NP-MRD: Showing NP-Card for 3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one (NP0288639)

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Record Information

Version

2.0

Created at

2022-09-09 18:25:19 UTC

Updated at

2022-09-09 18:25:19 UTC

NP-MRD ID

NP0288639

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one

Description

3-(2,6-Dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]Heptan-2-yl}-1,2-dihydropyridin-2-one belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. 3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one is found in Arthrinium arundinis. Based on a literature review very few articles have been published on 3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]Heptan-2-yl}-1,2-dihydropyridin-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092220252D          

 33 37  0  0  0  0            999 V2000
    8.6582    0.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3154   -0.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7851    0.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9727    0.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4424    0.8643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6299    0.7210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7245    1.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1942    2.2715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5370    1.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2889    3.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4764    3.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7925    2.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9461    3.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2283    4.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8798    1.2941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  3 33  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309092220252D          

 33 37  0  0  0  0            999 V2000
    8.6582    0.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8457    0.3756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0288639

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1(CCC(O)C2OC12)C1=CN(O)C(=O)C(C(=O)C2C(C)C=CC3CC(C)CCC23)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H33NO7/c1-12-4-7-15-14(10-12)6-5-13(2)18(15)21(29)19-20(28)16(11-26(31)24(19)30)25(32-3)9-8-17(27)22-23(25)33-22/h5-6,11-15,17-18,22-23,27-28,31H,4,7-10H2,1-3H3

> <INCHI_KEY>
RJLLKGPGZLQILJ-UHFFFAOYSA-N

> <FORMULA>
C25H33NO7

> <MOLECULAR_WEIGHT>
459.539

> <EXACT_MASS>
459.225702407

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.75111336768962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}-1,2-dihydropyridin-2-one

> <JCHEM_LOGP>
2.1223522083333326

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.810964492445187

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.1488820007005565

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1905390441392054

> <JCHEM_POLAR_SURFACE_AREA>
119.83000000000001

> <JCHEM_REFRACTIVITY>
121.52669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      16.162   0.434   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      14.645   0.701   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      13.655  -0.479   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.666   0.701   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.149   0.434   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      10.159   1.613   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       8.642   1.346   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.686   3.060   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.696   4.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.202   3.328   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.729   4.775   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.246   5.042   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.739   5.955   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.223   5.687   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.946   4.826   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.233   6.867   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.759   8.314   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.276   8.582   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.803  10.029   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.319  10.296   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.846  11.743   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.309   9.116   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.783   7.669   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.266   7.402   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.192   2.148   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.709   2.416   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.989  -1.249   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.989  -2.789   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.655  -3.559   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.655  -5.099   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.322  -2.789   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.988  -2.019   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.322  -1.249   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27   33                                             
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   25                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   24                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   18   13                                                  
CONECT   25   10    4   26                                                  
CONECT   26   25                                                            
CONECT   27    3   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31   33                                                       
CONECT   33   32   31    3                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₃NO₇

Average Mass

459.5390 Da

Monoisotopic Mass

459.22570 Da

IUPAC Name

3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}-1,2-dihydropyridin-2-one

Traditional Name

3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one

CAS Registry Number

Not Available

SMILES

COC1(CCC(O)C2OC12)C1=CN(O)C(=O)C(C(=O)C2C(C)C=CC3CC(C)CCC23)=C1O

InChI Identifier

InChI=1S/C25H33NO7/c1-12-4-7-15-14(10-12)6-5-13(2)18(15)21(29)19-20(28)16(11-26(31)24(19)30)25(32-3)9-8-17(27)22-23(25)33-22/h5-6,11-15,17-18,22-23,27-28,31H,4,7-10H2,1-3H3

InChI Key

RJLLKGPGZLQILJ-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
Arthrinium arundinis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Hydroxypyridine
Pyridinone
Oxepane
Dihydropyridine
Pyridine
Hydropyridine
Heteroaromatic compound
Vinylogous amide
Vinylogous acid
Cyclic alcohol
Secondary alcohol
Lactam
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.12	ChemAxon
pKa (Strongest Acidic)	6.15	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.53 m³·mol⁻¹	ChemAxon
Polarizability	48.75 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

163049463

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one (NP0288639)

MOL for NP0288639 (3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one)

3D MOL for NP0288639 (3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one)

3D SDF for NP0288639 (3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one)

3D-SDF for NP0288639 (3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one)

PDB for NP0288639 (3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one)

3D PDB for NP0288639 (3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one)

SMILES for NP0288639 (3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one)

INCHI for NP0288639 (3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one)

Structure for NP0288639 (3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one)

3D Structure for NP0288639 (3-(2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-1,4-dihydroxy-5-{5-hydroxy-2-methoxy-7-oxabicyclo[4.1.0]heptan-2-yl}pyridin-2-one)