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 2-methylbut-2-enoate (NP0315688)

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Record Information

Version

2.0

Created at

2022-09-11 14:26:50 UTC

Updated at

2022-09-11 14:26:50 UTC

NP-MRD ID

NP0315688

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 2-methylbut-2-enoate

Description

8-Benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylbut-2-enoate belongs to the class of organic compounds known as oxirane carboxylic acids. Oxirane carboxylic acids are compounds containing an oxirane ring bearing a carboxylic acid group. 8-Benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylbut-2-enoate is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241501482D          

 38 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241501482D          

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 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  4  0  0  0
 28 31  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 11 35  1  0  0  0  0
 35 36  2  0  0  0  0
  7 37  2  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0315688

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=NC(C(=O)NC2COC(=O)C(CC3=CC=CC=C3)C(OC(=O)C(C)=CC)C(C)OC2=O)=C1O

> <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)

> <INCHI_KEY>
NRCFYQYMBDTOBT-UHFFFAOYSA-N

> <FORMULA>
C27H30N2O9

> <MOLECULAR_WEIGHT>
526.542

> <EXACT_MASS>
526.195130554

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.132877646646115

> <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 2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
4.050238530000001

> <ALOGPS_LOGS>
-4.36

> <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>
150.35000000000002

> <JCHEM_REFRACTIVITY>
133.61300000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.28e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.784  -2.664   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.550  -3.434   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.550  -4.974   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.784  -5.744   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.784  -7.284   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.550  -8.054   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.884  -7.284   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.217  -8.054   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.551  -7.284   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -3.217  -9.594   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -4.551 -10.364   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.284 -11.881   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.054 -13.215   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.501 -13.741   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.501 -15.281   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -7.948 -13.215   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.938 -14.394   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.411 -15.842   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.895 -16.109   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.368 -17.556   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -7.358 -18.736   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.874 -18.468   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.401 -17.021   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.718 -11.881   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -10.235 -12.148   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -10.761 -13.596   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -9.771 -14.775   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -12.278 -13.863   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -12.805 -15.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -14.321 -15.578   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -13.268 -12.683   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.451 -10.364   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.784  -9.594   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -7.271  -9.375   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -5.731  -9.375   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -5.204  -7.927   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.884  -5.744   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.217  -4.974   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   16   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28                                                            
CONECT   32   24   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   11   36                                                  
CONECT   36   35                                                            
CONECT   37    7    3   38                                                  
CONECT   38   37                                                            
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-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 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 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 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC=NC(C(=O)NC2COC(=O)C(CC3=CC=CC=C3)C(OC(=O)C(C)=CC)C(C)OC2=O)=C1O

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)

InChI Key

NRCFYQYMBDTOBT-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxirane carboxylic acids. Oxirane carboxylic acids are compounds containing an oxirane ring bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Epoxides

Sub Class

Oxirane carboxylic acids and derivatives

Direct Parent

Oxirane carboxylic acids

Alternative Parents

Substituents

Oxirane carboxylic acid
Methyl ester
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	3.12	ALOGPS
logP	4.05	ChemAxon
logS	-4.4	ALOGPS
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	54.13 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

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

468591

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 2-methylbut-2-enoate (NP0315688)

MOL for NP0315688 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylbut-2-enoate)

3D MOL for NP0315688 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylbut-2-enoate)

3D SDF for NP0315688 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylbut-2-enoate)

3D-SDF for NP0315688 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylbut-2-enoate)

PDB for NP0315688 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylbut-2-enoate)

3D PDB for NP0315688 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylbut-2-enoate)

SMILES for NP0315688 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylbut-2-enoate)

INCHI for NP0315688 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylbut-2-enoate)

Structure for NP0315688 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylbut-2-enoate)

3D Structure for NP0315688 (8-benzyl-3-(3-hydroxy-4-methoxypyridine-2-amido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylbut-2-enoate)