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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:34 UTC

Update Date

2022-03-07 02:52:56 UTC

HMDB ID

HMDB0031360

Secondary Accession Numbers

HMDB31360

Metabolite Identification

Common Name

L-cis-Cyclo(aspartylphenylalanyl)

Description

L-cis-Cyclo(aspartylphenylalanyl), also known as L-cis-cyclo(phenylalanylaspartyl) or 3-CMB-DKP, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Based on a literature review very few articles have been published on L-cis-Cyclo(aspartylphenylalanyl).

Structure

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

HMDB0031360
     RDKit          3D
L-cis-Cyclo(aspartylphenylalanyl)
 33 34  0  0  0  0  0  0  0  0999 V2000
    5.2420   -0.0961    1.3380 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924   -0.3786    0.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4305    0.1391   -0.9227 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5858   -1.2601    0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5548   -0.6240    1.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247   -1.3618    1.1001 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0822   -0.7093    0.8211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782   -1.0396    1.5985 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0066    0.2372   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980    1.2422   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4663    0.7058   -0.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1442    0.5632    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4259    0.0262    1.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0470   -0.3799   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3717   -0.2376   -1.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1021    0.2965   -1.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2487    1.0124   -0.3776 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3254    0.7539    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1185    1.6468    0.8785 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0201    0.9105   -1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9158   -2.2427    0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729   -1.3881   -0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9692   -0.5411    2.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3680   -2.3723    1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466   -0.3530   -1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115    2.0147    0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809    1.8373   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6926    0.8835    1.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9752   -0.0983    1.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0596   -0.8111   -0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8675   -0.5553   -2.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5632    0.4123   -2.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3728    1.7673   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 18  5  1  0
 16 11  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  END


  Mrv0541 02241216082D          

 19 20  0  0  0  0            999 V2000
   -0.3567    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568   -0.8243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568    0.8242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841    0.8257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0704    0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140   -0.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990    0.4132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004    0.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2140    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2140   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004   -0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  2 13  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 14 15  2  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031360

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC1NC(=O)C(CC2=CC=CC=C2)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O4/c16-11(17)7-10-13(19)14-9(12(18)15-10)6-8-4-2-1-3-5-8/h1-5,9-10H,6-7H2,(H,14,19)(H,15,18)(H,16,17)

> <INCHI_KEY>
VNHJXYUDIBQDDX-UHFFFAOYSA-N

> <FORMULA>
C13H14N2O4

> <MOLECULAR_WEIGHT>
262.2613

> <EXACT_MASS>
262.095356946

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.21133184192519

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(5-benzyl-3,6-dioxopiperazin-2-yl)acetic acid

> <ALOGPS_LOGP>
-0.04

> <JCHEM_LOGP>
-0.05852353700000023

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.804717150197394

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.050431959074224

> <JCHEM_PKA_STRONGEST_BASIC>
-4.620707318280546

> <JCHEM_POLAR_SURFACE_AREA>
95.5

> <JCHEM_REFRACTIVITY>
65.24920000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5-benzyl-3,6-dioxopiperazin-2-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031360
     RDKit          3D
L-cis-Cyclo(aspartylphenylalanyl)
 33 34  0  0  0  0  0  0  0  0999 V2000
    5.2420   -0.0961    1.3380 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924   -0.3786    0.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4305    0.1391   -0.9227 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5858   -1.2601    0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5548   -0.6240    1.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247   -1.3618    1.1001 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0822   -0.7093    0.8211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782   -1.0396    1.5985 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0066    0.2372   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980    1.2422   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4663    0.7058   -0.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1442    0.5632    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4259    0.0262    1.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0470   -0.3799   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3717   -0.2376   -1.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1021    0.2965   -1.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2487    1.0124   -0.3776 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3254    0.7539    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1185    1.6468    0.8785 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0201    0.9105   -1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9158   -2.2427    0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729   -1.3881   -0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9692   -0.5411    2.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3680   -2.3723    1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466   -0.3530   -1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115    2.0147    0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809    1.8373   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6926    0.8835    1.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9752   -0.0983    1.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0596   -0.8111   -0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8675   -0.5553   -2.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5632    0.4123   -2.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3728    1.7673   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 18  5  1  0
 16 11  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.666   0.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.666  -0.769   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.666  -1.539   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.996  -0.769   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.996   0.771   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.666   1.539   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       3.330   1.541   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.998   1.541   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.330  -1.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.665  -0.769   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.999  -1.539   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.665   0.771   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.001  -1.539   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.333   0.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.667   1.536   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.999   0.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.999  -0.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.667  -1.541   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.333  -0.771   0.000  0.00  0.00           C+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    1    5                                                       
CONECT    7    5                                                            
CONECT    8    1   14                                                       
CONECT    9    4   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2                                                            
CONECT   14    8   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   14   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0031360
HETATM    1  O1  UNL     1       5.242  -0.096   1.338  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.792  -0.379   0.195  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.431   0.139  -0.923  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.586  -1.260   0.138  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.555  -0.624   1.035  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.325  -1.362   1.100  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.082  -0.709   0.821  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.878  -1.040   1.598  1.00  0.00           O  
HETATM    9  C5  UNL     1       0.007   0.237  -0.271  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.098   1.242  -0.248  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.466   0.706  -0.231  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.144   0.563   0.950  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.426   0.026   1.014  1.00  0.00           C  
HETATM   14  C10 UNL     1      -5.047  -0.380  -0.148  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.372  -0.238  -1.338  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.102   0.296  -1.379  1.00  0.00           C  
HETATM   17  N2  UNL     1       1.249   1.012  -0.378  1.00  0.00           N  
HETATM   18  C13 UNL     1       2.325   0.754   0.507  1.00  0.00           C  
HETATM   19  O4  UNL     1       3.118   1.647   0.879  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.020   0.910  -1.450  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.916  -2.243   0.542  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.273  -1.388  -0.895  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.969  -0.541   2.050  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.368  -2.372   1.353  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.047  -0.353  -1.233  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.912   2.015   0.545  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.981   1.837  -1.207  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.693   0.884   1.871  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.975  -0.098   1.935  1.00  0.00           H  
HETATM   30  H11 UNL     1      -6.060  -0.811  -0.121  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.867  -0.555  -2.267  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.563   0.412  -2.336  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.373   1.767  -1.091  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5   21   22
CONECT    5    6   18   23
CONECT    6    7   24
CONECT    7    8    8    9
CONECT    9   10   17   25
CONECT   10   11   26   27
CONECT   11   12   12   16
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15   30
CONECT   15   16   16   31
CONECT   16   32
CONECT   17   18   33
CONECT   18   19   19
END

HMDB0031360
     RDKit          3D
L-cis-Cyclo(aspartylphenylalanyl)
 33 34  0  0  0  0  0  0  0  0999 V2000
    5.2420   -0.0961    1.3380 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924   -0.3786    0.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4305    0.1391   -0.9227 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5858   -1.2601    0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5548   -0.6240    1.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247   -1.3618    1.1001 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0822   -0.7093    0.8211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782   -1.0396    1.5985 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0066    0.2372   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980    1.2422   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4663    0.7058   -0.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1442    0.5632    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4259    0.0262    1.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0470   -0.3799   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3717   -0.2376   -1.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1021    0.2965   -1.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2487    1.0124   -0.3776 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3254    0.7539    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1185    1.6468    0.8785 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0201    0.9105   -1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9158   -2.2427    0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729   -1.3881   -0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9692   -0.5411    2.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3680   -2.3723    1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466   -0.3530   -1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115    2.0147    0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809    1.8373   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6926    0.8835    1.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9752   -0.0983    1.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0596   -0.8111   -0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8675   -0.5553   -2.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5632    0.4123   -2.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3728    1.7673   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 18  5  1  0
 16 11  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S-cis)-(-)-5-Benzyl-3,6-dioxo-2-piperazineacetic acid	HMDB
(2S-cis)-5-Benzyl-3,6-dioxopiperazine-2-acetic acid	HMDB
3-Phenylmethyl-2,5-diketopiperazine-6-acetic acid	HMDB
Cyclo(aspartyl-phenylalanyl)	HMDB
L-cis-3,6-Dioxo-5-(phenylmethyl)-2-piperazineacetic acid	HMDB
L-cis-5-Benzyl-3,6-dioxo-2-piperazineacetic acid	HMDB
L-cis-5-Benzyldiketopiperazine-2-acetic acid	HMDB
L-cis-Cyclo(phenylalanylaspartyl)	HMDB
3-CMB-DKP	HMDB
2-(5-Benzyl-3,6-dihydroxy-2,5-dihydropyrazin-2-yl)acetate	HMDB
3-Carboxymethyl-6-benzyl-2,5-diketopiperazine	HMDB

Chemical Formula

C₁₃H₁₄N₂O₄

Average Molecular Weight

262.2613

Monoisotopic Molecular Weight

262.095356946

IUPAC Name

2-(5-benzyl-3,6-dioxopiperazin-2-yl)acetic acid

Traditional Name

(5-benzyl-3,6-dioxopiperazin-2-yl)acetic acid

CAS Registry Number

5262-10-2

SMILES

OC(=O)CC1NC(=O)C(CC2=CC=CC=C2)NC1=O

InChI Identifier

InChI=1S/C13H14N2O4/c16-11(17)7-10-13(19)14-9(12(18)15-10)6-8-4-2-1-3-5-8/h1-5,9-10H,6-7H2,(H,14,19)(H,15,18)(H,16,17)

InChI Key

VNHJXYUDIBQDDX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Dioxopiperazine
2,5-dioxopiperazine
Monocyclic benzene moiety
1,4-diazinane
Piperazine
Benzenoid
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031360)
Cytoplasm (HMDB: HMDB0031360)

Source

Endogenous

Endogenous (HMDB: HMDB0031360)

Exogenous

Food

Food (HMDB: HMDB0031360)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	256 - 258 °C	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	0.67 g/L	ALOGPS
logP	-0.04	ALOGPS
logP	-0.059	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.5 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.25 m³·mol⁻¹	ChemAxon
Polarizability	24.21 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	160.048	31661259
DarkChem	[M-H]-	157.191	31661259
DeepCCS	[M+H]+	156.175	30932474
DeepCCS	[M-H]-	153.779	30932474
DeepCCS	[M-2H]-	186.743	30932474
DeepCCS	[M+Na]+	162.135	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	163.9	32859911
AllCCS	[M+Na]+	164.9	32859911
AllCCS	[M-H]-	161.2	32859911
AllCCS	[M+Na-2H]-	161.1	32859911
AllCCS	[M+HCOO]-	161.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-cis-Cyclo(aspartylphenylalanyl)	OC(=O)CC1NC(=O)C(CC2=CC=CC=C2)NC1=O	4187.7	Standard polar	33892256
L-cis-Cyclo(aspartylphenylalanyl)	OC(=O)CC1NC(=O)C(CC2=CC=CC=C2)NC1=O	2135.2	Standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl)	OC(=O)CC1NC(=O)C(CC2=CC=CC=C2)NC1=O	2657.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-cis-Cyclo(aspartylphenylalanyl),1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1NC(=O)C(CC2=CC=CC=C2)NC1=O	2409.9	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),1TMS,isomer #2	C[Si](C)(C)N1C(=O)C(CC2=CC=CC=C2)NC(=O)C1CC(=O)O	2352.3	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),1TMS,isomer #3	C[Si](C)(C)N1C(=O)C(CC(=O)O)NC(=O)C1CC1=CC=CC=C1	2353.6	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1C(=O)NC(CC2=CC=CC=C2)C(=O)N1[Si](C)(C)C	2358.9	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1C(=O)NC(CC2=CC=CC=C2)C(=O)N1[Si](C)(C)C	2455.6	Standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),2TMS,isomer #2	C[Si](C)(C)OC(=O)CC1NC(=O)C(CC2=CC=CC=C2)N([Si](C)(C)C)C1=O	2352.0	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),2TMS,isomer #2	C[Si](C)(C)OC(=O)CC1NC(=O)C(CC2=CC=CC=C2)N([Si](C)(C)C)C1=O	2475.6	Standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),2TMS,isomer #3	C[Si](C)(C)N1C(=O)C(CC2=CC=CC=C2)N([Si](C)(C)C)C(=O)C1CC(=O)O	2308.4	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),2TMS,isomer #3	C[Si](C)(C)N1C(=O)C(CC2=CC=CC=C2)N([Si](C)(C)C)C(=O)C1CC(=O)O	2425.4	Standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1C(=O)N([Si](C)(C)C)C(CC2=CC=CC=C2)C(=O)N1[Si](C)(C)C	2319.3	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1C(=O)N([Si](C)(C)C)C(CC2=CC=CC=C2)C(=O)N1[Si](C)(C)C	2503.3	Standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1NC(=O)C(CC2=CC=CC=C2)NC1=O	2670.4	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)C(CC2=CC=CC=C2)NC(=O)C1CC(=O)O	2619.9	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)C(CC(=O)O)NC(=O)C1CC1=CC=CC=C1	2604.2	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1C(=O)NC(CC2=CC=CC=C2)C(=O)N1[Si](C)(C)C(C)(C)C	2850.5	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1C(=O)NC(CC2=CC=CC=C2)C(=O)N1[Si](C)(C)C(C)(C)C	2904.4	Standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC1NC(=O)C(CC2=CC=CC=C2)N([Si](C)(C)C(C)(C)C)C1=O	2829.5	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC1NC(=O)C(CC2=CC=CC=C2)N([Si](C)(C)C(C)(C)C)C1=O	2922.7	Standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)C(CC2=CC=CC=C2)N([Si](C)(C)C(C)(C)C)C(=O)C1CC(=O)O	2798.1	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)C(CC2=CC=CC=C2)N([Si](C)(C)C(C)(C)C)C(=O)C1CC(=O)O	2861.1	Standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1C(=O)N([Si](C)(C)C(C)(C)C)C(CC2=CC=CC=C2)C(=O)N1[Si](C)(C)C(C)(C)C	3035.0	Semi standard non polar	33892256
L-cis-Cyclo(aspartylphenylalanyl),3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1C(=O)N([Si](C)(C)C(C)(C)C)C(CC2=CC=CC=C2)C(=O)N1[Si](C)(C)C(C)(C)C	3112.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kbg-8940000000-7c805cd44ad858016a38	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) GC-MS (1 TMS) - 70eV, Positive	splash10-00vl-9361000000-31710fe31bc2ea726498	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) 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 - L-cis-Cyclo(aspartylphenylalanyl) 10V, Positive-QTOF	splash10-03dj-0090000000-a9b25afab4a8bc5fde82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) 20V, Positive-QTOF	splash10-0udi-1190000000-d4d6f1542ea5b5cbb304	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) 40V, Positive-QTOF	splash10-0006-9400000000-23be9d6b82d3dbcff622	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) 10V, Negative-QTOF	splash10-03xr-0390000000-ddf0fdb9e3de1ac967ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) 20V, Negative-QTOF	splash10-0006-9420000000-6521c630fd1cb42902ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) 40V, Negative-QTOF	splash10-0006-9200000000-2cd3d3b210b1b9a89459	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) 10V, Positive-QTOF	splash10-03di-0090000000-a2ee4d242ee88b598c17	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) 20V, Positive-QTOF	splash10-016s-0490000000-90698a7e5d1724180dd0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) 40V, Positive-QTOF	splash10-0fr6-5910000000-c92117a86b885dd0d6ac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) 10V, Negative-QTOF	splash10-014i-0090000000-fb815081bd7294709b23	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) 20V, Negative-QTOF	splash10-014l-5590000000-fe3cbf6bb80e6f097cf9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-cis-Cyclo(aspartylphenylalanyl) 40V, Negative-QTOF	splash10-0006-9400000000-25114f4b08257b56d5dc	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB003427

KNApSAcK ID

Not Available

Chemspider ID

106716

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119494

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for L-cis-Cyclo(aspartylphenylalanyl) (HMDB0031360)

MOL for HMDB0031360 (L-cis-Cyclo(aspartylphenylalanyl))

3D MOL for HMDB0031360 (L-cis-Cyclo(aspartylphenylalanyl))

3D SDF for HMDB0031360 (L-cis-Cyclo(aspartylphenylalanyl))

3D-SDF for HMDB0031360 (L-cis-Cyclo(aspartylphenylalanyl))

PDB for HMDB0031360 (L-cis-Cyclo(aspartylphenylalanyl))

3D PDB for HMDB0031360 (L-cis-Cyclo(aspartylphenylalanyl))

SMILES for HMDB0031360 (L-cis-Cyclo(aspartylphenylalanyl))

INCHI for HMDB0031360 (L-cis-Cyclo(aspartylphenylalanyl))

Structure for HMDB0031360 (L-cis-Cyclo(aspartylphenylalanyl))

3D Structure for HMDB0031360 (L-cis-Cyclo(aspartylphenylalanyl))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra