NP-MRD: Showing NP-Card for 4-{2-[(1e,3s,5s)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3h-pyridin-2-one (NP0330378)

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Record Information

Version

2.0

Created at

2022-09-12 15:39:39 UTC

Updated at

2022-09-12 15:39:39 UTC

NP-MRD ID

NP0330378

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{2-[(1e,3s,5s)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3h-pyridin-2-one

Description

368-19-4 Belongs to the class of organic compounds known as piperidinediones. Piperidinediones are compounds containing a piperidine ring which bears two ketones. Based on a literature review very few articles have been published on 368-19-4.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122217392D          

 19 20  0  0  1  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   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
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330378

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@H](C)C(=O)\C(C1)=C\CC1CC(O)=NC(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H21NO3/c1-9-5-10(2)15(19)12(6-9)4-3-11-7-13(17)16-14(18)8-11/h4,9-11H,3,5-8H2,1-2H3,(H,16,17,18)/b12-4+/t9-,10-/m0/s1

> <INCHI_KEY>
KWDFWSRTWRWCPS-JNCFRARESA-N

> <FORMULA>
C15H21NO3

> <MOLECULAR_WEIGHT>
263.337

> <EXACT_MASS>
263.15214354

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.115227033842164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{2-[(1E,3S,5S)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-2,3,4,5-tetrahydropyridin-2-one

> <JCHEM_LOGP>
2.3534647203333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6206525503543125

> <JCHEM_PKA_STRONGEST_BASIC>
-3.308081171304121

> <JCHEM_POLAR_SURFACE_AREA>
66.72999999999999

> <JCHEM_REFRACTIVITY>
72.77140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-{2-[(1E,3S,5S)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3H-pyridin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      10.669  -9.240   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -7.700   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
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7                                                       
CONECT   15    4   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₁NO₃

Average Mass

263.3370 Da

Monoisotopic Mass

263.15214 Da

IUPAC Name

4-{2-[(1E,3S,5S)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-2,3,4,5-tetrahydropyridin-2-one

Traditional Name

4-{2-[(1E,3S,5S)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3H-pyridin-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@H](C)C(=O)\C(C1)=C\CC1CC(O)=NC(=O)C1

InChI Identifier

InChI=1S/C15H21NO3/c1-9-5-10(2)15(19)12(6-9)4-3-11-7-13(17)16-14(18)8-11/h4,9-11H,3,5-8H2,1-2H3,(H,16,17,18)/b12-4+/t9-,10-/m0/s1

InChI Key

KWDFWSRTWRWCPS-JNCFRARESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidinediones. Piperidinediones are compounds containing a piperidine ring which bears two ketones.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Piperidinones

Direct Parent

Piperidinediones

Alternative Parents

Substituents

Piperidinedione
Delta-lactam
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Ketone
Lactam
Cyclic ketone
Carboxylic acid derivative
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
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	2.35	ChemAxon
pKa (Strongest Acidic)	3.62	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.73 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.77 m³·mol⁻¹	ChemAxon
Polarizability	29.12 Å³	ChemAxon
Number of Rings	2	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

4945456

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6441268

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{2-[(1e,3s,5s)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3h-pyridin-2-one (NP0330378)

MOL for NP0330378 (4-{2-[(1e,3s,5s)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3h-pyridin-2-one)

3D MOL for NP0330378 (4-{2-[(1e,3s,5s)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3h-pyridin-2-one)

3D SDF for NP0330378 (4-{2-[(1e,3s,5s)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3h-pyridin-2-one)

3D-SDF for NP0330378 (4-{2-[(1e,3s,5s)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3h-pyridin-2-one)

PDB for NP0330378 (4-{2-[(1e,3s,5s)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3h-pyridin-2-one)

3D PDB for NP0330378 (4-{2-[(1e,3s,5s)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3h-pyridin-2-one)

SMILES for NP0330378 (4-{2-[(1e,3s,5s)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3h-pyridin-2-one)

INCHI for NP0330378 (4-{2-[(1e,3s,5s)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3h-pyridin-2-one)

Structure for NP0330378 (4-{2-[(1e,3s,5s)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3h-pyridin-2-one)

3D Structure for NP0330378 (4-{2-[(1e,3s,5s)-3,5-dimethyl-2-oxocyclohexylidene]ethyl}-6-hydroxy-4,5-dihydro-3h-pyridin-2-one)