NP-MRD: Showing NP-Card for 5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione (NP0294185)

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Record Information

Version

2.0

Created at

2022-09-10 02:36:28 UTC

Updated at

2022-09-10 02:36:28 UTC

NP-MRD ID

NP0294185

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione

Description

5-Benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 5-Benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231520522D          

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M  END

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M  END


  Mrv1533004231520522D          

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    4.7709   -0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2243   -1.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5873   -2.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3202   -2.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012   -1.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -2.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1898   -2.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2258   -2.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7 35  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 14 20  1  0  0  0  0
 24 35  1  0  0  0  0
 20 21  2  0  0  0  0
 14 22  1  0  0  0  0
 22 23  2  0  0  0  0
  5 33  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 24 33  1  0  0  0  0
 22 24  1  0  0  0  0
 33 34  2  0  0  0  0
  5 20  1  0  0  0  0
  7  8  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
  2 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0294185

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC12CC3C(C4OC4(C)C)C(CC=C(C)C)(C1=O)C(=O)C(C(=O)C1=CC=CC=C1)(C2=O)C3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C33H40O5/c1-19(2)14-16-31-18-22-23(25-30(7,8)38-25)32(26(31)35,17-15-20(3)4)28(37)33(27(31)36,29(22,5)6)24(34)21-12-10-9-11-13-21/h9-15,22-23,25H,16-18H2,1-8H3

> <INCHI_KEY>
CVRGNVXISHMROR-UHFFFAOYSA-N

> <FORMULA>
C33H40O5

> <MOLECULAR_WEIGHT>
516.678

> <EXACT_MASS>
516.287574388

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
57.55960203262852

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione

> <ALOGPS_LOGP>
5.24

> <JCHEM_LOGP>
7.442234555333332

> <ALOGPS_LOGS>
-5.69

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.22447724723538

> <JCHEM_POLAR_SURFACE_AREA>
80.81

> <JCHEM_REFRACTIVITY>
148.7272

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione

> <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      -2.913  -6.681   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.852  -5.565   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.355  -5.926   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.767  -4.746   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.590  -3.096   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.217  -3.793   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.056  -2.318   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.056  -0.923   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.257  -0.118   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.991   1.236   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.796  -0.076   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.326   0.099   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.484  -1.454   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.429  -0.225   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.562   1.414   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.666   2.559   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.241   4.039   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.310   5.147   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.747   4.411   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.590  -1.701   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.237  -1.773   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.802  -0.923   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.099   0.028   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.802  -2.318   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.357  -2.772   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.631  -3.831   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.376  -1.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.888  -0.159   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.908   0.994   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.417   0.687   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.906  -0.773   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.885  -1.927   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.963  -3.793   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.331  -4.718   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.429  -3.016   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.598  -4.617   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.221  -4.955   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.288  -4.088   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20   33                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   11                                                       
CONECT   11   10    9   12   13                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15   20   22                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14    5   21                                                  
CONECT   21   20                                                            
CONECT   22   14   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   33   35                                             
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   24    5   34                                                  
CONECT   34   33                                                            
CONECT   35   24    7   36   37                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38    2                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₀O₅

Average Mass

516.6780 Da

Monoisotopic Mass

516.28757 Da

IUPAC Name

5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione

Traditional Name

5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione

CAS Registry Number

Not Available

SMILES

CC(C)=CCC12CC3C(C4OC4(C)C)C(CC=C(C)C)(C1=O)C(=O)C(C(=O)C1=CC=CC=C1)(C2=O)C3(C)C

InChI Identifier

InChI=1S/C33H40O5/c1-19(2)14-16-31-18-22-23(25-30(7,8)38-25)32(26(31)35,17-15-20(3)4)28(37)33(27(31)36,29(22,5)6)24(34)21-12-10-9-11-13-21/h9-15,22-23,25H,16-18H2,1-8H3

InChI Key

CVRGNVXISHMROR-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 alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Adamantanone
Aromatic monoterpenoid
Monoterpenoid
Benzoyl
Aryl alkyl ketone
Benzenoid
Monocyclic benzene moiety
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
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	5.24	ALOGPS
logP	7.44	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	80.81 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	148.73 m³·mol⁻¹	ChemAxon
Polarizability	57.56 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

21592370

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione (NP0294185)

MOL for NP0294185 (5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione)

3D MOL for NP0294185 (5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione)

3D SDF for NP0294185 (5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione)

3D-SDF for NP0294185 (5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione)

PDB for NP0294185 (5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione)

3D PDB for NP0294185 (5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione)

SMILES for NP0294185 (5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione)

INCHI for NP0294185 (5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione)

Structure for NP0294185 (5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione)

3D Structure for NP0294185 (5-benzoyl-8-(3,3-dimethyloxiran-2-yl)-6,6-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)adamantane-2,4,9-trione)