NP-MRD: Showing NP-Card for Histidinyl-Gamma-glutamate (NP0136508)

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Record Information

Version

2.0

Created at

2022-05-12 15:16:20 UTC

Updated at

2022-05-12 15:16:20 UTC

NP-MRD ID

NP0136508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Histidinyl-Gamma-glutamate

Description

Histidinyl-Gamma-glutamate, also known as H-ge dipeptide or histidinyl-g-glutamic acid, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. Histidinyl-Gamma-glutamate is a very strong basic compound (based on its pKa). It is an incomplete breakdown product of protein digestion or protein catabolism. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite. Histidinyl-Gamma-glutamate is a dipeptide composed of histidine and gamma-glutamate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.1707   -1.3398   -0.6783 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4846   -0.0795   -0.0148 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7494    1.0676   -0.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2745    0.9859   -0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5497    0.9431    0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1528    1.0198    1.7217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1322    0.8131    0.6351 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6229    0.7578   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1097    0.8172   -1.6734 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1157    0.6219   -0.5186 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6235    0.5907   -1.8519 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5327   -0.5915    0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0067   -0.6786    0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7876   -1.3424   -0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0898   -1.1616   -0.2620 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1158   -0.4093    0.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309   -0.1185    1.1701 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5646   -0.1445    1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0556    0.8389    2.0617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -1.2667    2.1330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9688   -1.9824   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4186   -1.7973   -0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6007    0.0627   -0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1738    1.2862   -1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533    2.0176   -0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9209    1.8591   -1.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9693    0.0940   -1.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371    0.7684    1.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5137    1.5251   -0.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6420    0.7221   -1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2297   -0.1445   -2.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1957   -0.5200    1.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442   -1.4881   -0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4523   -1.9134   -1.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0186   -0.1165    1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5922    0.4641    2.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5070   -2.1608    1.8066 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  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  2 18  1  0
 18 20  1  0
 18 19  2  0
 17 13  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
M  END


  Mrv1652304062013502D          

 20 20  0  0  0  0            999 V2000
    6.0409    0.1979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0409   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974   -1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -0.6271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    0.1979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3251   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286   -0.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806   -0.3495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5681    0.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2389    0.1934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7553   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4698   -0.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7553   -1.8646    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  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
 13 17  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CCC(=O)NC(=O)C(N)CC1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H17N5O4/c12-7(11(19)20)1-2-9(17)16-10(18)8(13)3-6-4-14-5-15-6/h4-5,7-8H,1-3,12-13H2,(H,14,15)(H,19,20)(H,16,17,18)

> <INCHI_KEY>
PFZUBGMULASFDW-UHFFFAOYSA-N

> <FORMULA>
C11H17N5O4

> <MOLECULAR_WEIGHT>
283.2838

> <EXACT_MASS>
283.128054057

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.73516540937054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-5-[2-amino-3-(1H-imidazol-5-yl)propanamido]-5-oxopentanoic acid

> <ALOGPS_LOGP>
-2.79

> <JCHEM_LOGP>
-5.154872534119894

> <ALOGPS_LOGS>
-1.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.600345322749984

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.023605293489854

> <JCHEM_PKA_STRONGEST_BASIC>
9.410495990925886

> <JCHEM_POLAR_SURFACE_AREA>
164.18999999999997

> <JCHEM_REFRACTIVITY>
68.09109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-5-[2-amino-3-(3H-imidazol-4-yl)propanamido]-5-oxopentanoic 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  N   UNK     0      11.276   0.369   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      11.276  -1.171   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.943  -1.941   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.609  -1.171   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.275  -1.941   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.275  -3.481   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       5.942  -1.171   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.608  -1.941   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.608  -3.481   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.274  -1.171   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       3.274   0.369   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.941  -1.941   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.607  -1.171   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.800  -1.797   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -1.830  -0.652   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.060   0.681   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       0.446   0.361   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      12.610  -1.941   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.944  -1.171   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.610  -3.481   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
CONECT   18    2   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
Histidinyl-g-glutamate	Generator
Histidinyl-g-glutamic acid	Generator
Histidinyl-gamma-glutamic acid	Generator
Histidinyl-γ-glutamate	Generator
Histidinyl-γ-glutamic acid	Generator
H-GE dipeptide	HMDB
HGE dipeptide	HMDB
His-gglu	HMDB
Histidine gamma-glutamate dipeptide	HMDB
Histidine-gamma-glutamate dipeptide	HMDB
Histidinylgamma-glutamate	HMDB
L-Histidinyl-L-gamma-glutamate	HMDB
2-Amino-4-{[2-amino-3-(1H-imidazol-5-yl)propanoyl]-C-hydroxycarbonimidoyl}butanoate	Generator

Chemical Formula

C₁₁H₁₇N₅O₄

Average Mass

283.2838 Da

Monoisotopic Mass

283.12805 Da

IUPAC Name

2-amino-5-[2-amino-3-(1H-imidazol-5-yl)propanamido]-5-oxopentanoic acid

Traditional Name

2-amino-5-[2-amino-3-(3H-imidazol-4-yl)propanamido]-5-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

NC(CCC(=O)NC(=O)C(N)CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C11H17N5O4/c12-7(11(19)20)1-2-9(17)16-10(18)8(13)3-6-4-14-5-15-6/h4-5,7-8H,1-3,12-13H2,(H,14,15)(H,19,20)(H,16,17,18)

InChI Key

PFZUBGMULASFDW-UHFFFAOYSA-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 histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
Glutamine or derivatives
Alpha-amino acid amide
Alpha-amino acid
Imidazolyl carboxylic acid derivative
Aralkylamine
N-acyl-amine
Azole
Carboxylic acid imide, n-unsubstituted
Carboxylic acid imide
Imidazole
Dicarboximide
Heteroaromatic compound
Amino acid
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	-2.8	ALOGPS
logP	-5.2	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	2.02	ChemAxon
pKa (Strongest Basic)	9.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.19 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	68.09 m³·mol⁻¹	ChemAxon
Polarizability	27.74 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

HMDB0028899

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

131750770

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Histidinyl-Gamma-glutamate (NP0136508)

MOL for NP0136508 (Histidinyl-Gamma-glutamate)

3D MOL for NP0136508 (Histidinyl-Gamma-glutamate)

3D SDF for NP0136508 (Histidinyl-Gamma-glutamate)

3D-SDF for NP0136508 (Histidinyl-Gamma-glutamate)

PDB for NP0136508 (Histidinyl-Gamma-glutamate)

3D PDB for NP0136508 (Histidinyl-Gamma-glutamate)

SMILES for NP0136508 (Histidinyl-Gamma-glutamate)

INCHI for NP0136508 (Histidinyl-Gamma-glutamate)

Structure for NP0136508 (Histidinyl-Gamma-glutamate)

3D Structure for NP0136508 (Histidinyl-Gamma-glutamate)