9575   -0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7296    2.0213   -0.9711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5140    2.5337   -1.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374    1.9809   -0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4221   -1.8435   -0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1435   -3.0227   -0.3346 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6524   -1.6020   -1.2397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160   -2.9231    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3064   -1.3791    2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544   -2.2375   -0.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3275    0.0965   -0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2125   -0.6538    0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5402    1.8661    1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7052   -1.5804    1.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2524   -0.3078   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961   -0.1045    1.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315    1.1790    0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5688   -0.4477    1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6866    0.5538    0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6587    2.4556   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    3.3710   -2.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3696    2.3610   -1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3713   -2.2295 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
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 18 20  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  6 26  1  0
  9 27  1  0
 10 28  1  6
 11 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 20 36  1  0
M  END

View in JSmol

Synonyms

Value	Source
alpha-Aspartylphenylalanine	ChEBI
Aspartyl-phenylalanine	ChEBI
Demethylaspartame	ChEBI
DF	ChEBI
L-alpha-Asp-L-phe	ChEBI
L-Asp-L-phe	ChEBI
L-Aspartyl-L-phenylalanine	ChEBI
a-Aspartylphenylalanine	Generator
Α-aspartylphenylalanine	Generator
L-a-Asp-L-phe	Generator
L-Α-asp-L-phe	Generator
3-Amino-N-(a-carboxyphenethyl)-succinamic acid stereoisomer	HMDB
3-Amino-N-(carboxyphenethyl)-succinamic acid stereoisomer	HMDB
a-L-Aspartyl-L-phenylalanine	HMDB
alpha-L-Aspartyl-L-phenylalanine	HMDB
L-a-Aspartyl-L-phenylalanine	HMDB
L-alpha-Aspartyl-L-phenylalanine	HMDB
N-L-a-Aspartyl-L-phenylalanine	HMDB
N-L-alpha-Aspartyl-L-phenylalanine	HMDB
N-L-Aspartyl-L-phenylalanine	HMDB
Asp-phe	HMDB
Aspartate phenylalanine dipeptide	HMDB
Aspartate-phenylalanine dipeptide	HMDB
Aspartic acid phenylalanine dipeptide	HMDB
Aspartic acid-phenylalanine dipeptide	HMDB
D-F Dipeptide	HMDB
DF Dipeptide	HMDB
L-Α-aspartyl-L-phenylalanine	HMDB
N-Aspartylphenylalanine	HMDB
N-L-alpha-Aspartylphenylalanine	HMDB
N-L-Α-aspartyl-L-phenylalanine	HMDB
N-L-Α-aspartylphenylalanine	HMDB
N-alpha-Aspartylphenylalanine	HMDB
N-alpha-L-Aspartyl-L-phenylalanine	HMDB
N-Α-aspartylphenylalanine	HMDB
N-Α-L-aspartyl-L-phenylalanine	HMDB
alpha-Asp-phe	HMDB
alpha-L-Asp-L-phe	HMDB
Α-asp-phe	HMDB
Α-L-asp-L-phe	HMDB
Α-L-aspartyl-L-phenylalanine	HMDB
Aspartylphenylalanine	ChEBI

Chemical Formula

C₁₃H₁₆N₂O₅

Average Mass

280.2765 Da

Monoisotopic Mass

280.10592 Da

IUPAC Name

(3S)-3-amino-3-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}propanoic acid

Traditional Name

L-aspartyl-L-phenylalanine

CAS Registry Number

13433-09-5

SMILES

N[C@@H](CC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C13H16N2O5/c14-9(7-11(16)17)12(18)15-10(13(19)20)6-8-4-2-1-3-5-8/h1-5,9-10H,6-7,14H2,(H,15,18)(H,16,17)(H,19,20)/t9-,10-/m0/s1

InChI Key

YZQCXOFQZKCETR-UWVGGRQHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Phenylalanine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Beta amino acid or derivatives
3-phenylpropanoic-acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Amino acid or derivatives
Amino acid
Carboximidic acid derivative
Carboxylic acid
Carboximidic acid
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:73830 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	236 - 239 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.14 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-2.8	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	8.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	68.45 m³·mol⁻¹	ChemAxon
Polarizability	27.38 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

External Links

HMDB ID

HMDB0000706

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002275

KNApSAcK ID

Not Available

Chemspider ID

84028

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5674

PubChem Compound

93078

PDB ID

Not Available

ChEBI ID

73830

Good Scents ID

Not Available

References

General References

Burton EG, Schoenhard GL, Hill JA, Schmidt RE, Hribar JD, Kotsonis FN, Oppermann JA: Identification of N-beta-L-aspartyl-L-phenylalanine as a normal constituent of human plasma and urine. J Nutr. 1989 May;119(5):713-21. [PubMed:2723819 ]
Tobey NA, Heizer WD: Intestinal hydrolysis of aspartylphenylalanine--the metabolic product of aspartame. Gastroenterology. 1986 Oct;91(4):931-7. [PubMed:3743970 ]
Mizuma T, Masubuchi S, Awazu S: Intestinal absorption of stable cyclic dipeptides by the oligopeptide transporter in rat. J Pharm Pharmacol. 1998 Feb;50(2):167-72. [PubMed:9530984 ]
Burgert SL, Andersen DW, Stegink LD, Takeuchi H, Schedl HP: Metabolism of aspartame and its L-phenylalanine methyl ester decomposition product by the porcine gut. Metabolism. 1991 Jun;40(6):612-8. [PubMed:1865825 ]
Benoiton NL, Chen FM: 2,4-Dimethyl-5(4H)-oxazolone as reagent for activation and coupling of N-substituted aspartic acid. Int J Pept Protein Res. 1994 Aug;44(2):139-42. [PubMed:7982757 ]
Goodman M, Mattern RH, Gantzel P, Santini A, Iacovino R, Saviano M, Benedetti E: X-ray structures of new dipeptide taste ligands. J Pept Sci. 1998 Jun;4(4):229-38. [PubMed:9680057 ]
Pattanaargson S, Sanchavanakit C: Aspartame degradation study using electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom. 2000;14(11):987-93. [PubMed:10844736 ]
Schwerdt G, Freudinger R, Silbernagl S, Gekle M: Apical uptake of radiolabelled ochratoxin A into Madin-Darby canine kidney cells. Toxicology. 1998 Nov 16;131(2-3):193-202. [PubMed:9928634 ]
Leung SS, Grant DJ: Solid state stability studies of model dipeptides: aspartame and aspartylphenylalanine. J Pharm Sci. 1997 Jan;86(1):64-71. [PubMed:9002461 ]

Showing NP-Card for Aspartylphenylalanine (NP0000870)

MOL for NP0000870 (Aspartylphenylalanine)

3D MOL for NP0000870 (Aspartylphenylalanine)

3D SDF for NP0000870 (Aspartylphenylalanine)

3D-SDF for NP0000870 (Aspartylphenylalanine)

PDB for NP0000870 (Aspartylphenylalanine)

3D PDB for NP0000870 (Aspartylphenylalanine)

SMILES for NP0000870 (Aspartylphenylalanine)

INCHI for NP0000870 (Aspartylphenylalanine)

Structure for NP0000870 (Aspartylphenylalanine)

3D Structure for NP0000870 (Aspartylphenylalanine)