NP-MRD: Showing NP-Card for [(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid (NP0246826)

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Record Information

Version

2.0

Created at

2022-09-07 08:24:54 UTC

Updated at

2022-09-07 08:24:54 UTC

NP-MRD ID

NP0246826

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid

Description

Leu-Gly-Gly, also known as L-leu-gly-gly or LGG, belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Leu-Gly-Gly is a very strong basic compound (based on its pKa). [(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid is found in Trypanosoma brucei. A tripeptide composed of one L-leucine and two glycine residues joined in sequence.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 35  0  0  0  0  0  0  0  0999 V2000
   -4.1303    0.9294    0.9160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6685   -0.0356   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6228   -1.2217   -0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926   -0.5523    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2367    0.5120    0.1336 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1381    1.2765   -1.0873 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984   -0.0608    0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7266   -0.9188   -0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869    0.2480    1.5054 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9953   -0.2966    1.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8389   -0.1087    0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0708    1.1596    0.1393 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3466   -1.1234    0.0296 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1813   -0.9524   -1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3473   -0.1209   -0.8078 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2033    0.1500   -1.6966 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5755    0.4014    0.4644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8381    1.9765    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2503    0.8972    1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6934    0.5971    1.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7666    0.4612   -1.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6422   -0.8240   -0.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3435   -2.0187   -0.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6935   -1.5637    0.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0360   -1.2249   -0.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2811   -1.1411    1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4984    1.2014    0.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1961    1.7376   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8340    2.0680   -1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6395   -0.7173   -1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8852   -1.3615    2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4131    0.2575    2.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2814    1.3484   -0.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4770   -1.9316   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5870   -0.4280   -1.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8086    1.3803    0.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
  5 27  1  1
  6 28  1  0
  6 29  1  0
  4 25  1  0
  4 26  1  0
  2 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 17 36  1  0
M  END


  Mrv0541 09041213002D          

 18 17  0  0  0  0            999 V2000
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
  7 11  1  6  0  0  0
 12  5  1  4  0  0  0
 12  8  2  0  0  0  0
 13  4  1  4  0  0  0
 13 10  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
  7 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0246826

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H19N3O4/c1-6(2)3-7(11)10(17)13-4-8(14)12-5-9(15)16/h6-7H,3-5,11H2,1-2H3,(H,12,14)(H,13,17)(H,15,16)/t7-/m0/s1

> <INCHI_KEY>
VWHGTYCRDRBSFI-ZETCQYMHSA-N

> <FORMULA>
C10H19N3O4

> <MOLECULAR_WEIGHT>
245.2756

> <EXACT_MASS>
245.137556111

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
25.615157783617782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid

> <ALOGPS_LOGP>
-1.99

> <JCHEM_LOGP>
-2.315754416448841

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.20273075200427

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.691044194277817

> <JCHEM_PKA_STRONGEST_BASIC>
9.606408452754035

> <JCHEM_POLAR_SURFACE_AREA>
128.5

> <JCHEM_REFRACTIVITY>
60.82130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3    6    7                                                       
CONECT    4    8   13                                                       
CONECT    5    9   12                                                       
CONECT    6    1    2    3                                                  
CONECT    7    3   10   11   18                                             
CONECT    8    4   12   14                                                  
CONECT    9    5   15   16                                                  
CONECT   10    7   13   17                                                  
CONECT   11    7                                                            
CONECT   12    5    8                                                       
CONECT   13    4   10                                                       
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18    7                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
L-Leu-gly-gly	ChEBI
Leucyl-glycyl-glycine	ChEBI
Leucylglycylglycine	ChEBI
LGG	ChEBI
N-(N-L-Leucylglycyl)glycine	ChEBI
Leucyl-glycyl-glycine, (DL-leu)-isomer	MeSH
L-Leucyl-glycyl-glycine	MeSH
Leucyl-glycyl-glycine, (D-leu)-isomer	MeSH

Chemical Formula

C₁₀H₁₉N₃O₄

Average Mass

245.2756 Da

Monoisotopic Mass

245.13756 Da

IUPAC Name

2-[(2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid

Traditional Name

[(2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CC(C)C)C(O)=NCC(O)=NCC(O)=O

InChI Identifier

InChI=1S/C10H19N3O4/c1-6(2)3-7(11)10(17)13-4-8(14)12-5-9(15)16/h6-7H,3-5,11H2,1-2H3,(H,12,14)(H,13,17)(H,15,16)/t7-/m0/s1

InChI Key

VWHGTYCRDRBSFI-ZETCQYMHSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Amino acid or derivatives
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tripeptide (CHEBI:74538 )

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	ALOGPS
logP	-2.3	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.69	ChemAxon
pKa (Strongest Basic)	9.61	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	128.5 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	60.82 m³·mol⁻¹	ChemAxon
Polarizability	25.62 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

Not Available

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

70910

PDB ID

Not Available

ChEBI ID

74538

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid (NP0246826)

MOL for NP0246826 ([(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid)

3D MOL for NP0246826 ([(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid)

3D SDF for NP0246826 ([(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid)

3D-SDF for NP0246826 ([(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid)

PDB for NP0246826 ([(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid)

3D PDB for NP0246826 ([(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid)

SMILES for NP0246826 ([(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid)

INCHI for NP0246826 ([(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid)

Structure for NP0246826 ([(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid)

3D Structure for NP0246826 ([(2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]acetic acid)