NP-MRD: Showing NP-Card for (2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid (NP0239710)

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Record Information

Version

2.0

Created at

2022-09-06 23:21:43 UTC

Updated at

2022-09-06 23:21:44 UTC

NP-MRD ID

NP0239710

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid

Description

Astin J belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. (2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid is found in Aster tataricus. (2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid was first documented in 1995 (PMID: 7728933). Based on a literature review very few articles have been published on Astin J.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072201212D          

 37 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072201212D          

 37 38  0  0  1  0            999 V2000
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 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  4  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 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
 24 28  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239710

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](NC(=O)C1=CC=CN1)C(O)=N[C@@H](CO)C(O)=N[C@H](CC(O)=N[C@@H](CC)C(O)=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H33N5O7/c1-3-16(28-23(34)18-11-8-12-26-18)22(33)30-20(14-31)24(35)29-19(15-9-6-5-7-10-15)13-21(32)27-17(4-2)25(36)37/h5-12,16-17,19-20,26,31H,3-4,13-14H2,1-2H3,(H,27,32)(H,28,34)(H,29,35)(H,30,33)(H,36,37)/t16-,17-,19+,20-/m0/s1

> <INCHI_KEY>
MSWRFBPAGLGJCX-XEYPJELSSA-N

> <FORMULA>
C25H33N5O7

> <MOLECULAR_WEIGHT>
515.567

> <EXACT_MASS>
515.237998423

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.20630327120372

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(3R)-3-{[(2S)-1,3-dihydroxy-2-{[(2S)-1-hydroxy-2-[(1H-pyrrol-2-yl)formamido]butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid

> <JCHEM_LOGP>
1.7359993281459603

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.041401507784045

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8451791064772913

> <JCHEM_PKA_STRONGEST_BASIC>
3.514598275542914

> <JCHEM_POLAR_SURFACE_AREA>
200.18999999999997

> <JCHEM_REFRACTIVITY>
133.78520000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(3R)-3-{[(2S)-1,3-dihydroxy-2-{[(2S)-1-hydroxy-2-(1H-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0     -14.670   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -13.337  -0.000   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0     -12.003  -0.770   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0     -13.337  -3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -9.336  -5.390   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      -6.668  -6.930   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -2.667  -7.700   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.580  -4.485   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.104  -3.020   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.564  -3.020   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -0.088  -4.485   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0     -16.004  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29    8   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35    3   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Value	Source
(Pyrrol-2-yl)carbonyl-2-aminobutyryl-seryl-beta-phenylalanyl-2-aminobutyric acid	MeSH
Pyrrole-abu-ser-beta-phe-abu	MeSH

Chemical Formula

C₂₅H₃₃N₅O₇

Average Mass

515.5670 Da

Monoisotopic Mass

515.23800 Da

IUPAC Name

(2S)-2-{[(3R)-3-{[(2S)-1,3-dihydroxy-2-{[(2S)-1-hydroxy-2-[(1H-pyrrol-2-yl)formamido]butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid

Traditional Name

(2S)-2-{[(3R)-3-{[(2S)-1,3-dihydroxy-2-{[(2S)-1-hydroxy-2-(1H-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid

CAS Registry Number

Not Available

SMILES

CC[C@H](NC(=O)C1=CC=CN1)C(O)=N[C@@H](CO)C(O)=N[C@H](CC(O)=N[C@@H](CC)C(O)=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C25H33N5O7/c1-3-16(28-23(34)18-11-8-12-26-18)22(33)30-20(14-31)24(35)29-19(15-9-6-5-7-10-15)13-21(32)27-17(4-2)25(36)37/h5-12,16-17,19-20,26,31H,3-4,13-14H2,1-2H3,(H,27,32)(H,28,34)(H,29,35)(H,30,33)(H,36,37)/t16-,17-,19+,20-/m0/s1

InChI Key

MSWRFBPAGLGJCX-XEYPJELSSA-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
Aster tataricus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
Alpha-dipeptide
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Serine or derivatives
Beta amino acid or derivatives
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
2-heteroaryl carboxamide
Pyrrole-2-carboxamide
Pyrrole-2-carboxylic acid or derivatives
Benzenoid
Substituted pyrrole
N-acyl-amine
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Pyrrole
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	1.74	ChemAxon
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	3.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	200.19 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	133.79 m³·mol⁻¹	ChemAxon
Polarizability	53.21 Å³	ChemAxon
Number of Rings	2	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

9930954

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11756251

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Morita H, Nagashima S, Takeya K, Itokawa H: Structure of a new peptide, astin J, from Aster tataricus. Chem Pharm Bull (Tokyo). 1995 Feb;43(2):271-3. doi: 10.1248/cpb.43.271. [PubMed:7728933 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid (NP0239710)

MOL for NP0239710 ((2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid)

3D MOL for NP0239710 ((2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid)

3D SDF for NP0239710 ((2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid)

3D-SDF for NP0239710 ((2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid)

PDB for NP0239710 ((2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid)

3D PDB for NP0239710 ((2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid)

SMILES for NP0239710 ((2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid)

INCHI for NP0239710 ((2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid)

Structure for NP0239710 ((2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid)

3D Structure for NP0239710 ((2s)-2-{[(3r)-3-{[(2s)-1,3-dihydroxy-2-{[(2s)-1-hydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanoic acid)