NP-MRD: Showing NP-Card for Phenylalanylserine (NP0136600)

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Record Information

Version

2.0

Created at

2022-05-12 15:18:43 UTC

Updated at

2022-05-12 15:18:44 UTC

NP-MRD ID

NP0136600

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phenylalanylserine

Description

Phe-Ser, also known as FS or L-phe-L-ser, 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-Ser is possibly neutral. A dipeptide that is the N-(L-phenylalanyl) derivative of L-serine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
    0.9973    1.5065   -1.6839 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4355    0.4539   -0.8951 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0611    0.3455    0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5025    0.0804    0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088   -1.1963    0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3580   -1.4568    0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2303   -0.3720    0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7555    0.9203    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3866    1.1314    0.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0276    0.6354   -0.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819    1.6009   -1.4140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865   -0.2457   -0.1180 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3086   -0.0871   -0.0415 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0107   -1.3620   -0.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3888   -1.2191   -0.4577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6704    0.0726    1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8204    0.0577    2.3044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0184    0.2412    1.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0191    1.5117   -1.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6133    1.4159   -2.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390   -0.5164   -1.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8284    1.3066    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806   -0.4671    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548   -2.0771    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7441   -2.4694    0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2990   -0.5566    0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4133    1.7790    0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0157    2.1669    0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461   -1.0518    0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6781    0.7848   -0.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7268   -2.2111    0.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7319   -1.5586   -1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6827   -0.2865   -0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2641    1.1230    2.1410 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
 13 16  1  0
 16 18  1  0
 16 17  2  0
  9  4  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  6
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  6
 14 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
M  END


  Mrv1652304062014062D          

 18 18  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
10001.085410000.2157    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
 9998.9455 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
 9998.9455 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
10001.085410001.0394    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
10001.799910001.4519    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
  9 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136600

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
ROHDXJUFQVRDAV-UWVGGRQHSA-N

> <FORMULA>
C12H16N2O4

> <MOLECULAR_WEIGHT>
252.27

> <EXACT_MASS>
252.111007003

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.253175519661447

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.08

> <JCHEM_LOGP>
-2.770914143970553

> <ALOGPS_LOGS>
-1.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.845032484974062

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.551884402674064

> <JCHEM_PKA_STRONGEST_BASIC>
8.009599951963539

> <JCHEM_POLAR_SURFACE_AREA>
112.64999999999999

> <JCHEM_REFRACTIVITY>
63.957400000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-hydroxypropanoic 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
HETATM   18  O   UNK     0    8670.0268669.377   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   18                                                       
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                                                            
CONECT   18    9                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
FS	ChEBI
L-Phe-L-ser	ChEBI
Phenylalanylserine	ChEBI
F-S dipeptide	HMDB
FS dipeptide	HMDB
L-Phenylalanyl-L-serine	HMDB
N-L-Phenylalanyl-L-serine	HMDB
N-Phenylalanylserine	HMDB
Phe-Ser	HMDB
Phenylalanine serine dipeptide	HMDB
Phenylalanine-serine dipeptide	HMDB
Phenylalanyl-serine	HMDB

Chemical Formula

C₁₂H₁₆N₂O₄

Average Mass

252.2700 Da

Monoisotopic Mass

252.11101 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

ROHDXJUFQVRDAV-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

Not Available

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
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Serine or derivatives
Alpha-amino acid or derivatives
Amphetamine or derivatives
Beta-hydroxy acid
Aralkylamine
Hydroxy acid
Fatty amide
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Carboxamide group
Amino acid or derivatives
Secondary carboxylic acid amide
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Primary amine
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:71032 )

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	-2.1	ALOGPS
logP	-2.8	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	8.01	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	25.25 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

167923

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193508

PDB ID

Not Available

ChEBI ID

71032

Good Scents ID

Not Available

References

General References

Showing NP-Card for Phenylalanylserine (NP0136600)

MOL for NP0136600 (Phenylalanylserine)

3D MOL for NP0136600 (Phenylalanylserine)

3D SDF for NP0136600 (Phenylalanylserine)

3D-SDF for NP0136600 (Phenylalanylserine)

PDB for NP0136600 (Phenylalanylserine)

3D PDB for NP0136600 (Phenylalanylserine)

SMILES for NP0136600 (Phenylalanylserine)

INCHI for NP0136600 (Phenylalanylserine)

Structure for NP0136600 (Phenylalanylserine)

3D Structure for NP0136600 (Phenylalanylserine)