NP-MRD: Showing NP-Card for Arginylserine (NP0136357)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-12 15:12:29 UTC

Updated at

2022-05-12 15:12:29 UTC

NP-MRD ID

NP0136357

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arginylserine

Description

Arginylserine, also known as RS or L-arg-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. Arginylserine is a very strong basic compound (based on its pKa). Arginylserine was first documented in 1993 (PMID: 8436546). It is an incomplete breakdown product of protein digestion or protein catabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 36  0  0  0  0  0  0  0  0999 V2000
   -6.2398   -2.1955   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2656   -1.2463   -0.5966 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2715   -0.4149   -0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5079    0.8586   -0.0089 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0182   -0.7470   -1.1932 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8304   -0.1381   -0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5807   -0.5570   -1.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3135    0.0017   -0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0195   -0.3059    0.6819 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9465    0.1629    1.6302 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3286    0.3133    0.9890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    1.1221    1.9429 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4622    0.0016    0.2280 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292    0.6165    0.5433 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6739   -0.5178    0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7813   -1.3771   -0.1820 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2424    1.2957   -0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5765    1.2611   -1.7181 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4668    1.9765   -0.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9797    1.1474    0.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1968    1.5304   -0.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9904   -1.3801   -1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9589    0.9474   -0.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8659   -0.5504    0.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6649   -0.1914   -2.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5212   -1.6650   -1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2434    1.0967   -0.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129   -0.4362   -1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1294   -1.4134    0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5923    0.1547    2.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3565    1.0883    1.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601   -0.6856   -0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024    1.2897    1.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6615   -0.0446    1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2843   -1.1033    1.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2862   -2.1840    0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8214    2.2889    0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 19  1  0
 17 18  2  0
 10 30  1  0
 10 31  1  0
  9 29  1  6
  8 27  1  0
  8 28  1  0
  7 25  1  0
  7 26  1  0
  6 23  1  0
  6 24  1  0
  5 22  1  0
  4 20  1  0
  4 21  1  0
  2  1  1  0
 13 32  1  0
 14 33  1  1
 15 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
M  END


  Mrv1652304062013242D          

 18 17  0  0  0  0            999 V2000
 2502.4990 2500.0010    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.7850 2499.5877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0710 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3570 2499.5877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2499.6429 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9289 2499.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2149 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5009 2499.5877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7869 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7869 2500.8255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2496.0729 2499.5877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3570 2498.7633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0710 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2130 2499.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.9270 2500.0010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2130 2498.7633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4990 2500.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2130 2501.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  0  0  0  0
  1 17  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 13  2  0  0  0  0
  4  5  1  0  0  0  0
  4 12  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136357

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H19N5O4/c10-5(2-1-3-13-9(11)12)7(16)14-6(4-15)8(17)18/h5-6,15H,1-4,10H2,(H,14,16)(H,17,18)(H4,11,12,13)/t5-,6-/m0/s1

> <INCHI_KEY>
IJYZHIOOBGIINM-WDSKDSINSA-N

> <FORMULA>
C9H19N5O4

> <MOLECULAR_WEIGHT>
261.282

> <EXACT_MASS>
261.143704112

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.26796890921769

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-hydroxypropanoic acid

> <ALOGPS_LOGP>
-3.79

> <JCHEM_LOGP>
-4.726983964033473

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.89886473465075

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4607350622009485

> <JCHEM_PKA_STRONGEST_BASIC>
11.964682320314262

> <JCHEM_POLAR_SURFACE_AREA>
174.54999999999995

> <JCHEM_REFRACTIVITY>
72.76419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-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    4671.3314666.669   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4669.9994665.897   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4668.6664666.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4667.3334665.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4666.0004666.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4664.6674665.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4663.3344666.669   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    4662.0024665.897   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    4660.6694666.669   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0    4660.6694668.208   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0    4659.3364665.897   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0    4667.3334664.358   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0    4668.6664668.208   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    4672.6644665.897   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    4673.9974666.669   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    4672.6644664.358   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    4671.3314668.208   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    4672.6644668.975   0.000  0.00  0.00           O+0
CONECT    1    2   14   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4                                                            
CONECT   13    3                                                            
CONECT   14    1   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    1   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
Arginyl-serine	ChEBI
L-Arg-L-ser	ChEBI
RS	ChEBI
Arg-ser	HMDB
Arginine serine dipeptide	HMDB
Arginine-serine dipeptide	HMDB
L-Arginyl-L-serine	HMDB
N-Arginylserine	HMDB
N-L-Arginyl-L-serine	HMDB
R-S Dipeptide	HMDB
RS Dipeptide	HMDB
Arginylserine	ChEBI

Chemical Formula

C₉H₁₉N₅O₄

Average Mass

261.2820 Da

Monoisotopic Mass

261.14370 Da

IUPAC Name

(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-hydroxypropanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-hydroxypropanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(O)=O

InChI Identifier

InChI=1S/C9H19N5O4/c10-5(2-1-3-13-9(11)12)7(16)14-6(4-15)8(17)18/h5-6,15H,1-4,10H2,(H,14,16)(H,17,18)(H4,11,12,13)/t5-,6-/m0/s1

InChI Key

IJYZHIOOBGIINM-WDSKDSINSA-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
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
Alpha-amino acid or derivatives
Beta-hydroxy acid
Fatty acyl
Fatty amide
Hydroxy acid
N-acyl-amine
Amino acid
Guanidine
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Monocarboxylic acid or derivatives
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73819 )

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	-3.8	ALOGPS
logP	-4.7	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	11.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	174.55 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	72.76 m³·mol⁻¹	ChemAxon
Polarizability	26.27 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0028718

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

7021454

PDB ID

Not Available

ChEBI ID

73819

Good Scents ID

Not Available

References

General References

Ezaki M, Shigematsu N, Yamashita M, Komori T, Umehara K, Imanaka H: Biphenomycin C, a precursor of biphenomycin A in mixed culture. J Antibiot (Tokyo). 1993 Jan;46(1):135-40. doi: 10.7164/antibiotics.46.135. [PubMed:8436546 ]

Showing NP-Card for Arginylserine (NP0136357)

MOL for NP0136357 (Arginylserine)

3D MOL for NP0136357 (Arginylserine)

3D SDF for NP0136357 (Arginylserine)

3D-SDF for NP0136357 (Arginylserine)

PDB for NP0136357 (Arginylserine)

3D PDB for NP0136357 (Arginylserine)

SMILES for NP0136357 (Arginylserine)

INCHI for NP0136357 (Arginylserine)

Structure for NP0136357 (Arginylserine)

3D Structure for NP0136357 (Arginylserine)