NP-MRD: Showing NP-Card for 8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2z)-2-methylbut-2-enoate (NP0268531)

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Record Information

Version

2.0

Created at

2022-09-08 13:41:21 UTC

Updated at

2022-09-08 13:41:21 UTC

NP-MRD ID

NP0268531

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2z)-2-methylbut-2-enoate

Description

[8-Benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] (Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. Based on a literature review very few articles have been published on [8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] (Z)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082215412D          

 38 40  0  0  0  0            999 V2000
    2.2154   11.4886    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


  Mrv1652309082215412D          

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 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0268531

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C(=NC=C1)C(=O)NC1COC(=O)C(CC2=CC=CC=C2)C(OC(=O)C(\C)=C/C)C(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30N2O9/c1-5-15(2)25(32)38-23-16(3)37-27(34)19(29-24(31)21-22(30)20(35-4)11-12-28-21)14-36-26(33)18(23)13-17-9-7-6-8-10-17/h5-12,16,18-19,23,30H,13-14H2,1-4H3,(H,29,31)/b15-5-

> <INCHI_KEY>
NRCFYQYMBDTOBT-WCSRMQSCSA-N

> <FORMULA>
C27H30N2O9

> <MOLECULAR_WEIGHT>
526.542

> <EXACT_MASS>
526.195130554

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.547020687256364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
4.050238530000001

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.115589109053921

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.146081074676182

> <JCHEM_PKA_STRONGEST_BASIC>
3.1264270789321036

> <JCHEM_POLAR_SURFACE_AREA>
150.35

> <JCHEM_REFRACTIVITY>
133.613

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       4.135  21.445   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.145  22.625   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.629  22.358   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.639  23.537   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.102  20.911   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.414  20.643   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.092  19.731   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.565  18.284   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.745  17.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.079  18.064   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.012  15.777   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.242  14.444   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.232  13.264   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.795  13.917   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.795  12.377   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.129  11.607   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.463  12.377   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.129  10.067   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       0.795   9.297   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       0.795   7.757   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.129   6.987   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.463   7.757   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.796   6.987   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.796   5.447   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.463   9.297   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.796  10.067   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.652  14.444   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.422  15.777   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.154  17.294   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.488  18.064   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.025  18.284   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.501  19.731   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.018  19.998   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.008  18.819   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.524  19.086   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.051  20.533   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.061  21.713   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.545  21.445   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                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   18   26                                                  
CONECT   26   25                                                            
CONECT   27   14   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    8   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
[8-Benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] (Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₇H₃₀N₂O₉

Average Mass

526.5420 Da

Monoisotopic Mass

526.19513 Da

IUPAC Name

8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2Z)-2-methylbut-2-enoate

Traditional Name

8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C(=NC=C1)C(=O)NC1COC(=O)C(CC2=CC=CC=C2)C(OC(=O)C(\C)=C/C)C(C)OC1=O

InChI Identifier

InChI=1S/C27H30N2O9/c1-5-15(2)25(32)38-23-16(3)37-27(34)19(29-24(31)21-22(30)20(35-4)11-12-28-21)14-36-26(33)18(23)13-17-9-7-6-8-10-17/h5-12,16,18-19,23,30H,13-14H2,1-4H3,(H,29,31)/b15-5-

InChI Key

NRCFYQYMBDTOBT-WCSRMQSCSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Pyridine carboxylic acid or derivatives
Tricarboxylic acid or derivatives
2-heteroaryl carboxamide
Alkyl aryl ether
Fatty acid ester
Hydroxypyridine
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxamide group
Carboxylic acid ester
Lactone
Secondary carboxylic acid amide
Oxacycle
Ether
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxide
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	4.05	ChemAxon
pKa (Strongest Acidic)	8.15	ChemAxon
pKa (Strongest Basic)	3.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	150.35 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	133.61 m³·mol⁻¹	ChemAxon
Polarizability	52.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

4976799

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6474917

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2z)-2-methylbut-2-enoate (NP0268531)

MOL for NP0268531 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0268531 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0268531 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0268531 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2z)-2-methylbut-2-enoate)

PDB for NP0268531 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0268531 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0268531 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0268531 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2z)-2-methylbut-2-enoate)

Structure for NP0268531 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0268531 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl (2z)-2-methylbut-2-enoate)