NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoic acid (NP0313941)

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Record Information

Version

2.0

Created at

2022-09-11 11:46:49 UTC

Updated at

2022-09-11 11:46:49 UTC

NP-MRD ID

NP0313941

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Asp-Leu-Phe-Val, also known as D-L-F-V or DLFV, 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. Asp-Leu-Phe-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-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoic acid is found in Trypanosoma brucei. Based on a literature review very few articles have been published on Asp-Leu-Phe-Val.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112213462D          

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M  END

     RDKit          3D

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  Mrv1652309112213462D          

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 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0313941

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H36N4O7/c1-13(2)10-17(26-21(31)16(25)12-19(29)30)22(32)27-18(11-15-8-6-5-7-9-15)23(33)28-20(14(3)4)24(34)35/h5-9,13-14,16-18,20H,10-12,25H2,1-4H3,(H,26,31)(H,27,32)(H,28,33)(H,29,30)(H,34,35)/t16-,17-,18-,20-/m0/s1

> <INCHI_KEY>
QBJCJWAZOPCNIX-JPLJXNOCSA-N

> <FORMULA>
C24H36N4O7

> <MOLECULAR_WEIGHT>
492.573

> <EXACT_MASS>
492.258399515

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
50.98404960171845

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
0.8266960742127619

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.56118807788731

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.008832029525028

> <JCHEM_PKA_STRONGEST_BASIC>
9.702299281633968

> <JCHEM_POLAR_SURFACE_AREA>
198.38999999999996

> <JCHEM_REFRACTIVITY>
127.27820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -4.001   2.310   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      -1.334   3.850   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0      -1.334   6.930   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334   8.470   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   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    5   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   18   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   29   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   70    0
END

View in JSmol

Synonyms

Value	Source
D-L-F-V	ChEBI
DLFV	ChEBI
L-Asp-L-leu-L-phe-L-val	ChEBI

Chemical Formula

C₂₄H₃₆N₄O₇

Average Mass

492.5730 Da

Monoisotopic Mass

492.25840 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H36N4O7/c1-13(2)10-17(26-21(31)16(25)12-19(29)30)22(32)27-18(11-15-8-6-5-7-9-15)23(33)28-20(14(3)4)24(34)35/h5-9,13-14,16-18,20H,10-12,25H2,1-4H3,(H,26,31)(H,27,32)(H,28,33)(H,29,30)(H,34,35)/t16-,17-,18-,20-/m0/s1

InChI Key

QBJCJWAZOPCNIX-JPLJXNOCSA-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
Phenylalanine or derivatives
Aspartic acid or derivatives
Leucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Valine or derivatives
Alpha-amino acid amide
Amphetamine or derivatives
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
N-acyl-amine
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty amide
Amino acid
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Carboxylic acid
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Primary amine
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tetrapeptide (CHEBI:73431 )

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	0.83	ChemAxon
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	9.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	198.39 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	127.28 m³·mol⁻¹	ChemAxon
Polarizability	50.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

28639309

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71464626

PDB ID

Not Available

ChEBI ID

73431

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoic acid (NP0313941)

MOL for NP0313941 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoic acid)

3D MOL for NP0313941 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoic acid)

3D SDF for NP0313941 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoic acid)

3D-SDF for NP0313941 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoic acid)

PDB for NP0313941 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoic acid)

3D PDB for NP0313941 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoic acid)

SMILES for NP0313941 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoic acid)

INCHI for NP0313941 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoic acid)

Structure for NP0313941 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoic acid)

3D Structure for NP0313941 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoic acid)