NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid (NP0327411)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 09:58:07 UTC

Updated at

2022-09-12 09:58:07 UTC

NP-MRD ID

NP0327411

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid

Description

Leu-Asn, also known as L-leu-L-asn or L-N, 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. Leu-Asn 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}-3-(c-hydroxycarbonimidoyl)propanoic acid is found in Trypanosoma brucei. (2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid was first documented in 2019 (PMID: 31724512). Based on a literature review a small amount of articles have been published on Leu-Asn (PMID: 35304505) (PMID: 33946694) (PMID: 33718631).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122211582D          

 17 16  0  0  1  0            999 V2000
   -0.1914   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -3.1895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -3.6020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  1  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
    1.2375    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    0.5230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    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
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327411

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H19N3O4/c1-5(2)3-6(11)9(15)13-7(10(16)17)4-8(12)14/h5-7H,3-4,11H2,1-2H3,(H2,12,14)(H,13,15)(H,16,17)/t6-,7-/m0/s1

> <INCHI_KEY>
MLTRLIITQPXHBJ-BQBZGAKWSA-N

> <FORMULA>
C10H19N3O4

> <MOLECULAR_WEIGHT>
245.279

> <EXACT_MASS>
245.137556104

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.00499291968102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(C-hydroxycarbonimidoyl)propanoic acid

> <JCHEM_LOGP>
-4.790602014901784

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.5451327252471434

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.328706767922692

> <JCHEM_PKA_STRONGEST_BASIC>
13.129695792462911

> <JCHEM_POLAR_SURFACE_AREA>
139.99

> <JCHEM_REFRACTIVITY>
70.7842

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(C-hydroxycarbonimidoyl)propanoic 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      -0.357  -9.034   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976  -8.264   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -9.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976  -6.724   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310  -5.954   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       3.644  -6.724   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.310  -4.414   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.976  -3.644   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       3.644  -3.644   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.310   0.206   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.976   0.976   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       3.644   0.976   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.977   0.206   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.311  -2.104   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   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   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
L-Leu-L-asn	ChEBI
L-N	ChEBI
Leucylasparagine	ChEBI
LN	ChEBI

Chemical Formula

C₁₀H₁₉N₃O₄

Average Mass

245.2790 Da

Monoisotopic Mass

245.13756 Da

IUPAC Name

(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(C-hydroxycarbonimidoyl)propanoic acid

Traditional Name

(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(C-hydroxycarbonimidoyl)propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H19N3O4/c1-5(2)3-6(11)9(15)13-7(10(16)17)4-8(12)14/h5-7H,3-4,11H2,1-2H3,(H2,12,14)(H,13,15)(H,16,17)/t6-,7-/m0/s1

InChI Key

MLTRLIITQPXHBJ-BQBZGAKWSA-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 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
Leucine or derivatives
Asparagine or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Branched fatty acid
Fatty amide
N-acyl-amine
Fatty acyl
Fatty acid
Amino acid or derivatives
Carboxamide group
Carboxylic acid salt
Amino acid
Primary carboxylic acid amide
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Organic salt
Hydrocarbon derivative
Amine
Primary aliphatic amine
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Organopnictogen compound
Organic zwitterion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73529 )

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	-4.8	ChemAxon
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	13.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	139.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	70.78 m³·mol⁻¹	ChemAxon
Polarizability	25 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

5379099

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7016077

PDB ID

Not Available

ChEBI ID

73529

Good Scents ID

Not Available

References

General References

Kheeree N, Kuptawach K, Puthong S, Sangtanoo P, Srimongkol P, Boonserm P, Reamtong O, Choowongkomon K, Karnchanatat A: Discovery of calcium-binding peptides derived from defatted lemon basil seeds with enhanced calcium uptake in human intestinal epithelial cells, Caco-2. Sci Rep. 2022 Mar 18;12(1):4659. doi: 10.1038/s41598-022-08380-0. [PubMed:35304505 ]
Wongsrangsap N, Chukiatsiri S: Purification and Identification of Novel Antioxidant Peptides from Enzymatically Hydrolysed Samia ricini Pupae. Molecules. 2021 Apr 29;26(9):2588. doi: 10.3390/molecules26092588. [PubMed:33946694 ]
Elsadek BEM, Hassan MH: Screening for new peptide substrates for the development of albumin binding anticancer pro-drugs that are cleaved by prostate-specific antigen (PSA) to improve the anti tumor efficacy. Biochem Biophys Rep. 2021 Mar 2;26:100966. doi: 10.1016/j.bbrep.2021.100966. eCollection 2021 Jul. [PubMed:33718631 ]
Lee JK, Li-Chan ECY, Cheung IWY, Jeon YJ, Ko JY, Byun HG: Neuroprotective Effect of beta-secretase Inhibitory Peptide from Pacific Hake (Merluccius productus) Fish Protein Hydrolysate. Curr Alzheimer Res. 2019;16(11):1028-1038. doi: 10.2174/1567205016666191113122046. [PubMed:31724512 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid (NP0327411)

MOL for NP0327411 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid)

3D MOL for NP0327411 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid)

3D SDF for NP0327411 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid)

3D-SDF for NP0327411 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid)

PDB for NP0327411 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid)

3D PDB for NP0327411 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid)

SMILES for NP0327411 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid)

INCHI for NP0327411 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid)

Structure for NP0327411 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid)

3D Structure for NP0327411 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid)