NP-MRD: Showing NP-Card for 3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol (NP0239484)

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Record Information

Version

2.0

Created at

2022-09-06 23:05:40 UTC

Updated at

2022-09-06 23:05:40 UTC

NP-MRD ID

NP0239484

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol

Description

3-[6-(4,6-Dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol 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]-5-(4-hydroxyphenyl)pyridine-2,4-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231514502D          

 32 34  0  0  0  0            999 V2000
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004231514502D          

 32 34  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0239484

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)CC(C)C=C(C)C1OC(CCC1C)C1=C(O)C(=CNC1=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H37NO4/c1-6-16(2)13-17(3)14-19(5)26-18(4)7-12-23(32-26)24-25(30)22(15-28-27(24)31)20-8-10-21(29)11-9-20/h8-11,14-18,23,26,29H,6-7,12-13H2,1-5H3,(H2,28,30,31)

> <INCHI_KEY>
YDGOHTBOOYAVOP-UHFFFAOYSA-N

> <FORMULA>
C27H37NO4

> <MOLECULAR_WEIGHT>
439.596

> <EXACT_MASS>
439.272258675

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.30680729769735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <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-(4-hydroxyphenyl)-1,2-dihydropyridin-2-one

> <ALOGPS_LOGP>
5.59

> <JCHEM_LOGP>
5.636519468333333

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.03932267311753

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.111906012815716

> <JCHEM_PKA_STRONGEST_BASIC>
-3.174854950648552

> <JCHEM_POLAR_SURFACE_AREA>
78.79

> <JCHEM_REFRACTIVITY>
129.75189999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.82e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.000   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.000   7.700   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       1.334   6.930   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.668  10.010   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667   9.240   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   24                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   18   25                                                  
CONECT   25   24                                                            
CONECT   26   21   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₇NO₄

Average Mass

439.5960 Da

Monoisotopic Mass

439.27226 Da

IUPAC Name

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

Traditional Name

3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-5-(4-hydroxyphenyl)-1H-pyridin-2-one

CAS Registry Number

Not Available

SMILES

CCC(C)CC(C)C=C(C)C1OC(CCC1C)C1=C(O)C(=CNC1=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C27H37NO4/c1-6-16(2)13-17(3)14-19(5)26-18(4)7-12-23(32-26)24-25(30)22(15-28-27(24)31)20-8-10-21(29)11-9-20/h8-11,14-18,23,26,29H,6-7,12-13H2,1-5H3,(H2,28,30,31)

InChI Key

YDGOHTBOOYAVOP-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
3-phenylpyridine
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
1-hydroxy-2-unsubstituted benzenoid
Dihydropyridine
Pyridinone
Hydroxypyridine
Phenol
Monocyclic benzene moiety
Pyridine
Oxane
Benzenoid
Hydropyridine
Vinylogous acid
Heteroaromatic compound
Lactam
Azacycle
Oxacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
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	5.59	ALOGPS
logP	5.64	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	9.11	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.79 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.75 m³·mol⁻¹	ChemAxon
Polarizability	51.31 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

Not Available

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]-5-(4-hydroxyphenyl)pyridine-2,4-diol (NP0239484)

MOL for NP0239484 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

3D MOL for NP0239484 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

3D SDF for NP0239484 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

3D-SDF for NP0239484 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

PDB for NP0239484 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

3D PDB for NP0239484 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

SMILES for NP0239484 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

INCHI for NP0239484 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

Structure for NP0239484 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

3D Structure for NP0239484 (3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)