NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid (NP0160595)

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Record Information

Version

2.0

Created at

2022-09-02 18:34:41 UTC

Updated at

2022-09-02 18:34:42 UTC

NP-MRD ID

NP0160595

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid

Description

Ile-Leu-Val-Tyr, also known as i-L-V-y or ILVY, 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. Ile-Leu-Val-Tyr 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-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid is found in Trypanosoma brucei. Based on a literature review very few articles have been published on Ile-Leu-Val-Tyr.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220342D          

 36 36  0  0  1  0            999 V2000
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022220342D          

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   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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
  3  4  1  6  0  0  0
  3  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
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  4  0  0  0
 15 17  2  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  4  0  0  0
 19 21  2  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 24 30  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 18 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160595

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@H](N)C(O)=N[C@@H](CC(C)C)C(O)=N[C@@H](C(C)C)C(O)=N[C@@H](CC1=CC=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H42N4O6/c1-7-16(6)21(27)24(33)28-19(12-14(2)3)23(32)30-22(15(4)5)25(34)29-20(26(35)36)13-17-8-10-18(31)11-9-17/h8-11,14-16,19-22,31H,7,12-13,27H2,1-6H3,(H,28,33)(H,29,34)(H,30,32)(H,35,36)/t16-,19-,20-,21-,22-/m0/s1

> <INCHI_KEY>
ZBYBKIQDPOSLDR-XSXWSVAESA-N

> <FORMULA>
C26H42N4O6

> <MOLECULAR_WEIGHT>
506.644

> <EXACT_MASS>
506.310435088

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.94399524838935

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.30

> <JCHEM_LOGP>
2.443141619266612

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.702297955123728

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.222190749251196

> <JCHEM_PKA_STRONGEST_BASIC>
9.898112944797319

> <JCHEM_POLAR_SURFACE_AREA>
181.32

> <JCHEM_REFRACTIVITY>
136.82030000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S,3S)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -6.668  11.550   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      -6.668   8.470   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      -5.335   4.620   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      -1.334   3.850   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    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   18                                                       
CONECT   18   17   19   34                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   24                                                       
CONECT   31   22   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   18   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

View in JSmol

Synonyms

Value	Source
I-L-V-y	ChEBI
ILVY	ChEBI
L-Ile-L-leu-L-val-L-tyr	ChEBI

Chemical Formula

C₂₆H₄₂N₄O₆

Average Mass

506.6440 Da

Monoisotopic Mass

506.31044 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@H](N)C(O)=N[C@@H](CC(C)C)C(O)=N[C@@H](C(C)C)C(O)=N[C@@H](CC1=CC=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C26H42N4O6/c1-7-16(6)21(27)24(33)28-19(12-14(2)3)23(32)30-22(15(4)5)25(34)29-20(26(35)36)13-17-8-10-18(31)11-9-17/h8-11,14-16,19-22,31H,7,12-13,27H2,1-6H3,(H,28,33)(H,29,34)(H,30,32)(H,35,36)/t16-,19-,20-,21-,22-/m0/s1

InChI Key

ZBYBKIQDPOSLDR-XSXWSVAESA-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 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
Tyrosine or derivatives
Phenylalanine or derivatives
Leucine or derivatives
Isoleucine or derivatives
N-acyl-alpha-amino acid
Valine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
3-phenylpropanoic-acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Fatty amide
N-acyl-amine
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Primary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Primary amine
Organooxygen compound
Organic oxide
Amine
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tetrapeptide (CHEBI:73519 )

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	0.3	ALOGPS
logS	-4.5	ALOGPS

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

28639352

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71464668

PDB ID

Not Available

ChEBI ID

73519

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid (NP0160595)

MOL for NP0160595 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

3D MOL for NP0160595 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

3D SDF for NP0160595 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

3D-SDF for NP0160595 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

PDB for NP0160595 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

3D PDB for NP0160595 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

SMILES for NP0160595 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

INCHI for NP0160595 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

Structure for NP0160595 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)

3D Structure for NP0160595 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoic acid)