NP-MRD: Showing NP-Card for (1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione (NP0322860)

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Record Information

Version

2.0

Created at

2022-09-12 01:53:47 UTC

Updated at

2022-09-12 01:53:48 UTC

NP-MRD ID

NP0322860

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione

Description

(1S,3S,5R,7S,8S)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-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. (1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione is found in Hypericum scabrum. Based on a literature review very few articles have been published on (1S,3S,5R,7S,8S)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122203542D          

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M  END

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M  END


  Mrv1652309122203542D          

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    1.3012   -1.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1785   -2.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1101   -2.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8 35  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 14 23  1  0  0  0  0
 27 35  1  0  0  0  0
 23 24  2  0  0  0  0
 14 25  1  0  0  0  0
 25 26  2  0  0  0  0
  6 33  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 27 33  1  0  0  0  0
 25 27  1  0  0  0  0
 33 34  2  0  0  0  0
  6 23  1  0  0  0  0
  8  9  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322860

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC[C@@]12C[C@H]3[C@H](C=C(C)C)[C@](C(=O)C4=CC=CC=C4)(C1=O)C(=O)[C@@](CC=C(C)C)(C2=O)C3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C33H40O4/c1-20(2)14-16-31-19-25-24(18-22(5)6)33(28(31)36,26(34)23-12-10-9-11-13-23)29(37)32(27(31)35,30(25,7)8)17-15-21(3)4/h9-15,18,24-25H,16-17,19H2,1-8H3/t24-,25-,31-,32+,33-/m0/s1

> <INCHI_KEY>
HZHJUCBGNDWAOV-IPFYIKBHSA-N

> <FORMULA>
C33H40O4

> <MOLECULAR_WEIGHT>
500.679

> <EXACT_MASS>
500.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
0.0

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,5R,7S,8S)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione

> <JCHEM_LOGP>
8.343016063666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.358254265938351

> <JCHEM_POLAR_SURFACE_AREA>
68.28

> <JCHEM_REFRACTIVITY>
149.9667

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,5R,7S,8S)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione

> <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      -3.041  -6.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.885  -5.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.187  -3.826   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.426  -5.829   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.850  -4.707   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.590  -3.096   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.217  -3.793   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.056  -2.318   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.056  -0.923   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.384  -0.036   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.955   0.301   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.429   1.766   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.988  -0.842   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       2.316   1.388   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.339   2.638   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.763   2.085   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.878   3.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.265   4.288   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.538   3.420   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.422   1.885   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.035   1.217   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.590  -1.701   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.318  -1.785   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.802  -0.923   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.097   0.073   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.802  -2.318   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.422  -2.710   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.718  -1.820   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.108  -2.483   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.229  -4.018   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.377  -1.610   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       3.437  -5.494   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       4.067  -3.960   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.072  -4.832   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23   33                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   23   25                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   14    6   24                                                  
CONECT   24   23                                                            
CONECT   25   14   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   33   35                                             
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   27    6   34                                                  
CONECT   34   33                                                            
CONECT   35   27    8   36   37                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₀O₄

Average Mass

500.6790 Da

Monoisotopic Mass

500.29266 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=CC[C@@]12C[C@H]3[C@H](C=C(C)C)[C@](C(=O)C4=CC=CC=C4)(C1=O)C(=O)[C@@](CC=C(C)C)(C2=O)C3(C)C

InChI Identifier

InChI=1S/C33H40O4/c1-20(2)14-16-31-19-25-24(18-22(5)6)33(28(31)36,26(34)23-12-10-9-11-13-23)29(37)32(27(31)35,30(25,7)8)17-15-21(3)4/h9-15,18,24-25H,16-17,19H2,1-8H3/t24-,25-,31-,32+,33-/m0/s1

InChI Key

HZHJUCBGNDWAOV-IPFYIKBHSA-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
Hypericum scabrum	LOTUS Database	35616633

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
Monoterpenoid
Aromatic monoterpenoid
Aryl alkyl ketone
Benzoyl
Benzenoid
Monocyclic benzene moiety
Organic oxide
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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

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

162819033

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione (NP0322860)

MOL for NP0322860 ((1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione)

3D MOL for NP0322860 ((1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione)

3D SDF for NP0322860 ((1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione)

3D-SDF for NP0322860 ((1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione)

PDB for NP0322860 ((1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione)

3D PDB for NP0322860 ((1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione)

SMILES for NP0322860 ((1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione)

INCHI for NP0322860 ((1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione)

Structure for NP0322860 ((1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione)

3D Structure for NP0322860 ((1s,3s,5r,7s,8s)-1-benzoyl-6,6-dimethyl-3,5-bis(3-methylbut-2-en-1-yl)-8-(2-methylprop-1-en-1-yl)adamantane-2,4,9-trione)