NP-MRD: Showing NP-Card for Glutamylvaline (NP0136454)

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Record Information

Version

2.0

Created at

2022-05-12 15:14:57 UTC

Updated at

2022-05-12 15:14:57 UTC

NP-MRD ID

NP0136454

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glutamylvaline

Description

Glutamylvaline, also known as alpha-glu-val or α-glu-val, 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. Glutamylvaline is a very strong basic compound (based on its pKa). Glutamylvaline is found in Trypanosoma brucei. Glutamylvaline was first documented in 1965 (PMID: 5867340). A glutamyl-L-amino acid that is the N-(L-alpha-glutamyl) derivative of L-leucine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 34  0  0  0  0  0  0  0  0999 V2000
   -3.5592    1.5594   -0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3328    0.7338   -0.4890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6752   -0.2080   -1.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8098    0.0284    0.7544 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6521   -0.7527    0.4683 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486   -0.4797    0.9657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8071    0.5191    1.7136 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8315   -1.3034    0.6552 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3571   -2.3926   -0.2170 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8887   -0.5819   -0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4514    0.6229    0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4865    1.2023   -0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7548    0.6927   -1.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979    2.3444   -0.0151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8749   -0.7218    1.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7712   -1.9423    1.7561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0642   -0.0991    1.7924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4781    1.9747    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5699    2.4242   -0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4720    0.9347   -0.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5502    1.4222   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794    0.2351   -2.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2111   -1.2137   -1.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7721   -0.3900   -1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763    0.8658    1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -1.5912   -0.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2481   -1.7426    1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401   -2.0366   -1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1669   -3.0491   -0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4771   -0.3545   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7217   -1.3035   -0.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0117    0.3191    1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7335    1.4199    0.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0155    2.7646    0.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3475    0.0995    2.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 14  1  0
 12 13  2  0
  4 15  1  0
 15 17  1  0
 15 16  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  6
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  1
  5 26  1  0
  8 27  1  1
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 14 34  1  0
 17 35  1  0
M  END

      
  Mrv1652304062013412D          

 17 16  0  0  0  0            999 V2000
 2501.7860 2500.0010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.0720 2499.5877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3580 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6419 2499.5877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.9279 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2139 2499.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4998 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7859 2499.5877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4998 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6419 2498.7633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3580 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5000 2499.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2140 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5000 2498.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7860 2500.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5000 2501.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0720 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 12  1  0  0  0  0
  1 15  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4 10  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
  7  9  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136454

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H18N2O5/c1-5(2)8(10(16)17)12-9(15)6(11)3-4-7(13)14/h5-6,8H,3-4,11H2,1-2H3,(H,12,15)(H,13,14)(H,16,17)/t6-,8-/m0/s1

> <INCHI_KEY>
SITLTJHOQZFJGG-XPUUQOCRSA-N

> <FORMULA>
C10H18N2O5

> <MOLECULAR_WEIGHT>
246.2603

> <EXACT_MASS>
246.121571696

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
24.684483436125653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4-amino-4-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}butanoic acid

> <ALOGPS_LOGP>
-2.95

> <JCHEM_LOGP>
-3.0870598443062156

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.246657564243728

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.429747502735709

> <JCHEM_PKA_STRONGEST_BASIC>
8.449795306283493

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
57.5807

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-amino-4-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    4670.0014666.669   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4668.6684665.897   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4667.3354666.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4665.9984665.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4664.6654666.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4663.3334665.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4662.0004666.669   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4660.6674665.897   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4662.0004668.208   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    4665.9984664.358   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0    4667.3354668.208   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4671.3334665.897   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4672.6664666.669   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4671.3334664.358   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4670.0014668.208   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    4671.3334668.975   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    4668.6684668.975   0.000  0.00  0.00           O+0
CONECT    1    2   12   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4                                                            
CONECT   11    3                                                            
CONECT   12    1   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
alpha-Glu-val	ChEBI
Glutamyl-valine	ChEBI
L-alpha-Glu-L-val	ChEBI
L-Glu-L-val	ChEBI
L-Glutamyl-L-valine	ChEBI
a-Glu-val	Generator
Α-glu-val	Generator
L-a-Glu-L-val	Generator
L-Α-glu-L-val	Generator
Α-L-glu-L-val	HMDB
Α-glutamylvaline	HMDB
Α-L-glutamyl-L-valine	HMDB
L-Α-glutamyl-L-valine	HMDB
N-Α-glutamylvaline	HMDB
N-Α-L-glutamyl-L-valine	HMDB
N-L-Α-glutamylvaline	HMDB
N-L-Α-glutamyl-L-valine	HMDB
alpha-L-Glu-L-val	HMDB
alpha-Glutamylvaline	HMDB
alpha-L-Glutamyl-L-valine	HMDB
L-alpha-Glutamyl-L-valine	HMDB
N-alpha-Glutamylvaline	HMDB
N-alpha-L-Glutamyl-L-valine	HMDB
N-L-alpha-Glutamylvaline	HMDB
N-L-alpha-Glutamyl-L-valine	HMDB
NSC 334345	HMDB
Glu-val	HMDB
N-Glutamylvaline	HMDB
N-L-Glutamyl-L-valine	HMDB
Glutamic acid valine dipeptide	HMDB
Glutamate valine dipeptide	HMDB
Glutamic acid-valine dipeptide	HMDB
Glutamate-valine dipeptide	HMDB
e-V Dipeptide	HMDB
EV dipeptide	HMDB
Glutamylvaline	HMDB, ChEBI

Chemical Formula

C₁₀H₁₈N₂O₅

Average Mass

246.2603 Da

Monoisotopic Mass

246.12157 Da

IUPAC Name

(4S)-4-amino-4-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}butanoic acid

Traditional Name

(4S)-4-amino-4-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}butanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](NC(=O)[C@@H](N)CCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C10H18N2O5/c1-5(2)8(10(16)17)12-9(15)6(11)3-4-7(13)14/h5-6,8H,3-4,11H2,1-2H3,(H,12,15)(H,13,14)(H,16,17)/t6-,8-/m0/s1

InChI Key

SITLTJHOQZFJGG-XPUUQOCRSA-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

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

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
Valine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Amino fatty acid
Branched fatty acid
Methyl-branched fatty acid
Fatty amide
N-acyl-amine
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Carboxamide group
Secondary carboxylic acid amide
Amino acid
Amino acid or derivatives
Carboxylic acid
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glutamyl-L-amino acid (CHEBI:68846 )

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	ALOGPS
logP	-3.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	8.45	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	57.58 m³·mol⁻¹	ChemAxon
Polarizability	24.68 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

HMDB0028832

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

6992567

PDB ID

Not Available

ChEBI ID

68846

Good Scents ID

Not Available

References

General References

Kanazawa A, Kakimoto Y, Nakajima T, Sano I: Identification of gamma-glutamylserine, gamma-glutamylalanine, gamma-glutamylvaline and S-methylglutathione of bovine brain. Biochim Biophys Acta. 1965 Nov 15;111(1):90-5. doi: 10.1016/0304-4165(65)90475-7. [PubMed:5867340 ]

Showing NP-Card for Glutamylvaline (NP0136454)

MOL for NP0136454 (Glutamylvaline)

3D MOL for NP0136454 (Glutamylvaline)

3D SDF for NP0136454 (Glutamylvaline)

3D-SDF for NP0136454 (Glutamylvaline)

PDB for NP0136454 (Glutamylvaline)

3D PDB for NP0136454 (Glutamylvaline)

SMILES for NP0136454 (Glutamylvaline)

INCHI for NP0136454 (Glutamylvaline)

Structure for NP0136454 (Glutamylvaline)

3D Structure for NP0136454 (Glutamylvaline)