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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:24:35 UTC

Update Date

2022-09-22 18:34:48 UTC

HMDB ID

HMDB0341322

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Gly-Phe-beta-naphthylamide

Description

Gly-Phe-beta-naphthylamide, also known as gly-L-phe 2-naphthylamide, 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. Based on a literature review a significant number of articles have been published on Gly-Phe-beta-naphthylamide.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092223022D          

 26 28  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    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
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  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
 17 22  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 15 24  1  0  0  0  0
 13 25  2  0  0  0  0
  3 26  2  0  0  0  0
M  END


  Mrv1652309092223022D          

 26 28  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    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
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  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
 17 22  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 15 24  1  0  0  0  0
 13 25  2  0  0  0  0
  3 26  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341322

> <DATABASE_NAME>
hmdb

> <SMILES>
NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NC1=CC2=C(C=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H21N3O2/c22-14-20(25)24-19(12-15-6-2-1-3-7-15)21(26)23-18-11-10-16-8-4-5-9-17(16)13-18/h1-11,13,19H,12,14,22H2,(H,23,26)(H,24,25)/t19-/m0/s1

> <INCHI_KEY>
YABDXPBHLDPMOA-IBGZPJMESA-N

> <FORMULA>
C21H21N3O2

> <MOLECULAR_WEIGHT>
347.418

> <EXACT_MASS>
347.163376928

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
37.82009585594819

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(2-aminoacetamido)-N-(naphthalen-2-yl)-3-phenylpropanamide

> <JCHEM_LOGP>
2.396110467666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.445793736557743

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.561362241601966

> <JCHEM_PKA_STRONGEST_BASIC>
7.838644897338284

> <JCHEM_POLAR_SURFACE_AREA>
84.22

> <JCHEM_REFRACTIVITY>
102.64730000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(2-aminoacetamido)-N-(naphthalen-2-yl)-3-phenylpropanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  N   UNK     0       0.000  -4.620   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334  -8.470   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334 -13.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334 -13.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.001  -6.930   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    5   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   17   21   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   15                                                       
CONECT   25   13                                                            
CONECT   26    3                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Gly-L-phe 2-naphthylamide	ChEBI
Gly-phe 2-naphthylamide	ChEBI
Gly-phe-naphthylamide	ChEBI
Glycylphenylalanine 2-naphthylamide	ChEBI
Gly-phe-b-naphthylamide	Generator
Gly-phe-β-naphthylamide	Generator
Glycyl-L-phenylalanine 2-naphthylamide	MeSH
Glycyl-L-phenylalanine-beta-naphthylamide	MeSH

Chemical Formula

C₂₁H₂₁N₃O₂

Average Molecular Weight

347.418

Monoisotopic Molecular Weight

347.163376928

IUPAC Name

(2S)-2-(2-aminoacetamido)-N-(naphthalen-2-yl)-3-phenylpropanamide

Traditional Name

(2S)-2-(2-aminoacetamido)-N-(naphthalen-2-yl)-3-phenylpropanamide

CAS Registry Number

Not Available

SMILES

NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NC1=CC2=C(C=CC=C2)C=C1

InChI Identifier

InChI=1S/C21H21N3O2/c22-14-20(25)24-19(12-15-6-2-1-3-7-15)21(26)23-18-11-10-16-8-4-5-9-17(16)13-18/h1-11,13,19H,12,14,22H2,(H,23,26)(H,24,25)/t19-/m0/s1

InChI Key

YABDXPBHLDPMOA-IBGZPJMESA-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 or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Naphthalene
N-arylamide
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Fatty amide
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Primary amine
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

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
logP	2.4	ChemAxon
pKa (Strongest Acidic)	12.56	ChemAxon
pKa (Strongest Basic)	7.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	84.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	102.65 m³·mol⁻¹	ChemAxon
Polarizability	37.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

134338

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

152423

PDB ID

Not Available

ChEBI ID

90734

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

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for Gly-Phe-beta-naphthylamide (HMDB0341322)

MOL for HMDB0341322 (Gly-Phe-beta-naphthylamide)

3D MOL for HMDB0341322 (Gly-Phe-beta-naphthylamide)

3D SDF for HMDB0341322 (Gly-Phe-beta-naphthylamide)

3D-SDF for HMDB0341322 (Gly-Phe-beta-naphthylamide)

PDB for HMDB0341322 (Gly-Phe-beta-naphthylamide)

3D PDB for HMDB0341322 (Gly-Phe-beta-naphthylamide)

SMILES for HMDB0341322 (Gly-Phe-beta-naphthylamide)

INCHI for HMDB0341322 (Gly-Phe-beta-naphthylamide)

Structure for HMDB0341322 (Gly-Phe-beta-naphthylamide)

3D Structure for HMDB0341322 (Gly-Phe-beta-naphthylamide)

Predicted Kovats Retention Indices