Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Show more...Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-30 15:52:35 UTC

Update Date

2021-09-14 15:37:02 UTC

HMDB ID

HMDB0013302

Secondary Accession Numbers

HMDB13302

Metabolite Identification

Common Name

Phenylalanylphenylalanine

Description

Phenylalanylphenylalanine (Phe-Phe) is a peptide made of two phenylalanine molecules. Phenylalanine is an essential amino acid and the precursor for the amino acid tyrosine. Like tyrosine, it is the precursor of catecholamines in the body (tyramine, dopamine, epinephrine and norepinephrine). The psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is a precursor of the neurotransmitters called catecholamines, which are adrenalin-like substances. Phenylalanine is highly concentrated in the human brain and plasma. The Phe-Phe recognition motif of Alzheimer's amyloid-beta peptide is the smallest peptide able to assemble into higher-order structures (PMID: 17172307 ).

Structure

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

HMDB0013302
     RDKit          3D
Phenylalanylphenylalanine
 43 44  0  0  0  0  0  0  0  0999 V2000
    1.3682   -2.1937    2.7586 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0119   -1.0667    2.0639 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0510   -1.6505    1.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8108   -0.6777    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9775   -0.0746    0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6501    0.8369    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    1.1707   -1.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0075    0.5886   -1.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3356   -0.3314   -0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9631   -0.3066    1.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2617    0.7346    0.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4102   -0.6700    1.4473 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460    0.0934    0.7734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1095   -0.7042   -0.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1662    0.0629   -1.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4824    0.0166   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4938    0.7257   -1.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2036    1.5231   -2.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    1.5782   -2.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8822    0.8740   -2.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3738    0.7190    1.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803    0.5000    2.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4427    1.5295    1.4123 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173   -1.8161    3.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9231   -2.8387    2.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4676   -0.4083    2.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -2.2263    1.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524   -2.3662    0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3713   -0.3273    1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5640    1.3040    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6663    1.8804   -1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6344    0.8649   -2.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297   -0.7430   -1.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6576   -1.5199    1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9203    0.9483    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3615   -1.1038   -1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211   -1.6102    0.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7236   -0.6116    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5321    0.6638   -0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9664    2.0902   -2.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6789    2.2074   -3.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8507    0.9124   -2.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2963    1.4222    1.9343 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13 21  1  0
 21 22  2  0
 21 23  1  0
  9  4  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  3 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 12 34  1  0
 13 35  1  6
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 23 43  1  0
M  END

  Mrv1652303062020282D          

 23 24  0  0  0  0            999 V2000
10001.8001 9999.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.085510000.2157    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3730 9999.8034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.659010000.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9456 9999.8034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.230210000.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9456 9998.9797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.659010001.0394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.085510001.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.800110001.4513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.373010001.4513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5187 9999.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.804210000.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0897 9999.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0896 9998.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8041 9998.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5187 9998.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.941110001.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.226610001.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.512110001.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.512010000.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2265 9999.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.941110000.2150    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  0  0  0  0
  2  9  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  1  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
  6 12  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 18  1  0  0  0  0
  1 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013302

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H20N2O3/c19-15(11-13-7-3-1-4-8-13)17(21)20-16(18(22)23)12-14-9-5-2-6-10-14/h1-10,15-16H,11-12,19H2,(H,20,21)(H,22,23)/t15-,16-/m0/s1

> <INCHI_KEY>
GKZIWHRNKRBEOH-HOTGVXAUSA-N

> <FORMULA>
C18H20N2O3

> <MOLECULAR_WEIGHT>
312.369

> <EXACT_MASS>
312.147392512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.56349312916071

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-phenylpropanoic acid

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
-0.06665742104886124

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.611178230307814

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7808946240619323

> <JCHEM_PKA_STRONGEST_BASIC>
8.009683851231957

> <JCHEM_POLAR_SURFACE_AREA>
92.41999999999999

> <JCHEM_REFRACTIVITY>
87.03270000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013302
     RDKit          3D
Phenylalanylphenylalanine
 43 44  0  0  0  0  0  0  0  0999 V2000
    1.3682   -2.1937    2.7586 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0119   -1.0667    2.0639 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0510   -1.6505    1.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8108   -0.6777    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9775   -0.0746    0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6501    0.8369    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    1.1707   -1.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0075    0.5886   -1.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3356   -0.3314   -0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9631   -0.3066    1.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2617    0.7346    0.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4102   -0.6700    1.4473 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460    0.0934    0.7734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1095   -0.7042   -0.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1662    0.0629   -1.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4824    0.0166   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4938    0.7257   -1.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2036    1.5231   -2.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    1.5782   -2.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8822    0.8740   -2.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3738    0.7190    1.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803    0.5000    2.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4427    1.5295    1.4123 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173   -1.8161    3.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9231   -2.8387    2.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4676   -0.4083    2.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -2.2263    1.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524   -2.3662    0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3713   -0.3273    1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5640    1.3040    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6663    1.8804   -1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6344    0.8649   -2.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297   -0.7430   -1.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6576   -1.5199    1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9203    0.9483    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3615   -1.1038   -1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211   -1.6102    0.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7236   -0.6116    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5321    0.6638   -0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9664    2.0902   -2.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6789    2.2074   -3.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8507    0.9124   -2.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2963    1.4222    1.9343 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13 21  1  0
 21 22  2  0
 21 23  1  0
  9  4  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  3 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 12 34  1  0
 13 35  1  6
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 23 43  1  0
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8670.0278666.300   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.6938667.069   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8667.3638666.300   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8666.0308667.069   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8664.6988666.300   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8663.3638667.069   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8664.6988664.762   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    8666.0308668.607   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8668.6938668.607   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8670.0278669.376   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8667.3638669.376   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8662.0358666.301   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8660.7018667.071   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8659.3678666.301   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8659.3678664.761   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8660.7018663.991   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.0358664.761   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8674.0238668.608   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8672.6908669.378   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8671.3568668.608   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8671.3568667.068   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8672.6898666.298   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8674.0238667.068   0.000  0.00  0.00           C+0
CONECT    1    2   21                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   12                                                       
CONECT    7    5                                                            
CONECT    8    4                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12   13   17    6                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   19   23                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22    1                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0013302
HETATM    1  N1  UNL     1       1.368  -2.194   2.759  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.012  -1.067   2.064  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.051  -1.650   1.170  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.811  -0.678   0.383  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.978  -0.075   0.796  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.650   0.837   0.006  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.168   1.171  -1.229  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.008   0.589  -1.671  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.336  -0.331  -0.864  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.963  -0.307   1.390  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.262   0.735   0.713  1.00  0.00           O  
HETATM   12  N2  UNL     1      -0.410  -0.670   1.447  1.00  0.00           N  
HETATM   13  C10 UNL     1      -1.446   0.093   0.773  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.109  -0.704  -0.309  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.166   0.063  -1.002  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.482   0.017  -0.594  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.494   0.726  -1.224  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.204   1.523  -2.311  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.891   1.578  -2.730  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.882   0.874  -2.105  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.374   0.719   1.735  1.00  0.00           C  
HETATM   22  O2  UNL     1      -2.180   0.500   2.969  1.00  0.00           O  
HETATM   23  O3  UNL     1      -3.443   1.529   1.412  1.00  0.00           O  
HETATM   24  H1  UNL     1       0.717  -1.816   3.484  1.00  0.00           H  
HETATM   25  H2  UNL     1       0.923  -2.839   2.100  1.00  0.00           H  
HETATM   26  H3  UNL     1       2.468  -0.408   2.837  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.759  -2.226   1.807  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.552  -2.366   0.480  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.371  -0.327   1.768  1.00  0.00           H  
HETATM   30  H7  UNL     1       6.564   1.304   0.339  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.666   1.880  -1.877  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.634   0.865  -2.658  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.430  -0.743  -1.289  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.658  -1.520   2.000  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.920   0.948   0.255  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.361  -1.104  -1.028  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.621  -1.610   0.117  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.724  -0.612   0.264  1.00  0.00           H  
HETATM   39  H16 UNL     1      -6.532   0.664  -0.870  1.00  0.00           H  
HETATM   40  H17 UNL     1      -5.966   2.090  -2.827  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.679   2.207  -3.584  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.851   0.912  -2.428  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.296   1.422   1.934  1.00  0.00           H  
CONECT    1    2   24   25
CONECT    2    3   10   26
CONECT    3    4   27   28
CONECT    4    5    5    9
CONECT    5    6   29
CONECT    6    7    7   30
CONECT    7    8   31
CONECT    8    9    9   32
CONECT    9   33
CONECT   10   11   11   12
CONECT   12   13   34
CONECT   13   14   21   35
CONECT   14   15   36   37
CONECT   15   16   16   20
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   40
CONECT   19   20   20   41
CONECT   20   42
CONECT   21   22   22   23
CONECT   23   43
END

HMDB0013302
     RDKit          3D
Phenylalanylphenylalanine
 43 44  0  0  0  0  0  0  0  0999 V2000
    1.3682   -2.1937    2.7586 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0119   -1.0667    2.0639 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0510   -1.6505    1.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8108   -0.6777    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9775   -0.0746    0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6501    0.8369    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    1.1707   -1.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0075    0.5886   -1.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3356   -0.3314   -0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9631   -0.3066    1.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2617    0.7346    0.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4102   -0.6700    1.4473 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460    0.0934    0.7734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1095   -0.7042   -0.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1662    0.0629   -1.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4824    0.0166   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4938    0.7257   -1.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2036    1.5231   -2.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    1.5782   -2.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8822    0.8740   -2.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3738    0.7190    1.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803    0.5000    2.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4427    1.5295    1.4123 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173   -1.8161    3.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9231   -2.8387    2.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4676   -0.4083    2.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -2.2263    1.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524   -2.3662    0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3713   -0.3273    1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5640    1.3040    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6663    1.8804   -1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6344    0.8649   -2.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297   -0.7430   -1.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6576   -1.5199    1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9203    0.9483    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3615   -1.1038   -1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211   -1.6102    0.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7236   -0.6116    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5321    0.6638   -0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9664    2.0902   -2.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6789    2.2074   -3.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8507    0.9124   -2.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2963    1.4222    1.9343 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13 21  1  0
 21 22  2  0
 21 23  1  0
  9  4  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  3 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 12 34  1  0
 13 35  1  6
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 23 43  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-{[(2S)-2-amino-3-phenylpropanoyl]amino}-3-phenylpropanoic acid	ChEBI
FF	ChEBI
H-L-Phe-L-phe-OH	ChEBI
H-Phe-phe-OH	ChEBI
L-Phe-L-phe	ChEBI
(2S)-2-{[(2S)-2-amino-3-phenylpropanoyl]amino}-3-phenylpropanoate	Generator
(Phenylalanyl)phenylalanine	HMDB
Diphenylalanine	HMDB
F-F Dipeptide	HMDB
FF Dipeptide	HMDB
L,L-Diphenylalanine	HMDB
L-Phe-L-phe-OH	HMDB
L-Phenylalanyl-L-phenylalanine	HMDB
N-L-Phenylalanyl-L-phenylalanine	HMDB
N-Phenylalanylphenylalanine	HMDB
Phe-phe	HMDB
Phenylalanine phenylalanine dipeptide	HMDB
Phenylalanine-phenylalanine dipeptide	HMDB
Phenylalanyl-phenylalanine	HMDB
Phenylalanylphenylalanine	ChEBI

Chemical Formula

C₁₈H₂₀N₂O₃

Average Molecular Weight

312.369

Monoisotopic Molecular Weight

312.147392512

IUPAC Name

(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-phenylpropanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-phenylpropanoic acid

CAS Registry Number

2577-40-4

SMILES

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

InChI Identifier

InChI=1S/C18H20N2O3/c19-15(11-13-7-3-1-4-8-13)17(21)20-16(18(22)23)12-14-9-5-2-6-10-14/h1-10,15-16H,11-12,19H2,(H,20,21)(H,22,23)/t15-,16-/m0/s1

InChI Key

GKZIWHRNKRBEOH-HOTGVXAUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Phenylalanine or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
3-phenylpropanoic-acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Aralkylamine
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Amino acid or derivatives
Carboxamide group
Carboxylic acid salt
Amino acid
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Organic salt
Hydrocarbon derivative
Primary aliphatic amine
Organic nitrogen compound
Amine
Organic oxygen compound
Carbonyl group
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic zwitterion
Primary amine
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:72723 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0013302)
Saliva (PMID: 22308371)

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)
Feces (PMID: 25486321)

Source

Endogenous

Endogenous (HMDB: HMDB0013302)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	0.043 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	-0.067	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	8.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	87.03 m³·mol⁻¹	ChemAxon
Polarizability	33.56 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
DeepCCS	[M+H]+	171.992	30932474
DeepCCS	[M-H]-	169.634	30932474
DeepCCS	[M-2H]-	203.667	30932474
DeepCCS	[M+Na]+	178.895	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylalanylphenylalanine	N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	4031.0	Standard polar	33892256
Phenylalanylphenylalanine	N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	2289.7	Standard non polar	33892256
Phenylalanylphenylalanine	N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	2782.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenylalanylphenylalanine,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC1=CC=CC=C1	2626.1	Semi standard non polar	33892256
Phenylalanylphenylalanine,1TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2689.5	Semi standard non polar	33892256
Phenylalanylphenylalanine,1TMS,isomer #3	C[Si](C)(C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)C(=O)O	2635.6	Semi standard non polar	33892256
Phenylalanylphenylalanine,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2659.3	Semi standard non polar	33892256
Phenylalanylphenylalanine,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2612.5	Standard non polar	33892256
Phenylalanylphenylalanine,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	3506.1	Standard polar	33892256
Phenylalanylphenylalanine,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C	2594.0	Semi standard non polar	33892256
Phenylalanylphenylalanine,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C	2615.3	Standard non polar	33892256
Phenylalanylphenylalanine,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C	3652.8	Standard polar	33892256
Phenylalanylphenylalanine,2TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2800.3	Semi standard non polar	33892256
Phenylalanylphenylalanine,2TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2725.0	Standard non polar	33892256
Phenylalanylphenylalanine,2TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	3670.3	Standard polar	33892256
Phenylalanylphenylalanine,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2670.9	Semi standard non polar	33892256
Phenylalanylphenylalanine,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2678.7	Standard non polar	33892256
Phenylalanylphenylalanine,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	3561.5	Standard polar	33892256
Phenylalanylphenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2793.4	Semi standard non polar	33892256
Phenylalanylphenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2718.6	Standard non polar	33892256
Phenylalanylphenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	3321.2	Standard polar	33892256
Phenylalanylphenylalanine,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2647.3	Semi standard non polar	33892256
Phenylalanylphenylalanine,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2665.4	Standard non polar	33892256
Phenylalanylphenylalanine,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3264.5	Standard polar	33892256
Phenylalanylphenylalanine,3TMS,isomer #3	C[Si](C)(C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	2791.7	Semi standard non polar	33892256
Phenylalanylphenylalanine,3TMS,isomer #3	C[Si](C)(C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	2781.2	Standard non polar	33892256
Phenylalanylphenylalanine,3TMS,isomer #3	C[Si](C)(C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	3395.0	Standard polar	33892256
Phenylalanylphenylalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2819.2	Semi standard non polar	33892256
Phenylalanylphenylalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2799.8	Standard non polar	33892256
Phenylalanylphenylalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	3149.5	Standard polar	33892256
Phenylalanylphenylalanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC1=CC=CC=C1	2904.2	Semi standard non polar	33892256
Phenylalanylphenylalanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2905.9	Semi standard non polar	33892256
Phenylalanylphenylalanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)C(=O)O	2906.5	Semi standard non polar	33892256
Phenylalanylphenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3101.6	Semi standard non polar	33892256
Phenylalanylphenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3001.0	Standard non polar	33892256
Phenylalanylphenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3623.7	Standard polar	33892256
Phenylalanylphenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3120.1	Semi standard non polar	33892256
Phenylalanylphenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3006.7	Standard non polar	33892256
Phenylalanylphenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3731.4	Standard polar	33892256
Phenylalanylphenylalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3261.2	Semi standard non polar	33892256
Phenylalanylphenylalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3067.6	Standard non polar	33892256
Phenylalanylphenylalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3686.8	Standard polar	33892256
Phenylalanylphenylalanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3119.6	Semi standard non polar	33892256
Phenylalanylphenylalanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3046.0	Standard non polar	33892256
Phenylalanylphenylalanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3659.0	Standard polar	33892256
Phenylalanylphenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3460.9	Semi standard non polar	33892256
Phenylalanylphenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3265.6	Standard non polar	33892256
Phenylalanylphenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3490.4	Standard polar	33892256
Phenylalanylphenylalanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3298.0	Semi standard non polar	33892256
Phenylalanylphenylalanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3222.6	Standard non polar	33892256
Phenylalanylphenylalanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3491.3	Standard polar	33892256
Phenylalanylphenylalanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	3450.8	Semi standard non polar	33892256
Phenylalanylphenylalanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	3303.5	Standard non polar	33892256
Phenylalanylphenylalanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	3553.2	Standard polar	33892256
Phenylalanylphenylalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3622.3	Semi standard non polar	33892256
Phenylalanylphenylalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3485.4	Standard non polar	33892256
Phenylalanylphenylalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3427.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylalanylphenylalanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylalanylphenylalanine 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 - Phenylalanylphenylalanine 10V, Positive-QTOF	splash10-03di-0659000000-2ea890b75b0b712a2818	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylphenylalanine 20V, Positive-QTOF	splash10-006x-7900000000-2c1f0b9be17a3ca8be0d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylphenylalanine 40V, Positive-QTOF	splash10-002f-9600000000-f47c1b3ad7e2a330a7c2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylphenylalanine 10V, Negative-QTOF	splash10-03di-0129000000-fb15b06ad7556b02f9e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylphenylalanine 20V, Negative-QTOF	splash10-03dm-4922000000-fcfe1e5ee3e54e1a7e9a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylphenylalanine 40V, Negative-QTOF	splash10-0f96-6910000000-e05747bda02a2e69e53d	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	0.03 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029369

KNApSAcK ID

Not Available

Chemspider ID

5361193

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6993089

PDB ID

Not Available

ChEBI ID

72723

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1911081

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Authors unspecified: [Proceedings of the Swiss Society of Gynecology and Obstetrics, annual meeting. Interlaken, 13-15 June 1991]. Arch Gynecol Obstet. 1991;249 Suppl:S1-189. [PubMed:1796831 ]
de Groot NS, Parella T, Aviles FX, Vendrell J, Ventura S: Ile-phe dipeptide self-assembly: clues to amyloid formation. Biophys J. 2007 Mar 1;92(5):1732-41. doi: 10.1529/biophysj.106.096677. Epub 2006 Dec 15. [PubMed:17172307 ]

Showing metabocard for Phenylalanylphenylalanine (HMDB0013302)

MOL for HMDB0013302 (Phenylalanylphenylalanine)

3D MOL for HMDB0013302 (Phenylalanylphenylalanine)

3D SDF for HMDB0013302 (Phenylalanylphenylalanine)

3D-SDF for HMDB0013302 (Phenylalanylphenylalanine)

PDB for HMDB0013302 (Phenylalanylphenylalanine)

3D PDB for HMDB0013302 (Phenylalanylphenylalanine)

SMILES for HMDB0013302 (Phenylalanylphenylalanine)

INCHI for HMDB0013302 (Phenylalanylphenylalanine)

Structure for HMDB0013302 (Phenylalanylphenylalanine)

3D Structure for HMDB0013302 (Phenylalanylphenylalanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra