NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-methylbutanoic acid (NP0198636)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 17:07:19 UTC

Updated at

2022-09-04 17:07:19 UTC

NP-MRD ID

NP0198636

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Leu-Val, also known as L-leu-L-val or leucylvaline, 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-Val 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-methylbutanoic acid is found in Trypanosoma brucei. (2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-methylbutanoic acid was first documented in 2022 (PMID: 35815580). Based on a literature review a small amount of articles have been published on Leu-Val (PMID: 35806175) (PMID: 35562605).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 37  0  0  0  0  0  0  0  0999 V2000
    3.9757   -2.1338   -0.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5377   -0.8969   -0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7612   -1.0924    1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1270   -0.5818   -0.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5826    0.6468    0.2287 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6266    0.3997    1.6400 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1838    0.8859   -0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0598    1.1094   -1.5860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8192    0.8943    0.5615 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625    1.1262    0.0972 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7636    2.3267    0.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0581    2.9442    1.5994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0371    2.7593    0.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0550   -0.0458    0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4483    0.2334   -0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282   -1.3368   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6854   -3.0285   -0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0881   -2.1360   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5862   -2.1563   -1.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2045   -0.0701   -0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6603   -1.7285    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0175   -0.1040    1.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9342   -1.5695    1.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0645   -0.4013   -1.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4508   -1.4321   -0.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1547    1.5581   -0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8035   -0.0997    2.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9059    1.2298    2.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3992    1.9850   -1.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1748    1.2882   -0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1950    3.6931    0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1127   -0.1861    1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0426    0.6648    0.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3844    0.9172   -0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9228   -0.7428   -0.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4692   -1.4555    0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5947   -1.3007   -1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1233   -2.1633    0.2617 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 14  1  0
 14 15  1  0
 14 16  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
  8 29  1  0
 10 30  1  6
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 13 31  1  0
M  END


  Mrv1652309042219072D          

 16 15  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  2  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
    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 C   0  0  0  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
  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  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0198636

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H22N2O3/c1-6(2)5-8(12)10(14)13-9(7(3)4)11(15)16/h6-9H,5,12H2,1-4H3,(H,13,14)(H,15,16)/t8-,9-/m0/s1

> <INCHI_KEY>
MDSUKZSLOATHMH-IUCAKERBSA-N

> <FORMULA>
C11H22N2O3

> <MOLECULAR_WEIGHT>
230.308

> <EXACT_MASS>
230.163042576

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
25.653267312942603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.621047505023964

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.659312889152917

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.721114377653379

> <JCHEM_PKA_STRONGEST_BASIC>
9.605404120179916

> <JCHEM_POLAR_SURFACE_AREA>
95.91000000000001

> <JCHEM_REFRACTIVITY>
60.985600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-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  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+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   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
L-Leu-L-val	ChEBI
L-V	ChEBI
Leucylvaline	ChEBI
LV	ChEBI

Chemical Formula

C₁₁H₂₂N₂O₃

Average Mass

230.3080 Da

Monoisotopic Mass

230.16304 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H22N2O3/c1-6(2)5-8(12)10(14)13-9(7(3)4)11(15)16/h6-9H,5,12H2,1-4H3,(H,13,14)(H,15,16)/t8-,9-/m0/s1

InChI Key

MDSUKZSLOATHMH-IUCAKERBSA-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
Valine 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
Methyl-branched fatty acid
Fatty amide
N-acyl-amine
Fatty acyl
Fatty acid
Amino acid or derivatives
Carboxamide group
Carboxylic acid salt
Amino acid
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
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Organic zwitterion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73579 )

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	-0.62	ChemAxon
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	9.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.91 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	60.99 m³·mol⁻¹	ChemAxon
Polarizability	25.65 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

5361219

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6993115

PDB ID

Not Available

ChEBI ID

73579

Good Scents ID

Not Available

References

General References

Ghosh S, Chatterjee S, Satpati P: Effect of Leu/Val Mutation on the Energetics of Antimicrobial Peptide:Micelle Binding. J Phys Chem B. 2022 Jul 21;126(28):5262-5273. doi: 10.1021/acs.jpcb.2c01293. Epub 2022 Jul 10. [PubMed:35815580 ]
Bojarska J, Breza M, Remko M, Czyz M, Gajos-Michniewicz A, Zimecki M, Kaczmarek K, Madura ID, Wojciechowski JM, Wolf WM: Structural and Biofunctional Insights into the Cyclo(Pro-Pro-Phe-Phe-) Scaffold from Experimental and In Silico Studies: Melanoma and Beyond. Int J Mol Sci. 2022 Jun 28;23(13):7173. doi: 10.3390/ijms23137173. [PubMed:35806175 ]
Vezenkov LT, Danalev DL, Iwanov I, Lozanov V, Atanasov A, Todorova R, Vassilev N, Karadjova V: Synthesis and biological study of new galanthamine-peptide derivatives designed for prevention and treatment of Alzheimer(')s disease. Amino Acids. 2022 Jun;54(6):897-910. doi: 10.1007/s00726-022-03167-z. Epub 2022 May 13. [PubMed:35562605 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-methylbutanoic acid (NP0198636)

MOL for NP0198636 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-methylbutanoic acid)

3D MOL for NP0198636 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-methylbutanoic acid)

3D SDF for NP0198636 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-methylbutanoic acid)

3D-SDF for NP0198636 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-methylbutanoic acid)

PDB for NP0198636 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-methylbutanoic acid)

3D PDB for NP0198636 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-methylbutanoic acid)

SMILES for NP0198636 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-methylbutanoic acid)

INCHI for NP0198636 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-methylbutanoic acid)

Structure for NP0198636 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-methylbutanoic acid)

3D Structure for NP0198636 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-methylbutanoic acid)