NP-MRD: Showing NP-Card for n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid (NP0232925)

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Record Information

Version

2.0

Created at

2022-09-06 14:19:36 UTC

Updated at

2022-09-06 14:19:37 UTC

NP-MRD ID

NP0232925

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid

Description

N-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydro-2H-pyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid is found in Pseudomonas fluorescens. N-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydro-2H-pyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171513182D          

 35 36  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171513182D          

 35 36  0  0  0  0            999 V2000
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 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0232925

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=CC=CC=CC(=O)NC(CC(=O)NC(C(C)C)C(=O)C1C(C)C(=O)NC1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H33N3O5/c1-5-6-7-8-12-15-21(31)28-20(19-13-10-9-11-14-19)16-22(32)29-24(17(2)3)25(33)23-18(4)26(34)30-27(23)35/h5-15,17-18,20,23-24H,16H2,1-4H3,(H,28,31)(H,29,32)(H,30,34,35)

> <INCHI_KEY>
OHDXGZAYYBMHCY-UHFFFAOYSA-N

> <FORMULA>
C27H33N3O5

> <MOLECULAR_WEIGHT>
479.577

> <EXACT_MASS>
479.242021175

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
51.28580918589593

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(2-{[3-methyl-1-(4-methyl-2,5-dioxopyrrolidin-3-yl)-1-oxobutan-2-yl]carbamoyl}-1-phenylethyl)octa-2,4,6-trienamide

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
3.0781243736666664

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.91923778339135

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.725632517055244

> <JCHEM_PKA_STRONGEST_BASIC>
-0.34558673638474013

> <JCHEM_POLAR_SURFACE_AREA>
121.44

> <JCHEM_REFRACTIVITY>
135.73579999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(2-{[3-methyl-1-(4-methyl-2,5-dioxopyrrolidin-3-yl)-1-oxobutan-2-yl]carbamoyl}-1-phenylethyl)octa-2,4,6-trienamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   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  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       8.002  -3.080   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003  -3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.915  -0.635   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.380  -1.111   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.439   0.830   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.345   2.076   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0       9.899   0.830   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       9.424  -0.635   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.959  -1.111   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22   29                                                  
CONECT   29   28                                                            
CONECT   30   11   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
N-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydro-2H-pyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidate	Generator

Chemical Formula

C₂₇H₃₃N₃O₅

Average Mass

479.5770 Da

Monoisotopic Mass

479.24202 Da

IUPAC Name

N-(2-{[3-methyl-1-(4-methyl-2,5-dioxopyrrolidin-3-yl)-1-oxobutan-2-yl]carbamoyl}-1-phenylethyl)octa-2,4,6-trienamide

Traditional Name

N-(2-{[3-methyl-1-(4-methyl-2,5-dioxopyrrolidin-3-yl)-1-oxobutan-2-yl]carbamoyl}-1-phenylethyl)octa-2,4,6-trienamide

CAS Registry Number

Not Available

SMILES

CC=CC=CC=CC(=O)NC(CC(=O)NC(C(C)C)C(=O)C1C(C)C(=O)NC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C27H33N3O5/c1-5-6-7-8-12-15-21(31)28-20(19-13-10-9-11-14-19)16-22(32)29-24(17(2)3)25(33)23-18(4)26(34)30-27(23)35/h5-15,17-18,20,23-24H,16H2,1-4H3,(H,28,31)(H,29,32)(H,30,34,35)

InChI Key

OHDXGZAYYBMHCY-UHFFFAOYSA-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
Pseudomonas fluorescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
1,3-dicarbonyl compound
Pyrroline
Ketone
N-acylimine
Lactim
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxygen 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	3.48	ALOGPS
logP	3.08	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	9.73	ChemAxon
pKa (Strongest Basic)	-0.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.44 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	135.74 m³·mol⁻¹	ChemAxon
Polarizability	51.29 Å³	ChemAxon
Number of Rings	2	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72728785

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid (NP0232925)

MOL for NP0232925 (n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid)

3D MOL for NP0232925 (n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid)

3D SDF for NP0232925 (n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid)

3D-SDF for NP0232925 (n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid)

PDB for NP0232925 (n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid)

3D PDB for NP0232925 (n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid)

SMILES for NP0232925 (n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid)

INCHI for NP0232925 (n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid)

Structure for NP0232925 (n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid)

3D Structure for NP0232925 (n-(2-{[1-(5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl)-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-1-phenylethyl)octa-2,4,6-trienimidic acid)