NP-MRD: Showing NP-Card for Phenylalanylalanine (NP0136588)

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Record Information

Version

2.0

Created at

2022-05-12 15:18:25 UTC

Updated at

2022-05-12 15:18:25 UTC

NP-MRD ID

NP0136588

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phenylalanylalanine

Description

Phe-Ala, also known as F-A or L-phe-L-ala, 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. Phe-Ala is possibly neutral. Phenylalanylalanine is found in Trypanosoma brucei. A dipeptide formed from L-phenylalanine and L-alanine residues.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.1683   -0.9657    1.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4583   -0.0423    0.2321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0333   -0.1094    0.3690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815   -0.4543   -0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7133   -0.7188   -1.8190 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2876   -0.5360   -0.5929 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8860   -0.9151   -1.8452 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8910    0.7533   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3653    0.5701    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1998    0.8905   -1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663    0.7275   -1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1483    0.2109    0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3346   -0.1188    1.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9598    0.0575    1.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9675    1.3195    0.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1978    2.2618    0.7434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3221    1.5629    0.3718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4488   -1.1995    2.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4121   -1.8966    0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1086   -0.5439    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7094   -0.3079   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6134    0.1143    1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5333   -1.3215    0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2445   -0.7868   -2.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319   -1.8786   -1.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6454    1.5938   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5243    0.9238    0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7054    1.2937   -1.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1983    0.9915   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2144    0.0646    0.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7787   -0.5187    2.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.2047    1.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7025    2.4351   -0.0229 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
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  2 15  1  0
 15 17  1  0
 15 16  2  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  6
  3 22  1  0
  6 23  1  1
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
M  END


  Mrv1652304062014042D          

 17 17  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  1  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
 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
10002.512010000.2149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.8005 9998.9784    0.0000 O   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  1  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
 10 11  2  0  0  0  0
 11 12  1  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 10  1  0  0  0  0
  6 10  1  0  0  0  0
  1 17  2  0  0  0  0
  1 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136588

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O3/c1-8(12(16)17)14-11(15)10(13)7-9-5-3-2-4-6-9/h2-6,8,10H,7,13H2,1H3,(H,14,15)(H,16,17)/t8-,10-/m0/s1

> <INCHI_KEY>
MIDZLCFIAINOQN-WPRPVWTQSA-N

> <FORMULA>
C12H16N2O3

> <MOLECULAR_WEIGHT>
236.271

> <EXACT_MASS>
236.116092383

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.478493207779067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.98

> <JCHEM_LOGP>
-1.7232460061604404

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.86783114937393

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7324042644610187

> <JCHEM_PKA_STRONGEST_BASIC>
8.009692164500533

> <JCHEM_POLAR_SURFACE_AREA>
92.41999999999999

> <JCHEM_REFRACTIVITY>
62.41370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-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  C   UNK     0    8662.0358666.301   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.7018667.071   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8659.3678666.301   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8659.3678664.761   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.7018663.991   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.0358664.761   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8671.3568667.068   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8670.0288664.760   0.000  0.00  0.00           O+0
CONECT    1    2   17   16                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   10                                                       
CONECT    7    5                                                            
CONECT    8    4                                                            
CONECT    9    2                                                            
CONECT   10   11   15    6                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    1                                                            
CONECT   17    1                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
F-A	ChEBI
FA	ChEBI
L-Phe-L-ala	ChEBI
Phenylalanylalanine	ChEBI
Phenylalanylalanine, (D-ala-phe)-isomer	MeSH
L-Phenylalanyl-L-alanine	MeSH
F-A dipeptide	HMDB
FA dipeptide	HMDB
N-L-Phenylalanyl-L-alanine	HMDB
N-Phenylalanylalanine	HMDB
Phe-Ala	HMDB
Phenylalanine alanine dipeptide	HMDB
Phenylalanine-alanine dipeptide	HMDB
Phenylalanyl-alanine	HMDB

Chemical Formula

C₁₂H₁₆N₂O₃

Average Mass

236.2710 Da

Monoisotopic Mass

236.11609 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H16N2O3/c1-8(12(16)17)14-11(15)10(13)7-9-5-3-2-4-6-9/h2-6,8,10H,7,13H2,1H3,(H,14,15)(H,16,17)/t8-,10-/m0/s1

InChI Key

MIDZLCFIAINOQN-WPRPVWTQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

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
Alanine or derivatives
Alpha-amino acid or derivatives
Amphetamine or derivatives
Aralkylamine
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Primary aliphatic amine
Amine
Organic oxygen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:73630 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.98	ALOGPS
logP	-1.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.73	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	5	ChemAxon
Refractivity	62.41 m³·mol⁻¹	ChemAxon
Polarizability	24.48 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

HMDB0028988

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4589716

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5488196

PDB ID

Not Available

ChEBI ID

73630

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Phenylalanylalanine (NP0136588)

MOL for NP0136588 (Phenylalanylalanine)

3D MOL for NP0136588 (Phenylalanylalanine)

3D SDF for NP0136588 (Phenylalanylalanine)

3D-SDF for NP0136588 (Phenylalanylalanine)

PDB for NP0136588 (Phenylalanylalanine)

3D PDB for NP0136588 (Phenylalanylalanine)

SMILES for NP0136588 (Phenylalanylalanine)

INCHI for NP0136588 (Phenylalanylalanine)

Structure for NP0136588 (Phenylalanylalanine)

3D Structure for NP0136588 (Phenylalanylalanine)