NP-MRD: Showing NP-Card for Phenylalanylglycine (NP0136595)

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Record Information

Version

2.0

Created at

2022-05-12 15:18:36 UTC

Updated at

2022-05-12 15:18:36 UTC

NP-MRD ID

NP0136595

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phenylalanylglycine

Description

Phe-Gly, also known as F-G or L-phe-gly, 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-Gly is possibly neutral. Phenylalanylglycine is found in Trypanosoma brucei. A dipeptide formed from L-phenylalanine and glycine residues.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    0.4452   -2.4952   -1.6048 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0759   -1.2029   -1.1452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3472   -1.4127   -0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9414   -0.1693    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6207    0.3074    1.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876    1.4677    1.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0695    2.1484    1.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3843    1.6630   -0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8298    0.4955   -0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9604   -0.4493   -0.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6803    0.7106   -0.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2471   -0.9595   -0.1429 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333   -0.1943    0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5061    1.0490   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9185    1.2934   -1.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4399    1.9323    0.3458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -2.7516   -2.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3323   -3.2066   -0.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3103   -0.6293   -2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0596   -1.9661   -1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1827   -2.0879    0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9160   -0.2525    2.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9324    1.8454    2.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5414    3.0788    1.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0833    2.2245   -0.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0895    0.1373   -1.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4884   -1.9142   -0.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8971    0.0597    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1685   -0.7780    0.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3320    2.0563   -0.1239 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 16  1  0
 14 15  2  0
  9  4  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 16 30  1  0
M  END


  Mrv1652304062014052D          

 16 16  0  0  0  0            999 V2000
 9998.937910000.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6525 9999.9804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.366410000.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0818 9999.9804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.797210000.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5105 9999.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.225910000.3927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.5105 9999.1561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.366410001.2174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6525 9999.1561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2230 9999.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.508610000.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7941 9999.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7940 9999.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5085 9998.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2231 9999.1556    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 10  1  1  0  0  0
  3  4  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
  1 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136595

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O3/c12-9(11(16)13-7-10(14)15)6-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,16)(H,14,15)/t9-/m0/s1

> <INCHI_KEY>
GLUBLISJVJFHQS-VIFPVBQESA-N

> <FORMULA>
C11H14N2O3

> <MOLECULAR_WEIGHT>
222.244

> <EXACT_MASS>
222.100442319

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.764249288715025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.90

> <JCHEM_LOGP>
-2.292126300574983

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.399565245921018

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.709022259922749

> <JCHEM_PKA_STRONGEST_BASIC>
8.010007600994834

> <JCHEM_POLAR_SURFACE_AREA>
92.42

> <JCHEM_REFRACTIVITY>
57.91980000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S)-2-amino-3-phenylpropanamido]acetic 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    8664.6848667.400   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.0188666.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.3518667.400   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8668.6868666.630   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8670.0218667.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.3538666.630   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8672.6888667.400   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8671.3538665.091   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8667.3518668.939   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    8666.0188665.091   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8663.3508666.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.0168667.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8660.6828666.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.6828665.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.0168664.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.3508665.090   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3                                                            
CONECT   10    2                                                            
CONECT   11   12   16    1                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
F-G	ChEBI
FG	ChEBI
L-Phe-gly	ChEBI
Phenylalanylglycine	ChEBI
F-G dipeptide	HMDB
FG dipeptide	HMDB
L-Phenylalanylglycine	HMDB
N-L-Phenylalanylglycine	HMDB
N-Phenylalanylglycine	HMDB
Phe-Gly	HMDB
Phenylalanine glycine dipeptide	HMDB
Phenylalanine-glycine dipeptide	HMDB
Phenylalanyl-glycine	HMDB

Chemical Formula

C₁₁H₁₄N₂O₃

Average Mass

222.2440 Da

Monoisotopic Mass

222.10044 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H14N2O3/c12-9(11(16)13-7-10(14)15)6-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,16)(H,14,15)/t9-/m0/s1

InChI Key

GLUBLISJVJFHQS-VIFPVBQESA-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-alpha amino acid or derivatives
Alpha-amino acid amide
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
Primary amine
Organopnictogen compound
Organic zwitterion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:73635 )

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	-0.9	ALOGPS
logP	-2.3	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.71	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	57.92 m³·mol⁻¹	ChemAxon
Polarizability	22.76 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

HMDB0028995

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5360444

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6992303

PDB ID

Not Available

ChEBI ID

73635

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Phenylalanylglycine (NP0136595)

MOL for NP0136595 (Phenylalanylglycine)

3D MOL for NP0136595 (Phenylalanylglycine)

3D SDF for NP0136595 (Phenylalanylglycine)

3D-SDF for NP0136595 (Phenylalanylglycine)

PDB for NP0136595 (Phenylalanylglycine)

3D PDB for NP0136595 (Phenylalanylglycine)

SMILES for NP0136595 (Phenylalanylglycine)

INCHI for NP0136595 (Phenylalanylglycine)

Structure for NP0136595 (Phenylalanylglycine)

3D Structure for NP0136595 (Phenylalanylglycine)