NP-MRD: Showing NP-Card for gamma-Glutamylhydroxyproline (NP0136723)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-12 15:21:50 UTC

Updated at

2022-05-12 15:21:50 UTC

NP-MRD ID

NP0136723

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gamma-Glutamylhydroxyproline

Description

Gamma-Glutamylhydroxyproline, also known as glutamate hydroxyproline dipeptide or γ-glu-hyp, 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. Gamma-Glutamylhydroxyproline is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
    4.4680    1.0005    1.5563 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5586    0.0112    0.9280 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2240    0.6680    0.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1556   -0.1917    0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.5758    0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1134    1.7239    0.8259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369    0.0106   -0.1764 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418   -1.2974   -0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7298   -1.2648   -1.5759 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5230   -0.8125   -2.8650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5741   -0.3253   -0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6131    0.6488   -0.1837 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0081    1.1178    1.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2224    0.8745    2.1189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1857    1.7959    1.4244 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0367   -0.2455   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9673    0.4722   -0.9264 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4547   -1.2644   -1.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3964    0.8185    1.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4111    0.8047    2.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5243   -0.9203    1.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8630    0.9555    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2438    1.6161    0.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943   -0.4394   -0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0190   -1.1518    0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5732   -1.5421   -1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5503   -2.0606    0.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1918   -2.2672   -1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0198   -1.3515   -3.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0192   -0.9297    0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3912    0.1323   -1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5170    1.5578   -0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2939    2.7920    1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7163   -1.5119   -2.1197 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
  2 16  1  0
 16 18  1  0
 16 17  2  0
 12  7  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
  4 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  6
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  6
 15 33  1  0
 18 34  1  0
M  END


  Mrv1652304062014282D          

 18 18  0  0  0  0            999 V2000
 9975.2567 9972.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9975.9687 9972.3618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9975.2567 9973.5977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9972.9654 9970.9265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9973.8734 9972.8567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9973.2061 9972.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9973.4610 9971.5870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9974.2861 9971.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9974.5410 9972.3717    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9973.8734 9973.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9973.1590 9974.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9974.5879 9974.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9972.4445 9973.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9971.7299 9974.0942    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9971.0156 9973.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.3011 9974.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9971.0156 9972.8567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9971.7299 9974.9169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  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
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  7  4  1  1  0  0  0
  9  1  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 17  2  0  0  0  0
 15 16  1  0  0  0  0
 14 18  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0136723

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CCC(=O)N1C[C@H](O)C[C@H]1C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N2O6/c11-6(9(15)16)1-2-8(14)12-4-5(13)3-7(12)10(17)18/h5-7,13H,1-4,11H2,(H,15,16)(H,17,18)/t5-,6+,7+/m1/s1

> <INCHI_KEY>
VKENMLSUUVOQLD-VQVTYTSYSA-N

> <FORMULA>
C10H16N2O6

> <MOLECULAR_WEIGHT>
260.246

> <EXACT_MASS>
260.100836243

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.59610019588006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4R)-1-[(4S)-4-amino-4-carboxybutanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-3.48

> <JCHEM_LOGP>
-4.702990781740703

> <ALOGPS_LOGS>
-0.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.706722524339043

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8403133022987372

> <JCHEM_PKA_STRONGEST_BASIC>
9.312081295366923

> <JCHEM_POLAR_SURFACE_AREA>
141.16000000000003

> <JCHEM_REFRACTIVITY>
57.59210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R)-1-[(4S)-4-amino-4-carboxybutanoyl]-4-hydroxypyrrolidine-2-carboxylic 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    8620.4798615.845   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8621.8088615.075   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8620.4798617.382   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8616.2028612.396   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0    8617.8978615.999   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8616.6518615.094   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8617.1278613.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8618.6678613.629   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8619.1438615.094   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8617.8978617.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8616.5638618.309   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8619.2318618.309   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8615.2308617.539   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8613.8968618.309   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8612.5628617.539   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8611.2298618.309   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8612.5628615.999   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0    8613.8968619.845   0.000  0.00  0.00           N+0
CONECT    1    2    3    9                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    7                                                            
CONECT    5    6    9   10                                                  
CONECT    6    7    5                                                       
CONECT    7    6    8    4                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5    1                                                  
CONECT   10    5   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   17   16                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
Γ-glu-hyp	HMDB
L-Γ-glu-L-hyp	HMDB
L-Γ-glutamyl-L-hydroxyproline	HMDB
Γ-glutamyl-hydroxyproline	HMDB
Glutamate hydroxyproline dipeptide	HMDB
Glutamate-hydroxyproline dipeptide	HMDB
Glutamic acid hydroxyproline dipeptide	HMDB
Glutamic acid-hydroxyproline dipeptide	HMDB
(4R)-L-Γ-glutamyl-4-hydroxy-L-proline	HMDB
Γ-glutamylhydroxyproline	HMDB
(4R)-L-gamma-Glutamyl-4-hydroxy-L-proline	HMDB
L-gamma-Glu-L-hyp	HMDB
L-gamma-Glutamyl-L-hydroxyproline	HMDB
gamma-Glu-hyp	HMDB
gamma-Glutamyl-hydroxyproline	HMDB
gamma-Glutamylhydroxyproline	HMDB
(2S,4R)-1-[(4S)-4-Amino-4-carboxybutanoyl]-4-hydroxypyrrolidine-2-carboxylate	Generator

Chemical Formula

C₁₀H₁₆N₂O₆

Average Mass

260.2460 Da

Monoisotopic Mass

260.10084 Da

IUPAC Name

(2S,4R)-1-[(4S)-4-amino-4-carboxybutanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

Traditional Name

(2S,4R)-1-[(4S)-4-amino-4-carboxybutanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CCC(=O)N1C[C@H](O)C[C@H]1C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C10H16N2O6/c11-6(9(15)16)1-2-8(14)12-4-5(13)3-7(12)10(17)18/h5-7,13H,1-4,11H2,(H,15,16)(H,17,18)/t5-,6+,7+/m1/s1

InChI Key

VKENMLSUUVOQLD-VQVTYTSYSA-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
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
Proline or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
L-alpha-amino acid
Alpha-amino acid or derivatives
Alpha-amino acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine carboxylic acid
N-acylpyrrolidine
Hydroxy fatty acid
Heterocyclic fatty acid
Fatty acyl
Fatty acid
Dicarboxylic acid or derivatives
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid
Secondary alcohol
Carboxamide group
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	-3.5	ALOGPS
logP	-4.7	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	1.84	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.16 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.59 m³·mol⁻¹	ChemAxon
Polarizability	24.6 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

HMDB0029150

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

118243642

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for gamma-Glutamylhydroxyproline (NP0136723)

MOL for NP0136723 (gamma-Glutamylhydroxyproline)

3D MOL for NP0136723 (gamma-Glutamylhydroxyproline)

3D SDF for NP0136723 (gamma-Glutamylhydroxyproline)

3D-SDF for NP0136723 (gamma-Glutamylhydroxyproline)

PDB for NP0136723 (gamma-Glutamylhydroxyproline)

3D PDB for NP0136723 (gamma-Glutamylhydroxyproline)

SMILES for NP0136723 (gamma-Glutamylhydroxyproline)

INCHI for NP0136723 (gamma-Glutamylhydroxyproline)

Structure for NP0136723 (gamma-Glutamylhydroxyproline)

3D Structure for NP0136723 (gamma-Glutamylhydroxyproline)