NP-MRD: Showing NP-Card for Serylphenylalanine (NP0136632)

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Record Information

Version

2.0

Created at

2022-05-12 15:19:32 UTC

Updated at

2022-05-12 15:19:32 UTC

NP-MRD ID

NP0136632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Serylphenylalanine

Description

Serylphenylalanine, also known as SF or L-ser-L-phe, 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. Serylphenylalanine is a very strong basic compound (based on its pKa). Serylphenylalanine is found in Arabidopsis thaliana. It is an incomplete breakdown product of protein digestion or protein catabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
    2.2435    0.6287    2.1955 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1758    1.4054    0.9743 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6019    1.5992    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176    0.3735    0.2587 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3757    0.6208    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2081    1.1447   -1.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8424   -0.6438    0.3595 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0588   -1.4778   -0.4734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0603   -0.8099   -1.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0881   -0.1834   -0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1830   -0.9364    0.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1662   -0.3883    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1154    0.9295    1.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0565    1.6878    0.8184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0573    1.1259    0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9082   -2.2130   -1.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466   -2.0506   -1.4048 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -3.0836   -2.3203 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6178    1.1698    3.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8765   -0.1838    1.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6954    2.3792    1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354    2.1755   -0.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833    2.0837    1.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9605    0.4472   -0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529   -0.9890    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5087   -2.1883    0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6640   -0.0930   -2.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5541   -1.6146   -1.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2420   -1.9695   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0050   -0.9886    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945    1.3641    1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0010    2.7297    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2597    1.7581   -0.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2708   -3.8092   -1.9349 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8 16  1  0
 16 18  1  0
 16 17  2  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  1
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
M  END


  Mrv1652304062014122D          

 18 18  0  0  0  0            999 V2000
 2500.7103 2500.6131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2500.7103 2499.7881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4330 2499.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1474 2499.8003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4330 2498.5638    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2500.7185 2498.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0041 2498.5638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1474 2498.1503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9958 2501.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4247 2501.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1392 2500.6131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4247 2501.8496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2821 2500.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5677 2501.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8531 2500.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8531 2499.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5676 2499.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2821 2499.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  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 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 13  1  0  0  0  0
  9 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136632

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O4/c13-9(7-15)11(16)14-10(12(17)18)6-8-4-2-1-3-5-8/h1-5,9-10,15H,6-7,13H2,(H,14,16)(H,17,18)/t9-,10-/m0/s1

> <INCHI_KEY>
PPQRSMGDOHLTBE-UWVGGRQHSA-N

> <FORMULA>
C12H16N2O4

> <MOLECULAR_WEIGHT>
252.27

> <EXACT_MASS>
252.111007003

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.03858956768135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.22

> <JCHEM_LOGP>
-2.7708145996027875

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.361854450892576

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.645033285934457

> <JCHEM_PKA_STRONGEST_BASIC>
7.8493617997764495

> <JCHEM_POLAR_SURFACE_AREA>
112.65

> <JCHEM_REFRACTIVITY>
63.95740000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-phenylpropanoic 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    4667.9934667.811   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4667.9934666.271   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4669.3424665.526   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4670.6754666.294   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4669.3424663.986   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4668.0084663.214   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    4666.6744663.986   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0    4670.6754663.214   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    4666.6594668.579   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4669.3264668.579   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    4670.6604667.811   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    4669.3264670.119   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    4665.3274667.811   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4663.9934668.581   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4662.6594667.810   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4662.6594666.271   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4663.9934665.501   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4665.3274666.271   0.000  0.00  0.00           C+0
CONECT    1    2    9   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    1   13                                                       
CONECT   10    1   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   14   18    9                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
L-Ser-L-phe	ChEBI
Serinylphenylalanine	ChEBI
SF	ChEBI
3-Phenyl-N-serylalanine	HMDB
L-3-Phenyl-N-serylalanine	HMDB
L-Seryl-L-phenylalanine	HMDB
N-L-Seryl-L-phenylalanine	HMDB
N-Serylphenylalanine	HMDB
S-F Dipeptide	HMDB
SF Dipeptide	HMDB
Ser-phe	HMDB
Serine phenylalanine dipeptide	HMDB
Serine-phenylalanine dipeptide	HMDB
Serinyl-phenylalanine	HMDB
Seryl-phenylalanine	HMDB

Chemical Formula

C₁₂H₁₆N₂O₄

Average Mass

252.2700 Da

Monoisotopic Mass

252.11101 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H16N2O4/c13-9(7-15)11(16)14-10(12(17)18)6-8-4-2-1-3-5-8/h1-5,9-10,15H,6-7,13H2,(H,14,16)(H,17,18)/t9-,10-/m0/s1

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:71029 )

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	-2.2	ALOGPS
logP	-2.8	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.65	ChemAxon
pKa (Strongest Basic)	7.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	112.65 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	63.96 m³·mol⁻¹	ChemAxon
Polarizability	25.04 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

HMDB0029046

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7009597

PDB ID

Not Available

ChEBI ID

71029

Good Scents ID

Not Available

References

General References

Showing NP-Card for Serylphenylalanine (NP0136632)

MOL for NP0136632 (Serylphenylalanine)

3D MOL for NP0136632 (Serylphenylalanine)

3D SDF for NP0136632 (Serylphenylalanine)

3D-SDF for NP0136632 (Serylphenylalanine)

PDB for NP0136632 (Serylphenylalanine)

3D PDB for NP0136632 (Serylphenylalanine)

SMILES for NP0136632 (Serylphenylalanine)

INCHI for NP0136632 (Serylphenylalanine)

Structure for NP0136632 (Serylphenylalanine)

3D Structure for NP0136632 (Serylphenylalanine)