NP-MRD: Showing NP-Card for {[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid (NP0181646)

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Record Information

Version

1.0

Created at

2022-09-03 20:12:02 UTC

Updated at

2022-09-03 20:12:02 UTC

NP-MRD ID

NP0181646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid

Description

Pro-Trp-Val-Gly, also known as p-W-V-g or PWVG, 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. Pro-Trp-Val-Gly 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)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid is found in Trypanosoma brucei. It was first documented in 2022 (PMID: 36057450). Based on a literature review a significant number of articles have been published on Pro-Trp-Val-Gly (PMID: 36057449) (PMID: 36057448) (PMID: 36057447) (PMID: 36057446).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032222122D          

 33 35  0  0  1  0            999 V2000
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   -0.6880   -4.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2400   -4.0623    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309032222122D          

 33 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0181646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H](N=C(O)[C@H](CC1=CNC2=CC=CC=C12)N=C(O)[C@@H]1CCCN1)C(O)=NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H31N5O5/c1-13(2)20(23(33)26-12-19(29)30)28-22(32)18(27-21(31)17-8-5-9-24-17)10-14-11-25-16-7-4-3-6-15(14)16/h3-4,6-7,11,13,17-18,20,24-25H,5,8-10,12H2,1-2H3,(H,26,33)(H,27,31)(H,28,32)(H,29,30)/t17-,18-,20-/m0/s1

> <INCHI_KEY>
MMFLWRSVOVXBDP-BJLQDIEVSA-N

> <FORMULA>
C23H31N5O5

> <MOLECULAR_WEIGHT>
457.531

> <EXACT_MASS>
457.232519118

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.03937247109313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-2-({hydroxy[(2S)-pyrrolidin-2-yl]methylidene}amino)-3-(1H-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid

> <JCHEM_LOGP>
-0.02963822573068016

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.6272528647008033

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.129414065181954

> <JCHEM_PKA_STRONGEST_BASIC>
9.74698755709439

> <JCHEM_POLAR_SURFACE_AREA>
162.89

> <JCHEM_REFRACTIVITY>
121.72879999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-2-{[hydroxy((2S)-pyrrolidin-2-yl)methylidene]amino}-3-(1H-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       0.222  -8.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.284  -8.727   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.760 -10.192   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.839  -6.118   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -0.887  -3.189   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -2.393  -3.509   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.869  -4.974   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.424  -2.365   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.104  -0.858   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.437  -0.088   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.582  -1.119   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      -4.955  -2.526   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      -3.821  -7.903   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.297  -9.368   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0      -4.852  -6.759   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -6.358  -7.079   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.388  -5.934   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -8.895  -6.255   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -6.912  -4.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   13                                                  
CONECT   19    8   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22                                                       
CONECT   27    4   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
L-Pro-L-TRP-L-val-gly	ChEBI
p-W-V-g	ChEBI
PWVG	ChEBI

Chemical Formula

C₂₃H₃₁N₅O₅

Average Mass

457.5310 Da

Monoisotopic Mass

457.23252 Da

IUPAC Name

2-{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-2-({hydroxy[(2S)-pyrrolidin-2-yl]methylidene}amino)-3-(1H-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid

Traditional Name

{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-2-{[hydroxy((2S)-pyrrolidin-2-yl)methylidene]amino}-3-(1H-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](N=C(O)[C@H](CC1=CNC2=CC=CC=C12)N=C(O)[C@@H]1CCCN1)C(O)=NCC(O)=O

InChI Identifier

InChI=1S/C23H31N5O5/c1-13(2)20(23(33)26-12-19(29)30)28-22(32)18(27-21(31)17-8-5-9-24-17)10-14-11-25-16-7-4-3-6-15(14)16/h3-4,6-7,11,13,17-18,20,24-25H,5,8-10,12H2,1-2H3,(H,26,33)(H,27,31)(H,28,32)(H,29,30)/t17-,18-,20-/m0/s1

InChI Key

MMFLWRSVOVXBDP-BJLQDIEVSA-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
Valine or derivatives
Proline or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Triptan
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Fatty amide
N-acyl-amine
Fatty acyl
Substituted pyrrole
Benzenoid
Pyrrolidine
Pyrrole
Heteroaromatic compound
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Carboxylic acid
Secondary aliphatic amine
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Amine
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrapeptide (CHEBI:73650 )

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	-0.03	ChemAxon
pKa (Strongest Acidic)	3.13	ChemAxon
pKa (Strongest Basic)	9.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	162.89 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	121.73 m³·mol⁻¹	ChemAxon
Polarizability	48.04 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

29368061

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71728362

PDB ID

Not Available

ChEBI ID

73650

Good Scents ID

Not Available

References

General References

Micalizzi E, Vaudano AE, Ballerini A, Talami F, Giovannini G, Turchi G, Cioclu MC, Giunta L, Meletti S: Ictal Apnea: a prospective monocentric study in patients with epilepsy. Eur J Neurol. 2022 Sep 3. doi: 10.1111/ene.15547. [PubMed:36057450 ]
Jiang S, Guo P, Heo HY, Zhang Y, Wu J, Jin Y, Laterra J, Eberhart CG, Lim M, Blakeley JO: Radiomics analysis of amide proton transfer-weighted and structural MR images for treatment response assessment in malignant gliomas. NMR Biomed. 2022 Sep 3:e4824. doi: 10.1002/nbm.4824. [PubMed:36057449 ]
Agarwal K, Saikia P, Podder I: Metabolic syndrome and Dyslipidemia in xanthelasma palpebrarum and associated risk-factors- a case-control study. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15353. [PubMed:36057448 ]
Lebel V, Argiropoulos N, Robins S, Charbonneau L, Feeley N: Family-centred care and breastfeeding self-efficacy determined how ready mothers were for their infants to be discharged from a neonatal intensive care unit. Acta Paediatr. 2022 Sep 3. doi: 10.1111/apa.16538. [PubMed:36057447 ]
Park JI, Kim SJ, Kim YJ, Lee SJ: Protective role of Caesalpinia sappan extract and its main component brazilin against blue light-induced damage in human fibroblasts. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15354. [PubMed:36057446 ]
LOTUS database [Link]

Showing NP-Card for {[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid (NP0181646)

MOL for NP0181646 ({[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid)

3D MOL for NP0181646 ({[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid)

3D SDF for NP0181646 ({[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid)

3D-SDF for NP0181646 ({[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid)

PDB for NP0181646 ({[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid)

3D PDB for NP0181646 ({[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid)

SMILES for NP0181646 ({[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid)

INCHI for NP0181646 ({[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid)

Structure for NP0181646 ({[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid)

3D Structure for NP0181646 ({[(2s)-1-hydroxy-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-3-methylbutylidene]amino}acetic acid)