NP-MRD: Showing NP-Card for michler's ketone (NP0203623)

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Record Information

Version

2.0

Created at

2022-09-04 23:07:36 UTC

Updated at

2022-09-04 23:07:37 UTC

NP-MRD ID

NP0203623

Secondary Accession Numbers

None

Natural Product Identification

Common Name

michler's ketone

Description

4-[4-(Dimethylamino)benzoyl]-N,N-dimethylaniline, also known as michler's ketone, belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. michler's ketone is found in Phellodendron chinense. 4-[4-(Dimethylamino)benzoyl]-N,N-dimethylaniline is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -5.7074   -1.3637   -1.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1954   -0.4810   -0.1459 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0451   -0.1469    0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8842    0.0143   -0.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708   -0.8375   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4866   -0.3856   -0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2242    0.9596   -0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0648    1.5065   -0.8861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006    2.6292   -1.5361 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3459    0.9886   -0.4896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669    0.1903    0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7997   -0.3124    0.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8833   -0.0085    0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1678   -0.5118    0.5239 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5540   -1.8104    0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0027    0.3138    1.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7102    0.7872   -0.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4815    1.2679   -1.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350    1.8211   -0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6082    1.3413   -0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0076   -0.7294   -2.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5893   -1.9121   -0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9181   -2.0548   -1.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2884   -1.0520    1.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6260    0.5880    1.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0450    0.2187    0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0019   -1.9037   -0.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6678   -1.0827   -0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6928   -0.0360    1.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701   -0.9360    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5266   -1.8779   -1.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9613   -2.6485    0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5953   -1.9943    0.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6915   -0.3445    1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4577    0.9227    2.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6073    1.0357    0.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5862    0.9987   -1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2968    1.9065   -2.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1460    2.8777   -0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4162    2.0617   -0.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7 19  1  0
 19 20  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 17  1  0
 17 18  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 20  4  1  0
 18 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
 19 39  1  0
 20 40  1  0
 11 29  1  0
 12 30  1  0
 17 37  1  0
 18 38  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END


  Mrv1572004191601102D          

 20 21  0  0  0  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 15 10  1  0  0  0  0
 16 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18 15  1  0  0  0  0
 19  3  1  0  0  0  0
 19  4  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0203623

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)C1=CC=C(C=C1)C(=O)C1=CC=C(C=C1)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C17H20N2O/c1-18(2)15-9-5-13(6-10-15)17(20)14-7-11-16(12-8-14)19(3)4/h5-12H,1-4H3

> <INCHI_KEY>
VVBLNCFGVYUYGU-UHFFFAOYSA-N

> <FORMULA>
C17H20N2O

> <MOLECULAR_WEIGHT>
268.36

> <EXACT_MASS>
268.157563272

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.356003238395733

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[4-(dimethylamino)benzoyl]-N,N-dimethylaniline

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
3.648686570666667

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.7304516934091496

> <JCHEM_POLAR_SURFACE_AREA>
23.55

> <JCHEM_REFRACTIVITY>
85.49069999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
michler's ketone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   6.160   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  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -1.334   8.470   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   19                                                            
CONECT    5    9   13                                                       
CONECT    6   10   13                                                       
CONECT    7   11   14                                                       
CONECT    8   12   14                                                       
CONECT    9    5   15                                                       
CONECT   10    6   15                                                       
CONECT   11    7   16                                                       
CONECT   12    8   16                                                       
CONECT   13    5    6   17                                                  
CONECT   14    7    8   17                                                  
CONECT   15    9   10   18                                                  
CONECT   16   11   12   19                                                  
CONECT   17   13   14   20                                                  
CONECT   18    1    2   15                                                  
CONECT   19    3    4   16                                                  
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Michler's ketone	Kegg
4,4'-Bis(dimethylamino)benzophenone	MeSH

Chemical Formula

C₁₇H₂₀N₂O

Average Mass

268.3600 Da

Monoisotopic Mass

268.15756 Da

IUPAC Name

4-[4-(dimethylamino)benzoyl]-N,N-dimethylaniline

Traditional Name

michler's ketone

CAS Registry Number

Not Available

SMILES

CN(C)C1=CC=C(C=C1)C(=O)C1=CC=C(C=C1)N(C)C

InChI Identifier

InChI=1S/C17H20N2O/c1-18(2)15-9-5-13(6-10-15)17(20)14-7-11-16(12-8-14)19(3)4/h5-12H,1-4H3

InChI Key

VVBLNCFGVYUYGU-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
Phellodendron chinense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzophenones

Direct Parent

Benzophenones

Alternative Parents

Substituents

Benzophenone
Diphenylmethane
Aryl-phenylketone
Benzoyl
Tertiary aliphatic/aromatic amine
Aryl ketone
Aniline or substituted anilines
Dialkylarylamine
Ketone
Tertiary amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzophenones (CHEBI:82347 )

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	3.74	ALOGPS
logP	3.65	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	3.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	85.49 m³·mol⁻¹	ChemAxon
Polarizability	31.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C19266

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7031

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for michler's ketone (NP0203623)

MOL for NP0203623 (michler's ketone)

3D MOL for NP0203623 (michler's ketone)

3D SDF for NP0203623 (michler's ketone)

3D-SDF for NP0203623 (michler's ketone)

PDB for NP0203623 (michler's ketone)

3D PDB for NP0203623 (michler's ketone)

SMILES for NP0203623 (michler's ketone)

INCHI for NP0203623 (michler's ketone)

Structure for NP0203623 (michler's ketone)

3D Structure for NP0203623 (michler's ketone)