NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-hydroxypropanoic acid (NP0291278)

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Record Information

Version

1.0

Created at

2022-09-09 22:18:25 UTC

Updated at

2022-09-09 22:18:26 UTC

NP-MRD ID

NP0291278

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Leu-Ser, also known as L-leu-L-ser or leucylserine, 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-Ser 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-hydroxypropanoic acid is found in Trypanosoma brucei. It was first documented in 2022 (PMID: 35938100). Based on a literature review a significant number of articles have been published on Leu-Ser (PMID: 35304505) (PMID: 35802984) (PMID: 35438991) (PMID: 35146413).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 32  0  0  0  0  0  0  0  0999 V2000
   -3.6359   -0.7107    0.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8825    0.4897    0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6197    1.0690   -0.9865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    0.1322   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -0.4155    0.9486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6271    0.5894    1.9864 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7203   -0.6650    0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8587   -1.5646   -0.5892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7135   -0.0729    0.9884 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0903   -0.1765    0.6682 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3820   -1.1824   -0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7831   -1.1782   -0.6276 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6563    1.1433    0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8659    1.1956   -0.0471 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8611    2.2736    0.2334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7262   -0.4582    0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4593   -1.6270    0.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4687   -0.8500    1.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8555    1.2391    0.9886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5272    1.6055   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569    1.7008   -1.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399    0.2220   -1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9789    1.0632   -0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694   -0.6157   -1.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784   -1.3494    1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2714    1.4886    1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5450    0.6776    2.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2988   -2.3931   -0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6730   -0.4680    1.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9166   -0.8896   -1.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0378   -2.1809   -0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2018   -1.2021    0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1383    3.1105    0.7476 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
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 15  1  0
 13 14  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  0
  6 27  1  0
  8 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
M  END


  Mrv1652309102200182D          

 15 14  0  0  1  0            999 V2000
    3.3000    1.4289    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
    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
    1.2375    0.7145    0.0000 C   0  0  2  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
    0.8250    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  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
   -1.6500   -1.4289    0.0000 O   0  0  0  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   -2.1434    0.0000 O   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
  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  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291278

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H18N2O4/c1-5(2)3-6(10)8(13)11-7(4-12)9(14)15/h5-7,12H,3-4,10H2,1-2H3,(H,11,13)(H,14,15)/t6-,7-/m0/s1

> <INCHI_KEY>
XGDCYUQSFDQISZ-BQBZGAKWSA-N

> <FORMULA>
C9H18N2O4

> <MOLECULAR_WEIGHT>
218.253

> <EXACT_MASS>
218.126657068

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
22.610493400924472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-2.567554181622755

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.3504685263394505

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.450207557431745

> <JCHEM_PKA_STRONGEST_BASIC>
9.605343029701112

> <JCHEM_POLAR_SURFACE_AREA>
116.14

> <JCHEM_REFRACTIVITY>
53.53370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-hydroxypropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.540   2.667   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.770  -1.334   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  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.770  -4.001   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.540  -2.667   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   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
L-Leu-L-ser	ChEBI
L-S	ChEBI
Leucylserine	ChEBI
LS	ChEBI

Chemical Formula

C₉H₁₈N₂O₄

Average Mass

218.2530 Da

Monoisotopic Mass

218.12666 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](CO)C(O)=O

InChI Identifier

InChI=1S/C9H18N2O4/c1-5(2)3-6(10)8(13)11-7(4-12)9(14)15/h5-7,12H,3-4,10H2,1-2H3,(H,11,13)(H,14,15)/t6-,7-/m0/s1

InChI Key

XGDCYUQSFDQISZ-BQBZGAKWSA-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 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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Serine or derivatives
Alpha-amino acid or derivatives
Beta-hydroxy acid
Fatty acyl
Fatty amide
Hydroxy acid
N-acyl-amine
Amino acid
Carboxylic acid salt
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organonitrogen compound
Organooxygen compound
Primary aliphatic amine
Primary alcohol
Primary amine
Organic zwitterion
Organic salt
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73523 )

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

5360279

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6992129

PDB ID

Not Available

ChEBI ID

73523

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 ]
Suo SK, Zheng SL, Chi CF, Luo HY, Wang B: Novel angiotensin-converting enzyme inhibitory peptides from tuna byproducts-milts: Preparation, characterization, molecular docking study, and antioxidant function on H(2)O(2)-damaged human umbilical vein endothelial cells. Front Nutr. 2022 Jul 22;9:957778. doi: 10.3389/fnut.2022.957778. eCollection 2022. [PubMed:35938100 ]
Yin Z, Yan R, Jiang Y, Feng S, Sun H, Sun J, Zhao D, Li H, Wang B, Zhang N: Identification of peptides in Qingke baijiu and evaluation of its angiotensin converting enzyme (ACE) inhibitory activity and stability. Food Chem. 2022 Nov 30;395:133551. doi: 10.1016/j.foodchem.2022.133551. Epub 2022 Jun 22. [PubMed:35802984 ]
Clements-Decker T, Rautenbach M, Khan S, Khan W: Metabolomics and Genomics Approach for the Discovery of Serrawettin W2 Lipopeptides from Serratia marcescens NP2. J Nat Prod. 2022 May 27;85(5):1256-1266. doi: 10.1021/acs.jnatprod.1c01186. Epub 2022 Apr 19. [PubMed:35438991 ]
Ni ZJ, Wei CK, Zheng AR, Thakur K, Zhang JG, Wei ZJ: Analysis of key precursor peptides and flavor components of flaxseed derived Maillard reaction products based on iBAQ mass spectrometry and molecular sensory science. Food Chem X. 2022 Jan 22;13:100224. doi: 10.1016/j.fochx.2022.100224. eCollection 2022 Mar 30. [PubMed:35146413 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-hydroxypropanoic acid (NP0291278)

MOL for NP0291278 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-hydroxypropanoic acid)

3D MOL for NP0291278 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-hydroxypropanoic acid)

3D SDF for NP0291278 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-hydroxypropanoic acid)

3D-SDF for NP0291278 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-hydroxypropanoic acid)

PDB for NP0291278 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-hydroxypropanoic acid)

3D PDB for NP0291278 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-hydroxypropanoic acid)

SMILES for NP0291278 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-hydroxypropanoic acid)

INCHI for NP0291278 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-hydroxypropanoic acid)

Structure for NP0291278 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-hydroxypropanoic acid)

3D Structure for NP0291278 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-hydroxypropanoic acid)