NP-MRD: Showing NP-Card for 3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one (NP0222889)

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Record Information

Version

2.0

Created at

2022-09-06 00:50:34 UTC

Updated at

2022-09-06 00:50:34 UTC

NP-MRD ID

NP0222889

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one

Description

3-[6-(4,6-Dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methyl-1,2-dihydropyridin-2-one belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. 3-[6-(4,6-Dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methyl-1,2-dihydropyridin-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171507172D          

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M  END

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  Mrv1533004171507172D          

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 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 27 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222889

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)CC(C)C=C(C)C1OC(CCC1C)C1=C(O)C(=CN(C)C1=O)C1(O)CCC(=O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C28H43NO5/c1-7-17(2)14-18(3)15-20(5)26-19(4)8-9-23(34-26)24-25(31)22(16-29(6)27(24)32)28(33)12-10-21(30)11-13-28/h15-19,23,26,31,33H,7-14H2,1-6H3

> <INCHI_KEY>
HCEYJWLXDYOMJQ-UHFFFAOYSA-N

> <FORMULA>
C28H43NO5

> <MOLECULAR_WEIGHT>
473.654

> <EXACT_MASS>
473.314123489

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.51423253219398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methyl-1,2-dihydropyridin-2-one

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
4.154273913

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.092464848367918

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.697675903044832

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5471526517164476

> <JCHEM_POLAR_SURFACE_AREA>
87.07

> <JCHEM_REFRACTIVITY>
135.89259999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one

> <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      -7.990   5.821   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.657   6.591   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.323   5.821   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.323   4.281   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.989   6.591   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.656   5.821   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.656   4.281   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.322   6.591   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.012   5.821   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.012   4.281   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.345   6.591   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.345   8.131   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.679   8.901   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.013   8.131   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.013   6.591   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.679   5.821   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.679   4.281   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.679  10.441   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.345  11.211   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.012  10.441   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.345  12.751   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.679  13.521   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       4.013  12.751   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       5.346  13.521   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.013  11.211   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.346  10.441   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.012  13.521   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.002  14.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.515  12.074   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.032  11.806   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.021  12.986   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.538  12.719   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.495  14.433   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.978  14.700   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                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16                                                            
CONECT   18   13   19   25                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18   26                                                  
CONECT   26   25                                                            
CONECT   27   21   28   29   34                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   27                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₃NO₅

Average Mass

473.6540 Da

Monoisotopic Mass

473.31412 Da

IUPAC Name

3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methyl-1,2-dihydropyridin-2-one

Traditional Name

3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one

CAS Registry Number

Not Available

SMILES

CCC(C)CC(C)C=C(C)C1OC(CCC1C)C1=C(O)C(=CN(C)C1=O)C1(O)CCC(=O)CC1

InChI Identifier

InChI=1S/C28H43NO5/c1-7-17(2)14-18(3)15-20(5)26-19(4)8-9-23(34-26)24-25(31)22(16-29(6)27(24)32)28(33)12-10-21(30)11-13-28/h15-19,23,26,31,33H,7-14H2,1-6H3

InChI Key

HCEYJWLXDYOMJQ-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 terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Dihydropyridine
Hydroxypyridine
Pyridinone
Hydropyridine
Oxane
Pyridine
Vinylogous acid
Tertiary alcohol
Heteroaromatic compound
Cyclic alcohol
Cyclic ketone
Ketone
Lactam
Oxacycle
Azacycle
Organoheterocyclic compound
Dialkyl ether
Ether
Hydrocarbon derivative
Organopnictogen compound
Alcohol
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen 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	4.08	ALOGPS
logP	4.15	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.7	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.07 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	135.89 m³·mol⁻¹	ChemAxon
Polarizability	54.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

76171672

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one (NP0222889)

MOL for NP0222889 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one)

3D MOL for NP0222889 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one)

3D SDF for NP0222889 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one)

3D-SDF for NP0222889 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one)

PDB for NP0222889 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one)

3D PDB for NP0222889 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one)

SMILES for NP0222889 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one)

INCHI for NP0222889 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one)

Structure for NP0222889 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one)

3D Structure for NP0222889 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(1-hydroxy-4-oxocyclohexyl)-1-methylpyridin-2-one)