NP-MRD: Showing NP-Card for Serylglutamic acid (NP0136626)

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Record Information

Version

2.0

Created at

2022-05-12 15:19:23 UTC

Updated at

2022-05-12 15:19:23 UTC

NP-MRD ID

NP0136626

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Serylglutamic acid

Description

Serylglutamic acid, also known as L-ser-L-glu or serylglutamate, 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. Serylglutamic acid was first documented in 2006 (PMID: 16499867). Serylglutamic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 29  0  0  0  0  0  0  0  0999 V2000
   -3.3120    0.7303   -0.0460 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193   -0.5516    0.5573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4184   -1.5883   -0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6293   -1.3109   -1.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5767   -0.7236    0.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1502   -1.7382    1.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6699    0.2499    0.3051 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841    0.1257    0.4914 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3506   -0.3031   -0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8197   -0.4229   -0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826    0.9014   -0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533    1.9962   -0.9904 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419    0.9951   -0.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3852    1.2337    1.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7083    2.3072    1.3251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6374    1.2037    1.7656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8752    1.5248    0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3312    0.8650   -0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692   -0.7607    1.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525   -2.5992   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4841   -1.5278   -0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325   -0.6617   -2.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0003    1.1119   -0.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8807   -0.8231    1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9285   -1.3328   -1.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417    0.3627   -1.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2106   -1.0012   -0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660   -0.9970   -1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1661    0.6546    0.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1639    2.0800    1.8904 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  1  0
 11 13  1  0
 11 12  2  0
  8 14  1  0
 14 16  1  0
 14 15  2  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
  8 24  1  1
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
 16 30  1  0
M  END


  Mrv1652304062014112D          

 16 15  0  0  0  0            999 V2000
 2502.3014 2502.2032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.3014 2501.3777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0245 2500.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.7373 2501.3900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0245 2500.1529    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2502.3096 2499.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.5948 2500.1529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.7373 2499.7393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.5866 2502.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.8718 2502.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.1570 2502.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.4421 2502.2032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.1570 2503.4401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0163 2502.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.7311 2502.2032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0163 2503.4401    0.0000 O   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 14  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136626

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H14N2O6/c9-4(3-11)7(14)10-5(8(15)16)1-2-6(12)13/h4-5,11H,1-3,9H2,(H,10,14)(H,12,13)(H,15,16)/t4-,5-/m0/s1

> <INCHI_KEY>
LAFKUZYWNCHOHT-WHFBIAKZSA-N

> <FORMULA>
C8H14N2O6

> <MOLECULAR_WEIGHT>
234.208

> <EXACT_MASS>
234.085186179

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.49298389407418

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.61

> <JCHEM_LOGP>
-5.109084844788743

> <ALOGPS_LOGS>
-0.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.973188600545929

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.143118595816952

> <JCHEM_PKA_STRONGEST_BASIC>
7.849385712001744

> <JCHEM_POLAR_SURFACE_AREA>
149.95

> <JCHEM_REFRACTIVITY>
50.128800000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.48e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]pentanedioic 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    4670.9634670.779   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4670.9634669.238   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4672.3124668.493   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4673.6434669.261   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4672.3124666.952   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4670.9784666.180   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    4669.6444666.952   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0    4673.6434666.180   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    4669.6284671.548   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4668.2944670.779   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4666.9604671.548   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    4665.6254670.779   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    4666.9604673.088   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    4672.2974671.548   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    4673.6314670.779   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    4672.2974673.088   0.000  0.00  0.00           O+0
CONECT    1    2    9   14                                                  
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   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    1   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
L-Ser-L-glu	ChEBI
SE	ChEBI
Serinyl-glutamate	ChEBI
Serinyl-glutamic acid	Generator
Serylglutamate	Generator
L-Seryl-L-glutamate	HMDB
L-Seryl-L-glutamic acid	HMDB
N-L-Seryl-L-glutamate	HMDB
N-L-Seryl-L-glutamic acid	HMDB
N-Serylglutamate	HMDB
N-Serylglutamic acid	HMDB
S-e Dipeptide	HMDB
SE dipeptide	HMDB
Ser-glu	HMDB
Serine glutamate dipeptide	HMDB
Serine glutamic acid dipeptide	HMDB
Serine-glutamate dipeptide	HMDB
Serine-glutamic acid dipeptide	HMDB
Serinylglutamate	HMDB
Serinylglutamic acid	HMDB
Seryl-glutamate	HMDB
Seryl-glutamic acid	HMDB
Serylglutamic acid	ChEBI

Chemical Formula

C₈H₁₄N₂O₆

Average Mass

234.2080 Da

Monoisotopic Mass

234.08519 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H14N2O6/c9-4(3-11)7(14)10-5(8(15)16)1-2-6(12)13/h4-5,11H,1-3,9H2,(H,10,14)(H,12,13)(H,15,16)/t4-,5-/m0/s1

InChI Key

LAFKUZYWNCHOHT-WHFBIAKZSA-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
Glutamic acid 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
Dicarboxylic acid or derivatives
Fatty acid
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Carbonyl group
Alcohol
Amine
Primary alcohol
Primary amine
Organic oxygen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:74813 )

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	-3.6	ALOGPS
logP	-5.1	ChemAxon
logS	-0.97	ALOGPS
pKa (Strongest Acidic)	3.14	ChemAxon
pKa (Strongest Basic)	7.85	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.95 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	50.13 m³·mol⁻¹	ChemAxon
Polarizability	21.49 Å³	ChemAxon
Number of Rings	0	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

HMDB0029038

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

7023503

PDB ID

Not Available

ChEBI ID

74813

Good Scents ID

Not Available

References

General References

Morii H, Saiki M, Konakahara T, Ishimura M: Peripheral region for core cross-beta plays important role in amyloidogenicity. Biochem Biophys Res Commun. 2006 Apr 14;342(3):808-16. doi: 10.1016/j.bbrc.2006.02.012. Epub 2006 Feb 14. [PubMed:16499867 ]

Showing NP-Card for Serylglutamic acid (NP0136626)

MOL for NP0136626 (Serylglutamic acid)

3D MOL for NP0136626 (Serylglutamic acid)

3D SDF for NP0136626 (Serylglutamic acid)

3D-SDF for NP0136626 (Serylglutamic acid)

PDB for NP0136626 (Serylglutamic acid)

3D PDB for NP0136626 (Serylglutamic acid)

SMILES for NP0136626 (Serylglutamic acid)

INCHI for NP0136626 (Serylglutamic acid)

Structure for NP0136626 (Serylglutamic acid)

3D Structure for NP0136626 (Serylglutamic acid)