NP-MRD: Showing NP-Card for {[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}acetic acid (NP0329005)

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Record Information

Version

2.0

Created at

2022-09-12 12:58:30 UTC

Updated at

2022-09-12 12:58:31 UTC

NP-MRD ID

NP0329005

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Leu-Ala-Gly, also known as L-a-g or L-leu-L-ala-gly, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Leu-Ala-Gly is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. {[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}acetic acid is found in Trypanosoma brucei. Based on a literature review very few articles have been published on Leu-Ala-Gly.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122214582D          

 18 17  0  0  1  0            999 V2000
    4.9500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 N   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
    0.8250    1.4289    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
    1.2375   -0.7145    0.0000 O   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
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  4  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  4  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329005

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H21N3O4/c1-6(2)4-8(12)11(18)14-7(3)10(17)13-5-9(15)16/h6-8H,4-5,12H2,1-3H3,(H,13,17)(H,14,18)(H,15,16)/t7-,8-/m0/s1

> <INCHI_KEY>
WNGVUZWBXZKQES-YUMQZZPRSA-N

> <FORMULA>
C11H21N3O4

> <MOLECULAR_WEIGHT>
259.306

> <EXACT_MASS>
259.153206168

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.098737314844175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-2.0288425924744025

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.924172539488725

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.313673572515106

> <JCHEM_PKA_STRONGEST_BASIC>
9.60540550625271

> <JCHEM_POLAR_SURFACE_AREA>
128.5

> <JCHEM_REFRACTIVITY>
65.31520000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       9.240  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.470  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.240  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.930  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.160   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       6.930   1.334   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       3.850   1.334   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
L-a-g	ChEBI
L-Leu-L-ala-gly	ChEBI
LAG	ChEBI

Chemical Formula

C₁₁H₂₁N₃O₄

Average Mass

259.3060 Da

Monoisotopic Mass

259.15321 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H21N3O4/c1-6(2)4-8(12)11(18)14-7(3)10(17)13-5-9(15)16/h6-8H,4-5,12H2,1-3H3,(H,13,17)(H,14,18)(H,15,16)/t7-,8-/m0/s1

InChI Key

WNGVUZWBXZKQES-YUMQZZPRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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 oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Leucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alanine or derivatives
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Primary aliphatic amine
Organic oxide
Organic nitrogen compound
Carbonyl group
Amine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tripeptide (CHEBI:73526 )

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

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

8010675

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9834954

PDB ID

Not Available

ChEBI ID

73526

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}acetic acid (NP0329005)

MOL for NP0329005 ({[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

3D MOL for NP0329005 ({[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

3D SDF for NP0329005 ({[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

3D-SDF for NP0329005 ({[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

PDB for NP0329005 ({[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

3D PDB for NP0329005 ({[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

SMILES for NP0329005 ({[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

INCHI for NP0329005 ({[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

Structure for NP0329005 ({[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}acetic acid)

3D Structure for NP0329005 ({[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}acetic acid)